CN113474324A - α位具有正丁酰氧基的异丁酸酯化合物、香料组合物和作为香料的用途 - Google Patents
α位具有正丁酰氧基的异丁酸酯化合物、香料组合物和作为香料的用途 Download PDFInfo
- Publication number
- CN113474324A CN113474324A CN202080016604.9A CN202080016604A CN113474324A CN 113474324 A CN113474324 A CN 113474324A CN 202080016604 A CN202080016604 A CN 202080016604A CN 113474324 A CN113474324 A CN 113474324A
- Authority
- CN
- China
- Prior art keywords
- fragrance
- formula
- isobutyrate
- compound
- methyl
- 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 description 73
- 239000000203 mixture Substances 0.000 title claims description 38
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 8
- 239000002304 perfume Substances 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- -1 and specifically Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 31
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- 239000000126 substance Substances 0.000 description 23
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 22
- 239000000463 material Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 239000000796 flavoring agent Substances 0.000 description 15
- 235000019634 flavors Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000006210 lotion Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 3
- 238000000451 chemical ionisation Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol 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 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UUQHKWMIDYRWHH-UHFFFAOYSA-N Methyl beta-orcinolcarboxylate Chemical compound COC(=O)C1=C(C)C=C(O)C(C)=C1O UUQHKWMIDYRWHH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 2
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000013361 beverage Nutrition 0.000 description 2
- JSLCOZYBKYHZNL-UHFFFAOYSA-N butylisobutyrate Chemical compound CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000000645 desinfectant Substances 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
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- KYWIYKKSMDLRDC-UHFFFAOYSA-N methyl n-nonyl ketone Natural products CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 2
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- 229930007850 β-damascenone Natural products 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 1
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- QEBNYNLSCGVZOH-NFAWXSAZSA-N (+)-valencene Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CCC=C21 QEBNYNLSCGVZOH-NFAWXSAZSA-N 0.000 description 1
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000001112 (2E)-1,1-diethoxy-3,7-dimethylocta-2,6-diene Substances 0.000 description 1
- 239000001414 (2E)-2-(phenylmethylidene)octanal Substances 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- 239000001890 (2R)-8,8,8a-trimethyl-2-prop-1-en-2-yl-1,2,3,4,6,7-hexahydronaphthalene Substances 0.000 description 1
- VSRVCSJJKWDZSH-UHFFFAOYSA-N (3-pentyloxan-4-yl) acetate Chemical compound CCCCCC1COCCC1OC(C)=O VSRVCSJJKWDZSH-UHFFFAOYSA-N 0.000 description 1
- MTDAKBBUYMYKAR-SNVBAGLBSA-N (3r)-3,7-dimethyloct-6-enenitrile Chemical compound N#CC[C@H](C)CCC=C(C)C MTDAKBBUYMYKAR-SNVBAGLBSA-N 0.000 description 1
- MCFRBNBFXUUFGQ-UHFFFAOYSA-N (4-butylcyclohexyl) acetate Chemical compound CCCCC1CCC(OC(C)=O)CC1 MCFRBNBFXUUFGQ-UHFFFAOYSA-N 0.000 description 1
- MOKHYFNGZLUYRQ-UHFFFAOYSA-N (4-butylcyclohexyl) propanoate Chemical compound CCCCC1CCC(OC(=O)CC)CC1 MOKHYFNGZLUYRQ-UHFFFAOYSA-N 0.000 description 1
- KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 description 1
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- KRLBLPBPZSSIGH-CSKARUKUSA-N (6e)-3,7-dimethylnona-1,6-dien-3-ol Chemical compound CC\C(C)=C\CCC(C)(O)C=C KRLBLPBPZSSIGH-CSKARUKUSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- KHQDWCKZXLWDNM-KPKJPENVSA-N (e)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound CC\C(CO)=C/CC1CC=C(C)C1(C)C KHQDWCKZXLWDNM-KPKJPENVSA-N 0.000 description 1
- MTVBNJVZZAQKRV-BJMVGYQFSA-N (e)-2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound OCC(/C)=C/CC1CC=C(C)C1(C)C MTVBNJVZZAQKRV-BJMVGYQFSA-N 0.000 description 1
