JP4751884B2 - サリチル酸4−ヘプテン−2−イルおよびフレグランス成分としてのその使用 - Google Patents
サリチル酸4−ヘプテン−2−イルおよびフレグランス成分としてのその使用 Download PDFInfo
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- JP4751884B2 JP4751884B2 JP2007521770A JP2007521770A JP4751884B2 JP 4751884 B2 JP4751884 B2 JP 4751884B2 JP 2007521770 A JP2007521770 A JP 2007521770A JP 2007521770 A JP2007521770 A JP 2007521770A JP 4751884 B2 JP4751884 B2 JP 4751884B2
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- JP
- Japan
- Prior art keywords
- hepten
- fragrance
- salicylate
- salicylic acid
- 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.)
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- 239000003205 fragrance Substances 0.000 title claims description 40
- AWFJMMINHWORIB-UHFFFAOYSA-N hept-4-en-2-yl 2-hydroxybenzoate Chemical compound CCC=CCC(C)OC(=O)C1=CC=CC=C1O AWFJMMINHWORIB-UHFFFAOYSA-N 0.000 title description 10
- 239000004615 ingredient Substances 0.000 title description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 21
- 229960004889 salicylic acid Drugs 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- -1 cyclic oligosaccharides Chemical class 0.000 description 6
- 241000234435 Lilium Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229960001047 methyl salicylate Drugs 0.000 description 5
- 244000215777 Plumeria rubra Species 0.000 description 4
- CXVIEBMEWKSONY-UHFFFAOYSA-N hept-4-yn-2-ol Chemical compound CCC#CCC(C)O CXVIEBMEWKSONY-UHFFFAOYSA-N 0.000 description 4
- UYHCRBGMFLONOK-UHFFFAOYSA-N hept-4-yn-2-yl 2-hydroxybenzoate Chemical compound CCC#CCC(C)OC(=O)C1=CC=CC=C1O UYHCRBGMFLONOK-UHFFFAOYSA-N 0.000 description 4
- GTNCESCYZPMXCJ-UHFFFAOYSA-N 3-Phenylpropyl propanoate Chemical compound CCC(=O)OCCCC1=CC=CC=C1 GTNCESCYZPMXCJ-UHFFFAOYSA-N 0.000 description 3
- 240000006497 Dianthus caryophyllus Species 0.000 description 3
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000013087 Plumeria rubra Nutrition 0.000 description 3
- AWFJMMINHWORIB-PLNGDYQASA-N [(z)-hept-4-en-2-yl] 2-hydroxybenzoate Chemical compound CC\C=C/CC(C)OC(=O)C1=CC=CC=C1O AWFJMMINHWORIB-PLNGDYQASA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MPUDDMDNHKEYAK-PLNGDYQASA-N (z)-2-methylhex-3-en-1-ol Chemical compound CC\C=C/C(C)CO MPUDDMDNHKEYAK-PLNGDYQASA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-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
- 235000007173 Abies balsamea Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004857 Balsam Substances 0.000 description 2
- 241000597000 Freesia Species 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 244000018716 Impatiens biflora Species 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- SUHLUMKZPUMAFP-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1O SUHLUMKZPUMAFP-UHFFFAOYSA-N 0.000 description 2
- WHSXTWFYRGOBGO-UHFFFAOYSA-N o-cresotic acid Natural products CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
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- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- CRDAMVZIKSXKFV-YFVJMOTDSA-N (2-trans,6-trans)-farnesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO CRDAMVZIKSXKFV-YFVJMOTDSA-N 0.000 description 1
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
- WBNJCBPWAMSDMR-YFVJMOTDSA-N (2e,6e)-3,7,11-trimethyldodeca-2,6-dienal Chemical compound CC(C)CCC\C(C)=C\CC\C(C)=C\C=O WBNJCBPWAMSDMR-YFVJMOTDSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-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
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 1
- KZUFTCBJDQXWOJ-SNAWJCMRSA-N (e)-hept-4-en-2-ol Chemical compound CC\C=C\CC(C)O KZUFTCBJDQXWOJ-SNAWJCMRSA-N 0.000 description 1
- RNLHVODSMDJCBR-VURMDHGXSA-N (z)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C/C1CC=C(C)C1(C)C RNLHVODSMDJCBR-VURMDHGXSA-N 0.000 description 1
- KVDORLFQOZGRPI-CHNJZELVSA-N (z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO.CC\C=C/CCO KVDORLFQOZGRPI-CHNJZELVSA-N 0.000 description 1
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- YQYKESUTYHZAGG-BZNIZROVSA-N 1-[(1r,2s)-1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone Chemical compound C1([C@H]([C@@](CC2)(C)C(C)=O)C)=C2CCCC1(C)C YQYKESUTYHZAGG-BZNIZROVSA-N 0.000 description 1
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 1
- ZFGBKXBPHOUSJX-UHFFFAOYSA-N 3-methylcyclotetradec-5-en-1-one Chemical compound CC1CC=CCCCCCCCCC(=O)C1 ZFGBKXBPHOUSJX-UHFFFAOYSA-N 0.000 description 1
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 241000721662 Juniperus Species 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- AWFJMMINHWORIB-SNAWJCMRSA-N [(e)-hept-4-en-2-yl] 2-hydroxybenzoate Chemical compound CC\C=C\CC(C)OC(=O)C1=CC=CC=C1O AWFJMMINHWORIB-SNAWJCMRSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 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
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 235000009508 confectionery Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002088 nanocapsule Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
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- 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
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)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
−エッセンシャルオイルおよびエクストラクト、例えば、ラベンダーオイル、ジュニパーオイル、オークモスアブソリュート、ゼラニウムオイル、ジャスミンアブソリュート、パチョリオイル、ローズオイル、サンダルウッドオイル、レモンオイル、またはイラン−イランオイル。
−アルコール類、例えば、シトロネロール、Ebanol(R)、オイゲノール、ゲラニオール、スーパーミュゲ(Super Muguet)、リナロール、フェニルエチルアルコール、ネロリドール、3−ヘキセノール、Sandalore(R)、テルピネオール、またはTimberol(R)。
−エーテル類およびアセタール類、例えば、Ambrox(R)、ゲラニルメチルエーテル、ローズオキサイドまたはSpirambrene(R)。
−大環状分子類、例えば、アンブレトリド、エチレンブラシレート、Exaltolide(R)またはCosmoneTM。
−複素環類、例えば、イソブチルキノリン。
例1:サリチル酸4−ヘプテン−2−イル
a)サリチル酸4−ヘプチン−2−イル
