JP6054157B2 - Fragrance composition - Google Patents
Fragrance composition Download PDFInfo
- Publication number
- JP6054157B2 JP6054157B2 JP2012262669A JP2012262669A JP6054157B2 JP 6054157 B2 JP6054157 B2 JP 6054157B2 JP 2012262669 A JP2012262669 A JP 2012262669A JP 2012262669 A JP2012262669 A JP 2012262669A JP 6054157 B2 JP6054157 B2 JP 6054157B2
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- dimethyl
- octen
- examples
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003205 fragrance Substances 0.000 title claims description 84
- 239000000203 mixture Substances 0.000 title claims description 50
- UATRONWBYDQKSQ-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CCOCC=C(C)C UATRONWBYDQKSQ-UHFFFAOYSA-N 0.000 claims description 31
- VIZNHPNZAZKEPF-UHFFFAOYSA-N 4,7-dimethyloct-6-en-3-ol Chemical compound CCC(O)C(C)CC=C(C)C VIZNHPNZAZKEPF-UHFFFAOYSA-N 0.000 claims description 30
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 17
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 claims description 10
- 238000007259 addition reaction Methods 0.000 claims description 10
- 239000002537 cosmetic Substances 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 6
- -1 lactone compounds Chemical class 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 239000002304 perfume Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- WKQWDIFHKYWRTA-UHFFFAOYSA-N 4,7-dimethyloct-6-en-3-one Chemical compound CCC(=O)C(C)CC=C(C)C WKQWDIFHKYWRTA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 229940057995 liquid paraffin Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000020971 citrus fruits Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N (-)-Jasmonic acid Natural products CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- SCCDQYPEOIRVGX-UHFFFAOYSA-N Acetyleugenol Chemical compound COC1=CC(CC=C)=CC=C1OC(C)=O SCCDQYPEOIRVGX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 240000005385 Jasminum sambac Species 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 150000001656 butanoic acid esters Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- PZUDDXJZNSJESK-UHFFFAOYSA-N ethyl 2-cyclohexylpropanoate Chemical compound CCOC(=O)C(C)C1CCCCC1 PZUDDXJZNSJESK-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical group CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 150000002384 heptanoic acid esters Chemical class 0.000 description 2
- 150000002400 hexanoic acid esters Chemical class 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- ZNJFBWYDHIGLCU-UHFFFAOYSA-N jasmonic acid Natural products CCC=CCC1C(CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- FRISMOQHTLZZRP-UHFFFAOYSA-N nerol oxide Chemical compound CC(C)=CC1CC(C)=CCO1 FRISMOQHTLZZRP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 150000002969 pentanoic acid esters Chemical class 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- UTSGPHXOHJSDBC-UHFFFAOYSA-N rosefuran Chemical compound CC(C)=CCC=1OC=CC=1C UTSGPHXOHJSDBC-UHFFFAOYSA-N 0.000 description 2
- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 1
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- QEBNYNLSCGVZOH-NFAWXSAZSA-N (+)-valencene Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CCC=C21 QEBNYNLSCGVZOH-NFAWXSAZSA-N 0.000 description 1
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- ZHWLEUGSDGROJS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) ethyl carbonate Chemical compound CCOC(=O)OC1CCCCC1C(C)(C)C ZHWLEUGSDGROJS-UHFFFAOYSA-N 0.000 description 1
- 239000001112 (2E)-1,1-diethoxy-3,7-dimethylocta-2,6-diene Substances 0.000 description 1
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- 239000001890 (2R)-8,8,8a-trimethyl-2-prop-1-en-2-yl-1,2,3,4,6,7-hexahydronaphthalene Substances 0.000 description 1
- HLCSDJLATUNSSI-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dienenitrile Chemical compound CC(C)=CCC\C(C)=C\C#N HLCSDJLATUNSSI-JXMROGBWSA-N 0.000 description 1
- SDOFMBGMRVAJNF-KVTDHHQDSA-N (2r,3r,4r,5r)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-KVTDHHQDSA-N 0.000 description 1
- VSRVCSJJKWDZSH-UHFFFAOYSA-N (3-pentyloxan-4-yl) acetate Chemical compound CCCCCC1COCCC1OC(C)=O VSRVCSJJKWDZSH-UHFFFAOYSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- 239000001147 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran Substances 0.000 description 1
- VCOCESNMLNDPLX-BTXGZQJSSA-N (3s,6s)-2,2,8,8-tetramethyl-octahydro-1h-2,4a-methanonapthalene-10-one Chemical compound O=C1CCC(C)(C)[C@@]2(C3)C1C(C)(C)[C@H]3CC2 VCOCESNMLNDPLX-BTXGZQJSSA-N 0.000 description 1
- 229940098795 (3z)- 3-hexenyl acetate Drugs 0.000 description 1
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- KRLBLPBPZSSIGH-CSKARUKUSA-N (6e)-3,7-dimethylnona-1,6-dien-3-ol Chemical group CC\C(C)=C\CCC(C)(O)C=C KRLBLPBPZSSIGH-CSKARUKUSA-N 0.000 description 1
- 239000001244 (E)-1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one Substances 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- WMBOCUXXNSOQHM-FLIBITNWSA-N (Z)-3-butylidenephthalide Chemical compound C1=CC=C2C(=C/CCC)/OC(=O)C2=C1 WMBOCUXXNSOQHM-FLIBITNWSA-N 0.000 description 1
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical group CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- VPKMGDRERYMTJX-XEHSLEBBSA-N (e)-1-[(1r)-2,6,6-trimethylcyclohex-2-en-1-yl]pent-1-en-3-one Chemical compound CCC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C VPKMGDRERYMTJX-XEHSLEBBSA-N 0.000 description 1
- YYMCVDNIIFNDJK-XFQWXJFMSA-N (z)-1-(3-fluorophenyl)-n-[(z)-(3-fluorophenyl)methylideneamino]methanimine Chemical compound FC1=CC=CC(\C=N/N=C\C=2C=C(F)C=CC=2)=C1 YYMCVDNIIFNDJK-XFQWXJFMSA-N 0.000 description 1
- JRJBVWJSTHECJK-LUAWRHEFSA-N (z)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one Chemical compound CC(=O)C(\C)=C/C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-LUAWRHEFSA-N 0.000 description 1
- NTXGFKWLJFHGGJ-ACCUITESSA-N 1,1-Diethoxy-3,7-dimethyl-2,6-octadiene Chemical compound CCOC(OCC)\C=C(/C)CCC=C(C)C NTXGFKWLJFHGGJ-ACCUITESSA-N 0.000 description 1
- 239000001709 1,2-dimethylcyclohex-3-ene-1-carbaldehyde Substances 0.000 description 1
- MKEIDVFLAWJKMY-UHFFFAOYSA-N 1,7-dioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCCCCO1 MKEIDVFLAWJKMY-UHFFFAOYSA-N 0.000 description 1
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical group CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 1
- LMWNGLDCJDIIBR-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1=C(C)CCCC1(C)C LMWNGLDCJDIIBR-CMDGGOBGSA-N 0.000 description 1
- FAHUKNBUIVOJJR-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine Chemical compound C1=CC(F)=CC=C1C1C2=CC=CN2CCN1 FAHUKNBUIVOJJR-UHFFFAOYSA-N 0.000 description 1
- YBUIAJZFOGJGLJ-SWRJLBSHSA-N 1-cedr-8-en-9-ylethanone Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=C(C(C)=O)C2 YBUIAJZFOGJGLJ-SWRJLBSHSA-N 0.000 description 1
- AROCNZZBLCAOPH-UHFFFAOYSA-N 1-methyl-4-prop-2-enoxybenzene Chemical compound CC1=CC=C(OCC=C)C=C1 AROCNZZBLCAOPH-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- QYZSCAXYTWMYHH-UHFFFAOYSA-N 2,2,3,3,4,4-hexamethyl-5,6-dihydro-4ah-cyclopenta[h]chromene Chemical compound C1CC2C(C)(C)C(C)(C)C(C)(C)OC2=C2C=CC=C21 QYZSCAXYTWMYHH-UHFFFAOYSA-N 0.000 description 1
- OJMYKSVNVGQBRZ-UHFFFAOYSA-N 2,5-dimethyloct-2-ene Chemical compound CCCC(C)CC=C(C)C OJMYKSVNVGQBRZ-UHFFFAOYSA-N 0.000 description 1
- VVUMWAHNKOLVSN-UHFFFAOYSA-N 2-(4-ethoxyanilino)-n-propylpropanamide Chemical compound CCCNC(=O)C(C)NC1=CC=C(OCC)C=C1 VVUMWAHNKOLVSN-UHFFFAOYSA-N 0.000 description 1
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 1
- ZPENOSKWEKGDCX-UHFFFAOYSA-N 2-Benzyl-5-hydroxymethyl-1,3-dioxolane Chemical compound O1C(CO)COC1CC1=CC=CC=C1 ZPENOSKWEKGDCX-UHFFFAOYSA-N 0.000 description 1
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
- FLUWAIIVLCVEKF-UHFFFAOYSA-N 2-Methyl-1-phenyl-2-propanyl acetate Chemical compound CC(=O)OC(C)(C)CC1=CC=CC=C1 FLUWAIIVLCVEKF-UHFFFAOYSA-N 0.000 description 1
- SHSGYHAHMQLYRB-UHFFFAOYSA-N 2-Methyl-1-phenyl-2-propanyl butyrate Chemical compound CCCC(=O)OC(C)(C)CC1=CC=CC=C1 SHSGYHAHMQLYRB-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- SJWKGDGUQTWDRV-UHFFFAOYSA-N 2-Propenyl heptanoate Chemical compound CCCCCCC(=O)OCC=C SJWKGDGUQTWDRV-UHFFFAOYSA-N 0.000 description 1
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 description 1