- YYMCVDNIIFNDJK-XFQWXJFMSA-N (z)-1-(3-fluorophenyl)-n-[(z)-(3-fluorophenyl)methylideneamino]methanimine Chemical compound FC1=CC=CC(\C=N/N=C\C=2C=C(F)C=CC=2)=C1 YYMCVDNIIFNDJK-XFQWXJFMSA-N 0.000 description 1
- JRJBVWJSTHECJK-LUAWRHEFSA-N (z)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one Chemical compound CC(=O)C(\C)=C/C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-LUAWRHEFSA-N 0.000 description 1
- NTXGFKWLJFHGGJ-ACCUITESSA-N 1,1-Diethoxy-3,7-dimethyl-2,6-octadiene Chemical compound CCOC(OCC)\C=C(/C)CCC=C(C)C NTXGFKWLJFHGGJ-ACCUITESSA-N 0.000 description 1
- 239000001709 1,2-dimethylcyclohex-3-ene-1-carbaldehyde Substances 0.000 description 1
- FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 description 1
- WVIVQXUVAISQSW-UHFFFAOYSA-N 1-(2-phenylpropan-2-yloxy)ethane-1,1-diol Chemical compound CC(C)(C1=CC=CC=C1)OC(C)(O)O WVIVQXUVAISQSW-UHFFFAOYSA-N 0.000 description 1
- GQBVHGLNSHPKPG-UHFFFAOYSA-N 1-(2-tert-butylcyclohexyl)oxybutan-2-ol Chemical compound CCC(O)COC1CCCCC1C(C)(C)C GQBVHGLNSHPKPG-UHFFFAOYSA-N 0.000 description 1
- FVUGZKDGWGKCFE-ZBEGNZNMSA-N 1-[(2s,3s)-2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone Chemical compound CC1(C)CCCC2=C1C[C@@](C(C)=O)(C)[C@@H](C)C2 FVUGZKDGWGKCFE-ZBEGNZNMSA-N 0.000 description 1
- IGQOPTNWGSJHCD-UHFFFAOYSA-N 12-pentyl-oxacyclododecan-2-one Chemical compound CCCCCC1CCCCCCCCCC(=O)O1 IGQOPTNWGSJHCD-UHFFFAOYSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- VVUMWAHNKOLVSN-UHFFFAOYSA-N 2-(4-ethoxyanilino)-n-propylpropanamide Chemical compound CCCNC(=O)C(C)NC1=CC=C(OCC)C=C1 VVUMWAHNKOLVSN-UHFFFAOYSA-N 0.000 description 1
- AWNOGHRWORTNEI-UHFFFAOYSA-N 2-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethyl acetate Chemical compound CC(=O)OCCC1=CCC2C(C)(C)C1C2 AWNOGHRWORTNEI-UHFFFAOYSA-N 0.000 description 1
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
- UAQFADWTDBIBBZ-UHFFFAOYSA-N 2-[2-(2-naphthalen-2-ylethoxy)ethyl]naphthalene Chemical compound C1=CC=CC2=CC(CCOCCC=3C=C4C=CC=CC4=CC=3)=CC=C21 UAQFADWTDBIBBZ-UHFFFAOYSA-N 0.000 description 1
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 1
- UQURIQWAEZGLAC-UHFFFAOYSA-N 2-cyclohexylpropanal Chemical compound O=CC(C)C1CCCCC1 UQURIQWAEZGLAC-UHFFFAOYSA-N 0.000 description 1
- DVCHJFSLGUNEQZ-UHFFFAOYSA-M 2-ethenyl-2,6-dimethylhept-5-enoate Chemical compound CC(C)=CCCC(C)(C=C)C([O-])=O DVCHJFSLGUNEQZ-UHFFFAOYSA-M 0.000 description 1
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 1
- VYAGGOIWGCHHJR-UHFFFAOYSA-N 2-methylbuta-1,3-diene 2-methylpropanoic acid Chemical compound C=CC(C)=C.C(C(C)C)(=O)O VYAGGOIWGCHHJR-UHFFFAOYSA-N 0.000 description 1
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 1
- VNWOJVJCRAHBJJ-UHFFFAOYSA-N 2-pentylcyclopentan-1-one Chemical compound CCCCCC1CCCC1=O VNWOJVJCRAHBJJ-UHFFFAOYSA-N 0.000 description 1
- IYYUJCKJSSPXQQ-UHFFFAOYSA-N 2-pyridin-4-yl-1,3-thiazolidin-3-ium-4-carboxylate Chemical compound N1C(C(=O)O)CSC1C1=CC=NC=C1 IYYUJCKJSSPXQQ-UHFFFAOYSA-N 0.000 description 1
- BJLRAKFWOUAROE-UHFFFAOYSA-N 2500-83-6 Chemical compound C12C=CCC2C2CC(OC(=O)C)C1C2 BJLRAKFWOUAROE-UHFFFAOYSA-N 0.000 description 1
- FRUPGGSBENIUTJ-UHFFFAOYSA-N 3,5,6,6-tetramethyl-4-methylideneheptan-2-one Chemical compound CC(=O)C(C)C(=C)C(C)C(C)(C)C FRUPGGSBENIUTJ-UHFFFAOYSA-N 0.000 description 1
- OGHBUHJLMHQMHS-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 2-methylbut-2-enoate Chemical compound CC=C(C)C(=O)OCC=C(C)CCC=C(C)C OGHBUHJLMHQMHS-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- BWVZAZPLUTUBKD-UHFFFAOYSA-N 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol Chemical compound CC1(C)C(C)C2CC1CC2C1CCCC(O)C1 BWVZAZPLUTUBKD-UHFFFAOYSA-N 0.000 description 1
- GTNCESCYZPMXCJ-UHFFFAOYSA-N 3-Phenylpropyl propanoate Chemical compound CCC(=O)OCCCC1=CC=CC=C1 GTNCESCYZPMXCJ-UHFFFAOYSA-N 0.000 description 1
- VPXWZHXOBQZDNM-UHFFFAOYSA-N 4,4-dimethylcyclohex-2-ene-1-carbaldehyde Chemical compound CC1(CCC(C=O)C=C1)C VPXWZHXOBQZDNM-UHFFFAOYSA-N 0.000 description 1
