CN109516904A - 毛麝香醚及其组合物、制备方法和用途 - Google Patents
毛麝香醚及其组合物、制备方法和用途 Download PDFInfo
- Publication number
- CN109516904A CN109516904A CN201811441879.8A CN201811441879A CN109516904A CN 109516904 A CN109516904 A CN 109516904A CN 201811441879 A CN201811441879 A CN 201811441879A CN 109516904 A CN109516904 A CN 109516904A
- Authority
- CN
- China
- Prior art keywords
- mosquito
- compound
- ether
- repellent
- product
- 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.)
- Granted
Links
- 241000995168 Adenosma indianum Species 0.000 title claims abstract description 96
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000000077 insect repellent Substances 0.000 claims abstract description 58
- 241000255925 Diptera Species 0.000 claims abstract description 53
- 230000001846 repelling effect Effects 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 239000003205 fragrance Substances 0.000 claims abstract description 19
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 239000000341 volatile oil Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- -1 vaseline Chemical compound 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 239000011505 plaster Substances 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 8
- 235000019198 oils Nutrition 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000002674 ointment Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000002453 shampoo Substances 0.000 claims description 5
- 244000215068 Acacia senegal Species 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
- 229920000084 Gum arabic Polymers 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000205 acacia gum Substances 0.000 claims description 4
- 235000010489 acacia gum Nutrition 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 3
- 239000004166 Lanolin Substances 0.000 claims description 3
- 235000013871 bee wax Nutrition 0.000 claims description 3
- 239000012166 beeswax Substances 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 229960000541 cetyl alcohol Drugs 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 3
- 235000019388 lanolin Nutrition 0.000 claims description 3
- 229940039717 lanolin Drugs 0.000 claims description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 3
- 229940055577 oleyl alcohol Drugs 0.000 claims description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 3
- 229940093609 tricaprylin Drugs 0.000 claims description 3
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 3
