CN114384162A - Method for evaluating residual fragrance property of perfume, residual fragrance imparting agent, and residual fragrance property improving method - Google Patents
Method for evaluating residual fragrance property of perfume, residual fragrance imparting agent, and residual fragrance property improving method Download PDFInfo
- Publication number
- CN114384162A CN114384162A CN202111233042.6A CN202111233042A CN114384162A CN 114384162 A CN114384162 A CN 114384162A CN 202111233042 A CN202111233042 A CN 202111233042A CN 114384162 A CN114384162 A CN 114384162A
- Authority
- CN
- China
- Prior art keywords
- aroma
- fragrance
- compound
- residual
- odor
- 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.)
- Pending
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 239
- 238000000034 method Methods 0.000 title claims abstract description 80
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 26
- 239000002304 perfume Substances 0.000 title claims description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 238000011156 evaluation Methods 0.000 claims abstract description 71
- 239000000796 flavoring agent Substances 0.000 claims abstract description 71
- 239000000126 substance Substances 0.000 claims abstract description 30
- 238000004458 analytical method Methods 0.000 claims abstract description 23
- 229940126062 Compound A Drugs 0.000 claims abstract description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 50
- 210000004209 hair Anatomy 0.000 claims description 30
- 239000002537 cosmetic Substances 0.000 claims description 12
- 239000000341 volatile oil Substances 0.000 claims description 11
- PYCLZSZCVOERTA-UHFFFAOYSA-N C(C)(C)=C1CC2(CC1)C(=CCCC2C)C=O Chemical compound C(C)(C)=C1CC2(CC1)C(=CCCC2C)C=O PYCLZSZCVOERTA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 2
- 229940126534 drug product Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000003599 detergent Substances 0.000 description 12
- 238000004817 gas chromatography Methods 0.000 description 12
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 238000013329 compounding Methods 0.000 description 8
- 241000402754 Erythranthe moschata Species 0.000 description 7
- 235000019634 flavors Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- -1 natural fragrances Chemical class 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000002781 deodorant agent Substances 0.000 description 5
- 239000000118 hair dye Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 241000984061 Aquilaria Species 0.000 description 3
- 241000271309 Aquilaria crassna Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019629 palatability Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 235000015961 tonic Nutrition 0.000 description 3
- 230000001256 tonic effect Effects 0.000 description 3
- 229960000716 tonics Drugs 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 241000271307 Aquilaria malaccensis Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000001166 anti-perspirative effect Effects 0.000 description 2
- 239000003213 antiperspirant Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 229940071160 cocoate Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000077 insect repellent Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 230000008786 sensory perception of smell Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- CRIGTVCBMUKRSL-FNORWQNLSA-N 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-enone Chemical compound C\C=C\C(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-FNORWQNLSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 1
- 235000002598 Inula helenium Nutrition 0.000 description 1
- 244000116484 Inula helenium Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- CRIGTVCBMUKRSL-UHFFFAOYSA-N alpha-Damascone Natural products CC=CC(=O)C1C(C)=CCCC1(C)C CRIGTVCBMUKRSL-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 description 1
- 150000001588 beta-ionone derivatives Chemical class 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- MIZGSAALSYARKU-UHFFFAOYSA-N cashmeran Chemical compound CC1(C)C(C)C(C)(C)C2=C1C(=O)CCC2 MIZGSAALSYARKU-UHFFFAOYSA-N 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940071124 cocoyl glutamate Drugs 0.000 description 1
- 239000008294 cold cream Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000002690 dihydrocarvone group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 229940093503 ethyl maltol Drugs 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 239000008269 hand cream Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process 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
- 230000000813 microbial effect Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/64—Electrical detectors
- G01N30/66—Thermal conductivity detectors
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/86—Signal analysis
- G01N30/8675—Evaluation, i.e. decoding of the signal into analytical information
- G01N30/8679—Target compound analysis, i.e. whereby a limited number of peaks is analysed
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/065—Preparation using different phases to separate parts of sample
Abstract
The present invention addresses the problem of providing a residual fragrance property evaluation method for identifying a fragrance compound having a high residual fragrance property contained in a fragrance component of an odor substance, a method for evaluating the fragrance characteristics of the fragrance compound based on the degree of contribution of fragrance and the residual fragrance property, a method for imparting residual fragrance properties to a fragrance product, and other novel methods and residual fragrance property imparting agents that relate to residual fragrance properties. A method for evaluating residual fragrance of a selected fragrance compound contained in a odorous substance, the method comprising the steps of: a step 1 of leaving the odorous substance in a space where the temperature and humidity are constant, a step 2 of extracting the aroma components contained in the odorous substance after a predetermined time from the start of the leaving, a step 3 of subjecting the extracted aroma components to gas chromatography-odor (GCO) analysis to detect the presence or absence of an odor of each aroma compound constituting the aroma components, a step 4 of measuring the longest leaving time (T) for each aroma compound in which the odor of each aroma compound constituting the odorous substance can be detected, and a step 5 of using the longest standing time (Ta) during which the odor of the specific aroma compound A can be detected in the step 4, and a step of setting the Ta/Tx value as the residual aroma evaluation value of the aroma compound A contained in the odorant, wherein the longest standing time (Tx) of the aroma compound X with the longest T among the aroma compounds constituting the odorant is capable of detecting the odor.
Description
Technical Field
The present invention relates to a method for evaluating an aromatic compound having a high residual fragrance and a high contribution degree to fragrance from a mixture of aromatic compounds such as natural fragrances, and also relates to a residual fragrance-imparting agent found by the method, and a method for improving a fragrance composition which has the same fragrance profile and further has improved residual fragrance by analyzing the characteristics of the aromatic components by the method.
Background
Among aromatic products represented by perfumes, cosmetic products, skin care products, hair care products, toiletry products, household products, aromatic agents, and the like, the lasting of fragrance for a long time (having residual fragrance) is an important factor in bringing satisfaction, feeling of pleasure, feeling of heightened mood to consumers and improving commodity value. Therefore, it is important to develop a cosmetic perfume (fragrance) used in a fragrance product to improve the residual fragrance of the fragrance product. Here, the residual fragrance refers to a property of fragrance lasting or sustaining for a long time.
In the perfume industry, in order to overcome the problem of disappearance of fragrance in a short time when a perfume component having high volatility or low residual property is used, a method of encapsulating a perfume component in a microcapsule to physically suppress volatilization of a perfume component (patent document 1) and a method of using a derivative (pro fragance) capable of prolonging the effect of an active ingredient (patent document 2) have been studied.