- UAQFADWTDBIBBZ-UHFFFAOYSA-N 2-[2-(2-naphthalen-2-ylethoxy)ethyl]naphthalene Chemical compound C1=CC=CC2=CC(CCOCCC=3C=C4C=CC=CC4=CC=3)=CC=C21 UAQFADWTDBIBBZ-UHFFFAOYSA-N 0.000 description 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 1
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 1
- UQURIQWAEZGLAC-UHFFFAOYSA-N 2-cyclohexylpropanal Chemical compound O=CC(C)C1CCCCC1 UQURIQWAEZGLAC-UHFFFAOYSA-N 0.000 description 1
- DVCHJFSLGUNEQZ-UHFFFAOYSA-M 2-ethenyl-2,6-dimethylhept-5-enoate Chemical compound CC(C)=CCCC(C)(C=C)C([O-])=O DVCHJFSLGUNEQZ-UHFFFAOYSA-M 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 1
- VNWOJVJCRAHBJJ-UHFFFAOYSA-N 2-pentylcyclopentan-1-one Chemical compound CCCCCC1CCCC1=O VNWOJVJCRAHBJJ-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- PDGPIBIURNPBSE-UHFFFAOYSA-N 2-phenylethyl pentanoate Chemical compound CCCCC(=O)OCCC1=CC=CC=C1 PDGPIBIURNPBSE-UHFFFAOYSA-N 0.000 description 1
- IYYUJCKJSSPXQQ-UHFFFAOYSA-N 2-pyridin-4-yl-1,3-thiazolidin-3-ium-4-carboxylate Chemical compound N1C(C(=O)O)CSC1C1=CC=NC=C1 IYYUJCKJSSPXQQ-UHFFFAOYSA-N 0.000 description 1
- BJLRAKFWOUAROE-UHFFFAOYSA-N 2500-83-6 Chemical compound C12C=CCC2C2CC(OC(=O)C)C1C2 BJLRAKFWOUAROE-UHFFFAOYSA-N 0.000 description 1
- FRUPGGSBENIUTJ-UHFFFAOYSA-N 3,5,6,6-tetramethyl-4-methylideneheptan-2-one Chemical compound CC(=O)C(C)C(=C)C(C)C(C)(C)C FRUPGGSBENIUTJ-UHFFFAOYSA-N 0.000 description 1
- MTDAKBBUYMYKAR-UHFFFAOYSA-N 3,7-dimethyloct-6-enenitrile Chemical compound N#CCC(C)CCC=C(C)C MTDAKBBUYMYKAR-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- OGHBUHJLMHQMHS-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 2-methylbut-2-enoate Chemical compound CC=C(C)C(=O)OCC=C(C)CCC=C(C)C OGHBUHJLMHQMHS-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- GTNCESCYZPMXCJ-UHFFFAOYSA-N 3-Phenylpropyl propanoate Chemical compound CCC(=O)OCCCC1=CC=CC=C1 GTNCESCYZPMXCJ-UHFFFAOYSA-N 0.000 description 1
- UJVMVSBNTJTGOO-UHFFFAOYSA-N 3-chloro-n-(5-fluoro-2-methylphenyl)propanamide Chemical compound CC1=CC=C(F)C=C1NC(=O)CCCl UJVMVSBNTJTGOO-UHFFFAOYSA-N 0.000 description 1
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
- VPXWZHXOBQZDNM-UHFFFAOYSA-N 4,4-dimethylcyclohex-2-ene-1-carbaldehyde Chemical compound CC1(CCC(C=O)C=C1)C VPXWZHXOBQZDNM-UHFFFAOYSA-N 0.000 description 1
- CNJLMVZFWLNOEP-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(C)CCC2C(C)(C)C12 CNJLMVZFWLNOEP-UHFFFAOYSA-N 0.000 description 1
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 1
- YXVSKJDFNJFXAJ-UHFFFAOYSA-N 4-cyclohexyl-2-methylbutan-2-ol Chemical compound CC(C)(O)CCC1=CC=CC=C1 YXVSKJDFNJFXAJ-UHFFFAOYSA-N 0.000 description 1
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 1
- NKNGVPNCSFZRSM-ONEGZZNKSA-N 5-(3-hexenyl)dihydro-2(3h)-furanone Chemical compound CC\C=C\CCC1CCC(=O)O1 NKNGVPNCSFZRSM-ONEGZZNKSA-N 0.000 description 1
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 1
- ZJTBNMCGJKZICN-UHFFFAOYSA-N 6,7-dimethyloct-6-en-3-ol Chemical compound CCC(O)CCC(C)=C(C)C ZJTBNMCGJKZICN-UHFFFAOYSA-N 0.000 description 1
- IBXZBBOCKADXLI-UHFFFAOYSA-N 7-methyl-4,5-dihydro-1,2-benzodioxepin-3-one Chemical compound O1OC(=O)CCC2=CC(C)=CC=C21 IBXZBBOCKADXLI-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- OKJADYKTJJGKDX-UHFFFAOYSA-N Butyl pentanoate Chemical compound CCCCOC(=O)CCCC OKJADYKTJJGKDX-UHFFFAOYSA-N 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000984090 Cistus Species 0.000 description 1
- 235000002548 Cistus Nutrition 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- KNYRCCKTQMBSFP-UHFFFAOYSA-N Citronellyl hexanoate Chemical compound CCCCCC(=O)OCCC(C)CCC=C(C)C KNYRCCKTQMBSFP-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 240000004784 Cymbopogon citratus Species 0.000 description 1
- 235000017897 Cymbopogon citratus Nutrition 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- RZTOWFMDBDPERY-UHFFFAOYSA-N Delta-Hexanolactone Chemical compound CC1CCCC(=O)O1 RZTOWFMDBDPERY-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VXCUURYYWGCLIH-UHFFFAOYSA-N Dodecanenitrile Chemical compound CCCCCCCCCCCC#N VXCUURYYWGCLIH-UHFFFAOYSA-N 0.000 description 1
- 240000002943 Elettaria cardamomum Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- 244000165082 Lavanda vera Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- JBVVONYMRFACPQ-UHFFFAOYSA-N Linalylformate Natural products CC(=C)CCCC(C)(OC=O)C=C JBVVONYMRFACPQ-UHFFFAOYSA-N 0.000 description 1
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 description 1
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000078639 Mentha spicata Species 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- ALHUZKCOMYUFRB-OAHLLOKOSA-N Muscone Chemical compound C[C@@H]1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-OAHLLOKOSA-N 0.000 description 1
- 244000270834 Myristica fragrans Species 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 235000007265 Myrrhis odorata Nutrition 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- ZOZIRNMDEZKZHM-UHFFFAOYSA-N Phenethyl phenylacetate Chemical compound C=1C=CC=CC=1CCOC(=O)CC1=CC=CC=C1 ZOZIRNMDEZKZHM-UHFFFAOYSA-N 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 235000012550 Pimpinella anisum Nutrition 0.000 description 1
- 240000002505 Pogostemon cablin Species 0.000 description 1
- 235000011751 Pogostemon cablin Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- POPNTVRHTZDEBW-UHFFFAOYSA-N Propionsaeure-citronellylester Natural products CCC(=O)OCCC(C)CCC=C(C)C POPNTVRHTZDEBW-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- WNVCMFHPRIBNCW-UHFFFAOYSA-N Quercuslactone a Chemical compound CCCCC1OC(=O)CC1C WNVCMFHPRIBNCW-UHFFFAOYSA-N 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 240000006909 Tilia x europaea Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 244000284012 Vetiveria zizanioides Species 0.000 description 1
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 1
- NIONDZDPPYHYKY-UHFFFAOYSA-N Z-hexenoic acid Natural products CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 description 1
- FMFHUEMLVAIBFI-BQYQJAHWSA-N [(e)-2-phenylethenyl] acetate Chemical compound CC(=O)O\C=C\C1=CC=CC=C1 FMFHUEMLVAIBFI-BQYQJAHWSA-N 0.000 description 1
- JNWQKXUWZWKUAY-XYLIHAQWSA-N [(e)-hex-3-enyl] (e)-2-methylbut-2-enoate Chemical compound CC\C=C\CCOC(=O)C(\C)=C\C JNWQKXUWZWKUAY-XYLIHAQWSA-N 0.000 description 1
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 229940011037 anethole Drugs 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000001518 benzyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- NGHOLYJTSCBCGC-QXMHVHEDSA-N benzyl cinnamate Chemical compound C=1C=CC=CC=1\C=C/C(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-QXMHVHEDSA-N 0.000 description 1
- YZJCDVRXBOPXSQ-UHFFFAOYSA-N benzyl pentanoate Chemical compound CCCCC(=O)OCC1=CC=CC=C1 YZJCDVRXBOPXSQ-UHFFFAOYSA-N 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- 229940115397 bornyl acetate Drugs 0.000 description 1
- FZJUFJKVIYFBSY-UHFFFAOYSA-N bourgeonal Chemical compound CC(C)(C)C1=CC=C(CCC=O)C=C1 FZJUFJKVIYFBSY-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 235000005300 cardamomo Nutrition 0.000 description 1
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 description 1
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 description 1
- 229940026455 cedrol Drugs 0.000 description 1
- PCROEXHGMUJCDB-UHFFFAOYSA-N cedrol Natural products CC1CCC2C(C)(C)C3CC(C)(O)CC12C3 PCROEXHGMUJCDB-UHFFFAOYSA-N 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- WJSDHUCWMSHDCR-VMPITWQZSA-N cinnamyl acetate Natural products CC(=O)OC\C=C\C1=CC=CC=C1 WJSDHUCWMSHDCR-VMPITWQZSA-N 0.000 description 1
- NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
- NGHOLYJTSCBCGC-UHFFFAOYSA-N cis-cinnamic acid benzyl ester Natural products C=1C=CC=CC=1C=CC(=O)OCC1=CC=CC=C1 NGHOLYJTSCBCGC-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BLBJUGKATXCWET-UHFFFAOYSA-N cyclaprop Chemical compound C12CC=CC2C2CC(OC(=O)CC)C1C2 BLBJUGKATXCWET-UHFFFAOYSA-N 0.000 description 1
- NUQDJSMHGCTKNL-UHFFFAOYSA-N cyclohexyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1CCCCC1 NUQDJSMHGCTKNL-UHFFFAOYSA-N 0.000 description 1
- MCNKZOMTVSVVSJ-UHFFFAOYSA-N cyclooctyl methyl carbonate Chemical compound COC(=O)OC1CCCCCCC1 MCNKZOMTVSVVSJ-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- 229940095104 dimethyl benzyl carbinyl acetate Drugs 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- ZCSDUGXKKBIICL-MDZDMXLPSA-N ethyl (e)-non-2-enoate Chemical compound CCCCCC\C=C\C(=O)OCC ZCSDUGXKKBIICL-MDZDMXLPSA-N 0.000 description 1