- 229940099259 vaseline Drugs 0.000 claims description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 2
- 235000004433 Simmondsia californica Nutrition 0.000 claims description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 2
- 229940092738 beeswax Drugs 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 229940012831 stearyl alcohol Drugs 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000001069 triethyl citrate Substances 0.000 claims description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000013769 triethyl citrate Nutrition 0.000 claims description 2
- 229940045136 urea Drugs 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 241000221096 Simmondsia chinensis Species 0.000 claims 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 42
- 239000000126 substance Substances 0.000 abstract description 13
- 239000000796 flavoring agent Substances 0.000 abstract description 2
- 235000019634 flavors Nutrition 0.000 abstract description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 82
- 238000012360 testing method Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002386 air freshener Substances 0.000 description 4
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Chemical group CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 4
- 235000007746 carvacrol Nutrition 0.000 description 4
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229960001673 diethyltoluamide Drugs 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Chemical group CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 244000153234 Hibiscus abelmoschus Species 0.000 description 3
- 241001416180 Moschidae Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 3
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241001375490 Adenosma Species 0.000 description 2
- 241000256173 Aedes albopictus Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001166 anti-perspirative effect Effects 0.000 description 2
- 239000003213 antiperspirant Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005253 cladding Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 235000012907 honey Nutrition 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229930003658 monoterpene Natural products 0.000 description 2
- 235000002577 monoterpenes Nutrition 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 1
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
- ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000722824 Ardisia crenata Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 235000018959 Chrysanthemum indicum Nutrition 0.000 description 1
- 208000034657 Convalescence Diseases 0.000 description 1
- 241000744766 Cymbopogon winterianus Species 0.000 description 1
- 241001518935 Eragrostis Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 240000001341 Reynoutria japonica Species 0.000 description 1
- 235000018167 Reynoutria japonica Nutrition 0.000 description 1
- 244000044822 Simmondsia californica Species 0.000 description 1
- 241001062472 Stokellia anisodon Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000007824 aliphatic compounds Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 238000013096 assay test Methods 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007822 carvacrol derivatives Chemical group 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002072 distortionless enhancement with polarization transfer spectrum Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000003694 hair properties Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- RRLOOYQHUHGIRJ-UHFFFAOYSA-M sodium;ethyl sulfate Chemical compound [Na+].CCOS([O-])(=O)=O RRLOOYQHUHGIRJ-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/253—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
- C11D9/442—Perfumes
-
- 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
- C07B2200/07—Optical 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Birds (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biomedical Technology (AREA)
- Emergency Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及日用化学品领域,特别涉及驱蚊产品、香精香料和化妆品领域,具体涉及毛麝香醚及其组合物、制备方法和用途。特别地,本发明涉及如下结构式所示的化合物,所述化合物的制备方法,以所述化合物作为有效成分的用于驱避蚊虫的组合物,所述化合物用于制备蚊虫驱避产品的用途以及作为香料的用途。
Description
技术领域
本发明涉及日用化学品领域,特别涉及驱蚊产品、香精香料和化妆品领域,具体涉及毛麝香醚及其组合物、制备方法和用途。
背景技术
勐腊毛麝香(Adenosma buchneroides Bonati)为玄参科毛麝香属一年生草本植物,为我国云南特有种。该植物具有特殊的香气,为西双版纳勐腊县的僾伲人(为哈尼族的一个支系)民间使用的一种药用植物,由于其特殊的用途及寓意,当地人也将其称为爱情草、跳蚤草。爱尼妇女很喜欢这种草的香气,常将此草穿在自己的耳朵上,随时可闻到香气并且还有驱虫、驱蚊的作用;此草放入被子里、垫单下还可用于防治跳蚤。勐腊毛麝香虽然在僾伲人的生活中占有重要的位置,但相关研究非常少,仅许勇等人报道了其作为一种新香料植物的初步研究结果。目前对勐腊毛麝香还未很好的认识及开发利用。
勐腊毛麝香的茎叶、花序芳香且富含精油。精油又称挥发油、芳香油,是芳香植物含有的一类具有挥发性和脂溶性的油状物质。精油化学成分比较复杂,按结构可分为萜类化合物、芳香族化合物、脂肪族化合物、含硫含氮杂环化合物、有巨环内酯结构的特殊化合物等。精油具有多种生理活性,包括抗菌、消炎、抗病毒、镇痛、抗肿瘤、驱蚊虫、促渗透、抗氧化等。勐腊毛麝香富含精油,是其所含的一类重要次生代谢产物,目前还缺乏相关的研究与开发利用。
发明内容
为了开发利用勐腊毛麝香,本发明以该植物的民间利用为背景开展了相关的研究。现有技术中未见勐腊毛麝香精油在驱蚊方面的利用,本发明对精油的驱蚊活性物质进行了活性追踪分离,阐明了勐腊毛麝香精油的驱蚊活性物质基础,发现了一个新的具有驱蚊活性的挥发性二单萜醚化合物——毛麝香醚A,由此提供了下述发明:
毛麝香醚A及其制备方法
在一个方面,本申请提供了如下结构式所示的化合物毛麝香醚A,