However, there have been proposed problems that capsules and polymers used for encapsulating perfumes and fragrance precursors (Profragrance) are physically difficult to break and have low biodegradability, thereby imposing a burden on the natural environment.
Further, although pleasantness and unpleasant feeling to the smell depend on personal feelings, a popular fragrance having excellent palatability is not likely to give unpleasant feeling to most people. Therefore, as a perfume used in a fragrance product, a perfume having excellent both residual fragrance and preference is used empirically.
As such a technique, for example, a method of blending a fragrance by attaching a fragrance raw material for blending a fragrance and a natural or synthetic fragrance used to a fragrance paper and selecting a fragrance that leaves the fragrance for 2 hours, 6 hours, or 6 hours or more on the fragrance paper has been proposed (patent document 3).
However, in natural perfumes composed of a wide variety of fragrance components, effective components contributing to residual fragrance in natural perfumes have not been clarified so far, and therefore development of novel perfumes has been made only by fragrance notes, and therefore, there has been no method using a natural perfume containing a wide variety of fragrance components other than the natural perfume itself.
However, in this method, it is necessary to ensure residual fragrance properties while always balancing the fragrance (quality, character, type of smell) of the natural perfume itself with the target fragrance of a new perfume, and selection and blending amount of the natural perfume to be used require extensive trial and error based on the experience of a perfumer, which greatly affects the labor, time, and cost required for developing a new product.
Therefore, a technique has been studied which can improve only the residual fragrance property without using a natural perfume. For example, a method of sustaining a floral, fruity, or green type fragrance by adding a retention agent for adjusting the retention of a fragrant substance has been proposed (patent document 4); a method of using a vinylpyrrolidone/vinyl acetate copolymer as an aromatic extender (patent document 5); a method of using 1-methyl-3, 4-dioxy (cyclopropanone) benzene having high aromaticity (patent document 6); a method of using a persistent perfume composition containing a component having a calculated logarithmic value (ClogP) of not less than 3.0(P is an octanol/water partition coefficient) and a boiling point of not less than 250 ℃ (patent document 7); a method for producing a perfume composition having a high residual fragrance by using a perfume component which is solid at a temperature of 25 ℃ and has a low volatility (patent document 8).
In recent years, there has been an interest and a desire for using natural perfume components that are highly palatable and less loaded on the natural environment. However, there has been no method for searching for and evaluating a highly persistent aroma compound from natural aroma, and improving an aroma composition or developing an aroma composition having a high residual aroma based on the data.
On the other hand, as a method for analyzing the aroma characteristics of each aroma component in natural flavors, a method has been proposed in which aroma components in a coffee aroma concentrate are separated by Gas Chromatography (GC), and the separated aroma components are mixed with a coffee extract for evaluation and subjected to sensory evaluation to measure the contribution of the separated aroma components (patent document 9); a method of continuously mixing an aroma component in a coffee aroma concentrate separated by GC with a headspace sample of a coffee extract and evaluating the aroma (patent document 10); a method of calculating an FD factor of each aroma component by combining a GCO analysis method of sensory evaluation (sniffing) of the aroma component separated by GC by olfaction with an aroma extract dilution analysis method (AEDA), and converting the concentration of a trace amount of aroma component in coffee beans by integrating the threshold value of each aroma component to the FD factor (patent document 11).
However, in any of the above methods, although qualitative and quantitative determination of the aroma components contained and the aroma compounds constituting the aroma components can be performed, it is not a method for accurately evaluating the residual aroma of the aroma compounds in natural aroma, and it has not been achieved to find out aroma components having high residual aroma and high palatability.
In general, sensory evaluation methods are used to evaluate the flavor and Gas Chromatography (GC) is used to analyze the aroma components, but these methods have difficulty in identifying the active ingredients and aroma compounds that contribute to the residual aroma of natural flavors and in finding out the ingredients and aroma compounds that have high residual aroma in detail.
Therefore, the present inventors have found and provided a novel method for finding and evaluating aroma compounds having high residual aroma from a large amount of components contained in a familiar fragrance used since ancient times or a fragrance having a pleasant feeling due to natural aroma, which is a natural fragrance having high palatability.
Further, a method for evaluating the fragrance characteristics based on the correlation between the numerical data obtained by the residual fragrance evaluation method and the numerical data on the degree of contribution of the fragrance characteristics in the natural fragrance of the compound, a residual fragrance imparting agent found by the method, a method for imparting residual fragrance to a fragrance product, a method for improving fragrance having excellent residual fragrance and preference, and a method for developing a fragrance composition using a novel method have been found and provided.
Documents of the prior art
Patent document
Patent document 1: japanese Kokai publication No. 2010-520928
Patent document 2: japanese Kokai publication No. 2008-531761
Patent document 3: japanese patent laid-open publication No. 2002-327193
Patent document 4: japanese patent No. 5025845
Patent document 5: japanese Kohyo publication (Kohyo publication) No. 2017-520543
Patent document 6: japanese patent No. 5011254
Patent document 7: japanese Kohyo publication Hei 10-507789
Patent document 8: japanese patent laid-open publication No. 2009 and 242298
Patent document 9: japanese patent laid-open publication No. 2007-163198
Patent document 10: japanese patent laid-open publication No. 2003-107067
Patent document 11: japanese patent laid-open publication No. 2004-325116
Non-patent document
Non-patent document 1: measurement of flavor of instrument for Horiki's hui-Seng' the forefront ", Japanese cosmetic technical personnel will explain Vol.32, No.3 (No. 9 1998), pages 253-262
Disclosure of Invention
The present invention addresses the problem of providing a residual fragrance evaluation method for identifying and digitizing a high-residual-fragrance-content compound contained in a fragrance substance, a method for evaluating the fragrance characteristics of a fragrance compound contained in a fragrance substance based on a fragrance contribution degree and a residual-fragrance evaluation value, and various new methods for improving the residual fragrance of a fragrance such as a residual-fragrance-providing agent.
Namely, the present invention is as follows.