- KQCNXVHFHZAHDW-UHFFFAOYSA-N ethyl 3-nonenoate Chemical compound CCCCCC=CCC(=O)OCC KQCNXVHFHZAHDW-UHFFFAOYSA-N 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 229930007090 gamma-ionone Natural products 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- FQMZVFJYMPNUCT-UHFFFAOYSA-N geraniol formate Natural products CC(C)=CCCC(C)=CCOC=O FQMZVFJYMPNUCT-UHFFFAOYSA-N 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Chemical group CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- IUSBVFZKQJGVEP-SNAWJCMRSA-N isoeugenol acetate Chemical compound COC1=CC(\C=C\C)=CC=C1OC(C)=O IUSBVFZKQJGVEP-SNAWJCMRSA-N 0.000 description 1
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229930007503 menthone Natural products 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- ZWNPUELCBZVMDA-HJWRWDBZSA-N methyl 2-nonenoate Chemical compound CCCCCC\C=C/C(=O)OC ZWNPUELCBZVMDA-HJWRWDBZSA-N 0.000 description 1
- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
- JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ALHUZKCOMYUFRB-UHFFFAOYSA-N muskone Natural products CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 1
- FALTVGCCGMDSNZ-UHFFFAOYSA-N n-(1-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C1=CC=CC=C1 FALTVGCCGMDSNZ-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- WMBOCUXXNSOQHM-UHFFFAOYSA-N n-butylidenephthalide Natural products C1=CC=C2C(=CCCC)OC(=O)C2=C1 WMBOCUXXNSOQHM-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- OJEQSSJFSNLMLB-UHFFFAOYSA-N p-Tolyl phenylacetate Chemical compound C1=CC(C)=CC=C1OC(=O)CC1=CC=CC=C1 OJEQSSJFSNLMLB-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- FGPPDYNPZTUNIU-UHFFFAOYSA-N pentyl pentanoate Chemical compound CCCCCOC(=O)CCCC FGPPDYNPZTUNIU-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 238000005464 sample preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- YUVKTUCPWGPBLJ-UHFFFAOYSA-N tert-butyl 2-cyclohexylacetate Chemical compound CC(C)(C)OC(=O)CC1CCCCC1 YUVKTUCPWGPBLJ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- IUSBVFZKQJGVEP-UHFFFAOYSA-N trans-isoeugenol acetate Natural products COC1=CC(C=CC)=CC=C1OC(C)=O IUSBVFZKQJGVEP-UHFFFAOYSA-N 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- SFEOKXHPFMOVRM-BQYQJAHWSA-N γ-ionone Chemical compound CC(=O)\C=C\C1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-BQYQJAHWSA-N 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Description
本発明は、特定の2種の化合物を一定比率で含有する香料組成物に関する。 The present invention relates to a perfume composition containing two specific compounds in a certain ratio.
香りは製品等の嗜好性や高級感、安心感、効果への期待感などを演出する重要な要素である。更に特徴ある香りは製品識別効果、顧客吸引力を与える。 The scent is an important factor that produces a taste of products, a sense of luxury, a sense of security, and a sense of expectation for effects. Furthermore, the characteristic fragrance gives a product identification effect and customer suction power.
一つの香りを創作する際に、香りの質をより嗜好性の高いものにし、香りの拡散性、持続性、感覚強度を自在に調節し、また自他識別力のある香りを得るために、多種類の香料素材が組み合わされて使用されるのが通常である。香り創作の自由度を上げるために、香料素材のバリエーションの拡大は常に望まれており、特に、フローラル、フルーティの香調を併せ持つ香料素材は、香りの嗜好性を高め、また高級感を演出するために欠かせないものである。 When creating one scent, in order to make the quality of the scent more tasteful, freely adjust the diffusibility, persistence, and sensory intensity of the scent, and to obtain a scent with discriminating ability, It is usual to use a combination of a variety of fragrance materials. In order to increase the degree of freedom in creating fragrances, it is always desirable to expand the variety of fragrance materials. In particular, fragrance materials that combine floral and fruity fragrances enhance the taste of fragrance and produce a high-class feel. It is indispensable for.
従来、フローラル、フルーティの要素を併せ持つ香料素材としては、ジャスミン香ラクトンのようなラクトン系化合物や、幾つかの蟻酸エステル、酢酸エステル等のエステル系化合物が知られているが、これらは、花の香りに特有な重厚感や、フルーツのようなグルマン調の甘さ、植物に特有の青臭さを強調するものが多く、フレッシュなフローラル香を有しつつ、フルーティな甘さを付与できる化合物は稀であった。 Conventionally, as fragrance materials having both floral and fruity elements, lactone compounds such as jasmine fragrance lactones and some ester compounds such as formate esters and acetate esters are known. Many compounds emphasize the aroma and peculiar fragrance, Gurman-like sweetness like fruits, and the blue odor characteristic of plants. There are rare compounds that have a fresh floral aroma and can give a fruity sweetness. Met.
特許文献1には、4,7-ジメチル-6-オクテン-3-オールが香料として有用な化合物であり、柑橘様の香調であることが開示されている。また、非特許文献1には、ジプレニルエーテルが香料として有用な化合物であり、フレッシュで草様の甘さを持つ香調であることが開示されている。 Patent Document 1 discloses that 4,7-dimethyl-6-octen-3-ol is a useful compound as a fragrance and has a citrus-like fragrance. Further, Non-Patent Document 1 discloses that diprenyl ether is a compound useful as a fragrance and has a fresh and grass-like sweetness.
本発明者らは調香の自由度を上げるため、フレッシュなフローラル香を有しつつ、フルーティな甘さを付与できる素材を開発すべく、従来知られているラクトンやエステル系化合物ではなく、アルコール系やエーテル系化合物に注目して、種々の化合物を探索した。しかし、フレッシュなフローラル香と共にフルーティな甘さを付与できる化合物は稀であり、特許文献1、非特許文献1に記載されている化合物も、目的とする香りを有するものではなかった。 In order to increase the degree of freedom of the fragrance, the present inventors have developed a material that has a fresh floral fragrance and can impart a fruity sweetness. Various compounds were searched by paying attention to compounds and ether compounds. However, the compound which can provide fruity sweetness with a fresh floral fragrance is rare, and the compounds described in Patent Document 1 and Non-Patent Document 1 did not have the intended fragrance.
本発明の課題は、フレッシュなフローラル香を有しつつ、フルーティな甘さを付与し得る香料組成物を提供することにある。 The subject of this invention is providing the fragrance | flavor composition which can provide fruity sweetness, having a fresh floral fragrance.
本発明者らは、柑橘様のフレッシュなフローラル様の香気を有する4,7-ジメチル-6-オクテン-3-オールに対し、グリーンフルーティ様の香気を有するジプレニルエーテルを特定の比率で添加混合した際、フレッシュなフローラル香と共にフルーティな甘さを付与できることを見出した。更に意外なことに、このようにして得られた香料組成物は匂いの閾値が低下することを見出した。 The present inventors added and mixed diprenyl ether having a green fruity-like odor at a specific ratio to 4,7-dimethyl-6-octen-3-ol having a fresh citrus-like floral-like odor. When found, it was found that fruity sweetness can be imparted with a fresh floral scent. More surprisingly, it has been found that the fragrance composition thus obtained has a reduced odor threshold.
本発明は4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2の質量比で含有する香料組成物を提供するものである。 The present invention provides a fragrance composition containing 4,7-dimethyl-6-octen-3-ol and diprenyl ether in a mass ratio of 97.0 / 3.0 to 99.8 / 0.2.
更に本発明は、上記の香料組成物を含む家庭用製品及び香粧品を提供するものである。 Furthermore, this invention provides the household product and cosmetics containing said fragrance | flavor composition.
更に本発明は、塩化プレニルとジエチルケトンとの付加反応を行った後、還元反応を行う請求項1記載の香料組成物の製造方法を提供するものである。 Furthermore, this invention provides the manufacturing method of the fragrance | flavor composition of Claim 1 which performs a reductive reaction after performing the addition reaction of a prenyl chloride and diethyl ketone.
本発明の香料組成物は、匂いの閾値が低く、フレッシュなフローラル香と共にフルーティな甘さを付与することができる。 The fragrance composition of the present invention has a low odor threshold and can impart a fruity sweetness together with a fresh floral fragrance.
〔香料組成物〕
本発明の香料組成物は、4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルを特定の比率で含有する。これにより、4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテル自身が有する香りとは異なり、フレッシュなフローラル香気を維持したまま、良好なフルーティ感を有する香りとなる。更に意外なことに、4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルそれぞれが有する香り閾値より香りの閾値が下がるため、香りを認識しやすくなる。
[Perfume composition]
The perfume composition of the present invention contains 4,7-dimethyl-6-octen-3-ol and diprenyl ether in a specific ratio. Thus, unlike the scent of 4,7-dimethyl-6-octen-3-ol and diprenyl ether itself, the scent has a good fruity feeling while maintaining a fresh floral scent. More surprisingly, the scent threshold is lower than the scent threshold of each of 4,7-dimethyl-6-octen-3-ol and diprenyl ether, making it easier to recognize the scent.
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの含有比率は、香り閾値低下及びフレッシュなフローラル香気を維持したまま、良好なフルーティ感を付与する観点から、97.0/3.0〜99.8/0.2の質量比とするが、更には99.3/0.7〜99.8/0.2の質量比とすることがより好ましい。 The content ratio of 4,7-dimethyl-6-octen-3-ol and diprenyl ether is 97.0 / 3.0 to 99.8 from the viewpoint of imparting a good fruity feeling while maintaining a low fragrance threshold and a fresh floral fragrance. However, it is more preferable that the mass ratio be 99.3 / 0.7 to 99.8 / 0.2.