本申请还提供了本发明的化合物的制备方法,包括从勐腊毛麝香精油中分离出本发明的化合物。
在某些实施方案中,所述方法包括以下步骤:
步骤1:从勐腊毛麝香地上部分经蒸馏法提取获得精油;
步骤2:通过色谱方法从精油中分离出本发明的化合物。
在某些实施方案中,步骤1包括:
步骤1-1:称取勐腊毛麝香地上部分,在水中蒸馏(例如蒸馏1-5h,例如蒸馏3h);
步骤1-2:取馏出液上层挥发油,并使用干燥剂(例如无水硫酸钠)干燥,得到精油。
在某些实施方案中,所述勐腊毛麝香地上部分经过干燥粉碎。
在某些实施方案中,所述勐腊毛麝香地上部分为勐腊毛麝香鲜茎叶或花序。
在某些实施方案中,步骤1中精油提取的得率为0.3%-0.7%(例如0.5%)。
在某些实施方案中,步骤2中的色谱方法为硅胶柱层析法。
在某些实施方案中,步骤2包括:
步骤2-1:将步骤1得到的精油以200-300目硅胶装柱,湿法上样,以石油醚-乙酸乙酯***为流动相进行梯度洗脱;经TLC薄层色谱分析后合并相似组分,得到5个流分Fr.1-Fr.5;
步骤2-2:将流分Fr.4以薄层硅胶H装柱,湿法上样,采用正相减压硅胶柱层析法,以石油醚-氯仿***为流动相进行梯度洗脱,得到本发明的化合物。
用于驱避蚊虫的组合物和蚊虫驱避产品
本申请发明人发现,本发明的化合物具有驱蚊作用,因此,本申请提供了一种以本发明的化合物作为有效成分的用于驱避蚊虫的组合物。
所述组合物可以是任何合适形式,例如,液体、固体、半固体、气体等多种形式。本发明的化合物可与常规无毒的、药学或日化产品中可接受载体和/或赋形剂制成溶液剂、喷雾剂、气雾剂、乳剂、混悬剂、软膏剂、凝胶剂、贴剂和适合使用的其他形式。
所述载体和/或赋形剂包括,例如,水、乙醇、丙二醇、荷荷巴油、明胶、***树胶、吐温80、硬脂酸甘油酯、三辛酸甘油酯、鲸蜡醇、羊毛脂、尿素、凡士林、硬脂醇、蜂蜡、聚氧乙烯油醇醚,还包括适合在制备液体、固体、半固体、气体形式等的制剂中使用的其他载体和/或赋形剂。所述组合物可以另外含有稳定剂,增稠剂,着色剂和/或香料。
本发明中,用于驱避蚊虫的组合物可以本发明的化合物作为单一有效成分,也可以包含其他具有驱避蚊虫作用的化合物。
本申请还涉及本发明化合物用于制备蚊虫驱避产品的用途。
本申请还涉及一种蚊虫驱避产品,其以本发明化合物作为蚊虫驱避有效成分。在某些实施方案中,所述蚊虫驱避产品以本发明化合物作为蚊虫驱避的单一有效成分。在某些实施方案中,所述蚊虫驱避产品可以包含其他具有驱避蚊虫作用的化合物。
本发明中的蚊虫驱避产品可以为液体、软膏、挂件或便捷贴。本发明中的蚊虫驱避产品可以是化妆品。本发明中,化妆品指的是以涂擦、喷洒或其他类似方法,散布于人体表面任何部位(例如皮肤、毛发、指甲、***等)以达到清洁、消除不良气味、护肤、美容和修饰的日用化学工业产品。本发明中的蚊虫驱避产品可以是驻留类化妆品或淋洗类化妆品。
本发明中的蚊虫驱避产品可以是蚊虫驱避剂(例如油基型制剂、醇基型制剂、水基型制剂),也可以是驱蚊贴、驱蚊霜、驱蚊膏、驱蚊洗发用品、驱蚊空气清新剂等。
本发明的用于驱避蚊虫的组合物或蚊虫驱避产品中,毛麝香醚A的添加量可以为组合物或产品总质量百分数的0.1%-30%(例如0.1%-1%、1%-5%、5%-10%、10%-20%或20%-30%)。
在某些实施方案中,所述蚊虫驱避产品为蚊虫驱避剂,所述蚊虫驱避剂为油基型制剂,以毛麝香醚A为有效成分,辅以植物油;毛麝香醚A的添加量为蚊虫驱避剂总质量百分数的0.1-30%。所述蚊虫驱避剂为澄清的无色流动液体,具有毛麝香醚A特有的香气。
在某些实施方案中,所述蚊虫驱避产品为蚊虫驱避剂,所述蚊虫驱避剂为醇基型制剂,以毛麝香醚A为有效成分,辅以乙醇和水,毛麝香醚A的添加量为蚊虫驱避剂总质量百分数的0.1-30%。所述蚊虫驱避剂为澄清的无色流动液体,具有毛麝香醚A特有的香气。
在某些实施方案中,所述蚊虫驱避产品为蚊虫驱避剂,所述蚊虫驱避剂为水基型制剂,以毛麝香醚A为有效成分,辅以明胶、***树胶、去离子水,毛麝香醚A的添加量为蚊虫驱避剂总质量百分数的0.1-30%。所述蚊虫驱避剂为澄清的无色流动液体,具有毛麝香醚A特有的香气。
在某些实施方案中,所述蚊虫驱避产品为驱蚊贴,所述驱蚊贴以毛麝香醚A为有效成分,与高分子凝胶基质相结合,利用微滴包覆和恒速缓释控制技术制成驱蚊贴,毛麝香醚A的添加量为驱蚊贴总质量百分数的0.1-30%。
本申请还涉及一种驱避蚊虫的方法,包括使用有效量的本发明的化合物、或本发明的用于驱避蚊虫的组合物、或本发明的蚊虫驱避产品。
在某些实施方案中,所述蚊虫为伊蚊,例如白纹伊蚊。
香料香精
本发明的化合物毛麝香醚A具有浓郁纯正的木香味(woody)、琥珀香味(amber),类似紫苏和野菊花香气,气味强烈而无刺激性,留香持久,令人愉悦,具备良好的定香作用,适宜用做具有东方木香味的香水后调。
因此,本申请提供了本发明化合物作为香料的用途。本发明中,香料又称香原料,是一种能被嗅感嗅出的气味或被味感品出香味的物质,一般作为调制香精的原料。
本申请还提供了一种包含本发明化合物的香精。本发明中,香精是由两种或两种以上的香料按一定比例混合调配出来的混合物,也称为调和香料。在某些实施方案中,本发明化合物在所述香精中的重量百分含量为0.001%-20%。
本发明的香精可以为油溶性香精。所述香精可以包含溶剂,例如乙醇、异丙醇、二甘醇单***、一缩二丙二醇、邻苯二甲酸二乙酯、柠檬酸三乙酯、肉豆蔻酸异丙酯中的一种或多种。
本申请还涉及包含所述香精的产品,例如:织物洗涤粉、洗液、和其它织物护理产品;清洁剂和家用清洗、洗涤和消毒产品;空气清新剂、室内喷剂和香盒;皂、沐浴和淋浴凝胶、香波、护发素和其它个人清洁产品;化妆品例如香水、乳膏、软膏、花露水、护肤蜜、皮肤和其它洗液、滑石粉、身体除臭剂和防汗剂等。
本申请同时涉及以下技术方案:
1.如下结构式所示的毛麝香醚A,
