WO2022124003A1 - 香料組成物 - Google Patents
香料組成物 Download PDFInfo
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- WO2022124003A1 WO2022124003A1 PCT/JP2021/041663 JP2021041663W WO2022124003A1 WO 2022124003 A1 WO2022124003 A1 WO 2022124003A1 JP 2021041663 W JP2021041663 W JP 2021041663W WO 2022124003 A1 WO2022124003 A1 WO 2022124003A1
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- WIPO (PCT)
- Prior art keywords
- formula
- compound represented
- cis
- fragrance composition
- trans
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 177
- 239000003205 fragrance Substances 0.000 title claims abstract description 159
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims abstract description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 claims description 15
- SBUXRMKDJWEXRL-ROUUACIJSA-N cis-body Chemical compound O=C([C@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ROUUACIJSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 10
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000341 volatile oil Substances 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 8
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 5
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 5
- 150000001241 acetals Chemical class 0.000 claims description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 150000002596 lactones Chemical class 0.000 claims description 5
- 239000004571 lime Substances 0.000 claims description 5
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- 150000002825 nitriles Chemical class 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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- 239000012459 cleaning agent Substances 0.000 description 21
- GQBVHGLNSHPKPG-UHFFFAOYSA-N 1-(2-tert-butylcyclohexyl)oxybutan-2-ol Chemical compound CCC(O)COC1CCCCC1C(C)(C)C GQBVHGLNSHPKPG-UHFFFAOYSA-N 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- GQBVHGLNSHPKPG-LWNNLKQOSA-N 1-[(1r,2r)-2-tert-butylcyclohexyl]oxybutan-2-ol Chemical compound CCC(O)CO[C@@H]1CCCC[C@@H]1C(C)(C)C GQBVHGLNSHPKPG-LWNNLKQOSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- PZUDDXJZNSJESK-UHFFFAOYSA-N ethyl 2-cyclohexylpropanoate Chemical compound CCOC(=O)C(C)C1CCCCC1 PZUDDXJZNSJESK-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- 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 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 2
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- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-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
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- SCCDQYPEOIRVGX-UHFFFAOYSA-N Acetyleugenol Chemical compound COC1=CC(CC=C)=CC=C1OC(C)=O SCCDQYPEOIRVGX-UHFFFAOYSA-N 0.000 description 2
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- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
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- 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
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- NUQDJSMHGCTKNL-UHFFFAOYSA-N cyclohexyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1CCCCC1 NUQDJSMHGCTKNL-UHFFFAOYSA-N 0.000 description 2
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- 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
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- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
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- FGPPDYNPZTUNIU-UHFFFAOYSA-N pentyl pentanoate Chemical compound CCCCCOC(=O)CCCC FGPPDYNPZTUNIU-UHFFFAOYSA-N 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
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 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
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 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
- 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
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000010679 vetiver oil 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
- 229930007850 β-damascenone Natural products 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to a fragrance composition.
- ⁇ - (2-alkylcyclohexyloxy) - ⁇ -alkanol especially 1- (2-t-butylcyclohexyloxy) -2-alkanol, has a wood-like and amber-like fragrance, and has excellent residual fragrance. It is a useful fragrance material that can be manufactured at low cost (Japanese Patent Laid-Open No. 4-2179937).
- 1- (2-t-butylcyclohexyloxy) -2-butanol is widely known as amber core, a fragrance with a woody amber-like scent (a refreshing cypress-like scent) and a high residual scent.
- amber core a fragrance with a woody amber-like scent (a refreshing cypress-like scent) and a high residual scent.
- the trans body has a particularly strong woody amber-like scent.
- cis and trans mean whether the functional groups bonded to cyclohexane are cis or trans.
- the cis form and the trans form of the amber core each include the following three-dimensional structures.
- the present invention is a fragrance composition containing a cis form and a trans form.
- the cis form comprises a compound represented by the formula (Ia), a compound represented by the formula (Ib), a compound represented by the formula (IIa) and a compound represented by the formula (IIb).
- the trans form contains a compound represented by the formula (IIIa), a compound represented by the formula (IIIb), a compound represented by the formula (IVa), and a compound represented by the formula (IVb).
- a fragrance composition in which the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 65:35 or more and 95: 5 or less.
- R 1 is an alkyl group having 1 or more carbon atoms and 5 or less carbon atoms.
- R 2 is a hydrogen atom or an alkyl group having 1 or more and 4 or less carbon atoms.
- An object of the present invention is to focus on a cis form of ⁇ - (2-alkylcyclohexyloxy) - ⁇ -alkanol, which has not been noticed in amber core, and to provide a new fragrance composition.
- the present inventors have predominantly the ratio of the cis form in the fragrance composition containing the trans form and the cis form of ⁇ - (2-alkylcyclohexyloxy) - ⁇ -alkanol, specifically, the above-mentioned. It was found that when the mass ratio of the cis body to the trans body [cis body: trans body] is 65:35 or more and 95: 5 or less, a soft and fresh impression of wood is felt. This impression is a new impression that is different from Amber Core.
- the present invention is a fragrance composition containing a cis form and a trans form.
- the cis form comprises a compound represented by the formula (Ia), a compound represented by the formula (Ib), a compound represented by the formula (IIa) and a compound represented by the formula (IIb).
- the trans form contains the compound represented by the formula (IIIa), the compound represented by the formula (IIIb), the compound represented by the formula (IVa) and the compound represented by the formula (IVb), and the cis form.
- the fragrance composition has a mass ratio [cis-form: trans-form] of 65:35 or more and 95: 5 or less.
- the compound represented by the formula (Ia), the compound represented by the formula (Ib), the compound represented by the formula (IIa) and the compound represented by the formula (IIb) are ⁇ - (2-alkylcyclohexyloxy).
