JP2007536285A - 脂環式カルボン酸オキシカルボニルメチルエステル類および着臭剤としてのこれらの使用 - Google Patents
脂環式カルボン酸オキシカルボニルメチルエステル類および着臭剤としてのこれらの使用 Download PDFInfo
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- JP2007536285A JP2007536285A JP2007511828A JP2007511828A JP2007536285A JP 2007536285 A JP2007536285 A JP 2007536285A JP 2007511828 A JP2007511828 A JP 2007511828A JP 2007511828 A JP2007511828 A JP 2007511828A JP 2007536285 A JP2007536285 A JP 2007536285A
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- JP
- Japan
- Prior art keywords
- ester
- carboxylic acid
- octane
- formula
- cyclopropoxycarbonylmethyl
- 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.)
- Ceased
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- 239000003205 fragrance Substances 0.000 title claims abstract description 34
- -1 carboxylic acid oxycarbonylmethyl esters Chemical class 0.000 title description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 14
- SFDDJGIMHONNHU-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-(3,3-dimethylcyclohexyl)propanoate Chemical compound CCOC(=O)COC(=O)C(C)C1CCCC(C)(C)C1 SFDDJGIMHONNHU-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- JHIRZNSVBGSOFD-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2,7,7-trimethylspiro[2.5]octane-2-carboxylate Chemical compound CCOC(=O)COC(=O)C1(C)CC11CC(C)(C)CCC1 JHIRZNSVBGSOFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002304 perfume Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- JKRGTFRNUAEIHZ-UHFFFAOYSA-N (2-cyclopropyloxy-2-oxoethyl) 2,7,7-trimethylspiro[2.5]octane-2-carboxylate Chemical compound C1CC1OC(=O)COC(=O)C1(C)CC11CCCC(C)(C)C1 JKRGTFRNUAEIHZ-UHFFFAOYSA-N 0.000 claims 1
- PPXXHLDZUPHDFL-UHFFFAOYSA-N (2-cyclopropyloxy-2-oxoethyl) 2,7-dimethylspiro[2.5]octane-2-carboxylate Chemical compound C1C(C)CCCC11C(C(=O)OCC(=O)OC2CC2)(C)C1 PPXXHLDZUPHDFL-UHFFFAOYSA-N 0.000 claims 1
- HDCMFDOJLHAMLU-UHFFFAOYSA-N (2-cyclopropyloxy-2-oxoethyl) 2-(3,3-dimethylcyclohexyl)propanoate Chemical compound C1CC1OC(=O)COC(=O)C(C)C1CCCC(C)(C)C1 HDCMFDOJLHAMLU-UHFFFAOYSA-N 0.000 claims 1
- MLCSSGRQSXZLHZ-UHFFFAOYSA-N (2-cyclopropyloxy-2-oxoethyl) 2-(3-methylcyclohexyl)propanoate Chemical compound C1CC1OC(=O)COC(=O)C(C)C1CCCC(C)C1 MLCSSGRQSXZLHZ-UHFFFAOYSA-N 0.000 claims 1
- REKFLIURODXBEK-UHFFFAOYSA-N (2-cyclopropyloxy-2-oxoethyl) 2-cyclohexylpropanoate Chemical compound C1CC1OC(=O)COC(=O)C(C)C1CCCCC1 REKFLIURODXBEK-UHFFFAOYSA-N 0.000 claims 1
- DPAIXEQPNMQLJQ-UHFFFAOYSA-N (2-cyclopropyloxy-2-oxoethyl) 2-methylspiro[2.5]octane-2-carboxylate Chemical compound C1CC1OC(=O)COC(=O)C1(C)CC11CCCCC1 DPAIXEQPNMQLJQ-UHFFFAOYSA-N 0.000 claims 1
- UGEBBCSDCVVJSD-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2,7-dimethylspiro[2.5]octane-2-carboxylate Chemical compound CCOC(=O)COC(=O)C1(C)CC11CC(C)CCC1 UGEBBCSDCVVJSD-UHFFFAOYSA-N 0.000 claims 1
- OYQUOZKFLPVLKQ-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-(3-methylcyclohexyl)propanoate Chemical compound CCOC(=O)COC(=O)C(C)C1CCCC(C)C1 OYQUOZKFLPVLKQ-UHFFFAOYSA-N 0.000 claims 1
- RZMYWFNMHVTNLI-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-cyclohexylpropanoate Chemical compound CCOC(=O)COC(=O)C(C)C1CCCCC1 RZMYWFNMHVTNLI-UHFFFAOYSA-N 0.000 claims 1