2.具有驱蚊作用的组合物,含有方案1所述的化合物毛麝香醚A和日化产品可接受的载体。
3.方案1所述的化合物毛麝香醚A在制备具有驱蚊作用的日化品中的应用。
4.方案1所述的化合物毛麝香醚A在制备具有驱蚊作用的香精中的应用。
5.方案1所述的化合物毛麝香醚A在制备不同香调香精中的应用。
6.方案1所述的化合物毛麝香醚A的制备方法,称取干燥粉碎后或新鲜切碎后的勐腊毛麝香地上部分或茎叶或花序,置于3L圆底烧瓶中,加入1.5L蒸馏水,水中蒸馏3h提取挥发性成分,取出馏出液上层挥发油,并加入无水硫酸钠干燥,得到浅黄色勐腊毛麝香精油;勐腊毛麝香精油以200-300目硅胶装柱,湿法上样,石油醚-乙酸乙酯***为流动相进行梯度洗脱,减压旋蒸回收溶剂,经TLC薄层色谱分析后合并相似组分,得到5个流分Fr.1-Fr.5;流分Fr.4以薄层硅胶H装柱,湿法上样,采用正相减压硅胶柱层析法,以石油醚-氯仿***为流动相进行梯度洗脱,得到化合物毛麝香醚A。
7.一种含毛麝香醚A的驱蚊产品,其特征在于所述驱蚊产品以方案1所述的毛麝香醚A为有效成分,辅以辅料,毛麝香醚A的添加量为驱蚊产品总质量百分数的0.1-30%。
8、一种含毛麝香醚A的蚊虫驱避剂,其特征在于所述蚊虫驱避剂以方案1所述的毛麝香醚A为有效成分,辅以植物油,毛麝香醚A的添加量为驱蚊剂总质量百分数的0.1-30%,蚊虫驱避剂为油基型制剂。
9、一种含毛麝香醚A的蚊虫驱避剂,其特征在于所述蚊虫驱避剂以方案1所述的毛麝香醚A为有效成分,辅以乙醇和水,毛麝香醚A的添加量为驱蚊剂总质量百分数的0.1-30%,蚊虫驱避剂为醇基型制剂。
10、一种含毛麝香醚A的蚊虫驱避剂,其特征在于所述蚊虫驱避剂以方案所述的毛麝香醚A为有效成分,加上明胶、***树胶、去离子水,毛麝香醚A的添加量为驱蚊剂总质量百分数的0.1-30%,蚊虫驱避剂为水基型制剂。
11、一种含毛麝香醚A的驱蚊贴,其特征在于所述蚊虫驱蚊贴以方案1所述的毛麝香醚A为有效成分,与高分子凝胶基质相结合,利用微滴包覆和恒速缓释控制技术制成驱蚊贴,毛麝香醚A的添加量为驱蚊剂总质量百分数的0.1-30%,蚊虫驱避剂为便捷贴。
12、含毛麝香醚A的香调香精产品,其特征在于其是只含毛麝香醚A一种香料或含毛麝香醚A的香料组合物的香调香精产品,产品中的毛麝香醚A的量按重量为0.001%-20%。
13、根据方案5所述的化合物毛麝香醚A在制备不同香调香精中的应用,其特征在于所述的应用为毛麝香醚A在下列产品中的应用:织物洗涤粉、洗液、清洁剂、消毒剂、空气清新剂、室内喷剂、香盒、皂、沐浴和淋浴凝胶、香波、护发素、香水、乳膏、软膏、花露水、护肤蜜、洗液、滑石粉、身体除臭剂、防汗剂。
有益效果
本发明提供了一种新的具有蚊虫驱避活性的挥发性二单萜醚化合物——毛麝香醚A。含毛麝香醚A的蚊虫驱避产品具有绿色、环保的特点。毛麝香醚A具有令人愉悦的香气,因此以其作为有效成分的蚊虫驱避产品容易被消费者所接受。毛麝香醚A具有防蚊效果显著、对皮肤无刺激、天然、环保、安全的特点,可制成油基型、醇基型、水基型蚊虫驱避剂、以及驱蚊贴等蚊虫驱避产品。
下面将结合附图和实施例对本发明的实施方案进行详细描述,但是,本领域技术人员将理解,下列附图和实施例仅用于说明本发明,而不是对本发明的范围的限定。根据附图和优选实施方案的下列详细描述,本发明的各种目的和有利方面对于本领域技术人员来说将变得显然。
附图说明
图1显示了本发明化合物毛麝香醚A的化学结构、关键1H-1H COSY和HMBC相关。
图2显示了本发明化合物毛麝香醚A的关键ROESY相关。
具体实施方式
下面将结合实施例对本发明的实施方案进行详细描述,但是本领域技术人员将会理解,下列实施例仅用于说明本发明,而不应视为限定本发明的范围。实施例中未注明具体条件者,按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者,均为可以通过市购获得的常规产品。
实施例1
1.化合物毛麝香醚A的制备。
分离流程:称取干燥粉碎后的勐腊毛麝香地上部分0.5kg,置于3L圆底烧瓶中,加入1.5L蒸馏水,水中蒸馏3h提取挥发性成分,取出馏出液上层挥发油,并加入无水硫酸钠干燥,累计水中蒸馏12次,得到浅黄色勐腊毛麝香精油70.2g,干品得率为1.17%。取勐腊毛麝香精油60.0g,以1.4kg 200-300目硅胶装柱,湿法上样,石油醚-乙酸乙酯***(P/E100:0,7.2L;98:2,10.8L;95:5,8.1L;90:10,7.2L;80:20,4.5L;50:50,9.9L;25:75,6.3L)为流动相,进行梯度洗脱,减压旋蒸回收溶剂,经TLC薄层色谱分析后合并相似组分,得到5个流分Fr.1-Fr.5;流分取Fr.4(186mg),经正相减压硅胶柱层析(流动相为石油醚-氯仿P/C 1:0,400mL;7:1,300mL;3:1,120mL)得到化合物毛麝香醚A(151mg)。
2.毛麝香醚A的结构解析:
无色油状;(c 0.25,MeOH);UV(MeOH)λmax(nm)(logε):203(4.86),219(4.37),277(3.67)。根据ESI-MS谱中的准分子离子峰m/z325[M+Na]+,并结合13C NMR和DEPT谱分析,可推断该化合物分子分子式为C20H30O2。高分辨质谱HREI-MS给出准分子离子峰的精确相对分子质量为m/z 325.2139[M+Na]+(计算值C20H30O2Na,325.2138),进一步确定该化合物的分子式为C20H30O2,具有6个不饱和度。红外吸收谱IR中特征峰νmax 3437,1631,1251cm-1,说明分别存在羟基、苯环和醚基。3个呈ABX偶合***的芳香质子信号[δH 6.76(1H,d,1.5),6.74(1H,dd,7.5,1.5),7.06(1H,d,7.5)],说明存在一个1',2',4'-三取代苯环。进一步的13C NMR分析,发现该化合物与香芹酚信号十分相似,只是香芹酚C-1'和C-2'信号(δC 120.8,153.6)分别移到了更低场(δC 125.0,156.0),推测香芹酚2'-OH被另一片段所取代而形成醚基。分析剩余的碳信号(δC72.0,80.2,117.6,147.1,25.0,33.5,21.9,34.5,21.5,21.5),发现另一片段与(1R,2R)-(-)-3-p-menthen-l,2-diol的碳信号十分相似,只是后者C-2和C-3信号(δC 74.8,121.0)分别往低场方向移至δC 80.2和δC 117.7,说明后者2-OH是与香芹酚2'-OH脱水缩合形成醚基,恰好与上述推测一致。通过HMBC相关谱分析(图1),所有信号得到归属(表1),尤其是H-2(δH 4.68)/C-2'(δC 156.0)相关,佐证了C-2是与C-2'通过醚键相连。尽管该化合物的绝对构型没有通过直接实验手段而得到测定,但在ROESY相关谱中并没有观察到其H-2与H-7有任何空间相关(图2),说明H-2与1-CH3处于异侧,即C-1和C-2构型为(1R,2R)-型或(1S,2S)-型。结合文献数据,发现天然来源的p-menthen-l,2-diol都是(1R,2R)-型,而(1S,2S)-型都是人工合成产物。且该化合物由C-1和C-2的手性碳所导致的旋光方向[(c 0.25,MeOH)]与(1R,2R)-(-)-3-p-menthen-l,2-diol的旋光方向是相同的,而与(1S,2S)-型的旋光方向刚好相反,进一步可佐证其为(1R,2R)-型。因此,该化合物鉴定为(1R,2R)-(-)-2-[2'-(1'-methyl-4'-isopropyl)-phenoxyl]-1-methyl-4-isopropy l-3-en-1-cyclohexanol,命名为毛麝香醚A(adenosminA)。其结构式为:
表1化合物毛麝香醚A的波谱数据(chloroform-d)
实施例2
1、毛麝香醚A的驱蚊实验
本发明采用毛麝香醚A作为蚊虫驱避产品的功效成分,为确认本发明所述的毛麝香醚A在驱蚊上的功效,本发明采用笼内驱蚊模型(In-cage mosquito repellentbioassay)对毛麝香醚A进行了驱蚊试验,并与阳性对照驱蚊胺DEET(N,N-二乙基-3-甲基苯甲酰胺)进行了比较,具体的方法和结果(表2)如下:
①选取约500(±10%)只供试蚊虫置于试验蚊笼(45cm×37.5cm×35cm)内,适应25(±2.5)min后开始试验。②精密称取待测物150mg置于西林瓶中,用2mL无水乙醇溶解。充分摇匀后,取走一半溶液置于瓶子内,放入50cm2(5cm×10cm)纱布使其全部均匀浸润,成为1.5mg/cm2的初始浓度;剩余1mL加无水乙醇再稀释至2mL,依次取半浸润、留半稀释配成在纱布上为0.75、0.375、0.094、0.047、0.023、0.011mg/cm2等一系列稀释浓度。瓶子密封保存于-4℃环境中,测试时再启用(通常<48h)。取出瓶内的纱布并置于卡片纸上,放入干燥箱3-5min,然后可开始试验。③志愿者的手上先戴上一个及臂的长手套,然后再戴上聚乙烯材料的塑料手套;在手腕至肘部中间开一个4×8cm的小口,用以评价蚊虫的停落和叮咬行为,开口应当允许皮肤表面释放的气体能吸引到蚊子。测试中,在开口区域贴上待测物处理的纱布。④首先用中间浓度(e.g.,0.187mg/cm2)的纱布贴在开口处,如果有0-4bites/min,则认为该浓度有效,那么接着用浓度更低的纱布测试,直到无效为止;如果有≥5bites/min,则认为无效,那么接着用浓度更高的纱布测试,直到有效为止。最后,有效浓度与无效浓度的临界浓度即为最低有效剂量MED。一般重复测试至少3次,计算MED平均值和标准差。为防止被试蚊虫由于长期暴露对气味敏感度下降,每阶段测试只允许10次连续测试,中间需有一个15min的恢复期。⑤4名以上志愿者(男女各半)两人一组交替参与,每块纱布测试时间为1min。同一浓度纱布一旦使用超过10min就不能用于测试,以免因待测物挥发导致偏差。该实验参照GB/T 17322.10-2009(农药登记用卫生杀虫剂室内药效试验及评价第9部分:驱避剂)的测试标准,志愿者攻击力测试合格后,所有受试者须签订知情同意书,其协议由昆明市疾病预防控制中心批准。
表2毛麝香醚A驱避白蚊伊蚊的最低有效剂量MED(mean±sd mg/cm2)
化合物 | MED |
毛麝香醚A | 0.063±0.027(强) |
DEET | 0.031±0.014(强) |
实验结果表明,毛麝香醚A与阳性对照驱蚊胺DEET的MED相当,说明在驱蚊强度上其与DEET一样具有显著的驱蚊效果。
2.采用MTT法测试毛麝香醚A的细胞毒活性。
①接种细胞:用含10%胎牛血清的RMPI 1640培养液配成单个细胞悬液,以每孔15000个细胞接种到96孔板,每孔体积100μL,细胞提前12-24h接种培养。②加入待测化合物溶液:化合物用DMSO溶解,提取物初筛以100μg/mL浓度初筛,化合物初筛以40μM浓度,化合物复筛以100、20、4、0.8、0.16μg/mL浓度,每孔终体积200μL,每种处理均设3个复孔。③显色:37℃培养48h后,悬浮细胞弃100μL培养上清液,每孔加20μL的MTS溶液;设3个空白复孔(MTS溶液20μL和培养液100μL的混合液),继续孵育4h,使反应充分进行后测定光吸收值。④比色:选择492nm波长,多功能酶标仪(MULTISKAN FC)读取各孔光吸收值,记录结果,数据处理后以浓度为横坐标,细胞存活率为纵坐标绘制细胞生长曲线,应用两点法(Reed andMuench法)计算化合物的IC50值(表3)。
表3毛麝香醚A的细胞毒活性
NC=在最高浓度40μM下未显示毒性
实验结果表明,在最高浓度40μM下,毛麝香醚A对人真皮成纤维细胞HDFa未表现出细胞毒性,从细胞水平上说明毛麝香醚A用于驱蚊产品具有安全性优势。
实施例3制备含毛麝香醚A的驱蚊空气清新剂
按质量配比将毛麝香醚A 20份溶于无水乙醇20份中,再加入60份的蒸馏水及吐温80增溶剂0.5份,充分搅拌混合均匀。
实施例4制备含毛麝香醚A的驱蚊剂
按质量配比将毛麝香醚A 10份和香茅精油10份溶于无水乙醇20份中,再加入60份的蒸馏水及吐温80增溶剂0.5份,充分搅拌混合均匀。
实施例5含毛麝香醚A的驱蚊霜
配方如下:硬脂酸甘油酯16%、三辛酸甘油酯5.0%、鲸蜡醇1.0%、羊毛脂5.0%、丙二醇5.0%、毛麝香醚A 5.0%、去离子水62%。
实施例6含毛麝香醚A的驱蚊膏。
配方如下:毛麝香醚A 5.0%、尿素20%、凡士林40%、硬脂醇4.5%、蜂蜡20%、聚氧乙烯油醇醚0.5%、去离子水10.5%。
实施例7含毛麝香醚A的洗发水。
配方如下:蒸馏水约65%、月桂醇聚醚硫酸酯钠12%、十二烷基硫酸钠3%、十二烷基甜菜碱2%、椰油二乙醇酰胺4%、棕榈酸异丙酯2%、硅氧烷0.6%、甘油2%、珠光剂4%、尼泊金甲酯0.3%、何首乌根提取物5%、柠檬酸适量、色素适量、毛麝香醚A 0.03%。
以上所述的具体实施例,对本发明的目的、技术方案和有益效果进行了进一步详细说明,所应理解的是,以上所述仅为本发明的具体实施例而已,并不用于限定本发明的保护范围,凡在本发明的精神和原则之内,所做的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (9)
1.如下结构式所示的化合物,
2.制备权利要求1的化合物方法,包括从勐腊毛麝香精油中分离出所述化合物;
优选地,所述方法包括以下步骤:
步骤1:从勐腊毛麝香地上部分经蒸馏法提取获得精油;
步骤2:通过色谱方法从精油中分离出所述化合物。
3.一种以权利要求1的化合物作为有效成分的用于驱避蚊虫的组合物;
优选地,所述组合物包含载体和/或赋形剂;
优选地,所述载体和/或赋形剂选自水、乙醇、丙二醇、荷荷巴油、明胶、***树胶、吐温80、硬脂酸甘油酯、三辛酸甘油酯、鲸蜡醇、羊毛脂、尿素、凡士林、硬脂醇、蜂蜡、聚氧乙烯油醇醚;
优选地,所述组合物含有稳定剂,增稠剂,着色剂和/或香料;
优选地,所述组合物中,权利要求1的化合物的添加量为组合物总质量的0.1%-30%。
4.权利要求1的化合物用于制备蚊虫驱避产品的用途。
5.一种蚊虫驱避产品,其以权利要求1的化合物作为蚊虫驱避有效成分;
优选地,所述蚊虫驱避产品为液体、软膏、挂件或便捷贴;
优选地,所述蚊虫驱避产品为化妆品;
优选地,所述蚊虫驱避产品为蚊虫驱避剂(例如油基型制剂、醇基型制剂、水基型制剂);
优选地,所述蚊虫驱避产品选自驱蚊贴、驱蚊霜、驱蚊膏、驱蚊洗发用品、驱蚊空气清新剂;
优选地,所述蚊虫驱避产品中,权利要求1的化合物的添加量为所述产品总质量的0.1%-30%。
6.一种驱避蚊虫的方法,包括使用有效量的权利要求1的化合物、权利要求3的用于驱避蚊虫的组合物或权利要求5的蚊虫驱避产品。
7.权利要求1的化合物作为香料的用途。
8.一种包含权利要求1的化合物的香精;
优选地,所述化合物在所述香精中的重量百分含量为0.001%-20%;
优选地,所述香精包含溶剂,例如乙醇、异丙醇、二甘醇单***、一缩二丙二醇、邻苯二甲酸二乙酯、柠檬酸三乙酯、肉豆蔻酸异丙酯中的一种或多种。
9.包含权利要求8的香精的产品。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2018104949589 | 2018-05-22 | ||
CN201810494958.9A CN108558620A (zh) | 2018-05-22 | 2018-05-22 | 毛麝香醚及其组合物和其在日化品和香精中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109516904A true CN109516904A (zh) | 2019-03-26 |
CN109516904B CN109516904B (zh) | 2020-05-08 |
Family
ID=63539593
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810494958.9A Pending CN108558620A (zh) | 2018-05-22 | 2018-05-22 | 毛麝香醚及其组合物和其在日化品和香精中的应用 |
CN201811441879.8A Active CN109516904B (zh) | 2018-05-22 | 2018-11-29 | 毛麝香醚及其组合物、制备方法和用途 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810494958.9A Pending CN108558620A (zh) | 2018-05-22 | 2018-05-22 | 毛麝香醚及其组合物和其在日化品和香精中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (2) | CN108558620A (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108558620A (zh) * | 2018-05-22 | 2018-09-21 | 中国科学院昆明植物研究所 | 毛麝香醚及其组合物和其在日化品和香精中的应用 |
CN116492404B (zh) * | 2023-06-30 | 2024-01-26 | 中国科学院昆明植物研究所 | 一种勐腊毛麝香提取物及其制备方法和应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108558620A (zh) * | 2018-05-22 | 2018-09-21 | 中国科学院昆明植物研究所 | 毛麝香醚及其组合物和其在日化品和香精中的应用 |
-
2018
- 2018-05-22 CN CN201810494958.9A patent/CN108558620A/zh active Pending
- 2018-11-29 CN CN201811441879.8A patent/CN109516904B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108558620A (zh) * | 2018-05-22 | 2018-09-21 | 中国科学院昆明植物研究所 | 毛麝香醚及其组合物和其在日化品和香精中的应用 |
Also Published As
Publication number | Publication date |
---|---|
CN108558620A (zh) | 2018-09-21 |
CN109516904B (zh) | 2020-05-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105997703B (zh) | 橄榄叶提取物以及包含该提取物的化妆品 | |
JP4299374B2 (ja) | 細胞賦活剤及びその応用 | |
JPH08283172A (ja) | 活性酸素消去剤及びこれを含有する皮膚外用剤 | |
JP2007290968A (ja) | 防臭組成物、デオドラント剤、および繊維防臭剤 | |
BRPI0719468A2 (pt) | "processo para a preparação de um produto de reação, composição da matéria ou um artigo de fabricação e método para proporcionar a fragrância, ou revitalizar, a pele, couro, pêlos, peles, penas ou outra superfície" | |
DE69920567T2 (de) | Methode zur Verhütung des Körpergeruchs von alten Leute | |
CN103340761A (zh) | 木酚素化合物用于抗皱治疗的用途 | |
KR20190080011A (ko) | 천연 추출 성분을 함유하는 모기 기피제 조성물 | |
CN109516904B (zh) | 毛麝香醚及其组合物、制备方法和用途 | |
JP2006052198A5 (zh) | ||
WO2006008917A1 (ja) | デオドラント剤、デオドラント製剤、および繊維デオドラント処理方法 | |
KR101561408B1 (ko) | 작약 식물 태좌 세포 배양 추출물을 함유한 모공 축소, 미백, 피부 보습용 화장료 조성물 | |
CN105997579A (zh) | 勐腊毛麝香精油为有效成分的驱蚊产品及其应用 | |
JP3619185B2 (ja) | 化粧料 | |
JPH06128143A (ja) | 皮膚外用剤 | |
KR101533213B1 (ko) | 아네모네 식물 태좌 세포 배양 추출물을 함유한 항노화, 항염, 항산화 화장료 조성물 | |
CN112175733B (zh) | 香草精油提取物的制造方法及包括香草精油提取物的化妆品组合物 | |
KR20190006888A (ko) | 황근 추출물, 황근 추출물의 분획물 및 황근 추출물의 분획물로부터 분리된 화합물을 포함하는 피부 안티폴루션용 조성물 | |
KR101533217B1 (ko) | 수련화 식물 태좌 세포 배양 추출물을 함유한 항노화, 항염, 항산화 화장료 조성물 | |
Ghanwat et al. | Formulation and Evaluation of Herbal Soap | |
US20040047831A1 (en) | Use of a cell extract of at least a plant of the family pontederiaceae as anti-pollution agent | |
CN109497060B (zh) | 香芹酚类似物在驱蚊产品中的应用 | |
KR20030004499A (ko) | 멜라닌 생성 억제 활성을 갖는 식물 추출물을 함유하는피부미백용 화장료 | |
US11684564B2 (en) | Cosmetic composition for improving skin containing taraxacum coreanum phytoplacenta culture extract that has moisturizing and soothing effects for extremely dry skin such as atopic dermatitis, and skin barrier strengthening effect | |
KR101533214B1 (ko) | 노루귀 식물 태좌 세포 배양 추출물을 함유한 항노화, 항염, 항산화 화장료 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
OL01 | Intention to license declared |