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 1
- DKRZBJWBTFUHRG-UHFFFAOYSA-N 4-hexyl-2-hydroxybenzoic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)C(O)=C1 DKRZBJWBTFUHRG-UHFFFAOYSA-N 0.000 description 1
- YVSNOTITPICPTB-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)oxan-4-ol Chemical compound CC(C)CC1CC(C)(O)CCO1 YVSNOTITPICPTB-UHFFFAOYSA-N 0.000 description 1
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 1
- CCOQPGVQAWPUPE-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC(O)CC1 CCOQPGVQAWPUPE-UHFFFAOYSA-N 0.000 description 1
- 229940091886 4-tert-butylcyclohexanol Drugs 0.000 description 1
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 1
- ZJVRYPHKSDHLTC-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloctan-2-ol Chemical compound COC(C)(C)CCCC(C)C(C)O ZJVRYPHKSDHLTC-UHFFFAOYSA-N 0.000 description 1
- 240000004507 Abelmoschus esculentus Species 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- VHOMAPWVLKRQAZ-UHFFFAOYSA-N Benzyl propionate Chemical compound CCC(=O)OCC1=CC=CC=C1 VHOMAPWVLKRQAZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- YFDUWSBGVPBWKF-UHFFFAOYSA-N Butyl salicylate Chemical compound CCCCOC(=O)C1=CC=CC=C1O YFDUWSBGVPBWKF-UHFFFAOYSA-N 0.000 description 1
- ALSCSLPRMRDNQF-UHFFFAOYSA-N CCCC(O)(O)OC(C)(C)C1=CC=CC=C1 Chemical compound CCCC(O)(O)OC(C)(C)C1=CC=CC=C1 ALSCSLPRMRDNQF-UHFFFAOYSA-N 0.000 description 1
- JYHGOMYCFLUYEA-UHFFFAOYSA-N CCCCC(OC(=O)CCC)c1ccccc1 Chemical compound CCCCC(OC(=O)CCC)c1ccccc1 JYHGOMYCFLUYEA-UHFFFAOYSA-N 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 240000003538 Chamaemelum nobile Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- ZKVZSBSZTMPBQR-UHFFFAOYSA-N Civetone Natural products O=C1CCCCCCCC=CCCCCCCC1 ZKVZSBSZTMPBQR-UHFFFAOYSA-N 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 240000002943 Elettaria cardamomum Species 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 1
- WVRPFQGZHKZCEB-UHFFFAOYSA-N Isopropyl 2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)C WVRPFQGZHKZCEB-UHFFFAOYSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 244000165082 Lavanda vera Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 241000234269 Liliales Species 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- JBVVONYMRFACPQ-UHFFFAOYSA-N Linalylformate Natural products CC(=C)CCCC(C)(OC=O)C=C JBVVONYMRFACPQ-UHFFFAOYSA-N 0.000 description 1
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 description 1
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000078639 Mentha spicata Species 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
- KVWWIYGFBYDJQC-GHMZBOCLSA-N Methyl dihydrojasmonate Chemical compound CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-GHMZBOCLSA-N 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- ALHUZKCOMYUFRB-OAHLLOKOSA-N Muscone Chemical compound C[C@@H]1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-OAHLLOKOSA-N 0.000 description 1
- 244000270834 Myristica fragrans Species 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 240000009023 Myrrhis odorata Species 0.000 description 1
- 235000007265 Myrrhis odorata Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- 235000012550 Pimpinella anisum Nutrition 0.000 description 1
- 240000002505 Pogostemon cablin Species 0.000 description 1
- 235000011751 Pogostemon cablin Nutrition 0.000 description 1
- POPNTVRHTZDEBW-UHFFFAOYSA-N Propionsaeure-citronellylester Natural products CCC(=O)OCCC(C)CCC=C(C)C POPNTVRHTZDEBW-UHFFFAOYSA-N 0.000 description 1
- AZFUASHXSOTBNU-UHFFFAOYSA-N Propyl 2-methylpropanoate Chemical compound CCCOC(=O)C(C)C AZFUASHXSOTBNU-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 244000284012 Vetiveria zizanioides Species 0.000 description 1
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 description 1
- FMFHUEMLVAIBFI-BQYQJAHWSA-N [(e)-2-phenylethenyl] acetate Chemical compound CC(=O)O\C=C\C1=CC=CC=C1 FMFHUEMLVAIBFI-BQYQJAHWSA-N 0.000 description 1