- )-A cis form of ⁇ -alkanol which is a compound represented by the formula (IIIa), a compound represented by the formula (IIIb), a compound represented by the formula (IVa), and a compound represented by the formula (IVb).
- R 1 is an alkyl group having 1 or more carbon atoms and 5 or less carbon atoms.
- R 2 is a hydrogen atom or an alkyl group having 1 or more and 4 or less carbon atoms.
- the fragrance composition of the present invention contains a cis form of ⁇ - (2-alkylcyclohexyloxy) - ⁇ -alkanol in a specific ratio, has excellent harmony with various other fragrances, and has a characteristic scent when blended. It is possible to create the effect of.
- the present invention is, as described above, a fragrance composition containing a cis form and a trans form.
- the cis form comprises a compound represented by the formula (Ia), a compound represented by the formula (Ib), a compound represented by the formula (IIa) and a compound represented by the formula (IIb).
- the trans form contains a compound represented by the formula (IIIa), a compound represented by the formula (IIIb), a compound represented by the formula (IVa), and a compound represented by the formula (IVb).
- the mass ratio of the cis body to the trans body [cis body: trans body] has an excellent balance of wood-like soft and fresh impression, natural-like, and residual fragrance, and the usefulness of fragrance as a fragrance material.
- the mass ratio of the cis body to the trans body [cis body: trans body] has an excellent balance of wood-like soft and fresh impression, natural-like, and residual fragrance, and is useful as a fragrance material. From the viewpoint, it is preferably 68:32 or more and 90:10 or less, more preferably 68:32 or more and 85:15 or less, and further preferably 68:32 or more and 75:25 or less.
- the mass ratio of the cis body to the trans body is 65:35 or more, preferably 68:32 or more, more preferably 82. : 18 or more, more preferably 85:15 or more.
- the mass ratio of the cis form to the trans form [cis form: trans form] is 95: 5 or less, preferably 90:10 or less, more preferably 85 :. It is 15 or less, more preferably 78:22 or less, and even more preferably 75:25 or less.
- the mass ratio of the cis body to the trans body is preferably 82:18 or more and 95: 5 or less, more preferably 82: from the viewpoint of a soft and fresh impression of wood. It is 18 or more and 90:10 or less, more preferably 85:15 or more and 90:10 or less.
- the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is preferably 65:35 or more and 78:22 or less, more preferably 68:32, from the viewpoint of natural appearance, strength and residual fragrance. 78:22 or more, more preferably 68:32 or more and 75:25 or less.
- R 1 is an alkyl group having 1 or more carbon atoms and 5 or less carbon atoms.
- R 2 is a hydrogen atom or an alkyl group having 1 or more and 4 or less carbon atoms.
- the cis form includes a compound represented by the formula (Ia), a compound represented by the formula (Ib), a compound represented by the formula (IIa), and a compound represented by the formula (IIb). ..
- cis isomer ratio is a natural citrus scent with a sparkling-like top sparkling impression and a floral scent with green and woody nuances that make you feel like you are in a flower shop. From the viewpoint of imparting a floral feeling, it is preferably 55:45 or more and 68:32 or less, more preferably 55.5: 44.5 or more and 66:34 or less, and further preferably 56:44 or more and 62:38 or less. Is.
- the mass concentration of the cis form is, for example, preferably 65% by mass or more, more preferably 66% by mass or more, from the viewpoint of a wood-like soft and fresh impression and a natural appearance. It is more preferably 67% by mass or more, further preferably 68% by mass or more, still more preferably 69% by mass or more, and for example, preferably 95% by mass or less, more preferably 95% by mass or less from the viewpoint of natural appearance, strength and residual fragrance. It is 85% by mass or less, more preferably 80% by mass or less, still more preferably 75% by mass or less.
- the fragrance composition in such a ratio is excellent in harmony with various other fragrances, and it is possible to create a characteristic scent effect by blending.
- the compound represented by the formula (IIIb), the compound represented by the formula (IVa) and the compound represented by the formula (IVb) are produced by a conventionally known method, for example, the method described in JP-A-4-217937. can do.
- the compound represented by the formula (IIIb), the compound represented by the formula (IVa) and the compound represented by the formula (IVb) can be produced, for example, by the following methods.
- R 1 is an alkyl group having 1 or more carbon atoms and 5 or less carbon atoms.
- R 2 is a hydrogen atom or an alkyl group having 1 or more and 4 or less carbon atoms.
- the compound of the formula (X) and the compound of the formula (XI) are heated under the presence condition of a base (for example, sodium hydroxide) to obtain the compound of the formula (XII).
- a base for example, sodium hydroxide
- the compound of formula (XII) is hydrogenated in the presence of a catalyst (eg, a palladium catalyst) and hydrogen to obtain the compound of formula (XIII).
- the obtained compound of the formula (XIII) is a compound represented by the formula (Ia), a compound represented by the formula (Ib), a compound represented by the formula (IIa) and a compound represented by the formula (IIb).
- the obtained compound of the formula (XIII) can be separated by distillation or column chromatography to isolate the high-purity cis-form or trans-form. If necessary, the compound of the formula (XIII) (a mixture of the cis-form and the trans-form in a specific ratio) and the high-purity cis-form (a compound represented by the formula (Ia), represented by the formula (Ib)).
- Including the compound represented by the formula (IIa) and the compound represented by the formula (IIb)) or the trans-form having high purity (the compound represented by the formula (IIIa), the compound represented by the formula (IIIb)).
- a compound represented by the above, a compound represented by the formula (IVa) and a compound represented by the formula (IVb)) can be mixed to obtain a mixture containing a desired ratio of a trans form and a cis form. ..
- R 1 is an alkyl group having 1 or more carbon atoms and 5 or less carbon atoms.