本発明の香料組成物は、4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルを所定の濃度で混合することで得られる。4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルは、一般的な有機化学反応を用いて合成することができ、その製造方法に制限はない。例えば4,7-ジメチル-6-オクテン-3-オールは特許文献1に記載される合成方法で得ることができる。また、ジプレニルエーテルは非特許文献1に記載されている合成方法で得ることができる。 The fragrance composition of the present invention can be obtained by mixing 4,7-dimethyl-6-octen-3-ol and diprenyl ether at a predetermined concentration. 4,7-dimethyl-6-octen-3-ol and diprenyl ether can be synthesized using a general organic chemical reaction, and the production method is not limited. For example, 4,7-dimethyl-6-octen-3-ol can be obtained by the synthesis method described in Patent Document 1. Diprenyl ether can be obtained by the synthesis method described in Non-Patent Document 1.
また、例えば、以下の反応式のように、塩化プレニルとジエチルケトンとの付加反応を行った後、還元反応を行う工程を行えば、式(I)で表される4,7-ジメチル-6-オクテン-3-オールと式(II)で表されるジプレニルエーテルとを同時に製造することができる。 In addition, for example, as shown in the following reaction formula, if a reduction reaction is performed after an addition reaction between prenyl chloride and diethyl ketone, 4,7-dimethyl-6 represented by the formula (I) is performed. -Octen-3-ol and the diprenyl ether represented by the formula (II) can be produced simultaneously.
塩化プレニルとジエチルケトンとの付加反応は、塩基を用いることにより反応が進行する。塩基としては、アルカリ金属の水酸化物が好ましく、水酸化ナトリウム、水酸化カリウム等が挙げられる。また、水酸化ナトリウムや水酸化カリウムの溶解性の点から、用いる反応溶媒としては水性の溶媒が好ましい。用いる塩基量は1〜5当量、更には1.5〜4当量が好ましい。 The addition reaction between prenyl chloride and diethyl ketone proceeds by using a base. As the base, an alkali metal hydroxide is preferable, and examples thereof include sodium hydroxide and potassium hydroxide. From the viewpoint of solubility of sodium hydroxide or potassium hydroxide, an aqueous solvent is preferable as the reaction solvent to be used. The amount of base used is preferably 1 to 5 equivalents, more preferably 1.5 to 4 equivalents.
反応条件は、付加反応が進行する条件であればどのような条件でも良いが、例えば反応温度は40〜100℃、更には50〜80℃が好ましい。また、反応時間は3〜20時間、更には5〜10時間が好ましい。 The reaction conditions may be any conditions as long as the addition reaction proceeds. For example, the reaction temperature is preferably 40 to 100 ° C, more preferably 50 to 80 ° C. The reaction time is preferably 3 to 20 hours, more preferably 5 to 10 hours.
用いる塩化プレニルとジエチルケトンの比率は、塩化プレニルに対してジエチルケトンが1.5〜10当量、更には3〜7当量とするのが好ましい。 The ratio of prenyl chloride to diethyl ketone used is preferably 1.5 to 10 equivalents, more preferably 3 to 7 equivalents of diethyl ketone with respect to prenyl chloride.
付加反応で得られた生成物を還元するために用いる還元剤としては、水素化ホウ素ナトリウム、水素化アルミニウムリチウム、水素化ジイソブチルアルミニウム等が挙げられるが、製造工程の簡便性の点から水素化ホウ素ナトリウムが好ましい。用いる還元剤量は1〜4当量が好ましい。 Examples of the reducing agent used for reducing the product obtained by the addition reaction include sodium borohydride, lithium aluminum hydride, diisobutylaluminum hydride, and the like. Sodium is preferred. The amount of reducing agent used is preferably 1 to 4 equivalents.
反応条件は、還元反応が進行する条件であればどのような条件でも良いが、例えば反応温度は10〜40℃、更には15〜30℃が好ましい。また、反応時間は1〜3時間が好ましい。 The reaction conditions may be any conditions as long as the reduction reaction proceeds. For example, the reaction temperature is preferably 10 to 40 ° C, more preferably 15 to 30 ° C. The reaction time is preferably 1 to 3 hours.
この方法で得られた4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの混合物を精製してそれぞれを単離した上で、所定の濃度で混合してもよいが、本製造方法で得られた反応混合物中の両化合物の比率が前述の範囲内にある限り、この反抗混合物をそのまま、又は後述するその他の香料を適宜添加して、香料組成物として使用してもよい。製造工程の簡便さ、香りの質、更には匂いの閾値の観点から、本方法で得られた4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの混合物をそのまま用いてもよい。 The mixture of 4,7-dimethyl-6-octen-3-ol and diprenyl ether obtained by this method may be purified and isolated, and then mixed at a predetermined concentration. As long as the ratio of both compounds in the reaction mixture obtained by the method is within the above-mentioned range, this repellent mixture may be used as it is or by adding other fragrances described later as appropriate. From the viewpoint of simplicity of the production process, fragrance quality, and odor threshold, the mixture of 4,7-dimethyl-6-octen-3-ol and diprenyl ether obtained by this method may be used as it is. .
本発明の香料組成物における4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテルの合計含有量は、フレッシュなフローラル香気を維持したまま良好なフルーティ感を付与する観点より、好ましくは0.01〜99質量%、より好ましくは0.1〜15質量%、更に好ましくは0.3〜5質量%である。 The total content of 4,7-dimethyl-6-octen-3-ol and diprenyl ether in the fragrance composition of the present invention is preferably from the viewpoint of imparting a good fruity feeling while maintaining a fresh floral aroma. It is 0.01-99 mass%, More preferably, it is 0.1-15 mass%, More preferably, it is 0.3-5 mass%.
また、本発明の香料組成物は、4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテル以外に、その他の香料として、通常用いられる香料成分や、所望組成の調合香料を含有させ、例えば、フローラル調、フルーティ調、ハーバル調、スパイシー調、グリーン調、ウッディ調、バルサミック調の香気を付与することができる。 In addition to the 4,7-dimethyl-6-octen-3-ol and diprenyl ether, the fragrance composition of the present invention contains other commonly used fragrance ingredients and blended fragrances having a desired composition. For example, a floral, fruity, herbal, spicy, green, woody, and balsamic aroma can be imparted.
本発明の香料組成物において、4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテルと組み合わせて用いることができるその他の香料としては、アルコール類、炭化水素類、フェノール類、エステル類、カーボネート類、アルデヒド類、ケトン類、アセタール類、エーテル類、カルボン酸、ラクトン類、ニトリル類、シッフ塩基類、天然精油、天然抽出物等の香料成分を挙げられる。これら、その他の香料としては、アルコール類、エステル類、アルデヒド類が好ましく、中でも、アルコール類及びエステル類がより好ましい。 Examples of other fragrances that can be used in combination with 4,7-dimethyl-6-octen-3-ol and diprenyl ether in the fragrance composition of the present invention include alcohols, hydrocarbons, phenols, and esters. Perfume ingredients such as carbonates, aldehydes, ketones, acetals, ethers, carboxylic acids, lactones, nitriles, Schiff bases, natural essential oils, natural extracts and the like. As these other fragrances, alcohols, esters and aldehydes are preferable, and alcohols and esters are more preferable.
アルコール類としては、テルペン系アルコール、芳香族アルコール、脂肪族アルコール等が挙げられる。これらの中でもテルペン系アルコール、芳香族アルコールが好ましい。 Examples of alcohols include terpene alcohols, aromatic alcohols and aliphatic alcohols. Among these, terpene alcohol and aromatic alcohol are preferable.
テルペン系アルコールとしては、リナロール、シトロネロール、ゲラニオール、ネロール、ターピネオール、α-ターピネオール、ジヒドロミルセノール、ファルネソール、ネロリドール、セドロール、メントール、ボルネオール等が挙げられる。 Examples of the terpene alcohol include linalool, citronellol, geraniol, nerol, terpineol, α-terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, borneol and the like.
芳香族アルコールとしては、フェニルエチルアルコール、ベンジルアルコール、ジメチルベンジルカルビノール、フェニルエチルジメチルカルビノール、フェニルヘキサノール等が挙げられる。 Examples of the aromatic alcohol include phenylethyl alcohol, benzyl alcohol, dimethylbenzyl carbinol, phenylethyldimethylcarbinol, and phenylhexanol.
脂肪族アルコールとしては、エチルリナロール、シス-3-ヘキセノール、1-(2,2,6-トリメチルシクロヘキシル)-3-ヘキサノール、アンバーコア(花王株式会社商品名)、サンダルマイソールコア(花王株式会社商品名)、マグノール(花王株式会社商品名)等が挙げられる。 Aliphatic alcohols include ethyl linalool, cis-3-hexenol, 1- (2,2,6-trimethylcyclohexyl) -3-hexanol, amber core (trade name of Kao Corporation), sandal mysol core (product of Kao Corporation) Name), magnole (trade name of Kao Corporation), and the like.
炭化水素類としては、リモネン、α-ピネン、β-ピネン、テルピネン、セドレン、ロンギフォレン、バレンセン等が挙げられる。 Examples of the hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.
フェノール類としては、グアヤコール、オイゲノール、イソオイゲノール、チモール、パラクレゾール、バニリン、エチルバニリン等が挙げられる。 Examples of phenols include guaiacol, eugenol, isoeugenol, thymol, paracresol, vanillin, ethyl vanillin and the like.
エステル類としては、ギ酸エステル、酢酸エステル、プロピオン酸エステル、酪酸エステル、吉草酸エステル、ヘキサン酸エステル、ヘプタン酸エステル、ノネン酸エステル、安息香酸エステル、桂皮酸エステル、サリチル酸エステル、ブラシル酸エステル、チグリン酸エステル、ジャスモン酸エステル、グリシド酸エステル、アントラニル酸エステル等が挙げられる。これらのエステル類の中でも、酢酸エステル、ジャスモン酸エステルが好ましく使用される。 Esters include formic acid ester, acetic acid ester, propionic acid ester, butyric acid ester, valeric acid ester, hexanoic acid ester, heptanoic acid ester, nonenic acid ester, benzoic acid ester, cinnamic acid ester, salicylic acid ester, brassylic acid ester, tigulin Acid ester, jasmonic acid ester, glycidic acid ester, anthranilic acid ester and the like can be mentioned. Among these esters, acetate esters and jasmonate esters are preferably used.