[ 1] A method for evaluating residual fragrance properties of a selected fragrance compound contained in a odorous substance, the method being used for selecting a compound having a high residual fragrance property, the method comprising the steps of:
step 1. a step of leaving the odorous substance in a space in which the temperature and humidity are kept constant,
a step 2 of extracting the aroma component contained in the odorant after a predetermined time from the start of the standing,
step 3. subjecting the extracted aroma components to gas chromatography-olfactive (GCO) analysis to detect the presence or absence of an odor of each aroma compound constituting the aroma components,
a step 4 of measuring the longest standing time (T) for each aroma compound, which enables detection of the odor of each aroma compound constituting the aroma substance, and,
and a step 5 of using the longest standing time (Ta) during which the odor of the specific aroma compound a can be detected in the step 4 and the longest standing time (Tx) during which the odor of the aroma compound X having the longest T among the aroma compounds constituting the odor can be detected, and setting the Ta/Tx value as the residual odor evaluation value of the aroma compound a contained in the odorant.
[ 2] A method for evaluating the aroma characteristics of an aroma compound A based on the degree of aroma contribution of the aroma compound A contained in an odorous substance and the residual aroma evaluation value (Ta/Tx) of the aroma compound A obtained by the method of 1.
[ 3] A residual fragrance imparting agent comprising 1, 2-dihydrokara-one and/or 2-isopropylidene-10-methyl-spiro [4,5] -6-decene-6-carbaldehyde as an active ingredient.
[ 4] A fragrance composition (excluding fragrance compositions containing agilawood essential oil) comprising the residual fragrance imparting agent of the above 3.
[ 5] A fragrance composition having improved residual fragrance, which comprises the fragrance composition of item 4 above.
[ 6] according to the fragrance product of the above 5, the above product is a perfume, a cosmetic product, a skin care product, a hair care product, a personal care product as a toilet product, a household product, or a quasi drug.
[ 7] A method for imparting residual fragrance to a fragrance product by blending the fragrance composition according to the above 4.
[ 8] the method for imparting residual aroma according to the above 7, wherein the fragrance product is a perfume, a cosmetic product, a skin care product, a hair care product, a personal care product as a toiletry product, a household product or a quasi-drug.
[ 9] A method for improving the aroma of an odorous substance, comprising the steps of:
step 1: a step of determining a residual aroma evaluation value (P), an aroma contribution degree (Q) and a note of aroma based on the method [ 1] for each aroma compound constituting the aroma of the odorant,
and a step 2: a step of classifying a compound having 0 < P < 0.5 and 0 < Q < 0.5 as a compound group A, a compound having 0 < P < 0.5 and 0.5. ltoreq. Q.ltoreq.1 as a compound group B, a compound having 0.5. ltoreq. P.ltoreq.1 and 0 < Q < 0.5 as a compound group C, and a compound having 0.5. ltoreq. P.ltoreq.1 and 0.5. ltoreq. Q.ltoreq.1 as a compound group D for each aroma compound,
and 3. a step of replacing the aroma compound B classified into the compound group B with an aroma compound D classified into the compound group D and having a similar aroma tone to that of the aroma compound B.
[ 10] A method for designing a perfume composition, comprising the steps of:
a step of making a database of the correlation between the residual aroma evaluation value and the note with respect to a large amount of aroma compounds by the method of 9,
and selecting a constituent component from the data when designing a perfume composition whose fragrance changes with time.
According to the present invention, even with a complicated composition such as a natural perfume or a natural essential oil, it is possible to find and clarify components having high importance in both residual fragrance and contribution to fragrance, and to improve the residual fragrance without giving unpleasant feeling by adding the thus-found fragrance compound to another perfume composition as a residual fragrance imparting agent.
Therefore, in the development of a new perfume composition for a fragrance product, and in the improvement and improvement of conventional products, the operation and process steps of numerous trial and error, which have been conventionally required for selecting a perfume and determining the amount to be blended, can be greatly shortened, simplified, and made efficient and labor-saving.
As a result, the labor, time, and cost required for product development can be significantly reduced, and product design, development, and improvement in response to consumer demand can be performed in a short time and in a timely manner.
Drawings
FIG. 1 is a schematic view of the standing time and the sample number.
Fig. 2 is a correlation diagram of the residual aroma evaluation value and the aroma contribution degree.
Detailed Description
In the present invention, a gas chromatography-Olfactometry (GCO) analysis method in which odor of an odor compound remaining in a sample of an odor substance left standing for an arbitrary period of time is smelled at a discharge port of a Gas Chromatography (GC) and obtained information is superimposed on GC information is used to find out an odor compound having residual odor, and the strength (persistence of odor) of the odor compound is quantified and evaluated.
Further, by numerically evaluating the contribution degree of each aroma compound to the whole odor by the aeca (aroma Extract Dilution analysis) and classifying (sorting) the aroma compounds by the binary data of the residual aroma evaluation value and the aroma contribution degree, it is possible to identify and select an active ingredient having a high aroma contribution degree and residual aroma from a large amount of aroma ingredients contained in the natural aroma.
The present invention will be described in detail below with reference to embodiments.
[ 1] method for evaluating residual fragrance
The method for evaluating residual fragrance property for identifying a compound having high residual fragrance property contained in a odorous substance according to the present invention comprises the following steps (steps).
In step 1, the odorant is allowed to stand in a space where the temperature and humidity are kept constant.
In step 2, the aroma component contained in the odorant is extracted after a predetermined time from the start of standing.
In step 3, the extracted aroma components are subjected to gas chromatography-olfactive analysis (GCO) to detect the presence or absence of odor of each aroma compound constituting the aroma components.
In step 4, the longest standing time (T) for each aroma compound is measured, in which the odor of each aroma compound constituting the odor substance can be detected.
In step 5, the value Ta/Tx is used as the residual aroma evaluation value of the aroma compound a contained in the odorant, using the longest standing time (Ta) during which the odor of the specific aroma compound a can be detected in step 4 and the longest standing time (Tx) during which the odor of the aroma compound X having the longest T among the aroma compounds constituting the odorant can be detected.
The above-described steps will be described in further detail below.
(1) Step 1
Examples of odorants to be evaluated include natural plant perfumes obtained from flowers, fruits, fruit juices, trees, vegetables, fruits, seeds, spices, etc., natural animal perfumes obtained from Ambergris (Ambergris), Musk (Musk), dried fish, etc., synthetic perfumes obtained by chemical or microbial methods and composed of 2 or more odorous compounds, and commercially available odorous foods and beverages, cosmetics, etc. These odorous substances can be purified and used by a method known in the field of perfumery, for example, extraction, leaching, squeezing, evaporation, and the like.
In the evaluation, first, a sample in which an odor substance is permeated into the filter paper is prepared, and then, in consideration of the use environment of the fragrance product, adjustment is performed under conditions in which the temperature, humidity, illuminance, and the like are kept constant during the standing. The space for standing is, for example, a thermostatic chamber, a thermostat, a dryer, or the like.