- R 2 is a hydrogen atom or an alkyl group having 1 or more and 4 or less carbon atoms.
- R 1 is preferably an alkyl group having 1 or more and 4 or less carbon atoms, more preferably an alkyl group having 3 or more and 4 or less carbon atoms, and further preferably a t-butyl group. Further, R 2 is preferably a methyl group or an ethyl group.
- the fragrance composition of the present invention contains the cis form and the trans form in a specific ratio, it is excellent in harmony with various other fragrances, and it is possible to create a characteristic scent effect by blending. Is.
- the fragrance composition of the present invention can be combined with other fragrance components usually used as fragrances other than the cis-form and the trans-form, or a blended fragrance having a desired composition.
- fragrances other than the cis and trance fragrances for example, the sparkling-like popping impression of the top and the natural floral feeling of being in a flower shop with the addition of green and woody nuances along with the floral scent.
- the fragrance composition of the present invention is preferably a composition further containing a fragrance other than the group consisting of the cis-form and the trans-form.
- fragrances that can be used in combination with the cis form and the trans form include alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, and acetal.
- fragrance components such as, ethers, carboxylic acids, lactones, nitriles, shift bases, natural essential oils and natural extracts (excluding the cis form and the trans form).
- alcohols phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, natural essential oils and natural extracts are preferable.
- each fragrance means a single compound or a mixture of two or more compounds.
- alcohols examples include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Of these, fatty alcohols are preferred.
- terpene alcohols examples include limonene, linalool, citronellol, geraniol, nerol, turpineol, ⁇ -terpineol, dihydromilsenol, farnesol, nerolidol, sedrol, menthol, borneol, florol (florosa) and the like.
- aromatic alcohol examples include phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbinol, phenylethyldimethylcarbinol, phenylhexanol and the like.
- fatty alcohols cis-3-hexanol, 1- (2,2,6-trimethylcyclohexanol) -3-hexanol, sandal mysol core (trade name of Kao Co., Ltd., 2-methyl-4- (2,2)) 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol), magnol (trade name of Kao Co., Ltd., a mixture containing ethylnorbonylcyclohexanol as a main component), Undecavertor (Givaudan stock) Company trade name, 4-methyl-3-decene-5-ol), isobornylcyclohexanol, and the like.
- glycols such as dipropylene glycol, fluorosa (trade name of Givaudan, chemical name: 4-methyl-2- (2-methylpropyl) tetrahydro-2H-4-pyranol) and the like.
- hydrocarbons examples include limonene, ⁇ -pinene, ⁇ -pinene, terpinene, cedrene, longifolene, valencene and the like.
- phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, paracresol, vanillin, ethylvanillin and the like.
- esters examples include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.
- Examples of the aliphatic carboxylic acid forming the aliphatic carboxylic acid ester include linear and branched carboxylic acids having 1 to 18 carbon atoms, and among them, carboxylic acids having 1 to 6 carbon atoms such as formic acid, acetic acid and propionic acid. , Especially acetic acid is important.
- Examples of the aromatic carboxylic acid forming the aromatic carboxylic acid ester include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, anthranyl acid and the like.
- Examples of the alcohol forming the aliphatic and aromatic esters include linear and branched aliphatic alcohols having 1 to 5 carbon atoms and the above-mentioned fragrance component alcohols.
- Examples of formic acid ester include linalyl formate, citronellyl formate, geranyl formate and the like.
- acetate As acetate, ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopill acetate, Bornyl acetate, isobornyl acetate, acetyl eugenol, acetyl isooigenol, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, phenylethyl acetate, styralyl acetate, Examples thereof include cinnamyl acetate, dimethylbenzyl car
- propionic acid ester examples include citronellyl propionate, tricyclodecenyl propionate, allylcyclohexylpropionate, ethyl2-cyclohexylpropionate, benzylpropionate, styralylpropionate and the like.
- fatty acid ester examples include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, tricyclodecenylisobutyrate and the like.
- Examples of the enanthic acid ester include methylheptanoate and allylheptanoate.
- nonene acid ester examples include methyl 2-nonenoate, ethyl2-nonenoate, ethyl3-nonenoate and the like.
- benzoic acid ester examples include methylbenzoate, benzylbenzoate, 3,6-dimethylbenzoate and the like.
- Examples of the cinnamic acid ester include methyl cinnamate and benzyl cinnamate.
- salicylic acid ester examples include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.
- examples of the brush acid ester include ethylene brassylate and the like.
- Examples of the tiglic acid ester include geranyl titrate, 1-hexyl titrate, cis-3-hexenyl titrate and the like.
- jasmonic acid ester examples include methyl jasmonate and methyl dihydro jasmonate.
- glycidic acid ester examples include methyl 2,4-dihydroxy-ethylmethylphenylglycidate, 4-methylphenylethylglycidate and the like.
- anthranilic acid ester examples include methyl anthranilate, ethyl anthranilate, dimethyl anthranilate and the like.
- glycolic acid ester examples include allylcyclohexylglycolate.
- esters include ethyl safranate (trade name of Dibodan Co., Ltd., ethyl dihydrocyclogeranate), poirenate (trade name of Kao Co., Ltd., ethyl-2-cyclohexylpropionate), and flutate (trade name of Kao Co., Ltd., ethyl).
- carbonates examples include refarome (FIF brand name, cis-3-hexenylmethyl carbonate), jasmacyclat (Kao Corporation trade name, methyl-cyclooctyl carbonate), and floramat (Kao Corporation trade name, ethyl-2-t). -Butylcyclohexyl carbonate) and the like.
- aldehydes examples include n-octanal, n-nonanal, n-decanaal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, and triplar (IFF trade name, IFF trade name, 2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde), cyclobertal (trade name of Kao Co., Ltd., dimethyl-3-cyclohexenyl-1-carboxyaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, synamic Aldehyde, dimethyltetrahydrobenzaldehyde, bulgeonal (Givaudan trade name, 3- (4-tert-butylphenyl) propanal), Rilal (IFF trade name, hydroxymyracaldehyde), Polenal II
- Ketones include methylheptenone, dimethyloctenone, 3-octanone, hexylcyclopentanone, dihydrojasmon, beruton (Filmenich trade name, 2,2,5-trimethyl-5-pentylcyclopentanone), and nectaryl (divodan).
- acetals include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethylacetaldehyde ethylene glycol acetal, boazambrenforte (trade name of Kao Corporation), troenan (trade name of Kao Corporation) and the like. ..
- Ethers include ethyllinalol, sedrill methyl ether, estragor, anetol, ⁇ -naphthylmethyl ether, ⁇ -naphthylethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, and ambro.
- Xan (trade name of Kao Co., Ltd., [3aR- (3a ⁇ , 5a ⁇ , 9a ⁇ , 9b ⁇ )] dodecahydro-3a, 6,6,9a-tetramethylnaphtho [2,1-b] furan), Herbaval (product of Kao Co., Ltd.) Name, 3,3,5-trimethylcyclohexylethyl ether), galaxoride (trade name of IFF, hexamethylhexahydrocyclopentabenzopyrane), phenylacetaldehyde dimethyl acetal and the like.
- carboxylic acids examples include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, fatty acid, 2-hexenoic acid and the like.
- lactones examples include ambrettolide, ⁇ -decalactone, ⁇ -decalactone, ⁇ -valerolactone, ⁇ -nononalactone, ⁇ -undecalactone, ⁇ -hexalactone, ⁇ -jasmolactone, whiskey lactone, coumarin, and cyclopenta.
- lactones include decanolide, cyclohexadecanolide, 11-oxahexadecanolide, butylidenephthalide and the like.
- nitriles examples include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, dodecane nitrile and the like.
- Schiff bases examples include auranthial, ligantral and the like.
- Natural essential oils and extracts include orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, camomill, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, Iran Iran, Examples include annis, cloves, ginger, nutmeg, cardamon, cedar, hinoki, vetiver, patchouli, lemongrass, lavender, grapefruit, and essential oil.
- the fragrance composition of the present invention may further contain one or more selected from lime essential oil, limonene, and menthol from the viewpoint of giving a sparkling-like popping impression of the top of the citrus-like scent. preferable.
- the fragrance composition of the present invention has fluorolol, hexyl acetate, and methyl from the viewpoint of imparting a natural floral feeling as if it were in a flower shop by adding nuances such as green and woody together with a floral scent. It is preferable to further contain one or more selected from dihydrojasmonate.
- the content of these other fragrances can be appropriately selected depending on the type of the blended fragrance, the type of the desired fragrance, the intensity of the fragrance, and the like, but each of them is preferable in the composition containing the fragrance composition of the present invention. Is 0.0001% by mass or more, more preferably 0.001% by mass or more, and preferably 99.99% by mass or less, more preferably 80% by mass or less.
- the total content of other fragrances is preferably 5% by mass or more, more preferably 50% by mass or more, and preferably 99.99% by mass or less in the composition containing the fragrance composition of the present invention. More preferably, it is 99.95% by mass or less.
- the fragrance composition of the present invention can be combined with an oil agent which does not have an odor by itself as a base.
- an oil agent can evenly mix the fragrance components, can be easily blended into the product, and can easily perfume an fragrance having an appropriate intensity.
- the oil agent include polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol and dipropylene glycol, esters such as isopropyl myristate, dibutyl adipate and diethyl sebacate, liquid paraffins and hydrocarbons such as squalane, and poly.
- surfactants such as oxyethylene alkyl ether and sorbitan fatty acid ester.
- the content of the oil is preferably 0.01% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass or more in the fragrance composition. It is 0% by mass or less, more preferably 80% by mass or less.
- the present invention also provides a cleaning agent composition containing the fragrance composition of the present invention, a cosmetic containing the fragrance composition of the present invention, and a fiber treatment composition containing the fragrance composition of the present invention.
- a body cleaning agent composition, a clothing cleaning agent composition, and a hard surface cleaning agent composition are preferable, and a body cleaning agent composition and a clothing cleaning agent composition are more preferable.
- a cleaning composition for clothing is more preferable.
- Examples of the body cleansing composition include a skin cleansing composition, a hair cleansing composition, and a soap composition, and a skin cleansing composition is preferable.
- hard surface cleaning agent composition examples include a multipurpose cleaning agent (All purpose Cleaner) and a tableware cleaning agent composition.
- a softener composition is preferable.
- perfume As the cosmetic of the present invention, perfume, milky lotion, cosmetic water, sunscreen are preferable, and perfume is more preferable.
- the detergent composition of the present invention preferably contains an anionic surfactant in addition to the fragrance composition of the present invention, and further comprises a nonionic surfactant, a pH adjuster, a viscosity regulator, a solvent, an oil agent, and the like. Preservatives, water, etc. can be blended.
- the fiber treatment composition of the present invention preferably contains a cationic surfactant, and may further contain a pH adjuster, a solvent, an oil agent, a preservative, water and the like. can.
- a solvent, water, or the like can be added to the perfume of the present invention.
- the fragrance composition of the present invention containing the cis form and the trans form in a specific ratio gives a soft and fresh impression like wood. Further, as described above, when this fragrance composition is formulated with other ingredients as a fragrance material, the fragrance composition of the present invention has a sparkling-like popping impression of the top of a citrus-like scent and a floral scent. It can give a new impression that nuances such as green and woody are added and a natural floral feeling like being in a flower shop is given.