酢酸エステルとしては、ヘキシルアセテート、シス-3-ヘキセニルアセテート、リナリルアセテート、シトロネリルアセテート、ゲラニルアセテート、ネリルアセテート、テルピニルアセテート、ノピルアセテート、ボルニルアセテート、イソボルニルアセテート、アセチルオイゲノール、アセチルイソオイゲノール、o-tert-ブチルシクロヘキシルアセテート、p-tert-ブチルシクロヘキシルアセテート、トリシクロデセニルアセテート、ベンジルアセテート、フェニルエチルアセテート、スチラリルアセテート、シンナミルアセテート、ジメチルベンジルカルビニルアセテート、フェニルエチルフェニルアセテート、3-ペンチルテトラヒドロピラン-4-イルアセテート、パラクレジルフェニルアセテート等が挙げられる。 Acetic acid esters include hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyrucetate, bornyl acetate, isobornyl acetate, acetyleugenol, acetyl Isoeugenol, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, phenylethyl acetate, styryl acetate, cinnamyl acetate, dimethylbenzylcarbinyl acetate, phenylethylphenyl Acetate, 3-pentyltetrahydropyran-4-yl acetate, para-cresyl phenyl acetate and the like can be mentioned.
ジャスモン酸エステルとしては、メチルジャスモネート、メチルジヒドロジャスモネート等が挙げられる。 Examples of the jasmonic acid ester include methyl jasmonate and methyl dihydrojasmonate.
ギ酸エステルとしては、リナリルホルメート、シトロネリルホルメート、ゲラニルホルメート等が挙げられる。 Examples of the formate include linalyl formate, citronellyl formate, and geranyl formate.
プロピオン酸エステルとしては、シトロネリルプロピオネート、トリシクロデセニルプロピオネート、アリルシクロヘキシルプロピオネート、エチル2-シクロヘキシルプロピオネート、ベンジルプロピオネート、スチラリルプロピオネート等が挙げられる。 Examples of the propionate include citronellyl propionate, tricyclodecenyl propionate, allyl cyclohexyl propionate, ethyl 2-cyclohexyl propionate, benzyl propionate, and styryl propionate.
酪酸エステルとしては、シトロネリルブチレート、ジメチルベンジルカルビニルn-ブチレート、トリシクロデセニルイソブチレート等が挙げられる。 Examples of the butyric acid ester include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, tricyclodecenyl isobutyrate, and the like.
吉草酸エステルとしては、メチルバレレート、エチルバレレート、ブチルバレレート、アミルバレレート、ベンジルバレレート、フェニルエチルバレレート等;ヘキサン酸エステルとしては、メチルヘキサノエート、エチルヘキサノエート、アリルヘキサノエート、リナリルヘキサノエート、シトロネリルヘキサノエート等が挙げられる。 Examples of valeric acid esters include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, phenyl ethyl valerate, etc .; and hexanoic acid esters include methyl hexanoate, ethyl hexanoate, allyl hexa Noate, linalyl hexanoate, citronellyl hexanoate and the like.
ヘプタン酸エステルとしては、メチルヘプタノエート、アリルヘプタノエート等が挙げられる。 Examples of heptanoic acid esters include methyl heptanoate and allyl heptanoate.
ノネン酸エステルとしては、メチル2-ノネノエート、エチル2-ノネノエート、エチル3-ノネノエート等が挙げられる。 Nonene esters include methyl 2-nonenoate, ethyl 2-nonenoate, ethyl 3-nonenoate and the like.
安息香酸エステルとしては、メチルベンゾエート、ベンジルベンゾエート、3,6-ジメチルベンゾエート等が挙げられる。 Examples of benzoic acid esters include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate.
桂皮酸エステルとしては、メチルシンナメート、ベンジルシンナメート等が挙げられる。 Examples of cinnamic acid esters include methyl cinnamate and benzyl cinnamate.
サリチル酸エステルとしては、メチルサリシレート、n-ヘキシルサリシレート、シス-3-ヘキセニルサリシレート、シクロヘキシルサリシレート、ベンジルサリシレート等が挙げられる。 Examples of the salicylic acid ester include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.
ブラシル酸エステルとしては、エチレンブラシレート等が挙げられる。 Examples of the brassylic acid ester include ethylene brush rate.
チグリン酸エステルとしては、ゲラニルチグレート、1-ヘキシルチグレート、シス-3-ヘキセニルチグレート等が挙げられる。 Examples of the tiglic acid ester include geranyl tiglate, 1-hexyl tiglate, cis-3-hexenyl tiglate and the like.
グリシド酸エステルとしては、メチル2,4-ジヒドロキシ−エチルメチルフェニルグリシデート、4-メチルフェニルエチルグリシデート等が挙げられる。 Examples of the glycidic acid ester include methyl 2,4-dihydroxy-ethylmethylphenyl glycidate and 4-methylphenylethyl glycidate.
アントラニル酸エステルとしては、メチルアントラニレート、エチルアントラニレート、ジメチルアントラニレート等が挙げられる。 Examples of the anthranilate ester include methyl anthranilate, ethyl anthranilate, dimethyl anthranilate and the like.
更にその他のエステルとしては、メチルアトラレート、アリルシクロヘキシルグリコレート、フルーテート(花王株式会社商品名)、ポワレネート(花王株式会社商品名)、ペラナット(花王株式会社商品名)、メルサット(花王株式会社商品名)、イロチル(花王株式会社商品名)等が挙げられる。 Other esters include methyl atrate, allyl cyclohexyl glycolate, fluate (trade name of Kao Corporation), Poirenate (trade name of Kao Corporation), Peranat (trade name of Kao Corporation), Mersat (trade name of Kao Corporation) ), Irotil (trade name of Kao Corporation) and the like.
カーボネート類としては、リファローム(IFF社商品名,シス-3-ヘキセニルメチルカーボネート)、ジャスマシクラット(花王株式会社商品名)、フロラマット(花王株式会社商品名)等が挙げられる。 Examples of carbonates include rifarom (trade name of IFF, cis-3-hexenylmethyl carbonate), jasma cyclat (trade name of Kao Corporation), Floramat (trade name of Kao Corporation), and the like.
アルデヒド類としては、n-オクタナール、n-ノナナール、n-デカナ−ル、n-ドデカナール、2-メチルウンデカナール、10-ウンデセナール、シトロネラール、シトラール、ヒドロキシシトロネラール、トリプラール、シクロベルタール(花王株式会社商品名)、ベンズアルデヒド、フェニルアセトアルデヒド、フェニルプロピルアルデヒド、シンナミックアルデヒド、ジメチルテトラヒドロベンズアルデヒド、ブルゲオナール(Givaudan社商品名,3-(p-tert-ブチルフェニル)-プロパナール)、リラール(IFF社、商品名)、ポレナールII(花王株式会社商品名,2-シクロヘキシルプロパナール)、リリアール(Givaudan社商品名,p-tert-ブチル-α-メチルヒドロシンナミックアルデヒド)、p-イソプロピル-α-メチルヒドロシンナミックアルデヒド、フロラロゾン(IFF社商品名,p-エチル-α,α-ジメチルヒドロシンナミックアルデヒド)、α-アミルシンナミックアルデヒド、α-ヘキシルシンナミックアルデヒド、ヘリオトロピン、ヘリオナール(IFF社商品名,α-メチル-3,4-メチレンジオキシヒドロシンナミックアルデヒド)等が挙げられる。 Aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, tripral, and cyclobeltal (Kao stock) Company product name), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, burgeonal (Givaudan product name, 3- (p-tert-butylphenyl) -propanal), laral (IFF company, product) Name), Polenal II (trade name of Kao Corporation, 2-cyclohexylpropanal), Liliar (trade name of Givaudan, p-tert-butyl-α-methylhydrocinnamic aldehyde), p-isopropyl-α-methylhydrocin Namic aldehyde, florarozone IFF brand name, p-ethyl-α, α-dimethylhydrocinnamic aldehyde), α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, heliotropin, helional (IFF product name, α-methyl-3, 4-methylenedioxyhydrocinnamic aldehyde) and the like.
ケトン類としては、α-イオノン、β-イオノン、γ-イオノン、α-メチルイオノン、β-メチルイオノン、γ-メチルイオノン、ダマセノン、メチルヘプテノン、4-メチレン-3,5,6,6-テトラメチル-2-ヘプタノン、アセトフェノン、アミルシクロペンタノン、ジヒドロジャスモン、ローズケトン、カルボン、メントン、樟脳、アセチルセドレン、イソロンギフォラノン、ヌートカトン、ベンジルアセトン、アニシルアセトン、メチルβ-ナフチルケトン、2,5-ジメチル-4-ヒドロキシ-3(2H)-フラノン、マルトール、ムスコン、シベトン、シクロペンタデカノン、カロン(Firmenich社商品名,7-メチル-3,5-ジヒドロ−2H−ベンゾジオキセピン-3-オン)、ラズベリーケトン等が挙げられる。 Ketones include α-ionone, β-ionone, γ-ionone, α-methylionone, β-methylionone, γ-methylionone, damasenone, methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2- Heptanone, acetophenone, amylcyclopentanone, dihydrojasmon, rose ketone, carvone, menthone, camphor, acetyl cedrene, isolongifolanone, nootkatone, benzylacetone, anisylacetone, methyl β-naphthylketone, 2,5-dimethyl -4-Hydroxy-3 (2H) -furanone, maltol, muscone, sibeton, cyclopentadecanone, caron (Firmenich trade name, 7-methyl-3,5-dihydro-2H-benzodioxepin-3-one ), And raspberry ketone.