- AFZZHFUARFGHFH-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-methylspiro[2.5]octane-2-carboxylate Chemical compound CCOC(=O)COC(=O)C1(C)CC11CCCCC1 AFZZHFUARFGHFH-UHFFFAOYSA-N 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
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- 239000002244 precipitate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000402754 Erythranthe moschata Species 0.000 description 3
- PSSKAIMYKSRYIQ-UHFFFAOYSA-N ethyl 2-(3,3-dimethylcyclohexylidene)propanoate Chemical compound CCOC(=O)C(C)=C1CCCC(C)(C)C1 PSSKAIMYKSRYIQ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- SMUBYRSPILIFEE-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-(3,3-dimethylcyclohexylidene)propanoate Chemical compound CCOC(=O)COC(=O)C(C)=C1CCCC(C)(C)C1 SMUBYRSPILIFEE-UHFFFAOYSA-N 0.000 description 2
- MMTRVRVLQXOINK-UHFFFAOYSA-N 2,7,7-trimethylspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1(C)CC11CC(C)(C)CCC1 MMTRVRVLQXOINK-UHFFFAOYSA-N 0.000 description 2
- ZDNDDXBTIZOZDR-UHFFFAOYSA-N 2-(3,3-dimethylcyclohexylidene)propanoic acid Chemical compound OC(=O)C(C)=C1CCCC(C)(C)C1 ZDNDDXBTIZOZDR-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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 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
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- YZAFURQSICZZHZ-UHFFFAOYSA-N ethyl 2,7,7-trimethylspiro[2.5]octane-2-carboxylate Chemical compound CCOC(=O)C1(C)CC11CC(C)(C)CCC1 YZAFURQSICZZHZ-UHFFFAOYSA-N 0.000 description 2
- BVSRWCMAJISCTD-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylpropanoate Chemical compound CCOC(=O)C(C)P(=O)(OCC)OCC BVSRWCMAJISCTD-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
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- 239000012044 organic layer Substances 0.000 description 2
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- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
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- 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
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- VRLUSLNMNQAPOH-UHFFFAOYSA-N 2-cyclohexylpropanoic acid Chemical class OC(=O)C(C)C1CCCCC1 VRLUSLNMNQAPOH-UHFFFAOYSA-N 0.000 description 1
- GUXRZQZCNOHHDO-UHFFFAOYSA-N 2-phosphonopropanoic acid Chemical compound OC(=O)C(C)P(O)(O)=O GUXRZQZCNOHHDO-UHFFFAOYSA-N 0.000 description 1
- ZVJQBBYAVPAFLX-UHFFFAOYSA-N 3,3-dimethylcyclohexan-1-one Chemical compound CC1(C)CCCC(=O)C1 ZVJQBBYAVPAFLX-UHFFFAOYSA-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
- 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
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 230000001953 sensory effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000009466 transformation Effects 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
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic 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
-
- 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
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/50—Spiro compounds
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)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
Description
−エーテル油および抽出物、例えば海狸香、コスタス根油、オークモスアブソリュート、ゼラニウム油、ジャスミンアブソリュート、パチョリ油、ローズ油、ビャクダン油またはイランイラン油。
−アルコール類、例えばシトロネロール、エバノール(Ebanol)(登録商標)、オイゲノール、ゲラニオール、スーパーミューゲ(Super Muguet)、リナロール、フェニルエチルアルコール、サンダロア(Sandalore)(登録商標)、テルピネオールまたはチンベロール(Timberol)(登録商標)。