- JNWQKXUWZWKUAY-XYLIHAQWSA-N [(e)-hex-3-enyl] (e)-2-methylbut-2-enoate Chemical compound CC\C=C\CCOC(=O)C(\C)=C\C JNWQKXUWZWKUAY-XYLIHAQWSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- UKKUVAOJBOSXOX-UHFFFAOYSA-N acetic acid 3-phenylprop-2-enal Chemical compound CC(O)=O.O=CC=CC1=CC=CC=C1 UKKUVAOJBOSXOX-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229940072717 alpha-hexylcinnamaldehyde Drugs 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-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
- 229940011037 anethole Drugs 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- 229940115397 bornyl acetate Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000005300 cardamomo Nutrition 0.000 description 1
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 description 1
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 description 1
- 229940026455 cedrol Drugs 0.000 description 1
- PCROEXHGMUJCDB-UHFFFAOYSA-N cedrol Natural products CC1CCC2C(C)(C)C3CC(C)(O)CC12C3 PCROEXHGMUJCDB-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 239000010632 citronella oil Substances 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- ZKVZSBSZTMPBQR-UPHRSURJSA-N civetone Chemical compound O=C1CCCCCCC\C=C/CCCCCCC1 ZKVZSBSZTMPBQR-UPHRSURJSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940019836 cyclamen aldehyde Drugs 0.000 description 1
- BLBJUGKATXCWET-UHFFFAOYSA-N cyclaprop Chemical compound C12CC=CC2C2CC(OC(=O)CC)C1C2 BLBJUGKATXCWET-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- LXJDKGYSHYYKFJ-UHFFFAOYSA-N cyclohexadecanone Chemical compound O=C1CCCCCCCCCCCCCCC1 LXJDKGYSHYYKFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PZUDDXJZNSJESK-UHFFFAOYSA-N ethyl 2-cyclohexylpropanoate Chemical compound CCOC(=O)C(C)C1CCCCC1 PZUDDXJZNSJESK-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940093468 ethylene brassylate Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- FQMZVFJYMPNUCT-UHFFFAOYSA-N geraniol formate Natural products CC(C)=CCCC(C)=CCOC=O FQMZVFJYMPNUCT-UHFFFAOYSA-N 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- GOKKOFHHJFGZHW-UHFFFAOYSA-N hexyl propanoate Chemical compound CCCCCCOC(=O)CC GOKKOFHHJFGZHW-UHFFFAOYSA-N 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940024423 isopropyl isobutyrate Drugs 0.000 description 1
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229930007503 menthone Natural products 0.000 description 1
- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- ALHUZKCOMYUFRB-UHFFFAOYSA-N muskone Natural products CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 1
- FALTVGCCGMDSNZ-UHFFFAOYSA-N n-(1-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C1=CC=CC=C1 FALTVGCCGMDSNZ-UHFFFAOYSA-N 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UTNKPINVMZDAHQ-UHFFFAOYSA-N propan-2-yl 2-hydroxy-2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)(C)O UTNKPINVMZDAHQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RGFNRWTWDWVHDD-UHFFFAOYSA-N sec-butyl ester of butyric acid Natural products CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- YUVKTUCPWGPBLJ-UHFFFAOYSA-N tert-butyl 2-cyclohexylacetate Chemical compound CC(C)(C)OC(=O)CC1CCCCC1 YUVKTUCPWGPBLJ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 229940117960 vanillin Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
式(1)表示的化合物。式(1)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。
Description
技术领域
本发明涉及α位具有正丁酰氧基的异丁酸酯化合物、香料组合物以及作为香料的用途。
背景技术
已知异丁酸酯中存在作为香料有用的化合物。例如，非专利文献1中记载了各种异丁酸酯主要用作调味剂，具体而言异丁酸甲酯为甜杏样的香味、异丁酸丙酯为浓郁的菠萝样的香味、异丁酸丁酯为新鲜的苹果和香蕉样的香味、异丁酸异戊酯为甜杏和菠萝样的香味等，都是果香味的调味剂物质(Flavor material)。
另外，专利文献1中公开了作为α位具有与氧成键的异丁酸酯，α－烷氧基异丁酸的直链或支链的碳原子数4～12的烷基酯作为香料有用，记载了α－乙氧基异丁酸正己基酯具有薰衣草般的香气。
现有技术文献
专利文献
专利文献1:美国专利第3368943号说明书
非专利文献
非专利文献1:“合成香料化学和商品知识增补新版”，化学工业日报社，2016年，580～582页
发明内容
本发明要解决的课题在于提供作为香料和调合香料材料有用的α位具有正丁酰氧基的异丁酸酯化合物。本发明要解决的课题还在于提供含有上述化合物作为有效成分的香料组合物以及该化合物作为香料的用途。
本发明人等合成了各种化合物，对其香气进行深入研究，发现α位具有正丁酰氧基的异丁酸的特定酯化合物作为香料和调合香料材料有用。
即，本发明如下。
＜1＞式(1)表示的化合物。