The residual fragrance properties under various environments can be evaluated by appropriately setting the temperature, humidity, illuminance, and the like when the sheet is left to stand. For example, the temperature is 0-30 ℃, the relative humidity is 40-90%, and the illumination is 0-100000 lux.
When a sample is prepared, the residual fragrance of the fragrance for hair care products such as hair dye can be accurately evaluated by using hair instead of filter paper, and the residual fragrance of the fragrance for household goods such as detergent and soft finishing agent can be accurately evaluated by using garment materials.
Here, the fragrance product refers to perfume, aromatic, cosmetic product, toilet product, skin care product, hair care product, and household product as shown below.
The term "perfume" means perfume, cologne, etc., and may be in the form of bottle, ball or spray, depending on the intended use.
"cosmetic products" are used for the purpose of beautifying, protecting the skin, bringing fun and satisfaction.
Make-up cosmetics such as foundation make-up, lipstick, blush, eyeliner, mascara, eye shadow, eyebrow pencil, loose powder, pressed powder, nail polish, etc., nail beautifying, nail polish removing lotion, etc.
The skin care product plays roles in removing sweat and dirt, tightening the skin, maintaining proper nutrition and moisture, assisting normal skin state, protecting the skin from being damaged by ultraviolet rays and the like.
The face cleansing cream, the vanishing cream, the facial cleanser, the cleansing cream, the cold cream, the sunscreen cream, the emulsion, the astringent, the packing agent, the makeup remover, the after-shave lotion, the toilet powder, the lipstick, the hand cream, the antiperspirant and the face care (cleansing foam, the makeup remover oil, the oil absorption paper, etc.).
"Hair care products" are used for cleaning and protecting hair and scalp, and for styling hair, and include shampoos, hair dyes, hair conditioners, hair tonics and hair oils for improving scalp blood circulation, hair rinses, hair sticks, hair lotions, hair setting agents, hair sprays, hair foams, hair dressings and other hair styling agents, hair dyes such as hair dyes, acid hair dyes, bleaches, hair blackers and the like, hair conditioners such as permanent wave agents, hair curlers and the like, hair tonics such as hair rinses and the like, hair tonics and the like.
The toilet products include body care products such as perfumed soaps, hand sanitizers, bath salts, bath agents, lipsticks and the like, oral care products such as sun screens, antiperspirant deodorants, shavers (shavers, hair waste disposal razors, shaving foams and the like), toothpastes, mouth washes, dental flosses, denture cleaners and the like, wet tissues, paper diapers, physiological products and the like.
"household articles" include clothing articles such as detergents and softening agents used in ordinary households, house and furniture articles such as detergents and waxes, kitchen articles such as bleaching agents and garbage deodorants, daily sundry goods such as office glues and paints, liquid detergents for clothing, powder detergents for clothing, solid soaps for clothing, softening agents for clothing, bleaching agents for clothing, kitchen detergents, detergents for dish washers, bathroom detergents, glass detergents, mold removers, detergents for drain pipes, smoke detergents, mosquito-repellent incense, insecticides, insect repellents, and toilet detergents.
The "aromatic agent" includes aqueous liquid aromatic agent, oily liquid aromatic agent, aqueous gel aromatic agent, oily gel aromatic agent, aromatic spray, aromatic aerosol, impregnated aromatic agent, joss stick, aromatic deodorant, deodorant spray, deodorant aerosol, etc.
(2) Step 2
Next, as shown in fig. 1, after a certain time (Tn) from the start of standing, the odor substance (Sn) remaining on the filter paper was recovered. The interval of the standing time can be appropriately adjusted according to the purpose, but if the interval is too short, the number of experiments increases and becomes complicated, and conversely, if the interval is too long, it becomes difficult to obtain a difference in residual fragrance among the fragrance compounds, and thus the accuracy of the result becomes low. Preferably, the setting is made at intervals of equal difference or equal ratio from several tens of minutes to several hours or so.
The recovery method is suitably selected from solvent extraction, solid-phase extraction of headspace gas, direct injection of headspace gas, and the like.
(3) Step 3 to step 5
In the method for evaluating the residual aroma of the present invention, qualitative analysis of aroma components in the odorant (Sn) is performed after n hours from the start of standing (To) by a conventionally known GCO analysis.
Here, the GCO analysis is an analysis method in which a gas chromatography and a detection means based on human olfaction are combined, and is a method in which an outlet of a column of the gas chromatography is branched, one is connected to a detector (FID, MS, etc.), and the other is connected to a port capable of smelling a smell, and an apparatus is controlled so that the detector and the smell sniffing port can simultaneously detect the smell, thereby analyzing the characteristics of the smell (non-patent document 1).
As the apparatus for GCO analysis, a commercially available apparatus can be suitably used.
The aroma components were allowed to stand and GCO analysis was continued until no odor was present, and the longest standing time (Tx) for which the odor of either component was perceived was determined.
When the longest standing time (Ta) during which the odor of a specific aroma compound a can be detected and the longest standing time (Tx) during which the odor of an aroma compound X among aroma compounds constituting an odorant can be detected are set after the start of standing, the Ta/Tx value (value exceeding 0 and ranging to 1) is used as the residual aroma evaluation value of the aroma compound a contained in the odorant.
[ 2] evaluation method for combination of residual fragrance evaluation value and fragrance contribution degree
By using the residual aroma evaluation value of the aroma compound contained in the aroma substance and the aroma contribution degree of the aroma compound together, the aroma characteristics of the aroma compound can be evaluated more readily, and the evaluation can contribute to the improvement of the aroma substance and the development of new fragrances.
That is, the method is a method for evaluating the aroma characteristics of the aroma compound a contained in the odorant based on the aroma contribution degree obtained by evaluating the aroma contribution degree of the aroma compound a contained in the odorant and the residual aroma evaluation value (Ta/Tx) of the aroma compound a.
The method for measuring the aroma contribution degree can flexibly use a dilution analysis method. The Dilution analysis method is a method using GCO of an Aroma component eluted from a column of GC by human nose sniffing, and includes aeda (Aroma Extract Dilution analysis), charm (combined heavy Aroma Response measurement) analysis, and the like.
The aroma contribution degree by AEDA is obtained by sequentially diluting the odorant of the analyte at a predetermined ratio, repeating GCO analysis of each component until no odor is observed by sequentially increasing the dilution ratio, and defining the final dilution ratio at which odor is perceived for each component as the FD factor of the component. That is, this is a method of identifying the component which finally senses the odor as a component having a high degree of contribution.
The aroma contribution degree based on CHARM analysis is a method of simultaneously recording the time when AEDA is performed while the aroma is sensed, and two-dimensionally recording the contribution degree of the odor of each component as a peak area (CHARM Value) of a chromatogram.
The residual aroma Ta/Tx obtained by GCO analysis of aroma components in the odor substance after standing and the aroma contribution degree obtained by dilution analysis can be regulated, so that the residual aroma and the contribution degree of each aroma compound contained in the odor substance can be thoroughly evaluated.
Fig. 2 shows an example of evaluation based on the residual aroma evaluation value (Ta/Tx) and the aroma contribution degree.
The classification from a to D in fig. 2 is as follows.
A: aroma compound having low residual aroma evaluation value and low aroma contribution degree
B: aroma compound having low residual aroma evaluation value and high aroma contribution degree
C: aroma compound having high residual aroma evaluation value but low aroma contribution degree
D: aroma compound having high residual aroma evaluation value and high aroma contribution degree
Further, if the residual fragrance evaluation value is represented by P and the fragrance contribution degree is represented by Q (here, 0 < P.ltoreq.1 and 0 < Q.ltoreq.1), then compounds with 0 < P < 0.5 and 0 < Q < 0.5 can be classified as compound group A, compounds with 0 < P < 0.5 and 0.5. ltoreq.Q.ltoreq.1 can be classified as compound group B, compounds with 0.5. ltoreq.P.ltoreq.1 and 0 < Q < 0.5 can be classified as compound group C, and compounds with 0.5. ltoreq.P.ltoreq.1 and 0.5. ltoreq.Q.ltoreq.1 can be classified as compound group D. Further, the higher the P value is, the more excellent the residual fragrance is (P > 0.7), and the higher the Q value is, the more excellent the fragrance contribution is, the more excellent the Q value is (P > 0.7).
[ 3] fragrance imparting agent
The present inventors analyzed and studied various aroma compounds contained in agilawood (representative incense wood) having high preference used since ancient times, by using the above-described method for evaluating residual aroma, and method for evaluating two-dimensional aroma contribution degree.
Then, 1, 2-dihydrokara-tone and 2-isopropylidene-10-methyl-spiro [4,5] -6-decene-6-formaldehyde were found to be effective as residual aroma-imparting agents for aroma from the aroma compounds contained in eaglewood. In particular, 1, 2-dihydrokara ketone is excellent in both residual fragrance and fragrance contribution degree.
Aquilaria is a primitive plant such as Aquilaria (Aquilaria) belonging to Thymaceae, and is a sap extracted from bark of a tree to prevent invasion of bacteria, and is extracted from the bark. The essential oil extracted from lignum Aquilariae Resinatum contains terpene alcohol.
1, 2-dihydrokara ketone (CAS No.19598-45-9) has the structure of formula 1, and has radix aucklandiae and fumigating incense. Aroma components contained in eaglewood, which is an incense wood, and the like are known, but the use as an aroma compound is not known.
2-isopropylidene-10-methyl-spiro [4,5] -6-decene-6-carbaldehyde (J-GLOBALID:200907023404424459, Nikkaji number: J664.750B) has a structure represented by the following formula 2, and is an aroma component having elecampane. The use as aroma compounds has not been known to date.
Examples
The present invention will be further specifically described below with reference to examples, but the present invention is not limited to these examples.
[ test example 1] Aquilaria agallocha essential oil
(sample preparation)
7 pieces of eaglewood essential oil (sold product) produced in Thailand were added dropwise to 5. mu.L of an odorant on a filter paper having a diameter of 1cm, and the filter paper was left to stand at 25 ℃ at room temperature for 6 hours, 12 hours, 24 hours, 48 hours, 96 hours, and 192 hours, and collected in a vial, 1mL of methylene chloride was added thereto, and solvent extraction was performed for 10 minutes to obtain samples S0, S6, S12, S24, S48, S96, and S192.
(evaluation of residual fragrance)
Samples extracted after each elapsed time were subjected to GCO analysis under the conditions described below, and the presence or absence of odor, strength, flavor (character), and the like were evaluated.
The remaining fragrance evaluation value (Ta/Tx) was obtained by assuming that Ta was the longest standing time for which the odor of the fragrance component a was perceived and Tx was the standing time for which the fragrance component having the longest time among the odorous substances and being capable of detecting the odor. In test example 1, Tx is 96.
(evaluation of degree of contribution of fragrance)
The Thailand Aquilaria agallocha essential oil was supplied to GCO, and FD factors of each component in which odor was sensed were determined using AEDA method.
A 256-fold dilution of thailand agilawood essential oil with 1mL of dichloromethane was obtained. Subsequently, the samples were diluted 4-fold in sequence and measured by GCO until no odor was detected. Furthermore, the dilution ratio (1/4) when the odor of each aroma compound is not sensedn) The FD factor n was determined.
Next, the ratio of the FD factor of each aroma compound to the highest FD factor among the odorants was evaluated as the aroma contribution degree (Q).
(GCO analysis conditions)
The device comprises the following steps: agilent 6850 series gas chromatograph
A detector: thermal Conductivity Detector (TCD)
(Agilent Technologies,Palo Alto,USA)
Column: column of fused silica (internal diameter 30 m.times.0.25 mm, coated with 0.25 μm DB-Wax film; J & W Scientific, Folsom, USA)
Temperature rising conditions are as follows: the temperature is raised from 40 ℃ to 210 ℃ at the speed of 5 ℃/min,
carrier gas: he (1ml/min)
The evaluation values of residual aroma and the degree of aroma contribution of each aroma compound detected from the agilawood essential oil are summarized in table 1. "RI" in the table denotes Retention Index (Retention Index).
[ Table 1]
From the above results, the relationship between the residual aroma evaluation value and the aroma contribution degree is classified for each aroma compound according to fig. 2.
The aroma compounds having a high aroma contribution degree, that is, having a high aroma contribution degree to aroma and a high residual aroma evaluation value in agilawood essential oil, are classified into D, the aroma compounds having a low aroma contribution degree and a high residual aroma evaluation value are classified into C, the aroma compounds having a high aroma contribution degree and a low residual aroma evaluation value are classified into B, and the aroma compounds having a low aroma contribution degree and a low residual aroma evaluation value are classified into a. Next, table 2 summarizes the aroma compounds classified into a to D and identified.
The classifications A to D are as follows.
A: compounds having an evaluation value of residual fragrance of 0 < 0.5 and an aroma contribution of 0 < 0.5,
b: a compound having an evaluation value of residual fragrance of 0 < 0.5 and a contribution degree of fragrance of 0.5. ltoreq. 1,
c: a residual fragrance evaluation value of 0.5 or more and 1 or less and a fragrance contribution degree of 0 or more and 0.5 or less,
d: a residual fragrance evaluation value of 0.5. ltoreq. 1 and a fragrance contribution degree of 0.5. ltoreq. 1.
[ Table 2]
A | Butyric acid |
B | Guaiacol |
C | 2-isopropylidene-10-methyl-spiro [4,5]]-6-decene-6-carbaldehyde |
D | 1, 2-dihydrocarvones |
[ test example 2] floral fragrance composition
In a floral fragrance type perfume composition (manufactured by xiaochuan perfumer corporation) prepared by the formulation shown in table 4, 1, 2-dihydrokaratone (manufactured by xiaochuan perfumer corporation) classified as an aroma compound having a high aroma contribution degree and a high residual aroma property in test example 1 was mixed at the concentration shown in table 3, and the mixture was dropped on a filter paper in the same manner as in test example 1, and the residual aroma after being left standing for 12 hours under the same conditions was evaluated by 10 professional panelists trained in advance.
The evaluation results are shown in table 5 described later.
[ Table 3]
TABLE 3 formulation of 1, 2-dihydrokara-nones in floral fragrances
Comparative example 1 | Comparative example 2 | Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 3 | |
Floral type spice | 999 | 999 | 999 | 999 | 999 | 999 | 999 |
1,2 |
0 | 0.00001 | 0.0001 | 0.005 | 0.01 | 0.1 | 0.5 |
Dipropylene glycol | 1 | 0.99999 | 0.9999 | 0.995 | 0.99 | 0.9 | 0.5 |
[ Table 4]
TABLE 4 floral fragrance formula
Compounding amount (g) | |
Phenylethanolic acid | 400 |
Geraniol | 300 |
Citronellol | 200 |
Damascenone | 1 |
Rose ether | 2 |
Phenylethyl acetate | 5 |
Dipropylene glycol | 92 |
Total up to | 1000 |
[ Table 5]
TABLE 5 evaluation results
The evaluation contents are as follows.
Evaluation of residual fragrance: the numbers in the table indicate the number of evaluators.
Evaluation 1: the residual fragrance was the same as in comparative example 1.
Evaluation 2: the residual fragrance is slightly improved.
Evaluation 3: the residual fragrance is obviously improved.
The content of 1, 2-dihydrokara ketone is preferably 0.00001 to 0.01%, particularly preferably 0.00005 to 0.005%, and more particularly preferably 0.0001 to 0.002%.
[ test example 3] Musk-type perfume composition
The 1, 2-dihydrokaraanone (manufactured by kawa perfume co., ltd.) classified in test example 1 was mixed with the musk type perfume composition (manufactured by kawa perfume co., ltd.) prepared according to the formulation shown in table 7 at the concentration shown in table 6. The fragrance residue was dropped onto a filter paper in the same manner as in test example 1, and evaluated by 10 professional panelists trained in advance for fragrance residue after standing for 12 hours under the same conditions.
The evaluation results are shown in table 8 described later.
[ Table 6]
TABLE 6 compounding Table of 1, 2-dihydrokara-nones in musk type perfumes
Comparative example 4 | Comparative example 5 | Example 5 | Example 6 | Example 7 | Example 8 | Comparative example 6 | |
Musk type perfume | 999 | 999 | 999 | 999 | 999 | 999 | 999 |
1, 2- |
0 | 0.00001 | 0.0001 | 0005 | 0.01 | 0.1 | 0.5 |
Dipropylene glycol | 1 | 0.99999 | 0.9999 | 0.995 | 0.99 | 0.9 | 0.5 |
[ Table 7]
TABLE 7 Musk type perfume formulas
Compounding amount (g) | |
Kescomide (Cashmeran) | 30 |
Cyclopentadecanolide | 100 |
Ethylene glycol brassylate | 300 |
Musk ketene | 50 |
Muscolide | 100 |
Cyclopentadecenolide | 200 |
Dipropylene glycol | 220 |
Total up to | 1000 |
[ Table 8]
Table 8 evaluation results
The evaluation was as follows.
Evaluation of residual fragrance: the numbers in the table indicate the number of evaluators.
Evaluation 1: the residual fragrance was the same as in comparative example 4.
Evaluation 2: the residual fragrance is slightly improved.
Evaluation 3: the residual fragrance is obviously improved.
The content of 1, 2-dihydrokara ketone is preferably 0.00001 to 0.01%, particularly preferably 0.00005 to 0.005%, and more particularly preferably 0.0001 to 0.002%.
[ test example 4] fragrance composition of oriental odor type
1, 2-dihydrokaraya ketones (product of Xiaochuan Fujiu Co., Ltd.) classified in test example 1 was mixed with a fragrance composition of oriental flavor type (product of Xiaochuan Fujiu Co., Ltd.) prepared according to the formulation shown in Table 10 at the concentration shown in Table 9, dropped on a filter paper in the same manner as in test example 1, and the remaining fragrance after standing for 12 hours under the same conditions was evaluated by 10 professional panelists trained in advance.
The evaluation results are shown in table 11 described later.
[ Table 9]
TABLE 9 compounding table of 1, 2-dihydrocarvone in oriental flavor perfume
Comparative example 7 | Comparative example 8 | Example 9 | Example 10 | Example 11 | Example 12 | Comparative example 9 | |
Oriental fragrance type perfume | 999 | 999 | 999 | 999 | 999 | 999 | 999 |
1, 2- |
0 | 0.00001 | 0.0001 | 0.005 | 0.01 | 0.1 | 0.5 |
Dipropylene glycol | 1 | 0.99999 | 0.9999 | 0.995 | 0.99 | 0.9 | 0.5 |
[ Table 10]
Table 10 oriental fragrance perfume formula
Compounding amount (g) | |
Ethyl maltol | 1 |
Ethyl vanillin | 10 |
Hexyl cinnamic aldehyde | 100 |
Phenylethanolic acid | 200 |
Salicylic acid hexyl ester | 50 |
Iso E Super | 150 |
Ethylene glycol brassylate | 200 |
Pterocarpiol | 50 |
Beta-ionones | 30 |
Rose essential oil | 1 |
Bergamot oil | 50 |
Gamma undecalactones | 5 |
Alpha-damascone | 1 |
Dipropylene glycol | 152 |
Total up to | 1000 |
[ Table 11]
TABLE 11 evaluation results
The evaluation was as follows.
Evaluation of residual fragrance: the numbers in the table indicate the number of evaluators.
Evaluation 1: the residual fragrance was the same as in comparative example 7.
Evaluation 2: the residual fragrance is slightly improved.
Evaluation 3: the residual fragrance is obviously improved.
The content of 1, 2-dihydrokara ketone is preferably 0.00001 to 0.01%, particularly preferably 0.00005 to 0.005%, and more particularly preferably 0.0001 to 0.002%.
Similar evaluation tests were conducted on fruit-type, citrus-type, amber-type, and herbal-type fragrance compositions of fragrance notes other than those described above, and it was confirmed that the incorporation of 1, 2-dihydrokarainone in any of the fragrance note types brings about an effect of improving the residual fragrance of the fragrance composition.
Further, the same evaluation test as that for 1, 2-dihydrokara-6-carbaldehyde was also conducted for 2-isopropylidene-10-methyl-spiro [4,5] -6-decene-6-carbaldehyde, which is classified as an aroma compound having a low contribution degree but a high residual aroma, in test example 1, and it was confirmed that the same residual-property-improving effect was obtained by blending the compound in various types of perfume compositions, and that it was also effective even when 1, 2-dihydrokara-ne and 2-isopropylidene-10-methyl-spiro [4,5] -6-decene-6-carbaldehyde were used in combination.
By using the residual fragrance evaluation technique of the present invention, it is possible to easily screen a fragrance compound having a high residual fragrance and a fragrance tone thereof. Thus, in the absence of group D, which is preferred in the perfume of fig. 2, the fragrance of the perfume can be improved by supplementing the perfume with an aroma compound having a high residual fragrance in the notes of group B instead.
Further, by using aroma compounds having different residual aroma properties, cosmetic fragrances having a changing fragrance tone over time can be developed.
By making the screened residual fragrance and fragrance note into a database, a new fragrance can be developed by selecting a fragrance compound to be used from the viewpoint of residual fragrance.
Example 13 use of 1, 2-Dihydrocardone in perfumes
Fragrance samples were prepared by mixing the floral fragrance produced in example 2 of test example 2 above with ethanol according to the formulation of table 12 below.
The fragrance sample maintained the desired residual fragrance in the state of a perfume maintaining the floral style notes.
[ Table 12]
Perfume formula for table 12 perfume
Compounding amount (g) | |
Fragrance of example 2 | 10 |
Ethanol | 90 |
Total up to | 100 |
Example 14 use of 1, 2-Dihydrocardone in fragrances
A spray type fragrance was prepared by mixing methyl hydroxybenzoate, the floral fragrance prepared in example 2, Polyoxyethylene (POE) hardened castor oil, ethanol, and water in this order according to the formulation in table 13.
The desired residual fragrance is maintained in a state of the fragrance maintaining the fragrance of floral type.
[ Table 13]
Perfume formulation for table 13 fragrance
Compounding amount (g) | |
Hydroxy phenyl methyl ester | 0.1 |
Fragrance of example 2 | 1 |
POE hardened castor oil | 4.5 |
Ethanol | 10 |
Water (W) | Balance of |
Total up to | 100 |
Example 15 use of 1, 2-Dihydrocardone in skin Care products
A toner was prepared by adding PEG-20 sorbitan cocoate and the floral fragrance prepared in example 2, which were uniformly mixed in advance, to a toner base prepared by dissolving 1, 3-butanediol, glycerin, and methyl paraben in ethanol and mixing with water according to the formulation of 14.
The desired residual fragrance is maintained in the state of the lotion maintaining the fragrance tone of floral type.
[ Table 14]
Table 14 fragrance formulations for skin care products
Compounding amount (g) | |
Ethanol | 5.95 |
1, 3-butanediol | 3 |
Glycerol | 2 |
Hydroxy phenyl methyl ester | 0.1 |
Water (W) | Balance of |
PEG-20 sorbitan cocoate | 2 |
Fragrance of example 2 | 0.2 |
Total up to | 100 |
Example 16 use of 1, 2-Dihydrocardone in Hair Care products
According to the formulation shown in Table 15, water-based base materials were weighed in a beaker, uniformly mixed while heating at 85 ℃, then an activator such as Na cocoyl glutamate was added while stirring to uniformly dissolve the base materials, and 1% citric acid water and water were added to uniformly mix the base materials. Finally, a shampoo was prepared by adding the floral fragrance of example 2 to the resulting mixture.
The ideal residual fragrance is maintained in the state of the shampoo with fragrance of flower fragrance.
[ Table 15]
TABLE 15 fragrance formulations for hair care products
Example 17 application of 1, 2-Dihydrocardone in household articles
According to the formulation shown in Table 16, phase A was weighed in a beaker, and after uniformly mixing the phases while heating at 80 ℃, phase B uniformly mixed at 80 ℃ was added and stirred by a homomixer.
Finally, the perfume of example 2 was added to the resulting mixture to prepare a softener.
The desired residual fragrance is maintained in the state of the softener which maintains the fragrance tone of the floral type.
[ Table 16]
TABLE 16 fragrance formulations for household articles
Claims (10)
1. A method for evaluating residual fragrance of a selected fragrance compound contained in a odorous substance, the method comprising the steps of:
step 1. a step of leaving the odorous substance in a space where the temperature and humidity are constant,
a step 2 of extracting the aroma component contained in the odorant after a predetermined time from the start of the standing,
step 3. subjecting the extracted aroma components to gas chromatography-olfactive (GCO) analysis to detect the presence or absence of an odor of each aroma compound constituting the aroma components,
step 4. measuring the longest standing time T for each aroma compound, which is capable of detecting the odor of each aroma compound constituting the aroma substance, and
and a step 5 of using the longest standing time Ta during which the odor of the specific aroma compound a can be detected in the step 4 and the longest standing time Tx during which the odor of the aroma compound X having the longest T among the aroma compounds constituting the odor can be detected, and setting the Ta/Tx value as the residual odor evaluation value of the aroma compound a contained in the odorant.
2. A method for evaluating the aroma characteristics of an aroma compound A based on the degree of aroma contribution of the aroma compound A contained in an odorous substance and the residual aroma evaluation value Ta/Tx of the aroma compound A obtained by the method of claim 1.
3. A residual fragrance imparting agent contains 1, 2-dihydrokara-one and/or 2-isopropylidene-10-methyl-spiro [4,5] -6-decene-6-formaldehyde as effective component.
4. A perfume composition comprising the residual fragrance imparting agent according to claim 3, the perfume composition excluding perfume compositions comprising agilawood essential oil.
5. A fragrance product having improved residual fragrance, which comprises the fragrance composition according to claim 4.
6. The fragrance product of claim 5, wherein the fragrance product is a perfume, a cosmetic product, a skin care product, a hair care product, a personal care product as a toiletry product, a household product, or a quasi-drug product.
7. A method of imparting lingering fragrance to a fragrance product by formulating the fragrance composition of claim 4.
8. The method of imparting lingering fragrance of claim 7, wherein the fragrance product is a perfume, a cosmetic product, a skin care product, a hair care product, a personal care product as a toiletry product, a household product, or a quasi drug.
9. A method for improving the aroma of an odorous substance, which is characterized by comprising the following steps:
step 1: a step of determining a residual aroma evaluation value P, an aroma contribution degree Q and a note of aroma based on the method of claim 1 for each aroma compound constituting the aroma of an odorant,
and a step 2: a step of classifying a compound having 0 < P < 0.5 and 0 < Q < 0.5 as a compound group A, a compound having 0 < P < 0.5 and 0.5. ltoreq. Q.ltoreq.1 as a compound group B, a compound having 0.5. ltoreq. P.ltoreq.1 and 0 < Q < 0.5 as a compound group C, and a compound having 0.5. ltoreq. P.ltoreq.1 and 0.5. ltoreq. Q.ltoreq.1 as a compound group D for each aroma compound,
step 3: a step of replacing the aroma compound B classified into the compound group B with an aroma compound D classified into the compound group D and having a fragrance tone similar to that of the aroma compound B.
10. A method for designing a perfume composition, comprising the steps of:
a step of making a database of the correlation between the residual aroma evaluation value and the note of a large amount of aroma compounds by the method according to claim 9,
and selecting a constituent component from the data when designing a perfume composition whose fragrance changes with time.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020-177031 | 2020-10-22 | ||
JP2020177031 | 2020-10-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN114384162A true CN114384162A (en) | 2022-04-22 |
Family
ID=81195564
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111233042.6A Pending CN114384162A (en) | 2020-10-22 | 2021-10-22 | Method for evaluating residual fragrance property of perfume, residual fragrance imparting agent, and residual fragrance property improving method |
CN202111232395.4A Active CN114384161B (en) | 2020-10-22 | 2021-10-22 | Method for evaluating residual fragrance of perfume, residual fragrance imparting agent, and method for improving residual fragrance |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111232395.4A Active CN114384161B (en) | 2020-10-22 | 2021-10-22 | Method for evaluating residual fragrance of perfume, residual fragrance imparting agent, and method for improving residual fragrance |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP2022068828A (en) |
CN (2) | CN114384162A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7366308B1 (en) | 2023-06-09 | 2023-10-20 | 小川香料株式会社 | fragrance composition |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2927590B2 (en) * | 1991-12-19 | 1999-07-28 | 鐘紡株式会社 | Fragrance composition |
JP2001124749A (en) * | 1999-10-27 | 2001-05-11 | House Foods Corp | Analytical method for aroma preserving property of plastic packaging material for foods |
JP5681751B2 (en) * | 2013-05-27 | 2015-03-11 | 花王株式会社 | Fragrance composition |
CN111272822B (en) * | 2020-03-04 | 2022-11-11 | 浙江理工大学 | Electronic nose technology-based fabric fragrance retention lasting performance quantitative characterization method |
-
2021
- 2021-07-29 JP JP2021124121A patent/JP2022068828A/en active Pending
- 2021-10-22 CN CN202111233042.6A patent/CN114384162A/en active Pending
- 2021-10-22 CN CN202111232395.4A patent/CN114384161B/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2022068828A (en) | 2022-05-10 |
CN114384161B (en) | 2024-01-02 |
CN114384161A (en) | 2022-04-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10828242B2 (en) | Artificial sweat composition | |
JP6821553B2 (en) | Fragrance composition | |
CN114384161B (en) | Method for evaluating residual fragrance of perfume, residual fragrance imparting agent, and method for improving residual fragrance | |
CN106221911A (en) | A kind of perfume compositions and application thereof | |
KR20170093663A (en) | Perfume composition for expressing the fragrance of Freesia hybrida 'Shiny Gold' | |
JP2007137781A (en) | Cosmetic material and use of the same | |
JP2008101129A (en) | Perfume composition and cosmetic formulated with the same | |
Chisvert et al. | Perfumes in Cosmetics: Regulatory Aspects and Analytical Methods | |
KR102567074B1 (en) | Perfume composition for expressing the fragrance of hibiscus syriacus flower | |
KR20240059183A (en) | Perfume composition for expressing the fragrance of cestrum nocturnum flower | |
KR102460455B1 (en) | Perfume composition for expressing the fragrance of Leucocoryne hybrida | |
KR101608883B1 (en) | Perfume Composition having the fragrance of Cymbidium goeringii Reichb | |
Gomes | Engineering perfumes | |
JP6840168B2 (en) | Fragrance composition | |
KR20180023767A (en) | Perfume composition representing the fragrance of Aerides japonicum | |
KR101213071B1 (en) | Perfume composition representing the fragrance of coniferous forests | |
KR20230067869A (en) | Perfume composition for expressing the fragrance of Lantana camara | |
KR102598026B1 (en) | Perfume composition for expressing the fragrance of Tilia cordata honey | |
US7030079B1 (en) | Fragrance composition exhibiting varying olfactive characteristics when applied on different persons | |
KR101881669B1 (en) | Perfume composition representing the fragrance of Lonicera harai Makino | |
KR102512854B1 (en) | Perfume composition for expressing the fragrance of Carthamus tinctorius L. | |
KR20180064146A (en) | Perfume composition representing the fragrance of Lilium hansonii Leichtlin | |
KR20240062600A (en) | Perfume composition for expressing the fragrance of juniperus chinensis in ulleungdo | |
KR101644487B1 (en) | Perfume Composition having the fragrance of Rhododendron schlippenbachii | |
Chisvert et al. | Perfumes in Cosmetics. Analytical Methods |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20220422 |