アセタール類としては、アセトアルデヒドエチルフェニルプロピルアセタール、シトラールジエチルアセタール、フェニルアセトアルデヒドグリセリルアセタール、エチルアセトアセテートエチレングリコールアセタール、ボアザンブレンフォルテ(花王株式会社商品名)、トロエナン(花王株式会社商品名)等が挙げられる。 Examples of acetals include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetoacetate ethylene glycol acetal, boazambrenforte (trade name of Kao Corporation), Troenan (trade name of Kao Corporation), and the like. .
エーテル類としては、セドリルメチルエーテル、エストラゴール、アネトール、β−ナフチルメチルエーテル、β-ナフチルエチルエーテル、リモネンオキサイド、ローズオキサイド、ネロールオキサイド、1,8-シネオール、ローズフラン、アンブロキサン(花王株式会社商品名)、ハーバベール(花王株式会社商品名)、ガラクソリド(IFF社商品名,ヘキサメチルヘキサヒドロシクロペンタベンゾピラン)等が挙げられる。 Ethers include cedolyl methyl ether, estragole, anethole, β-naphthylmethyl ether, β-naphthylethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, ambroxan (Kao Trade name), Herbaval (trade name of Kao Corporation), Galaxolide (trade name of IFF, hexamethylhexahydrocyclopentabenzopyran), and the like.
カルボン酸類としては、安息香酸、フェニル酢酸、桂皮酸、ヒドロ桂皮酸、酪酸、2-ヘキセン酸等が挙げられる。 Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.
ラクトン類としては、γ-デカラクトン、δ-デカラクトン、γ-バレロラクトン、γ-ノナラクトン、γ-ウンデカラクトン、δ-ヘキサラクトン、γ-ジャスモラクトン、ウイスキーラクトン、クマリン、シクロペンタデカノリド、シクロヘキサデカノリド、アンブレットリド、11-オキサヘキサデカノリド、ブチリデンフタリド等が挙げられる。
ニトリル類としては、ゲラニルニトリル、シトロネリルニトリル、ドデカンニトリル等が挙げられる。
Lactones include γ-decalactone, δ-decalactone, γ-valerolactone, γ-nonalactone, γ-undecalactone, δ-hexalactone, γ-jasmolactone, whiskey lactone, coumarin, cyclopentadecanolide, Examples include cyclohexadecanolide, ambretlide, 11-oxahexadecanolide, butylidenephthalide, and the like.
Examples of nitriles include geranyl nitrile, citronellyl nitrile, and dodecane nitrile.
シッフ塩基類としては、オーランチオール、リガントラール等が挙げられる。 Examples of Schiff bases include auranthiol and ligantoral.
天然精油や天然抽出物としては、オレンジ、レモン、ライム、ベルガモット、バニラ、マンダリン、ペパーミント、スペアミント、ラベンダー、カモミル、ローズマリー、ユーカリ、セージ、バジル、ローズ、ロックローズ、ゼラニウム、ジャスミン、イランイラン、アニス、クローブ、ジンジャー、ナツメグ、カルダモン、セダー、ヒノキ、ベチバー、パチュリ、レモングラス、ラブダナム等が挙げられる。 Natural essential oils and natural extracts include orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, camomil, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, ylang ylang, Anise, cloves, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, lemongrass, lovedanum and the like.
これらのその他の香料の含有量は、調合香料の種類、目的とする香気の種類及び香気の強さ等により適宜選択することができるが、本発明の香料組成物中、それぞれ好ましくは0.001〜99.99質量%、より好ましくは0.1〜80質量%である。 The content of these other fragrances can be appropriately selected depending on the kind of the blended fragrance, the type of the target fragrance, the intensity of the fragrance, and the like, but preferably in the fragrance composition of the present invention, 0.001 to 99.99 It is 0.1 mass%, More preferably, it is 0.1-80 mass%.
本発明の香料組成物は、本発明のジメチルシクロヘキセニルアルケノン及びその他の香料素材を含有させるベースとして、それ自身は匂いを持たない油剤を含有させることができる。このような油剤は、香料成分を均一に混合させ、製品に配合しやすく、適度な強度の香りを賦香しやすくすることができる。前記油剤の例としては、エチレングリコール、プロピレングリコール、ブチレングリコール、ジプロピレングリコール等の多価アルコール、ミリスチン酸イソプロピル、アジピン酸ジブチル、セバシン酸ジエチル等のエステル、流動パラフィン、スクワラン等の炭化水素、ポリオキシエチレンアルキルエーテル、ソルビタン脂肪酸エステル等の界面活性剤が挙げられる。 The fragrance composition of the present invention can contain an oil agent that does not have an odor as a base for containing the dimethylcyclohexenyl alkenone of the present invention and other fragrance materials. Such an oil agent can mix a fragrance | flavor component uniformly, is easy to mix | blend with a product, and can make it easy to perfume the intensity | strength of moderate intensity | strength. Examples of the oil include polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol and dipropylene glycol, esters such as isopropyl myristate, dibutyl adipate and diethyl sebacate, hydrocarbons such as liquid paraffin and squalane, poly Surfactants such as oxyethylene alkyl ether and sorbitan fatty acid ester can be mentioned.
これらのなかでも、全ての香料成分の溶解性の観点から、前記油剤としては多価アルコール及びエステルが好ましく、ジプロピレングリコール及びミリスチン酸イソプロピルがより好ましい。かかる油剤の含有量は、香料組成物中、好ましくは0.01〜95質量%、より好ましくは0.1〜50質量%、更に好ましくは1〜30質量%である。 Among these, from the viewpoint of the solubility of all the perfume ingredients, the oil agent is preferably a polyhydric alcohol and an ester, and more preferably dipropylene glycol and isopropyl myristate. The content of the oil is preferably 0.01 to 95% by mass, more preferably 0.1 to 50% by mass, and further preferably 1 to 30% by mass in the fragrance composition.
〔香粧品、家庭用製品〕
本発明の香料組成物は、様々な形態の芳香性製品に配合又は適用することができる。その利用分野としては、例えば、香粧品、家庭用製品等がある。
[Cosmetics, household products]
The perfume composition of the present invention can be blended or applied to various forms of aromatic products. Examples of the application field include cosmetics and household products.
「香粧品」とは、人の身なりを清潔に又は美しくするための製品であり、具体的には石鹸、身体洗浄剤、頭髪洗浄剤、頭髪化粧料、化粧品(例えば、皮膚化粧料、仕上げ化粧料など)、香水、コロン、制汗剤、デオドラント剤、浴用剤等が挙げられる。 “Cosmetics” is a product for making a person's appearance clean or beautiful. Specifically, soaps, body cleaners, hair cleaners, hair cosmetics, cosmetics (for example, skin cosmetics, finish cosmetics). Etc.), perfumes, colons, antiperspirants, deodorants, bath agents and the like.
「家庭用製品」とは、家庭生活に必要な住居や家庭製品等の様々な物品の機能又は清潔性を維持するための製品であり、具体的には衣料用洗剤、衣料用柔軟剤、衣料用糊剤、住居用洗剤、風呂用洗剤、食器用洗剤、漂白剤、カビ取り剤、床用ワックス、芳香剤、消臭剤等が挙げられる。 “Household products” are products for maintaining the function or cleanliness of various articles such as houses and household products necessary for home life. Specifically, clothes detergents, clothing softeners, clothing Sizing agent, residential detergent, bath detergent, dish detergent, bleach, mold remover, floor wax, fragrance, deodorant and the like.
以上述べた実施形態に関し、以下に本発明の好ましい態様を更に開示する。 With respect to the embodiments described above, preferred aspects of the present invention will be further disclosed below.
<1>
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2、好ましくは99.3/0.7〜99.8/0.2の質量比で含有する香料組成物。
<1>
A fragrance composition containing 4,7-dimethyl-6-octen-3-ol and diprenyl ether in a mass ratio of 97.0 / 3.0 to 99.8 / 0.2, preferably 99.3 / 0.7 to 99.8 / 0.2.
<2>
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの合計量が、好ましくは0.01〜99質量%、より好ましくは0.1〜15質量%、更に好ましくは0.3〜5質量%である<1>に記載の香料組成物。
<2>
The total amount of 4,7-dimethyl-6-octen-3-ol and diprenyl ether is preferably 0.01 to 99% by mass, more preferably 0.1 to 15% by mass, and still more preferably 0.3 to 5% by mass < The fragrance composition according to 1>.
<3>
好ましくは<1>又は<2>記載の香料組成物を含む家庭用製品。
<3>
Preferably, a household product comprising the fragrance composition according to <1> or <2>.
<4>
好ましくは<1>又は<2>記載の香料組成物を含む香粧品。
<4>
Preferably a cosmetic comprising the fragrance composition according to <1> or <2>.
<5>
塩化プレニルとジエチルケトンとの付加反応を行った後、還元反応を行う<1>記載の香料組成物の製造方法。
<5>
<1> The method for producing a fragrance composition according to <1>, wherein a reduction reaction is performed after an addition reaction between prenyl chloride and diethyl ketone.
<6>
付加反応に好ましくは塩基、より好ましくはアルカリ金属の水酸化物、更に好ましくは水酸化ナトリウム、水酸化カリウムから選ばれるいずれか1以上を用いる<5>記載の製造方法。
<6>
<5> The production method according to <5>, wherein the addition reaction preferably uses a base, more preferably an alkali metal hydroxide, more preferably any one or more selected from sodium hydroxide and potassium hydroxide.
<7>
付加反応に用いる反応溶媒が、好ましくは水性の溶媒である<5>又は<6>に記載の製造方法。
<7>
The production method according to <5> or <6>, wherein the reaction solvent used in the addition reaction is preferably an aqueous solvent.
<8>
付加反応に用いる塩化プレニルとジエチルケトンの比率が、塩化プレニルに対してジエチルケトンが好ましくは1.5〜10当量、更に好ましくは3〜7当量である<5>〜<7>のいずれか1項に記載の製造方法。
<8>
<5> to <7>, wherein the ratio of prenyl chloride and diethyl ketone used in the addition reaction is preferably 1.5 to 10 equivalents, more preferably 3 to 7 equivalents with respect to prenyl chloride. The manufacturing method as described.