4−ヘプチン−2−オール(22g;0.2mol)およびサリチル酸メチル(30g;0.2mol)を、撹拌および窒素下で、120℃まで加熱する。チタニウム(IV)イソプロポキシド(0.5g;0.02mol)をシリンジを介して一部分で加え、反応物を減圧下(600mbar)で150°Cまで加熱し、その間にメタノールを蒸留する。24時間後(75%変換)フラスコの内容物を25℃まで冷ます。高真空(0.1Torr=0.133mbar)を加え、反応質量を短経路で蒸留し、最初の5gの4−ヘプチン−2−オール(23%)を得て、118°C/0.1Torr(0.133mbar)において35gのサリチル酸4−ヘプチン−2−イル(75%)を得る。
サリチル酸4−ヘプチン−2−イル(24.6g;0.1mol)を30mlの無水エタノールに溶解し、硫酸バリウム上のパラジウムの上(0.4g;0.02mol)および水素下で3時間撹拌する。セライト(Celite)でのろ過および減圧下でのエタノールの蒸発により、26.2gの粗生成物を得る、そしてそれをVigreuxカラムで蒸留し、23.5g(96%)のわずかに黄色がかったオイルを98°C/0.1Torr(0.133mbar)で得る。同じ条件下で、再蒸留し、21.6g(88%)の無色のサリチル酸(Z)−4−ヘプテン−2−イルを得る。
サリチル酸(Z)−2−メチル−3−ヘキセン−1−イルを、他の場所(Russian Journal of Organic Chemistry, 1992, 28, 220-225)に説明されている合成、(Z)−2−メチル−3−ヘキセン−1−オール、およびサリチル酸メチルから上記例1a)に説明されたように調製する。(Z)−2−メチル−3−ヘキセン−1−オール(5.9g、0.05mol)およびサリチル酸メチル(7.6g、0.05mol)から、このように、108〜112℃/0.3mbarで蒸留した後、7.5gのサリチル酸(Z)−2−メチル−3−ヘキセン−1−イル(64%)を得た。
2−ヒドロキシ−3−メチル安息香酸(Z)−3−ヘキセン−1−イルは、市販の(Z)−ヘキサ−3−エン−1−オールおよびo−クレソチン酸メチルから上記例1a)に説明されたように調製される。(Z)−ヘキサ−3−エン−1−オール(20.0g、0.2mol)およびo−クレソチン酸メチル(33.2g、0.2mol)から、したがって118°C/0.2mbarで蒸留した後、37.2gの2−ヒドロキシ−3−メチル安息香酸(Z)−3−ヘキセン−1−イル(79%)を得た。
当業者に既知の標準的な手順に従って、揮発性香料化合物の閾値を、においを嗅ぐポート(sniff port)を備えているガスクロマトグラフィで、訓練された評価者のパネルによって測定された。それぞれのパネリストによって嗅がれた最も低い濃度が、ngで表される個々の閾値として記録される(においを嗅ぐポートに送られる化合物の絶対量)。
Claims (4)
- サリチル酸(Z)−4−ヘプテン−2−イルおよびサリチル酸(E)−4−ヘプテン−2−イルから選択される化合物。
- サリチル酸(Z)−4−ヘプテン−2−イルおよびサリチル酸(E)−4−ヘプテン−2−イルから選択される少なくとも一つの化合物を含む、フレグランス組成物。
- サリチル酸(Z)−4−ヘプテン−2−イルおよびサリチル酸(E)−4−ヘプテン−2−イルから選択される化合物の、フレグランス成分としての使用。
- サリチル酸(Z)−4−ヘプテン−2−イルおよびサリチル酸(E)−4−ヘプテン−2−イルから選択される化合物、またはそれらの混合物の有効量を組み入れるステップを含む、フレグランス利用品の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0416428.1 | 2004-07-23 | ||
GBGB0416428.1A GB0416428D0 (en) | 2004-07-23 | 2004-07-23 | Organic compound |
PCT/CH2005/000435 WO2006007755A1 (en) | 2004-07-23 | 2005-07-22 | 4-hepten-2-yl salicylate and its use as fragrance ingredient |
Publications (2)
Publication Number | Publication Date |
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JP2008507479A JP2008507479A (ja) | 2008-03-13 |
JP4751884B2 true JP4751884B2 (ja) | 2011-08-17 |
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JP2007521770A Active JP4751884B2 (ja) | 2004-07-23 | 2005-07-22 | サリチル酸4−ヘプテン−2−イルおよびフレグランス成分としてのその使用 |
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US (1) | US7842660B2 (ja) |
EP (1) | EP1771407B1 (ja) |
JP (1) | JP4751884B2 (ja) |
KR (1) | KR20070039070A (ja) |
CN (1) | CN100551898C (ja) |
BR (1) | BRPI0513495B1 (ja) |
ES (1) | ES2513790T3 (ja) |
GB (1) | GB0416428D0 (ja) |
MX (1) | MX2007000554A (ja) |
WO (1) | WO2006007755A1 (ja) |
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CN104837895B (zh) * | 2013-07-01 | 2017-06-06 | Lg化学株式会社 | 聚硅氧烷化合物及其制备方法以及包含它的共聚碳酸酯树脂 |
JP6809073B2 (ja) * | 2015-11-13 | 2021-01-06 | 株式会社リコー | 立体造形材料セット、立体造形物の製造方法、及び立体造形物の製造装置 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56128732A (en) * | 1980-02-13 | 1981-10-08 | Firmenich & Cie | Ester of 1,3-dimethyl-but-3-ene-1-yl, method of improving or modifying smell properties of perfume or perfuming product or taste properties of food, animal feed and beverage and perfume, perfuming compound and flavoring product |
JP2000226357A (ja) * | 1998-12-04 | 2000-08-15 | Kuraray Co Ltd | シス型不飽和エステル、その製造方法及びそれを含有する香料組成物 |
JP2002155294A (ja) * | 2000-09-14 | 2002-05-28 | Firmenich Sa | 香り特性を付与、改善、増強又は変性する方法、香料組成物、付香物品並びに不飽和エステル化合物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0694417B2 (ja) | 1984-08-03 | 1994-11-24 | 株式会社資生堂 | 現代ローズ香料組成物及びその製造方法 |
EP0545556B1 (en) * | 1991-11-08 | 1997-07-23 | Quest International B.V. | Perfume composition |
EP1063229B1 (en) | 1999-05-27 | 2003-02-19 | Givaudan SA | Alpha, beta-unsaturated ketones |
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2004
- 2004-07-23 GB GBGB0416428.1A patent/GB0416428D0/en not_active Ceased
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2005
- 2005-07-22 US US11/572,218 patent/US7842660B2/en active Active
- 2005-07-22 CN CNB2005800237957A patent/CN100551898C/zh active Active
- 2005-07-22 JP JP2007521770A patent/JP4751884B2/ja active Active
- 2005-07-22 KR KR1020077001662A patent/KR20070039070A/ko not_active Application Discontinuation
- 2005-07-22 ES ES05760959.6T patent/ES2513790T3/es active Active
- 2005-07-22 WO PCT/CH2005/000435 patent/WO2006007755A1/en active Application Filing
- 2005-07-22 BR BRPI0513495A patent/BRPI0513495B1/pt active IP Right Grant
- 2005-07-22 MX MX2007000554A patent/MX2007000554A/es active IP Right Grant
- 2005-07-22 EP EP05760959.6A patent/EP1771407B1/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56128732A (en) * | 1980-02-13 | 1981-10-08 | Firmenich & Cie | Ester of 1,3-dimethyl-but-3-ene-1-yl, method of improving or modifying smell properties of perfume or perfuming product or taste properties of food, animal feed and beverage and perfume, perfuming compound and flavoring product |
JP2000226357A (ja) * | 1998-12-04 | 2000-08-15 | Kuraray Co Ltd | シス型不飽和エステル、その製造方法及びそれを含有する香料組成物 |
JP2002155294A (ja) * | 2000-09-14 | 2002-05-28 | Firmenich Sa | 香り特性を付与、改善、増強又は変性する方法、香料組成物、付香物品並びに不飽和エステル化合物 |
Also Published As
Publication number | Publication date |
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JP2008507479A (ja) | 2008-03-13 |
US20080261859A1 (en) | 2008-10-23 |
MX2007000554A (es) | 2007-03-07 |
US7842660B2 (en) | 2010-11-30 |
BRPI0513495A (pt) | 2008-05-06 |
BRPI0513495B1 (pt) | 2016-05-31 |
WO2006007755A1 (en) | 2006-01-26 |
KR20070039070A (ko) | 2007-04-11 |
CN1984870A (zh) | 2007-06-20 |
GB0416428D0 (en) | 2004-08-25 |
EP1771407A1 (en) | 2007-04-11 |
EP1771407B1 (en) | 2014-09-03 |
CN100551898C (zh) | 2009-10-21 |
ES2513790T3 (es) | 2014-10-27 |
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