(式(1)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。)
＜2＞根据＜1＞所述的化合物，其中，式(1)中，R选自甲基、乙基、正丙基、异丙基、正丁基以及异丁基。
＜3＞根据＜1＞或＜2＞所述的化合物，其中，式(1)中，R为甲基。
＜4＞根据＜1＞或＜2＞所述的化合物，其中，式(1)中，R为乙基。
＜5＞根据＜1＞或＜2＞所述的化合物，其中，式(1)中，R为正丙基。
＜6＞根据＜1＞或＜2＞所述的化合物，其中，式(1)中，R为异丙基。
＜7＞根据＜1＞或＜2＞所述的化合物，其中，式(1)中，R为正丁基。
＜8＞根据＜1＞或＜2＞所述的化合物，其中，式(1)中，R为异丁基。
＜9＞一种香料组合物，含有＜1＞～＜8＞中任一项所述的化合物作为有效成分。
＜10＞＜1＞～＜8＞中任一项所述的化合物作为香料的用途。
＜11＞根据＜10＞所述的用途，其中，＜3＞、＜4＞和＜6＞中任一项所述的化合物赋予大马士革样的果香调、花香调或木香调的香调。
根据本发明，能够提供作为香料和调合香料材料有用的α位具有正丁酰氧基的异丁酸酯化合物。此外根据本发明，能够提供含有上述化合物作为有效成分的香料组合物和该化合物作为香料的用途。
具体实施方式
[式(1)表示的化合物]
本发明的化合物由下述式(1)表示。以下，也将下述式(1)表示的化合物称为“本发明的异丁酸酯”或者“本发明的化合物”。
这里，式(1)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。
作为R的例子，具体而言可举出甲基、乙基、正丙基、异丙基、正丁基、异丁基(2－甲基丙基)、仲丁基(1－甲基丙基)、叔丁基、环丙基、环丁基等。
R具有不对称碳的情况下，本发明的化合物可以仅具有由其产生的光学异构体中的任一个，另外，也可以是以任意的比例含有多个光学异构体的混合物。
式(1)表示的化合物是新型化合物。
式(1)表示的本发明的异丁酸酯作为香料和调合香料材料有用，表现出花香调、绿调和果香调的香气。
特别优选R为甲基。
特别优选R为乙基。
特别优选R为正丙基。
特别优选R为异丙基。
特别优选R为正丁基。
特别优选R为异丁基。
本发明中，作为式(1)表示的化合物，例示以下的式(1－1)～(1－10)中任一个表示的化合物，特别优选的化合物是以下的式(1－1)～(1－6)中任一个表示的化合物。
近年来，存在极其重视化学物质的毒性、对环境的影响的趋势，这对于香料、香料组合物也不例外。由于对人体的敏感性、环境中的积蓄性等理由，以往一直使用的香料的使用条件受到严格限制，禁止使用的案件有增加的趋势。因此，现如今的状况是比以往任何时候都强烈要求环境负荷少的香料和香料组合物。因此，作为调合香料材料也优选生物降解性优异。
本发明的化合物含有生物降解性优异的化合物，从生物降解性的观点出发，R优选为选自甲基、乙基、正丙基、异丙基、正丁基和异丁基中的基团。
本发明的异丁酸酯其本身如后所述具有优异的香气，因此作为香料有用。另外，香料一般很少以单品使用，大多作为根据目的配合多个香料的调合香料(香料组合物)使用。本发明的异丁酸酯作为配合于调合香料(香料组合物)中的香料(也称为“调合香料材料”)有用。作为香料，上述式(1)表示的化合物可以单独使用1种，也可以并用2种以上。
另外，本发明的化合物在不损害本发明的效果的范围内，不排除含有少量的杂质、副产物、夹杂物等。
式(1)表示的本发明的异丁酸酯具有花香调、绿调、果香调等的香气，并且扩散性也优异。另外，由式(1－1)、式(1－2)、(1－4)任一者表示的本发明的异丁酸酯具有大马士革样的果香调、花香调、或者木香调的香气，并且扩散性也优异。
可以将本发明的异丁酸酯单独作为香料在各种化妆品类、以健康卫生材料为首的医药品、日用杂货品、食品等中添加使用而赋予香气，另外，也可以将本发明的异丁酸酯与其他调合香料材料等混合，制备后述的香料组合物(调合香料)，将其配合于各种的制品中赋予香气。其中，从得到目标的香气的观点出发，优选将本发明的化合物作为调合香料材料配合于香料组合物，将该香料组合物配合于制品而赋香。
[香料组合物]
本发明的香料组合物(调合香料)含有本发明的异丁酸酯作为有效成分。应予说明，只要含有至少1种以上的本发明的异丁酸酯就没有特别限定，可以含有2种以上的本发明的异丁酸酯。
本发明的香料组合物含有本发明的异丁酸酯作为有效成分即可，其他成分没有特别限定，优选进一步含有其他调合香料材料(以下，也称为“以往香料”)。
应予说明，“香料组合物(调合香料)”是将该香料组合物添加到各种化妆品类、医药品、食品、饮料等中而赋予香气的组合物，或者作为其本身用于香水等的组合物，除了以往香料以外根据需要还可以含有溶剂等添加剂。
本发明的异丁酸酯的配合量根据本发明的异丁酸酯的种类、目标香气的种类和香气的强度等而不同，但作为式(1)表示的本发明的异丁酸酯的量，在香料组合物中优选为0.001质量％以上，更优选为0.01质量％以上，进一步优选为0.1质量％以上，优选为90质量％以下，更优选为70质量％以下，进一步优选为50质量％以下。
以往香料只要是以往公知的香料成分就没有特别限制，可以使用范围广泛的香料，例如可以单独使用或者以任意的混合比率选择使用2种以上的下述中的物质。
例如，柠檬烯、α-蒎烯、β-蒎烯、萜品烯、雪松烯、长叶烯、瓦伦烯等烃类；芳樟醇、香茅醇、香叶醇、橙花醇、萜品醇、二氢月桂烯醇、乙基芳樟醇、法呢醇、橙花叔醇、顺式－3－己烯醇、雪松醇、薄荷醇、冰片、β－苯乙醇、苯甲醇、苯己醇、2,2,6－三甲基环己基－3－己醇、1－(2－叔丁基环己氧基)－2－丁醇、4－异丙基环己烷甲醇、4－叔丁基环己醇、4－甲基－2－(2－甲基丙基)四氢－2H－吡喃－4－醇、2－甲基－4－(2,2,3－三甲基－3－环戊烯－1－基)－2－丁烯－1－醇、2－乙基－4－(2,2,3－三甲基－3－环戊烯－1－基)－2－丁烯－1－醇、异莰基环己醇、3,7－二甲基－7－甲氧基辛烷－2－醇等醇类；丁香酚、百里酚、香草醛等酚类；甲酸芳樟酯、甲酸香茅酯、甲酸香叶酯、乙酸正己酯、顺式－3－己烯乙酸酯、乙酸芳樟酯、乙酸香茅酯、乙酸香叶酯、乙酸橙花酯、乙酸萜品酯、乙酸诺卜酯、乙酸龙脑酯、乙酸异冰片酯、乙酸邻叔丁基环己酯、乙酸对叔丁基环己酯、乙酸三环癸烯酯、乙酸苄酯、乙酸苯乙烯酯、乙酸肉桂醛、乙酸二甲基苄基原酯、3－戊基四氢吡喃－4－基乙酸酯、丙酸香茅酯、丙酸三环癸烯酯、环己基丙酸烯丙酯、2－环己基丙酸乙酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基原酯、异丁酸三环癸烯酯、2－壬酸甲酯、苯甲酸甲酯、苯甲酸苄酯、肉桂酸甲酯、水杨酸甲酯、水杨酸正己基酯、水杨酸顺式－3－己烯酯、惕各酸香叶酯、惕各酸顺－3－己烯酯、茉莉酮酸甲酯、二氢茉莉酮酸甲酯、2,4－二羟基－3,6－二甲基苯甲酸甲酯、甲基苯基代去水甘油酸乙酯、邻氨基苯甲酸甲酯、FRUITATE(三环癸烷羧酸乙酯)等酯类；正辛醛、正癸醛、正十二醛、2－甲基十一醛、10－十一醛、香茅醛、柠檬醛、羟基香茅醛、二甲基四氢苯甲醛、4(3)－(4－羟基－4－甲基戊基)－3－环己烯－1－甲醛、2－环己基丙醛、对叔丁基－α－甲基氢化肉桂醛、对异丙基－α－甲基氢化肉桂醛、对乙基－α,α－二甲基氢化肉桂醛、α－戊基肉桂醛、α－己基肉桂醛、胡椒醛、α－甲基－3,4－亚甲二氧基氢化肉桂醛等醛类；甲基庚烯酮、4－亚甲基－3,5,6,6－四甲基－2－庚酮、戊基环戊酮、3－甲基－2－(顺式－2－戊烯－1－基)－2－环戊烯－1－酮、甲基环戊烯醇酮、玫瑰酮、γ－甲基紫罗兰酮、α－紫罗兰酮、香芹酮、薄荷酮、樟脑、诺卡酮、苄基丙酮、茴香基丙酮、甲基β－萘酮、2,5－二甲基－4－羟基－3(2H)－呋喃酮、麦芽酚、7－乙酰基－1,2,3,4,5,6,7,8－八氢－1,1,6,7－四甲基萘、麝香酮、灵猫酮、环十五酮、环十六烯酮等酮类；乙醛乙基苯基丙基乙缩醛、柠檬醛二乙缩醛、苯乙醛甘油缩醛、乙酰乙酸乙酯乙二醇缩酮类的缩醛类和缩酮类；茴香脑、β－萘基甲基醚、β－萘基乙基醚、柠檬烯氧化物、玫瑰氧化物、1,8－桉树脑、外消旋体或者光学活性的十二氢－3a,6,6,9a－四甲基萘[2,1－b]呋喃等醚类；香茅腈等腈类；γ－壬内酯、γ－十一内酯、σ－癸内酯、γ－茉莉内酯、香豆素、环十五内酯、环十六内酯、麝子内酯、巴西酸亚乙酯、11－十六烷内酯等内酯类；橙子、柠檬、佛手柑、柑橘、薄荷、留兰香、薰衣草、洋甘菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、天竺葵、茉莉、依兰依兰、八角、丁香、姜、肉豆蔻、豆蔻、雪松、柏树、檀香、香根草、广藿香、劳丹脂等的天然精油、天然提取物；合成香料等其他香料物质等。
另外，香料组合物还可以含有聚氧乙烯十二烷基硫酸酯醚等表面活性剂；二丙二醇、邻苯二甲酸二乙酯、乙二醇、丙二醇、肉豆蔻酸甲酯、柠檬酸三乙酯等溶剂；抗氧化剂；着色剂等作为调合香料材料以外的构成成分。
式(1)表示的本发明的异丁酸酯因为具有花香调、绿调、果香调等的香气，所以可以与以往香料组合而赋予自然的花香调、绿调、果香调，因此添加到各种化妆品类、以保健卫生材料为代表的医药品、日用杂货品、食品等中赋予香气是有用的。另外，由式(1－1)、(1－2)、(1－4)中任一个表示的本发明的异丁酸酯因为具有大马士革样的果香调、花香调或者木香调的香气，所以与以往香料进行组合等而赋予香气是有用的。
作为为了赋予香气和对配合对象物的香气进行改进而能够添加含有式(1)表示的本发明的异丁酸酯的香料组合物的物质，可以举出化妆品类、健康卫生材料、杂货、饮料、食品、准医药品、医药品等各种制品，例如可以作为香水、古龙水类等香味产品；洗发水、染发剂类、生发油、发乳类、摩斯、啫喱、发蜡、喷雾其他头发用化妆品；爽肤水、精华液、面霜、乳液、面膜、粉底、蜜粉、口红、各种化妆品类等皮肤用化妆品；洗碗洗剂、洗衣用洗剂、柔软剂类、消毒用洗剂类、除臭洗剂类、室内芳香剂、家具护理、玻璃清洁剂、家具清洁剂、地板清洁剂、消毒剂、杀虫剂、漂白剂、杀菌剂、驱虫剂、其他各种健康卫生用洗剂类；牙膏、漱口水、浴盐、止汗产品、烫发液等的准医药品；卫生纸、纸巾等杂货；医药品等；食品等的香气成分使用。
上述制品中的香料组合物的配合量没有特别限定，香料组合物的配合量可以根据要赋香的制品的种类、性质和感受效果等在很宽的范围选择。例如，0.00001质量％以上，优选0.0001质量％以上，更优选0.001质量％以上，例如香水等香味产品的情况下可以为100质量％，优选为80质量％以下，更优选为60质量％以下，进一步优选为40质量％以下。
[本发明的异丁酸酯的制造方法]
式(1)表示的本发明的异丁酸酯的制造方法没有特别限制，可以从以往公知的方法中适当地选择使用。
例如，可举出通过在催化剂的存在下或者不存在下使α－羟基异丁酸酯与酰化剂反应而将α位的羟基酰化的方法。作为使用的酰化剂，可举出像丁酸那样的羧酸、像丁酸酐那样的羧酸酐、像丁酰氯、丁酰溴那样的羧酸卤化物、像乙烯酮那样的烯酮化合物等。另外，也可以将从其中选择的2个以上的酰化剂以任意的比率组合使用。
将使用羧酸、羧酸酐、羧酸卤化物时的反应式示于下述式(2)。
式(2)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。Y因酰化剂的种类而不同，例如表示羟基、正丁酰氧基、氯、溴、碘等。
将使用烯酮化合物时的反应式示于下述式(3)。
式(3)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。
另外，在催化剂的存在下使其他种类的α－正丁酰氧基异丁酸酯与醇进行酯交换反应，能够制造目标α－正丁酰氧基异丁酸酯。将该反应的反应式示于下述式(4)。
式(4)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。R’只要与R为不同的烷基就没有特别限制。
同样地在催化剂的存在下使α－正丁酰氧基异丁酸与醇进行酯化反应，能够制造目标α－正丁酰氧基异丁酸酯。将该反应的反应式示于下述式(5)。
式(5)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。
这些反应中使用的催化剂、反应方式、反应条件以及反应装置等均可以使用以往公知的催化剂、反应方法、反应条件以及反应装置，没有特别限制。另外，对得到的式(1)的化合物进行精制的方法也可以采用以往公知的精制方法，没有任何限制。
实施例
以下基于实施例对本发明进行更详细的说明，但本发明不受这些实施例限定。
反应成绩的评价按下述公式进行评价。
反应收率(％)＝[(反应液中的生成酯的摩尔数)/(进料液中的原料酯的摩尔数)]×100％
＜气相色谱分析(GC分析)＞
装置：GC－2010(株式会社岛津制作所制，制品名)
检测器：FID
色谱柱：DB－1(J&W制毛细管柱，制品名)(0.25mmφ×60m×0.25μm)
＜NMR谱分析＞
酯的鉴定通过1H－NMR测定和13C－NMR测定进行。测定条件如下所示。
装置：ECA500(日本电子株式会社制，制品名)
〔1H－NMR〕
核素：1H
测定频率：500MHz
测定试样：5％CDCl3溶液
〔13C－NMR〕
核素：13C
测定频率：125MHz
测定试样：5％CDCl3溶液
＜气相色谱－质谱联用(GC－MS分析)＞
化合物的鉴定也可以通过GC－MS测定(化学电离法[CI+]，高分辨率质谱法[millimas])确定出分子量来进行。测定条件如下述所示。
GC装置：Agilent 7890A(安捷伦公司制，商品名)
GC测定条件
色谱柱：DB－1(J&W制毛细管柱，制品名)(0.25mmφ×30m×0.25μm)
MS装置：JMS－T100GCV(日本电子株式会社制，制品名)
MS测定条件化学电离法
检测器条件：200eV，300μA
反应气：异丁烷
记录通过化学电离法以质子化的状态检测到的碎片的精确分子量值和由其归属的化学组成式。
＜通过色谱法分离产物＞
利用色谱法分离产物使用下述的材料。
填充剂：Wako Gel C－200(和光纯药工业株式会社制，商品名)
展开剂：乙酸乙酯－己烷
＜实施例1：α－正丁酰氧基异丁酸甲酯的合成＞
向具备冷却管、搅拌装置的200ml玻璃制圆底烧瓶中填充α－羟基异丁酸甲酯(三菱瓦斯化学株式会社制)20.0g、丁酸酐(和光纯药工业株式会社制)29.4g、吡啶(和光纯药工业株式会社制)13.6g、4－二甲基氨基吡啶(和光纯药工业株式会社制)2.1g，在室温～40℃进行24小时搅拌，使其反应。通过反应液的GC分析确认了α－羟基异丁酸甲酯因与丁酸酐的反应而被完全消耗，通过下述式(7)的反应以反应收率93％得到了α－正丁酰氧基异丁酸甲酯。其后，用10％碳酸氢钠水溶液进行3次清洗操作，用饱和氯化钠水溶液进行2次清洗操作，用硫酸镁干燥。其后通过柱色谱得到α－正丁酰氧基异丁酸甲酯21.2g(GC分析纯度(以下，也称为GC纯度)：＞99.9％)。产物的NMR谱分析和GC－MS分析的结果如下所示。
〔α－正丁酰氧基异丁酸甲酯〕
1H NMR(500MHz,CDCl3)δ0.96(3H,t,J＝7.5Hz),1.55(6H,s),1.65(2H,sext,J＝7.5Hz),2.29(2H,t,J＝7.5Hz),3.72(3H,s)
13C NMR(125MHz,CDCl3)δ13.46,18.34,24.59,36.14,52.27,77.83,172.65,173.19
精确分子量189.11383(C9H16O4,母峰)，157.08676(C8H12O3)
＜参考例1：α－羟基异丁酸乙酯的合成＞
在具备蒸馏管的300ml玻璃制烧瓶中填充α－羟基异丁酸甲酯(三菱瓦斯化学株式会社制)56.7g、乙醇(和光纯药工业株式会社制)33.2g、四乙氧基钛(和光纯药工业株式会社制)0.92g。常压下边加热回流边进行酯交换反应，边将生成的甲醇抽出到体系外边进行96小时反应。其结果，以反应收率97％得到α－羟基异丁酸乙酯。向反应体系中加水使催化剂失活后进行减压蒸馏，作为71mmHg、77℃的馏分得到α－羟基异丁酸乙酯46.9g(GC纯度：99.6％)。
＜参考例2～5：各种α－羟基异丁酸酯的合成＞
使用与参考例1相同的反应装置，使适量的α－羟基异丁酸甲酯(三菱瓦斯化学株式会社制)与各种醇(正丙醇、异丙醇、正丁醇、异丁醇)在四烷氧基钛和/或者醇钠这样的适当的催化剂的存在下，根据情况在己烷、甲苯这样的溶剂共存下，边加热边在适当的反应条件下进行酯交换反应。将由反应生成的甲醇在反应条件下通过蒸馏或者与反应溶剂的共沸向体系外抽出，完成酯交换反应，进行与参考例1相同的分离操作，分别得到以下的α－羟基异丁酸酯。一并标注得到的异丁酸酯的GC纯度。
α－羟基异丁酸正丙酯(GC纯度：99.8％)
α－羟基异丁酸异丙酯(GC纯度：99.6％)
α－羟基异丁酸正丁酯(GC纯度：99.9％)
α－羟基异丁酸异丁酯(GC纯度：99.6％)
＜实施例2：α－正丁酰氧基异丁酸乙酯的合成＞
使用与实施例1相同的反应装置，使用适量的参考例1中制备的α－羟基异丁酸乙酯、丁酸酐(和光纯药工业株式会社制)、吡啶(和光纯药工业株式会社制)、4－二甲基氨基吡啶(和光纯药工业株式会社制)进行反应。与实施例1同样地操作，得到α－正丁酰氧基异丁酸乙酯(GC纯度：99.83％)。产物的NMR谱分析和GC－MS分析的结果如下所示。
〔α－正丁酰氧基异丁酸乙酯〕
1H NMR(500MHz,CDCl3)δ0.96(3H,t,J＝7.5Hz),1.25(3H,t,J＝7.0Hz),1.54(6H,s),1.65(2H,sext,J＝7.5Hz),2.29(2H,t,J＝7.5Hz),4.18(2H,q,J＝7.0Hz)
13C NMR(125MHz,CDCl3)δ13.51,13.99,18.37,24.56,36.17,61.15,77.90,172.56,172.67
精确分子量203.13157(C10H18O4,母峰)，157.08746(C8H12O3)
＜实施例3～6：α－正丁酰氧基异丁酸酯的合成＞
使用与实施例2相同的反应装置，使用适量的参考例2～5中制备的α－羟基异丁酸酯、丁酸酐(和光纯药工业株式会社制)、吡啶(和光纯药工业株式会社制)、4－二甲基氨基吡啶(和光纯药工业株式会社制)进行反应。与实施例1同样地操作，通过柱色谱法分别得到下述的α－正丁酰氧基异丁酸酯类。一并标注得到的酯的GC纯度、NMR谱分析以及GC－MS分析的结果。
〔实施例3：α－正丁酰氧基异丁酸正丙酯〕
GC纯度：99.81％
1H NMR(500MHz,CDCl3)δ0.94(3H,t,J＝7.5Hz),0.96(3H,t,J＝7.5Hz),1.55(6H,s),1.61-1.69(4H,m),2.29(2H,t,J＝7.5Hz),4.08(2H,t,J＝6.5Hz)
13C NMR(125MHz,CDCl3)δ10.29,13.53,18.34,21.82,24.62,36.18,66.76,77.96,172.56,172.75
精确分子量217.14467(C11H20O4,母峰)，157.08749(C8H12O3)
〔实施例4：α－正丁酰氧基异丁酸异丙酯〕
GC纯度：99.96％
1H NMR(500MHz,CDCl3)δ0.97(3H,t,J＝7.5Hz),1.22(6H,d,J＝6.5Hz),1.53(6H,s),1.65(2H,sext,J＝7.5Hz),2.28(2H,t,J＝7.5Hz),5.03(1H,sep,J＝6.5Hz)
13C NMR(125MHz,CDCl3)δ13.59,18.42,21.55,24.53,36.22,68.57,77.98,172.15,172.48
精确分子量217.14709(C11H20O4,母峰)，175.09776(C8H14O4)
〔实施例5：α－正丁酰氧基异丁酸正丁酯〕
GC纯度：99.91％
1H NMR(500MHz,CDCl3)δ0.93(3H,t,J＝7.5Hz),0.96(3H,t,J＝7.5Hz),1.37(2H,sext,J＝7.5Hz),1.54(6H,s),1.58-1.69(4H,m),2.28(2H,t,J＝7.5Hz),4.12(2H,t,J＝6.5Hz)
13C NMR(125MHz,CDCl3)δ13.54,13.65,18.35,19.04,24.61,30.45,36.19,65.05,77.96,172.56,172.77
精确分子量231.16103(C12H22O4,母峰)，157.08815(C8H12O3)
〔实施例6：α－正丁酰氧基异丁酸异丁酯〕
GC纯度：99.62％
1H NMR(500MHz,CDCl3)δ0.93(6H,d,J＝6.5Hz),0.96(3H,t,J＝7.5Hz),1.56(6H,s),1.65(2H,sext,J＝7.5Hz),1.94(1H,m),2.29(2H,t,J＝7.5Hz),3.90(2H,d,J＝6.5Hz)
13C NMR(125MHz,CDCl3)δ13.57,18.33,19.00,24.66,27.65,36.20,71.24,78.01,172.56,172.72
精确分子量231.16303(C12H22O4,母峰)，157.08976(C8H12O3)
将由上述方法得到的各种α－正丁酰氧基异丁酸酯由调香师进行香气评价，将结果示于表1。
[表1]
表1
<香料材料的生物降解性评价>
化合物的生物降解性的评价方法之一有OECD测试指南301C，可以根据化合物与需氧型微生物共存的水溶液中的生化需氧量和实际耗氧率来判断化合物的生物降解性的优劣。
作为从被验物质的化学结构容易且高精度地推算根据该试验方法的化合物的生物降解的概率的方法，已知有称为“Biowin5”，“Biowin6”的计算软件。
该软件作为美国环境保护署(United States Environmental ProtectionAgency，EPA)为评价化学物质对环境的影响而制作的名为“The Estimations ProgramsInterface for Windows version4.1”的计算软件的模块之一面向公众发布，用于全球化学品统一分类和标签制度(GHS)的化合物分类、美美国环境保护署的新型化学物质审查。使用该软件评价现有的香料材料与本发明的化合物的生物降解性的差异。
作为与本发明的化合物类似的现有的香料材料的代表例，选择具有花香香调的(E)-α-大马酮、(E)-β-大马烯酮，与本发明的化合物一起进行评价。将用于软件输入的SMILES公式和基于“Biowin5(线性预测模型)”、“Biowin6(非性形预测模型)”的良好降解性的概率的输出结果示于表2～表3。结果的数字越大，表示降解性越良好，如果为0.5以上则判定为降解性良好(表中，为符号“A”)，如果小于0.5则判定为难降解性(表中为符号“B”)。
由表2～表3可知，相对于类似的现有的香料材料(E)-α-大马酮、(E)-β-大马烯酮，本发明的化合物得到可期待良好的生物降解性的结果。本发明的化合物作为香料向环境释放后容易生物降解，显示对环境的负荷更少的趋势。
[表2]
表2
[表3]
表3
<实施例7：LILY BOUQUET型的香料组合物>
在具有表4所示的组成的香料组合物95.0质量份中加入实施例4得到的α-正丁酰氧基异丁酸异丙酯5.0质量份，制备香料组合物。
调香师进行香气评价，通过在具有表4记载的组成的香料组合物中添加实施例4的α-正丁酰氧基异丁酸异丙酯，玫瑰样的花香和果香相加，得到了华丽的甜味和具有宽度的花香。其结果，得到了赋予了玫瑰样花香的甜味和果香的更像天然物的芬芳的铃兰调香气的香料组合物。
该香料组合物的香气适合于对洗发水、爽肤水、护肤霜、乳液、柔软剂、肥皂等赋香。
[表4]
| 配合成分 | 质量份 |
| 羟基香茅醛 | 10.0 |
| JASMIN BASE A-15363/FC(Yamamoto Perfumery) | 7.0 |
| ISO E SUPER(IFF) | 8.0 |
| 黄葵内酯(IFF) | 0.8 |
| 乙酸苄酯 | 1.0 |
| 丙酸苄酯 | 0.6 |
| 香茅油 | 0.1 |
| 香茅醇 | 8.0 |
| 仙客来醛 | 0.7 |
| 加乐麝香50BB(IFF) | 4.5 |
| 香叶醇 | 6.5 |
| 己基肉桂醛 | 1.5 |
| 吲哚素(Symrise) | 0.5 |
| 铃兰醛 | 20.0 |
| 芳樟醇 | 2.5 |
| HEDION(Firmenich) | 10.0 |
| 橙花醇 | 3.0 |
| 苯乙醛二甲基乙缩醛 | 0.3 |
| 苯乙醇 | 10.0 |
| 合计 | 95.0 |
产业上的可利用性
本发明的在α位具有正丁酰氧基的异丁酸酯化合物具有优异的香气，期待其本身作为香料使用，并且通过使用该化合物作为调合香料材料而得到香气性优异的香料组合物，通过配合于各种制品而发挥所希望的赋香性。
此外，还表明实施例中得到的化合物均具有优异的生物降解性，对环境的负荷低，适合于使用。
Claims (11)
1.一种式(1)表示的化合物，
式(1)中，R表示碳原子数1～4的直链状、支链状或者环状的烷基。
2.根据权利要求1所述的化合物，其中，式(1)中，R选自甲基、乙基、正丙基、异丙基、正丁基和异丁基。
3.根据权利要求1或2所述的化合物，其中，式(1)中，R为甲基。
4.根据权利要求1或2所述的化合物，其中，式(1)中，R为乙基。
5.根据权利要求1或2所述的化合物，其中，式(1)中，R为正丙基。
6.根据权利要求1或2所述的化合物，其中，式(1)中，R为异丙基。
7.根据权利要求1或2所述的化合物，其中，式(1)中，R为正丁基。
8.根据权利要求1或2所述的化合物，其中，式(1)中，R为异丁基。
9.一种香料组合物，含有权利要求1～8中任一项所述的化合物作为有效成分。
10.一种权利要求1～8中任一项所述的化合物的用途，用作香料。
11.根据权利要求10所述的用途，其中，权利要求3、4和6中任一项所述的化合物赋予大马士革样的果香调、花香调或木香调的香调。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019034484 | 2019-02-27 | ||
| JP2019-034484 | 2019-02-27 | ||
| PCT/JP2020/006278 WO2020175241A1 (ja) | 2019-02-27 | 2020-02-18 | α位にノルマルブチリルオキシを有するイソ酪酸エステル化合物、香料組成物、及び香料としての使用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113474324A true CN113474324A (zh) | 2021-10-01 |
Family
ID=72238449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080016604.9A Pending CN113474324A (zh) | 2019-02-27 | 2020-02-18 | α位具有正丁酰氧基的异丁酸酯化合物、香料组合物和作为香料的用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20220153681A1 (zh) |
| EP (1) | EP3932901B1 (zh) |
| JP (1) | JP7400800B2 (zh) |
| CN (1) | CN113474324A (zh) |
| ES (1) | ES2943559T3 (zh) |
| WO (1) | WO2020175241A1 (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4082621B1 (en) * | 2019-12-24 | 2024-02-28 | Mitsubishi Gas Chemical Company, Inc. | ISOBUTYRATE ESTER COMPOUND HAVING CARBONATE GROUP AT alpha-POSITION, AND FRAGRANCE COMPOSITION |
| CN112778131B (zh) * | 2021-01-04 | 2022-07-08 | 东莞波顿香料有限公司 | 具有荔枝香气的化合物及其制备方法和日用香精 |
| CN117377743A (zh) * | 2021-05-28 | 2024-01-09 | 三菱瓦斯化学株式会社 | 在α位具有烯酰基氧基的异丁酸酯化合物、香料组合物以及作为香料的应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3368943A (en) * | 1965-10-20 | 1968-02-13 | Allan H. Gilbert | alpha-alkoxyisobutyrates and alpha-halo-beta-alkoxyisovalerates in perfumes and cleaning products |
| JPH08113795A (ja) * | 1994-10-14 | 1996-05-07 | T Hasegawa Co Ltd | 香料組成物 |
| CN1275121A (zh) * | 1998-09-09 | 2000-11-29 | 弗门尼舍有限公司 | 具有麝香气味的酯类及其香料用途 |
| CN1714067A (zh) * | 2002-11-29 | 2005-12-28 | 吉万奥丹股份有限公司 | 作为具有麝香特征的芳香剂的脂族化合物 |
| CN102046587A (zh) * | 2008-06-04 | 2011-05-04 | 弗门尼舍有限公司 | 果味增味剂 |
| CN105378045A (zh) * | 2013-07-08 | 2016-03-02 | 弗门尼舍有限公司 | 作为加香成分的新戊酸1-异丙氧基-1-氧代丙-2-基酯 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3568771D1 (en) * | 1984-10-10 | 1989-04-20 | Givaudan & Cie Sa | Hexanoates, process for their preparation and perfumes and/or flavouring agents having a content of such compounds |
| EP3816268A4 (en) * | 2018-06-26 | 2021-08-04 | Mitsubishi Gas Chemical Company, Inc. | ISOBUTYRIC ESTER COMPOUND WITH A PROPANOYLOXY GROUP IN POSITION?, PERFUMED COMPOSITION AND USE AS PERFUME |
| EP3816267A4 (en) * | 2018-06-26 | 2021-08-11 | Mitsubishi Gas Chemical Company, Inc. | ISOBUTTERIC ACID ESTER COMPOUND WITH ACETOXY GROUP AT THE SS POSITION, PERFUME COMPOSITION AND USE AS PERFUME |
| US11401483B2 (en) * | 2018-06-26 | 2022-08-02 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having butyryloxy group or pivaloyloxy group at α-position and fragrance composition |
-
2020
- 2020-02-18 WO PCT/JP2020/006278 patent/WO2020175241A1/ja unknown
- 2020-02-18 EP EP20762322.4A patent/EP3932901B1/en active Active
- 2020-02-18 ES ES20762322T patent/ES2943559T3/es active Active
- 2020-02-18 JP JP2021502024A patent/JP7400800B2/ja active Active
- 2020-02-18 CN CN202080016604.9A patent/CN113474324A/zh active Pending
- 2020-02-18 US US17/433,028 patent/US20220153681A1/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3368943A (en) * | 1965-10-20 | 1968-02-13 | Allan H. Gilbert | alpha-alkoxyisobutyrates and alpha-halo-beta-alkoxyisovalerates in perfumes and cleaning products |
| JPH08113795A (ja) * | 1994-10-14 | 1996-05-07 | T Hasegawa Co Ltd | 香料組成物 |
| CN1275121A (zh) * | 1998-09-09 | 2000-11-29 | 弗门尼舍有限公司 | 具有麝香气味的酯类及其香料用途 |
| CN1714067A (zh) * | 2002-11-29 | 2005-12-28 | 吉万奥丹股份有限公司 | 作为具有麝香特征的芳香剂的脂族化合物 |
| CN102046587A (zh) * | 2008-06-04 | 2011-05-04 | 弗门尼舍有限公司 | 果味增味剂 |
| JP2011524437A (ja) * | 2008-06-04 | 2011-09-01 | フイルメニツヒ ソシエテ アノニム | フルーツ調の着臭剤 |
| CN105378045A (zh) * | 2013-07-08 | 2016-03-02 | 弗门尼舍有限公司 | 作为加香成分的新戊酸1-异丙氧基-1-氧代丙-2-基酯 |
Non-Patent Citations (1)
| Title |
|---|
| CH. RUCHARDT UND H . BRINKMANN: "Zur ambivalenten Reaktivitat von a-Acyloxycarbonsaurechloriden", CHEM. BER., vol. 108, pages 3224 - 3242, XP055763188, DOI: 10.1002/cber.19751081012 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3932901B1 (en) | 2023-04-12 |
| EP3932901A4 (en) | 2022-05-04 |
| JPWO2020175241A1 (zh) | 2020-09-03 |
| US20220153681A1 (en) | 2022-05-19 |
| JP7400800B2 (ja) | 2023-12-19 |
| WO2020175241A1 (ja) | 2020-09-03 |
| ES2943559T3 (es) | 2023-06-14 |
| EP3932901A1 (en) | 2022-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7302601B2 (ja) | α位にブチリルオキシ基又はピバロイルオキシ基を有するイソ酪酸エステル化合物及び香料組成物 | |
| JP7310813B2 (ja) | α位にアセトキシ基を有するイソ酪酸エステル化合物、香料組成物、及び香料としての使用 | |
| JP7380558B2 (ja) | α－ヒドロキシイソ酪酸エステル化合物、香料組成物、及び香料としての使用 | |
| CN113474324A (zh) | α位具有正丁酰氧基的异丁酸酯化合物、香料组合物和作为香料的用途 | |
| CN112352037B (zh) | 在α位具有甲酰氧基的异丁酸酯化合物、香料组合物及作为香料的用途 | |
| JP7310812B2 (ja) | α位にプロパノイルオキシ基を有するイソ酪酸エステル化合物、香料組成物、及び香料としての使用 | |
| CN114846126B (zh) | α位具有碳酸酯基的异丁酸酯化合物及香料组合物 | |
| CN114867829B (zh) | α－羟基异丁酸酯化合物和香料组合物 | |
| JP7310815B2 (ja) | α－メトキシイソ酪酸エステル化合物を含有する香料組成物及び香料としての使用 | |
| WO2022250166A1 (ja) | α位にアルケノイルオキシ基を有するイソ酪酸エステル化合物、香料組成物、及び香料としての使用 |
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 |