<9>
還元反応に用いる還元剤が、好ましくは水素化ホウ素ナトリウム、水素化アルミニウムリチウム、水素化ジイソブチルアルミニウムから選ばれるいずれか1以上である<5>〜<8>のいずれか1項に記載の製造方法。
<9>
The production method according to any one of <5> to <8>, wherein the reducing agent used for the reduction reaction is preferably one or more selected from sodium borohydride, lithium aluminum hydride, and diisobutylaluminum hydride. .
<10>
還元反応に用いる還元剤の量が、好ましくは1〜4当量である<5>〜<9>のいずれかに記載の製造方法
<10>
The production method according to any one of <5> to <9>, wherein the amount of the reducing agent used in the reduction reaction is preferably 1 to 4 equivalents.
<11>
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルとを、97.0/3.0〜99.8/0.2、好ましくは99.3/0.7〜99.8/0.2の質量比で含有する組成物の香料としての使用方法。
<12>
4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルの合計量が、好ましくは0.01〜99質量%、より好ましくは0.1〜15質量%、更に好ましくは0.3〜5質量%である<11>に記載の組成物の香料としての使用方法。
<11>
Use as a fragrance of a composition containing 4,7-dimethyl-6-octen-3-ol and diprenyl ether in a mass ratio of 97.0 / 3.0 to 99.8 / 0.2, preferably 99.3 / 0.7 to 99.8 / 0.2 Method.
<12>
The total amount of 4,7-dimethyl-6-octen-3-ol and diprenyl ether is preferably 0.01 to 99% by mass, more preferably 0.1 to 15% by mass, and still more preferably 0.3 to 5% by mass <11> The use method as a fragrance | flavor of composition.
以下の実施例及び比較例において行った化合物の同定方法の詳細を以下にまとめて示す。 Details of the identification methods of the compounds carried out in the following Examples and Comparative Examples are summarized below.
〔化合物の同定〕
製造例1及び2で得られた各化合物の構造を、核磁気共鳴スペクトル(1H-NMR)により同定した。核磁気共鳴スペクトルは、Varian社製の製品名「Mercury 400」装置を用い、400MHzで、テトラメチルシランを内部標準として測定した。
[Identification of compounds]
The structure of each compound obtained in Production Examples 1 and 2 was identified by nuclear magnetic resonance spectrum ( 1 H-NMR). The nuclear magnetic resonance spectrum was measured at 400 MHz using tetramethylsilane as an internal standard using a product name “Mercury 400” apparatus manufactured by Varian.
製造例1 4,7-ジメチル-6-オクテン-3-オンの製造
フラスコに、ジエチルケトン226g、50質量%水酸化ナトリウム水溶液125g、ステアリルトリメチルアンモニウムクロライド1.8gを混合し、70℃まで昇温した。塩化プレニル60gの滴下を3.5時間かけて行い、滴下終了後1時間熟成し、冷却を行った。冷却後、水150gを加えて分層し、反応混合物261gを得た(4,7-ジメチル-6-オクテン-3-オン含有率22質量%、59g)。収率72%。
同様にして更に2回反応を行い、反応混合物計685gを得た(4,7-ジメチル-6-オクテン-3-オンとして合計165g)。
得られた反応混合物からジエチルケトンを留去した後、単蒸留を行い(槽内〜170℃/7kPa)、4,7-ジメチル-6-オクテン-3-オンを91質量%含有する留分を168g得た。留分の一部は中圧カラムクロマトグラフィー(展開溶媒=n-ヘキサン:酢酸エチル=100:0〜99:5)を行い、99%純度の4,7-ジメチル-6-オクテン-3-オンを得た。
残りの蒸留留分は、4,7-ジメチル-6-オクテン-3-オールの製造に用いた。
Production Example 1 Production of 4,7-dimethyl-6-octen-3-one A flask was mixed with 226 g of diethyl ketone, 125 g of a 50 mass% aqueous sodium hydroxide solution and 1.8 g of stearyltrimethylammonium chloride, and the temperature was raised to 70 ° C. . 60 g of prenyl chloride was added dropwise over 3.5 hours, and after completion of the addition, the mixture was aged for 1 hour and cooled. After cooling, 150 g of water was added and the layers were separated to obtain 261 g of a reaction mixture (4,7-dimethyl-6-octen-3-one content 22 mass%, 59 g). Yield 72%.
In the same manner, the reaction was further performed twice to obtain a total of 685 g of the reaction mixture (a total of 165 g as 4,7-dimethyl-6-octen-3-one).
Diethyl ketone was distilled off from the resulting reaction mixture, followed by simple distillation (in the tank to 170 ° C./7 kPa), and a fraction containing 91% by mass of 4,7-dimethyl-6-octen-3-one was obtained. 168 g was obtained. Part of the fraction was subjected to medium pressure column chromatography (developing solvent = n-hexane: ethyl acetate = 100: 0 to 99: 5), and 99% pure 4,7-dimethyl-6-octen-3-one Got.
The remaining distillation fraction was used for the production of 4,7-dimethyl-6-octen-3-ol.
1H-NMR(CDCl3, 400MHz), δ1.03(3H, t, J=7.2Hz, Me)1.05(3H, d, J=6.8Hz, Me), 1.60(3H, s, Me), 1.68(3H, s, Me), 2.00-2.10(1H, m), 2.24-2.34(1H, m, Me), 2.44(1H, q, J=0.72Hz, CH2), 2.48-2.60(1H, m, CH), 4.98-5.08(1H, m, c=CH) 1 H-NMR (CDCl 3 , 400 MHz), δ1.03 (3H, t, J = 7.2 Hz, Me) 1.05 (3H, d, J = 6.8 Hz, Me), 1.60 (3H, s, Me), 1.68 (3H, s, Me), 2.00-2.10 (1H, m), 2.24-2.34 (1H, m, Me), 2.44 (1H, q, J = 0.72Hz, CH 2 ), 2.48-2.60 (1H, m , CH), 4.98-5.08 (1H, m, c = CH)
製造例2 4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテルの製造
フラスコに、メタノール20mL、イオン交換水4g、50質量%水酸化ナトリウム水溶液0.2g、水素化ホウ素ナトリウム1.5gを加え、氷浴下攪拌した。攪拌溶液の中に4,7-ジメチル-6-オクテン-3-オン蒸留留分(純度90%)20gをゆっくり滴下した。滴下後氷浴を外し室温にて熟成した。1時間後、6N硫酸を加えてpH4以下にし、その後50質量%水酸化ナトリウムでpH6〜7まで中和した。そのまま常圧でメタノールを蒸発させ、分層後上層を乾燥、ろ過後、エバポレーターにより溶媒を留去し、20gの反応混合物を得た。
得られた反応混合物を中圧カラムクロマトグラフィー(展開溶媒=n-ヘキサン:酢酸エチル=97:3)を行い、11gの4,7-ジメチル-6-オクテン-3-オールを得た。収率82%
また、カラムの残りの部分を更に中圧カラムクロマトグラフィー(展開溶媒=n-ヘキサン:酢酸エチル=99:1)を行い、0.4gのジプレニルエーテルを得た。
Production Example 2 Production of 4,7-dimethyl-6-octen-3-ol and diprenyl ether In a flask, 20 mL of methanol, 4 g of ion-exchanged water, 0.2 g of 50% by mass sodium hydroxide aqueous solution, and 1.5 g of sodium borohydride were added. The mixture was further stirred in an ice bath. 20 g of 4,7-dimethyl-6-octen-3-one distillation fraction (purity 90%) was slowly dropped into the stirring solution. After dropping, the ice bath was removed and the mixture was aged at room temperature. After 1 hour, 6N sulfuric acid was added to adjust the pH to 4 or less, and then neutralized with 50 mass% sodium hydroxide to pH 6-7. Methanol was evaporated as it was under normal pressure, and after separation, the upper layer was dried and filtered, and then the solvent was distilled off by an evaporator to obtain 20 g of a reaction mixture.
The obtained reaction mixture was subjected to medium pressure column chromatography (developing solvent = n-hexane: ethyl acetate = 97: 3) to obtain 11 g of 4,7-dimethyl-6-octen-3-ol. Yield 82%
Further, the remaining part of the column was further subjected to medium pressure column chromatography (developing solvent = n-hexane: ethyl acetate = 99: 1) to obtain 0.4 g of diprenyl ether.
4,7-ジメチル-6-オクテン-3-オール
1H-NMR(CDCl3, 400MHz), δ1.03(3H, t, J=7.2Hz, Me), 1.05(3H, d, J=6.8Hz, Me), 1.60(3H, s, Me), 1.68(3H, s, Me), 2.00-2.10(1H, m), 2.24-2.34(1H, m, Me), 2.44(1H, q, J=0.72Hz, CH2), 2.48-2.60(1H, m, CH), 4.98-5.08(1H, m, c=CH)
4,7-Dimethyl-6-octen-3-ol
1 H-NMR (CDCl 3 , 400 MHz), δ1.03 (3H, t, J = 7.2 Hz, Me), 1.05 (3H, d, J = 6.8 Hz, Me), 1.60 (3H, s, Me), 1.68 (3H, s, Me), 2.00-2.10 (1H, m), 2.24-2.34 (1H, m, Me), 2.44 (1H, q, J = 0.72Hz, CH2), 2.48-2.60 (1H, m , CH), 4.98-5.08 (1H, m, c = CH)
ジプレニルエーテル
1H-NMR(CDCl3, 400MHz), δ1.67(6H, s, Me×2), 1.74(6H, s, Me×2), 3.93-3.94(4H, d, J=6.8MHz, CH2×2), 5.33-5.37(2H, tt, C=CH×2)
Diprenyl ether
1 H-NMR (CDCl 3 , 400 MHz), δ 1.67 (6H, s, Me × 2), 1.74 (6H, s, Me × 2), 3.93-3.94 (4H, d, J = 6.8 MHz, CH 2 × 2), 5.33-5.37 (2H, tt, C = CH × 2)
試験例1〔香気評価〕
4,7-ジメチル-6-オクテン-3-オール及びジプレニルエーテルを用いて、表1に示す香料組成物を調製し、それぞれの香料組成物の香気を評価した。表中の数値は質量部である(以下同じ)。
Test Example 1 [Aroma Evaluation]
Using 4,7-dimethyl-6-octen-3-ol and diprenyl ether, the fragrance compositions shown in Table 1 were prepared, and the fragrance of each fragrance composition was evaluated. The numerical values in the table are parts by mass (the same applies hereinafter).