−エーテル類およびアセタール類、例えばアンブロックス(Ambrox)(登録商標)、ゲラニルメチルエーテル、ローズオキシドまたはスピランブレン(Spirambrene)(登録商標)。
−エステル類およびラクトン類、例えば酢酸ベンジル、酢酸セドリル、γ−デカラクトン、ヘルベトリド(Helvetolide)(登録商標)、γ−ウンデカラクトンまたは酢酸ベチベニル。
−大環状化合物、例えばアンブレットリド、エチレンブラシレートまたはエクサルトリド(Exaltolide)(登録商標)。
−複素環式化合物、例えばイソブチルキノリン。
本発明を、ここで、以下の非限定的な例を参照してさらに記載する。
2−ホスホノプロピオン酸トリエチル(79.8g、335mmol)を1,2−ジメトキシエタン(70ml)に溶解した溶液を、30分以内に、95%NaH(7.54g、300mmol)を1,2−ジメトキシエタン(350ml)に懸濁させた攪拌した懸濁液に滴加した。反応混合物を、加熱還流させ、3,3−ジメチルシクロヘキサノン(63.0g、500mmol)を、5分の時間の間加えた。15時間還流させた後に、反応混合物を、粉砕した氷(600g)上に注入し、AcOH(約18ml、315mmol)を加えることによりpH5に酸性化し、Et2O(2×1l)で抽出した。混ぜ合わせた有機抽出物を、水および飽和水性NaClで洗浄し、乾燥し(MgSO4)、ロータリーエバポレータ上で濃縮して、粗製のα,β−不飽和エステル(89.2g)を得た。真空中での蒸留により、89〜90℃/3mbarにおいて、2−(3,3−ジメチルシクロヘキシリデン)プロピオン酸エチル(61.3g、97%)が得られた。
N2雰囲気中で、AgOAc(120mg、0.719mmol)を、AcOH(125ml)に溶解した。還流において、Zn粉末(20.2g、309mmol)を、攪拌しながら加え、還流温度でさらに10分間攪拌した後に、加熱源を取り外した。上清をデカンテーションし、残留物を、AcOH(100ml)およびEt2O(5×100ml)で洗浄した。次に、不溶性の物質を、Et2O(250ml)中に懸濁させ、触媒量のAgウールを、N2下で加えた。この懸濁液に、室温で、激しく攪拌しながら、例1により調製した2−(3,3−ジメチルシクロヘキシリデン)プロピオン酸エチル(25.0g、119mmol)を加えた。その後、CH2I2(41.4g、155mmol)を、この温度で、攪拌しながら10分以内に滴加し、次に、反応混合物を、24時間還流させ、次にさらにCH2I2(20.7g、77.3mmol)を加えた。
例1および2の一般的な手順に従って、表1の化合物3〜12を、それに応じて調製することができる。
Claims (8)
- 2−(3,3−ジメチルシクロヘキシル)プロピオン酸エトキシカルボニルメチルエステル、
1,5,5−トリメチルスピロ[2.5]オクタン−1−カルボン酸エトキシカルボニルメチルエステル、
2−(3,3−ジメチルシクロヘキシル)プロピオン酸シクロプロポキシカルボニルメチルエステル、
2−(3−メチルシクロヘキシル)プロピオン酸エトキシカルボニルメチルエステル、
2−(3−メチルシクロヘキシル)プロピオン酸シクロプロポキシカルボニルメチルエステル、
2−シクロヘキシル−プロピオン酸エトキシカルボニルメチルエステル、
2−シクロヘキシルプロピオン酸シクロプロポキシカルボニルメチルエステル、
1,5,5−トリメチルスピロ[2.5]オクタン−1−カルボン酸シクロプロポキシカルボニルメチルエステル、
1,5−ジメチルスピロ[2.5]オクタン−1−カルボン酸エトキシカルボニルメチルエステル、
1,5−ジメチルスピロ[2.5]オクタン−1−カルボン酸シクロプロポキシカルボニルメチルエステル、
1−メチルスピロ[2.5]オクタン−1−カルボン酸エトキシカルボニルメチルエステルおよび
1−メチルスピロ[2.5]オクタン−1−カルボン酸シクロプロポキシカルボニルメチルエステル
からなる群から選択されている、請求項1に記載の化合物。 - 請求項1または2において定義した式(I)で表される化合物の、着臭剤としての使用。
- 請求項1または2において定義した式(I)で表される化合物を含む、風味剤または芳香組成物。
- 風味剤または芳香組成物の製造方法であって、請求項1または2において定義した式(I)で表される化合物を、ベース材料中に導入する段階を含む、前記方法。
- 芳香適用品の製造方法であって、請求項1または2において定義した式(I)で表される化合物を導入することを含む、前記方法。
- 芳香適用品を改善、増強または改変する方法であって、請求項1または2において定義した式(I)で表される化合物の嗅覚的に許容し得る量を加えることによる、前記方法。
- 芳香適用品が、香水、家庭用品、ランドリー製品、ボディーケア製品および化粧品からなる群から選択される、請求項6または7に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0410134.1A GB0410134D0 (en) | 2004-05-07 | 2004-05-07 | Organic compounds |
PCT/CH2005/000251 WO2005108534A1 (en) | 2004-05-07 | 2005-05-04 | Alicyclic carboxylic acid oxycarbonylmethyl esters and their use as odorants |
Publications (2)
Publication Number | Publication Date |
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JP2007536285A true JP2007536285A (ja) | 2007-12-13 |
JP2007536285A5 JP2007536285A5 (ja) | 2008-06-19 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2007511828A Ceased JP2007536285A (ja) | 2004-05-07 | 2005-05-04 | 脂環式カルボン酸オキシカルボニルメチルエステル類および着臭剤としてのこれらの使用 |
Country Status (12)
Country | Link |
---|---|
US (1) | US7687452B2 (ja) |
EP (1) | EP1743013B1 (ja) |
JP (1) | JP2007536285A (ja) |
KR (1) | KR20070006895A (ja) |
CN (1) | CN1950490A (ja) |
AT (1) | ATE381605T1 (ja) |
BR (1) | BRPI0509666A (ja) |
DE (1) | DE602005003937T2 (ja) |
ES (1) | ES2297694T3 (ja) |
GB (1) | GB0410134D0 (ja) |
MX (1) | MXPA06012767A (ja) |
WO (1) | WO2005108534A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011037761A (ja) * | 2009-08-11 | 2011-02-24 | T Hasegawa Co Ltd | 脂肪族エステル類、該化合物を含有する香料組成物および該化合物の製造法 |
US10407378B2 (en) | 2014-04-21 | 2019-09-10 | Takasago International Corporation | Compound, and flavor and/or fragrance composition containing said compound |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1842564B1 (en) * | 2006-04-05 | 2014-02-19 | The Procter and Gamble Company | Absorbent articles including odour control system |
US8835511B2 (en) * | 2007-04-04 | 2014-09-16 | The Procter & Gamble Company | Absorbent articles including an odor control system |
US8846723B2 (en) * | 2010-07-29 | 2014-09-30 | Eastman Chemical Company | Esters of O-substituted hydroxy carboxylic acids and preparations thereof |
US8613940B2 (en) | 2010-09-03 | 2013-12-24 | Eastman Chemical Company | Carbonate derivatives as skin care |
US8329938B2 (en) | 2011-02-21 | 2012-12-11 | Eastman Chemical Company | Hydroxyalkanoic acid and hydroxyalkanoice acid oligomer esters of retinol |
PL234189B1 (pl) * | 2017-12-01 | 2020-01-31 | Politechnika Wroclawska | (2E)-2-[(2S,5R)-5-metylo-2-(propan-2-ylo)cykloheksylideno]butanian etylu i sposób jego wytwarzania |
JP7227924B2 (ja) | 2017-12-22 | 2023-02-22 | 高砂香料工業株式会社 | ムスク様香気を有する化合物及びそれを含有する香料組成物 |
WO2024206466A1 (en) | 2023-03-30 | 2024-10-03 | International Flavors & Fragrances Inc. | Method for producing a musk fragrance intermediate using copper catalysts |
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2004
- 2004-05-07 GB GBGB0410134.1A patent/GB0410134D0/en not_active Ceased
-
2005
- 2005-05-04 WO PCT/CH2005/000251 patent/WO2005108534A1/en active IP Right Grant
- 2005-05-04 ES ES05732413T patent/ES2297694T3/es active Active
- 2005-05-04 MX MXPA06012767A patent/MXPA06012767A/es active IP Right Grant
- 2005-05-04 KR KR1020067023223A patent/KR20070006895A/ko not_active Application Discontinuation
- 2005-05-04 EP EP05732413A patent/EP1743013B1/en not_active Not-in-force
- 2005-05-04 CN CNA2005800146426A patent/CN1950490A/zh active Pending
- 2005-05-04 US US11/568,475 patent/US7687452B2/en not_active Expired - Fee Related
- 2005-05-04 AT AT05732413T patent/ATE381605T1/de not_active IP Right Cessation
- 2005-05-04 JP JP2007511828A patent/JP2007536285A/ja not_active Ceased
- 2005-05-04 BR BRPI0509666-9A patent/BRPI0509666A/pt not_active IP Right Cessation
- 2005-05-04 DE DE602005003937T patent/DE602005003937T2/de active Active
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JP2011037761A (ja) * | 2009-08-11 | 2011-02-24 | T Hasegawa Co Ltd | 脂肪族エステル類、該化合物を含有する香料組成物および該化合物の製造法 |
US10407378B2 (en) | 2014-04-21 | 2019-09-10 | Takasago International Corporation | Compound, and flavor and/or fragrance composition containing said compound |
Also Published As
Publication number | Publication date |
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BRPI0509666A (pt) | 2007-10-09 |
ATE381605T1 (de) | 2008-01-15 |
MXPA06012767A (es) | 2007-01-16 |
DE602005003937D1 (de) | 2008-01-31 |
WO2005108534A1 (en) | 2005-11-17 |
GB0410134D0 (en) | 2004-06-09 |
KR20070006895A (ko) | 2007-01-11 |
US7687452B2 (en) | 2010-03-30 |
EP1743013A1 (en) | 2007-01-17 |
CN1950490A (zh) | 2007-04-18 |
EP1743013B1 (en) | 2007-12-19 |
ES2297694T3 (es) | 2008-05-01 |
DE602005003937T2 (de) | 2008-12-18 |
US20070225201A1 (en) | 2007-09-27 |
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