- the present invention is a method of using the fragrance composition of the present invention containing the cis-form and the trans-form in a specific ratio as a fragrance component, specifically, a fragrance composition, a cleaning agent composition, and a cosmetic.
- a method used as a perfume component of a fiber treatment composition As the cleaning agent composition, a body cleaning agent composition, a clothing cleaning agent composition, and a hard surface cleaning agent composition are preferable, and a body cleaning agent composition and a clothing cleaning agent composition are more preferable, and clothing.
- Cleaning agent compositions for use are more preferred.
- the body cleansing composition include a skin cleansing composition, a hair cleansing composition, and a soap composition, and a skin cleansing composition is preferable.
- the hard surface cleaning agent composition include a multi-purpose cleaning agent (All purpose Cleaner) and a tableware cleaning agent composition. Perfume is preferable as the cosmetic.
- a softener composition is preferable.
- the fragrance composition of the present invention is preferably 0.00001% by mass or more, more preferably 0.0001% by mass or more, and based on the cleaning composition, cosmetic or softener composition. It is preferably used in an amount of 0.01% by mass or less, more preferably 0.001% by mass or less.
- this fragrance composition when used in this amount, when this fragrance composition is formulated with other ingredients as a fragrance material, it has a citrus-like scent top sparkling-like popping impression and a floral scent with green, woody-like nuances. It can give a new impression that it gives a natural floral feeling like being in a flower shop.
- the fragrance composition of the present invention may be combined with an oil agent which does not have an odor by itself.
- the oil agent is the same as that described in the fragrance composition.
- the fragrance composition of the present invention may contain other fragrance components usually used as other fragrances or a blended fragrance having a desired composition. Such other fragrances are the same as those described in the fragrance composition.
- a fragrance composition containing a cis form and a trans form comprises a compound represented by the formula (Ia), a compound represented by the formula (Ib), a compound represented by the formula (IIa), and a compound represented by the formula (IIb).
- the trans form contains a compound represented by the formula (IIIa), a compound represented by the formula (IIIb), a compound represented by the formula (IVa), and a compound represented by the formula (IVb).
- a fragrance composition in which the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 65:35 or more and 95: 5 or less.
- R 1 is an alkyl group having 1 or more carbon atoms and 5 or less carbon atoms.
- R 2 is a hydrogen atom or an alkyl group having 1 or more and 4 or less carbon atoms.
- ⁇ 4> The fragrance composition according to any one of ⁇ 1> to ⁇ 3>, wherein the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 68:32 or more and 75:25 or less.
- ⁇ 5> The fragrance composition according to any one of ⁇ 1> to ⁇ 4>, wherein the mass concentration of the cis form is 65% by mass or more and 95% by mass or less.
- ⁇ 6> The fragrance composition according to any one of ⁇ 1> to ⁇ 5>, wherein the cis-form has a mass concentration of 66% by mass or more and 85% by mass or less.
- ⁇ 7> The fragrance composition according to any one of ⁇ 1> to ⁇ 6>, wherein the mass concentration of the cis form is 67% by mass or more and 80% by mass or less.
- ⁇ 8> The fragrance composition according to any one of ⁇ 1> to ⁇ 7>, wherein the mass concentration of the cis form is 68% by mass or more and 75% by mass or less.
- ⁇ 12> The fragrance composition according to any one of ⁇ 1> to ⁇ 11>, wherein the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 65:35 or more and 78:22 or less.
- ⁇ 14> The fragrance composition according to any one of ⁇ 1> to ⁇ 13>, wherein the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 68:32 or more and 75:25 or less.
- ⁇ 15> The fragrance composition according to any one of ⁇ 1> to ⁇ 14>, wherein the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 82:18 or more and 95: 5 or less.
- ⁇ 16> The fragrance composition according to any one of ⁇ 1> to ⁇ 15>, wherein the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 82:18 or more and 90:10 or less.
- ⁇ 17> The fragrance composition according to any one of ⁇ 1> to ⁇ 16>, wherein the mass ratio of the cis-form to the trans-form [cis-form: trans-form] is 85:15 or more and 90:10 or less.
- fragrance composition according to any one of ⁇ 1> to ⁇ 23>, further comprising one or more selected from fluorolol, hexyl acetate, and methyl dihydrojasmonate.
- ⁇ 26> A cosmetic containing the fragrance composition according to any one of ⁇ 1> to ⁇ 25>.
- ⁇ 28> A method of using the fragrance composition according to any one of ⁇ 1> to ⁇ 25> as a fragrance-enhancing component.
- % is “mass%” unless otherwise specified.
- the mass of the catalyst is the mass in the dry state.
- GC device Agilent Technologies Co., Ltd. 7890B, hydrogen flame ionization detector
- Column When the yield was analyzed, DB-1 (capillary column, 100% dimethylpolysiloxane, inner diameter 0.25 mm, length 30 m, film thickness 0.25 ⁇ m, manufactured by Agilent Technologies, Inc.) was used.
- DB-WAX capillary column, polyethylene glycol, inner diameter 0.25 mm, length 30 m, film thickness 0.25 ⁇ m, manufactured by Agilent Technologies, Inc.
- Carrier gas He, 1.5 mL / min
- Injection conditions 300 ° C, split ratio 100/1
- Driving amount 1 ⁇ L
- Detection conditions FID method, 300 ° C
- Column temperature conditions Starting from 80 ° C., the temperature was raised to 300 ° C. at a rate of 10 ° C./min. Then, it was held at 300 ° C. for 10 minutes.
- 2-t-butylphenol (1) manufactured by Fuji Film Wako Pure Chemical Industries, Ltd., 350 g
- 48% sodium hydroxide aqueous solution (Kanto Chemical Co., Inc.) in a 1-liter round-bottom flask equipped with a gym funnel and a dropping funnel under a nitrogen stream.
- 35 g was added and heated to 80 ° C.
- 1,2-butylene oxide (2) (176 g, manufactured by Tokyo Chemical Industry Co., Ltd.) in about 2 hours, and then the mixture was stirred at 80 ° C. for 5 hours.
- the lower sodium hydroxide aqueous solution is separated from the organic layer, and the organic layer is distilled to obtain 1- (2-t-butylphenyloxy) -2-butanol (3) in a yield of 96%.
- the cis form is represented by a compound represented by the formula (Ia-1), a compound represented by the formula (Ib-1), a compound represented by the formula (IIa-1), and a compound represented by the formula (IIb-1).
- the trans compound includes a compound represented by the formula (IIIa-1), a compound represented by the formula (IIIb-1), a compound represented by the formula (IVa-1), and a compound represented by the formula (IVa-1).
- -1) Contains the compound represented by. Further, the isomer ratio of the cis isomer [total of the compound represented by the formula (Ia-1) and the compound represented by the formula (Ib-1): the compound represented by the formula (IIa-1) and the formula ( The total (mass ratio) of the compounds represented by IIb-1) was 48:52.
- the mass ratio of cis: trans and the isomer ratio of the cis form of the obtained fragrance composition are as follows.
- the fragrance composition of the present invention showed the effect of enhancing the soft and fresh impression of wood while maintaining the residual fragrance.
- the present invention it is possible to provide a fragrance composition that gives a soft and fresh impression of wood. Furthermore, when this fragrance composition is prescribed with other ingredients as a fragrance material, it gives the impression of popping like sparkling at the top and the nuances of green and woody along with the floral scent, giving it a natural floral feel that makes you feel like you are in a flower shop. Can give a new impression that is given.
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Abstract
Description
前記シス体が、式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物及び式(IIb)で表される化合物を含み、
前記トランス体が、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物を含み、
前記シス体と前記トランス体の質量比[シス体:トランス体]が、65:35以上95:5以下である香料組成物を提供する。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。]
前記シス体が、式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物及び式(IIb)で表される化合物を含み、
前記トランス体が、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物を含み、前記シス体と前記トランス体の質量比[シス体:トランス体]が、65:35以上95:5以下である香料組成物である。なお、式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物及び式(IIb)で表される化合物がα-(2-アルキルシクロヘキシルオキシ)-β-アルカノールのシス体であり、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物が、α-(2-アルキルシクロヘキシルオキシ)-β-アルカノールのトランス体である。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。
前記シス体が、式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物及び式(IIb)で表される化合物を含み、
前記トランス体が、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物を含み、
前記シス体と前記トランス体の質量比[シス体:トランス体]が、木様の柔らかで瑞々しい印象、天然様、及び残香性のバランスに優れた、香料素材としての香気の有用性の観点から、65:35以上95:5以下である香料組成物である。前記シス体と前記トランス体の質量比[シス体:トランス体]は、木様の柔らかで瑞々しい印象、天然様、及び残香性のバランスに優れた、香料素材としての香気の有用性の観点から、好ましくは68:32以上90:10以下であり、より好ましくは68:32以上85:15以下であり、更に好ましくは68:32以上75:25以下である。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。
R1は、好ましくは炭素数1以上4以下のアルキル基であり、より好ましくは炭素数3以上4以下のアルキル基であり、更に好ましくはt―ブチル基である。また、R2は、好ましくはメチル基又はエチル基である。
<1>
シス体とトランス体とを含む香料組成物であって、
前記シス体が、式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物及び式(IIb)で表される化合物を含み、
前記トランス体が、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物を含み、
前記シス体と前記トランス体の質量比[シス体:トランス体]が、65:35以上95:5以下である香料組成物。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。]
前記シス体と前記トランス体の質量比[シス体:トランス体]が、68:32以上90:10以下である、<1>に記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、68:32以上85:15以下である、<1>又は<2>に記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、68:32以上75:25以下である、<1>~<3>のいずれかに記載の香料組成物。
前記シス体の質量濃度が、65質量%以上95質量%以下である、<1>~<4>のいずれかに記載の香料組成物。
前記シス体の質量濃度が、66質量%以上85質量%以下である、<1>~<5>のいずれかに記載の香料組成物。
前記シス体の質量濃度が、67質量%以上80質量%以下である、<1>~<6>のいずれかに記載の香料組成物。
前記シス体の質量濃度が、68質量%以上75質量%以下である、<1>~<7>のいずれかに記載の香料組成物。
前記式(Ia)で表される化合物および式(Ib)で表される化合物の合計と、式(IIa)で表される化合物および式(IIb)で表される化合物の合計との質量比[前記式(Ia)で表される化合物および式(Ib)で表される化合物の合計:式(IIa)で表される化合物および式(IIb)で表される化合物の合計]が55:45以上68:32以下である、<1>~<8>のいずれかに記載の香料組成物。
前記式(Ia)で表される化合物および式(Ib)で表される化合物の合計と、式(IIa)で表される化合物および式(IIb)で表される化合物の合計との質量比55.5:44.5以上66:34以下である、<1>~<9>のいずれかに記載の香料組成物。
前記式(Ia)で表される化合物および式(Ib)で表される化合物の合計と、式(IIa)で表される化合物および式(IIb)で表される化合物の合計との質量比56:44以上62:38以下である、<1>~<10>のいずれかに記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、65:35以上78:22以下である、<1>~<11>のいずれかに記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、68:32以上78:22以下である、<1>~<12>のいずれかに記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、68:32以上75:25以下である、<1>~<13>のいずれかに記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、82:18以上95:5以下である、<1>~<14>のいずれかに記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、82:18以上90:10以下である、<1>~<15>のいずれかに記載の香料組成物。
前記シス体と前記トランス体の質量比[シス体:トランス体]が、85:15以上90:10以下である、<1>~<16>のいずれかに記載の香料組成物。
R1は、炭素数1以上4以下のアルキル基である、<1>~<17>のいずれかに記載の香料組成物。
R1は、炭素数3以上4以下のアルキル基である、<1>~<18>のいずれかに記載の香料組成物。
R1は、t-ブチル基である、<1>~<19>のいずれかに記載の香料組成物。
R2は、メチル基又はエチル基である、<1>~<20>のいずれかに記載の香料組成物。
前記式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物、式(IIb)で表される化合物、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物以外であって、アルコール類、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、ラクトン類、ニトリル類、天然精油および天然抽出物のうち1種以上をさらに含む、<1>~<21>のいずれかに記載の香料組成物。
さらに、ライム精油、リモネン、及びメントールから選ばれる一種以上を含む、<1>~<22>のいずれかに記載の香料組成物。
さらに、フロロール、ヘキシルアセテート、及びメチルジヒドロジャスモネートから選ばれる一種以上を含む、<1>~<23>のいずれかに記載の香料組成物。
<1>~<24>のいずれかに記載の香料組成物を含む、シトラス香調、またはフローラル香調の香料組成物。
<1>~<25>のいずれかに記載の香料組成物を含む化粧料。
<1>~<25>のいずれかに記載の香料組成物を含む洗浄剤組成物。
<1>~<25>のいずれかに記載の香料組成物を賦香成分として使用する方法。
<ガスクロマトグラフィーの装置及び分析条件>
GC装置:アジレント・テクノロジー株式会社製7890B、水素炎イオン化型検出器 カラム:
収率を分析する場合は、DB-1(キャピラリーカラム、100%ジメチルポリシロキサン、内径0.25mm、長さ30m、膜厚0.25μm、アジレント・テクノロジー株式会社製)を用いた。
シス体およびトランス体を分析する場合は、DB-WAX(キャピラリーカラム、ポリエチレングリコール、内径0.25mm、長さ30m、膜厚0.25μm、アジレント・テクノロジー株式会社製)を用いた。
キャリアガス:He、1.5mL/min
注入条件:300℃、スプリット比100/1
打ち込み量:1μL
検出条件:FID方式、300℃
カラム温度条件:80℃から出発し、10℃/分の速度で300℃まで昇温した。その後、300℃10分間保持した。
1-(2-t-ブチルフェニルオキシ)-2-ブタノール(3)の製造
1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(4)の製造
1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス体100%)の製造
なお、1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス体100%)とは、式(Ia-1)で表される化合物、式(Ib-1)で表される化合物、式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の混合物である。
参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%)1gに対して、参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス(質量比)=57:43)2.8gを加え、混合して香料組成物を得た。得られた香料組成物のシス:トランスの質量比と前記シス体の異性体比は、以下のとおりである。
<シス:トランスの質量比>
シス:トランス(質量比)=68:32
<前記シス体の異性体比>
式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計(質量比)=56.5:43.5。
実施例1の手順と同様に、参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%)1gに対して、参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス(質量比)=57:43)1.3gを加え、混合して香料組成物を得た。得られた香料組成物のシス:トランスの質量比と前記シス体の異性体比は、以下のとおりである。
<シス:トランスの質量比>
シス:トランス(質量比)=75:25
<前記シス体の異性体比>
式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計(質量比)=60.6:39.4。
実施例1、2と同様に、参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%)1gに対して、参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス(質量比)=57:43)0.8gを加え、混合して香料組成物を得た。得られた香料組成物のシス:トランスの質量比と前記シス体の異性体比は、以下のとおりである。
<シス:トランスの質量比>
シス:トランス(質量比)=80:20
<前記シス体の異性体比>
式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計(質量比)=63.1:36.9。
実施例1~3と同様に、参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%)1gに対して、参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス質量比=57:43)0.5gを加え、混合して香料組成物を得た。得られた香料組成物のシス:トランスの質量比と前記シス体の異性体比は、以下のとおりである。
<シス:トランスの質量比>
シス:トランス質量比=85:15
<前記シス体の異性体比>
式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計(質量比)=65.1:34.9。
実施例1~4と同様に、参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%)1gに対して、参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス質量比=57:43)0.3gを加え、混合して香料組成物を得た。得られた香料組成物のシス:トランスの質量比と前記シス体の異性体比は、以下のとおりである。
<シス:トランスの質量比>
シス:トランス(質量比)=90:10
<前記シス体の異性体比>
式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計(質量比)=66.8:33.2。
参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス(質量比)=57:43、シス体の異性体比は、式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計の比率(質量比)=48.0:52.0)を比較例1の香料組成物として官能評価に用いた。
実施例1~5と同様に、参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%)1gに対して、参考例2にて得られた1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス:トランス(質量比)=57:43)6.0gを加え、混合して香料組成物を得た。得られた香料組成物のシス:トランスの質量比と前記シス体の異性体比は、以下のとおりである。
<シス:トランスの質量比>
シス:トランス質量比=63:37
<前記シス体の異性体比>
式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計の比率(質量比)=53.0:47.0。
参考例3にて得られた1-(シス-2-t-ブチルシクロヘキシルオキシ)-2-ブタノール(シス100%、式(Ia-1)で表される化合物および式(Ib-1)で表される化合物の合計:式(IIa-1)で表される化合物および式(IIb-1)で表される化合物の合計の比率(質量比)=70:30)を比較例3の香料組成物として官能評価に用いた。
実施例1~5および比較例1~3で得られた香料組成物の匂いを専門パネラー3名で評価した。評価は匂い試験紙(大文字洋紙製、150mm×7mm)を用いて行い、匂い試験紙の先端に異性体比率が異なる実施例1~5および比較例1~3をそれぞれ賦香して、1時間後に室内にて評価を行った。官能評価は匂いの特性と強度の観点から行った。匂いの特性と強度については5段階で相対評価し、数値が大きいほうが好ましい形で記載した。残香に関しては、香気が何日持続するのかを確認し、持続した日数を表記した。また、官能評価において専門パネラー3名が感じられた香り全体の質や特徴に関しても記述した。得られた結果を表1に示す。
下記組成のシトラス香調(ライム・スパークリング調)の調合香料900質量部に、実施例1~5および比較例1~3で得られた香料組成物をそれぞれ100質量部加えた組成物の官能評価を実施した。得られた結果を表3に示す。評価の結果に関しては、効果の度合いを5段階で相対評価し、数値が大きいほうが好ましい。
調合例1と同様に、下記組成のフローラル香調(フローラルブーケ、ホワイトフローラル調)の調合香料900質量部に実施例1~5および比較例1~3で得られた香料組成物をそれぞれ100質量部加えた組成物の官能評価を実施した。得られた結果を表5に示す。評価の結果に関しては、効果の度合いを5段階で相対評価し、数値が大きいほうが好ましい。
2)カントキサール:IFF社商品名、2-メチル-3-(パラメトキシフェニル)プロパナール
3)トリプラール:IFF商品名、2,4-ジメチル-3-シクロヘキセン-1-カルボキシアルデヒド
Claims (14)
- シス体とトランス体とを含む香料組成物であって、
前記シス体が、式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物及び式(IIb)で表される化合物を含み、
前記トランス体が、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物を含み、
前記シス体と前記トランス体の質量比[シス体:トランス体]が、65:35以上95:5以下である香料組成物。
R1は、炭素数1以上5以下のアルキル基であり、
R2は、水素原子または炭素数1以上4以下のアルキル基である。] - 前記シス体の質量濃度が、65質量%以上95質量%以下である、請求項1に記載の香料組成物。
- 前記式(Ia)で表される化合物および式(Ib)で表される化合物の合計と、式(IIa)で表される化合物および式(IIb)で表される化合物の合計との質量比が55:45以上、68:32以下である、請求項1又は2に記載の香料組成物。
- 前記シス体と前記トランス体の質量比[シス体:トランス体]が、65:35以上78:22以下である、請求項1~3のいずれかに記載の香料組成物に記載の香料組成物。
- 前記シス体と前記トランス体の質量比[シス体:トランス体]が、82:18以上95:5以下である、請求項1~3のいずれかに記載の香料組成物に記載の香料組成物。
- R1は、t-ブチル基である、請求項1~5のいずれかに記載の香料組成物に記載の香料組成物。
- R2は、メチル基又はエチル基である、請求項1~6のいずれかに記載の香料組成物に記載の香料組成物。
- 前記式(Ia)で表される化合物、式(Ib)で表される化合物、式(IIa)で表される化合物、式(IIb)で表される化合物、式(IIIa)で表される化合物、式(IIIb)で表される化合物、式(IVa)で表される化合物及び式(IVb)で表される化合物以外であって、アルコール類、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、ラクトン類、ニトリル類、天然精油および天然抽出物のうち1種以上をさらに含む、請求項1~7のいずれかに記載の香料組成物。
- さらに、ライム精油、リモネン、及びメントールから選ばれる一種以上を含む、請求項1~8のいずれかに記載の香料組成物。
- さらに、フロロール、ヘキシルアセテート、及びメチルジヒドロジャスモネートから選ばれる一種以上を含む、請求項1~8のいずれかに記載の香料組成物。
- 請求項1~10のいずれか一項に記載の香料組成物を含む、シトラス香調又はフローラル香調の香料組成物。
- 請求項1~11のいずれか一項に記載の香料組成物を含む化粧料。
- 請求項1~11のいずれか一項に記載の香料組成物を含む洗浄剤組成物。
- 請求項1~11のいずれかに記載の香料組成物を賦香成分として使用する方法。
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Citations (4)
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JPH04217937A (ja) | 1990-07-18 | 1992-08-07 | Kao Corp | α−(アルキルシクロヘキシルオキシ)−β−アルカノール類及びこれを含有する香料組成物 |
JPH04327553A (ja) * | 1991-04-30 | 1992-11-17 | Kao Corp | α−(アルキルシクロヘキシルオキシ)−β−アルカノールの製造法 |
JPH0827056A (ja) * | 1994-07-20 | 1996-01-30 | Kao Corp | α−アルキルシクロヘキシルオキシケトン類及びこれを含有する香料組成物 |
WO2013099858A1 (ja) * | 2011-12-26 | 2013-07-04 | 花王株式会社 | 1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノールの製造方法 |
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JPH04217937A (ja) | 1990-07-18 | 1992-08-07 | Kao Corp | α−(アルキルシクロヘキシルオキシ)−β−アルカノール類及びこれを含有する香料組成物 |
JPH04327553A (ja) * | 1991-04-30 | 1992-11-17 | Kao Corp | α−(アルキルシクロヘキシルオキシ)−β−アルカノールの製造法 |
JPH0827056A (ja) * | 1994-07-20 | 1996-01-30 | Kao Corp | α−アルキルシクロヘキシルオキシケトン類及びこれを含有する香料組成物 |
WO2013099858A1 (ja) * | 2011-12-26 | 2013-07-04 | 花王株式会社 | 1-(2-t-ブチルシクロヘキシルオキシ)-2-ブタノールの製造方法 |
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CHRISTIAN MARGOT: "Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation", HELVETICA CHIMICA ACTA, vol. 87, no. 10, 1 October 2004 (2004-10-01), pages 2662 - 2684, XP055073512, DOI: 10.1002/hlca.200490237 * |
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