香気評価は、におい紙(幅6mm、長さ150mmの香料試験紙)の先端約5mmを試料に浸漬し、匂いの専門パネラーにより、香調を判定することで行った。結果を表中に併せて示す。 The fragrance evaluation was performed by immersing about 5 mm of the tip of an odor paper (fragrance test paper having a width of 6 mm and a length of 150 mm) in a sample, and determining the fragrance tone using a panel specializing in odor. The results are also shown in the table.
香料組成物1は、フレッシュなフローラル香が感じられるもののフルーティな甘さは感じられなかった。一方、香料組成物2〜6は、フレッシュなフローラル香を損なうことなく、フルーティな甘さが付与されていた。また、香料組成物7及び8は、グリーン香が強くなりフレッシュなフローラル香、フルーティな甘さ共に損なわれていた。 Although the fragrance composition 1 felt a fresh floral fragrance, it did not feel a fruity sweetness. On the other hand, the fragrance | flavor compositions 2-6 were provided with fruity sweetness, without impairing a fresh floral fragrance. Further, in the fragrance compositions 7 and 8, the green fragrance was strong and both the fresh floral fragrance and the fruity sweetness were impaired.
試験例2〔匂いの閾値測定〕
匂いの閾値計測にあたっては、Haring, H.G. et al., Journal of Agricultural Food Chemistry, VOL. 20, NO.5, 1972, pp.1018-1021に記載の方法により、4,7-ジメチル-6-オクテン-3-オール、ジプレニルエーテルのいずれか一方のみ、及び両化合物の組み合わせについて、各種濃度の流動パラフィン溶液1点と、ブランクとして流動パラフィンのみ3点の計4点を専門パネルに呈示し、ボトル口の匂い評価を行い、その中から1点匂いの付いているサンプルを挙げさせ、正答率をカウントした。その正答率が62.5%を越えた際のサンプル濃度を検知閾値とした。計測は20〜40代までの匂いの専門パネラー男女17名を対象に行った。
Test Example 2 [Odor threshold measurement]
The odor threshold was measured by the method described in Haring, HG et al., Journal of Agricultural Food Chemistry, VOL. 20, NO.5, 1972, pp. 1018-1021, and 4,7-dimethyl-6-octene. For either -3-ol, diprenyl ether alone, or a combination of both compounds, present a total of 4 points on the specialized panel, 1 point of liquid paraffin solution of various concentrations and 3 points of liquid paraffin as blank. Mouth odor evaluation was performed, and samples with one point of scent were listed, and the correct answer rate was counted. The sample concentration when the correct answer rate exceeded 62.5% was taken as the detection threshold. Measurements were made on 17 panelists and men with special smells from the 20s to 40s.
(サンプル調製方法)
4,7-ジメチル-6-オクテン-3-オール単独、4,7-ジメチル-6-オクテン-3-オールにジプレニルエーテルを質量比99.8/0.2になるように添加したもの、4,7-ジメチル-6-オクテン-3-オールにジプレニルエーテルを質量比99.6/0.4になるように添加したもの、ジプレニルエーテル単独、のそれぞれの2.0〜62.5ppmまでの全6種の濃度の流動パラフィン溶液を調製した。それぞれ50mLずつを100mLのメディアバイアル(マルエム社製)に入れた。また、ブランクとして流動パラフィンのみ50mLを100mLのメディアバイアルに入れたサンプルを調製した。
(Sample preparation method)
4,7-dimethyl-6-octen-3-ol alone, 4,7-dimethyl-6-octen-3-ol added with diprenyl ether in a mass ratio of 99.8 / 0.2, Liquid paraffin solution of dimethyl-6-octen-3-ol added with diprenyl ether in a mass ratio of 99.6 / 0.4 and diprenyl ether alone, each in a total of 6 concentrations from 2.0 to 62.5 ppm Was prepared. Each 50 mL was placed in a 100 mL media vial (manufactured by Maruemu). Moreover, the sample which put only 50 mL of liquid paraffin into the 100 mL media vial as a blank was prepared.
4,7-ジメチル-6-オクテン-3-オール、ジプレニルエーテルのいずれか単独の場合の閾値は31.3ppmであったが、両者を併用した場合の閾値は15.6ppmに低下した。 The threshold when either 4,7-dimethyl-6-octen-3-ol or diprenyl ether alone was 31.3 ppm, but the threshold when both were used together decreased to 15.6 ppm.
試験例3〔賦香品の匂い評価〕
製造例2で得られた4,7-ジメチル-6-オクテン-3-オールとジプレニルエーテルを用いて、表3に示す組成のシトラスフローラルタイプの洗剤、身体洗浄料用の香料組成物を調製した。
Test Example 3 [Odor evaluation of flavored products]
Using the 4,7-dimethyl-6-octen-3-ol obtained in Production Example 2 and diprenyl ether, a citrus floral type detergent having the composition shown in Table 3 and a fragrance composition for body washing are prepared. did.
表3に示す香料組成物A、B、Cについて、匂いの専門パネラー男女5名により、香りの官能評価を行った。評価はフレッシュ感、フローラル香、フルーティ感、全体の香りの調和、の各項目について行った。評価基準は下記のとおりとし、そのスコアの平均値を表4に示す。
(評価基準)
5:非常に強い
4:強い
3:ふつうに感じられる
2:弱い
1:非常に弱い
For the fragrance compositions A, B and C shown in Table 3, sensory evaluation of fragrance was performed by five odor specialist panelists and men. Evaluation was performed for each item of fresh feeling, floral fragrance, fruity feeling and harmony of the whole fragrance. The evaluation criteria are as follows, and the average value of the scores is shown in Table 4.
(Evaluation criteria)
5: Very strong 4: Strong 3: Normal feel 2: Weak 1: Very weak
香気評価の結果、香料組成物Aはシトラスのフレッシュ感が強調され、フローラル・フルーティ感が感じられにくくなっているのに対し、香料組成物Bおよび香料組成物Cではフレッシュ感と共に、フローラル香、フルーティ感が上昇した。特に、香料組成物Cでは4,7-ジメチル-6-オクテン-3-オールの賦香量が増えていないにも関わらず、フローラル・フルーティ感が強くなった。また、爽やかなシトラス香とフローラル・フルーティ感が調和して華やかな甘さが加わり、柑橘の果実を想起させる瑞々しい香りになった。 As a result of the fragrance evaluation, the fragrance composition A emphasizes the freshness of citrus and makes it less likely to feel a floral and fruity feeling, whereas the fragrance composition B and the fragrance composition C have a fresh feeling as well as a floral fragrance, The fruity feeling increased. In particular, in the perfume composition C, although the amount of 4,7-dimethyl-6-octen-3-ol perfumed was not increased, the feeling of floral fruity became stronger. In addition, a refreshing citrus fragrance and a floral fruity feeling harmoniously add a gorgeous sweetness, resulting in a refreshing fragrance reminiscent of citrus fruits.
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012262669A JP6054157B2 (en) | 2012-11-30 | 2012-11-30 | Fragrance composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012262669A JP6054157B2 (en) | 2012-11-30 | 2012-11-30 | Fragrance composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014108970A JP2014108970A (en) | 2014-06-12 |
JP6054157B2 true JP6054157B2 (en) | 2016-12-27 |
Family
ID=51029802
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012262669A Active JP6054157B2 (en) | 2012-11-30 | 2012-11-30 | Fragrance composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6054157B2 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106456473B (en) * | 2014-05-08 | 2020-04-03 | 弗门尼舍有限公司 | Floral and green scent agent |
JP7028552B2 (en) | 2016-11-24 | 2022-03-02 | 花王株式会社 | Heating equipment |
CN112321403A (en) * | 2020-12-02 | 2021-02-05 | 天津市安凯特科技发展有限公司 | Synthesis method of dimethyl octenone |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH425767A (en) * | 1963-10-25 | 1966-12-15 | Hoffmann La Roche | Process for the production of secondary alcohols |
JPS5365812A (en) * | 1976-11-26 | 1978-06-12 | Dainippon Ink & Chem Inc | Treatment of unsaturated ketone |
DE10160141A1 (en) * | 2001-12-07 | 2003-06-18 | Basf Ag | Process for the selective liquid phase hydrogenation of alpha, beta-unsaturated carbonyl compounds to unsaturated alcohols in the presence of a Pt / ZnO catalyst |
-
2012
- 2012-11-30 JP JP2012262669A patent/JP6054157B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2014108970A (en) | 2014-06-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5395981B2 (en) | Fragrance composition | |
JP5709969B1 (en) | Fragrance composition | |
JP5750542B1 (en) | ester | |
JP7380558B2 (en) | α-Hydroxyisobutyric acid ester compound, fragrance composition, and use as fragrance | |
JP4323271B2 (en) | Valerolactone compounds and perfume compositions | |
JP6054157B2 (en) | Fragrance composition | |
CN111936608B (en) | Musk-flavored composition | |
JP5137249B2 (en) | Fragrance composition | |
JP6202679B2 (en) | 4,8-dimethyl-4,9-decadienenitrile | |
JP5270194B2 (en) | Fragrance composition | |
JPH0867661A (en) | Camphorenealdehyde derivative,its production,and perfuming component containing it | |
JP5808704B2 (en) | Dimethylcyclohexenyl alkenone | |
JP2013256470A (en) | Kanforen derivative and fragrance composition containing the same | |
JP5912943B2 (en) | 3,7-dimethyl-2-methylene-6-octenenitrile | |
JP6091028B1 (en) | Cyclopropane compound | |
JP6077387B2 (en) | 4 (3)-(4-Hydroxy-4-methylpentyl) -3-cyclohexene-1-carbonitrile | |
JP5639884B2 (en) | Fragrance composition | |
WO2022249897A1 (en) | Perfume composition | |
JP2004527502A (en) | 2,3,5,5-tetramethylhexanal derivative |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150924 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20161109 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20161129 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20161130 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 6054157 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |