JP2000053613A - 保護されたヒドロキシ基を有する化合物 - Google Patents
保護されたヒドロキシ基を有する化合物Info
- Publication number
- JP2000053613A JP2000053613A JP11111199A JP11119999A JP2000053613A JP 2000053613 A JP2000053613 A JP 2000053613A JP 11111199 A JP11111199 A JP 11111199A JP 11119999 A JP11119999 A JP 11119999A JP 2000053613 A JP2000053613 A JP 2000053613A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ester
- dimethyl
- acid
- substituted
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title abstract description 3
- 239000002243 precursor Substances 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 42
- 150000002148 esters Chemical class 0.000 claims description 41
- 150000001299 aldehydes Chemical class 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 8
- 230000003213 activating effect Effects 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000009965 odorless effect Effects 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000001671 coumarin Nutrition 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000004718 beta keto acids Chemical class 0.000 claims description 2
- 150000004775 coumarins Chemical class 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000002587 enol group Chemical group 0.000 claims 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 229960000956 coumarin Drugs 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
- 230000000845 anti-microbial effect Effects 0.000 abstract description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000001632 sodium acetate Substances 0.000 abstract description 3
- 235000017281 sodium acetate Nutrition 0.000 abstract description 3
- 230000004936 stimulating effect Effects 0.000 abstract description 3
- DFFGXGLKNGYGOY-UHFFFAOYSA-N [3-(4-tert-butylphenyl)-2-methylprop-1-enyl] acetate Chemical compound CC(=O)OC=C(C)CC1=CC=C(C(C)(C)C)C=C1 DFFGXGLKNGYGOY-UHFFFAOYSA-N 0.000 abstract 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 abstract 1
- 210000000056 organ Anatomy 0.000 abstract 1
- -1 aromatic radicals Chemical class 0.000 description 67
- 239000003205 fragrance Substances 0.000 description 57
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 230000003111 delayed effect Effects 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KBWRWCSRYCKEOR-UHFFFAOYSA-N 3-capryl propionic acid Chemical compound CCCCCCCC(=O)CCC(O)=O KBWRWCSRYCKEOR-UHFFFAOYSA-N 0.000 description 10
- 239000003599 detergent Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000002596 lactones Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XEXIVNNTJNBUGV-UHFFFAOYSA-N 4-hydroxy-undecanoic acid Chemical compound CCCCCCCC(O)CCC(O)=O XEXIVNNTJNBUGV-UHFFFAOYSA-N 0.000 description 8
- SPUWOYCLMKSXKU-UHFFFAOYSA-N 4-oxo capric acid Chemical compound CCCCCCC(=O)CCC(O)=O SPUWOYCLMKSXKU-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 239000002979 fabric softener Substances 0.000 description 8
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000004367 Lipase Substances 0.000 description 7
- 102000004882 Lipase Human genes 0.000 description 7
- 108090001060 Lipase Proteins 0.000 description 7
- 235000019421 lipase Nutrition 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000002781 deodorant agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 230000000873 masking effect Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000001166 anti-perspirative effect Effects 0.000 description 5
- 239000003213 antiperspirant Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 4
- PRDIIROHTWNJDB-UHFFFAOYSA-N 3-caproyl propionic acid Chemical compound CCCCCC(=O)CCC(O)=O PRDIIROHTWNJDB-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 4
- RBBLRYOHDSHTKL-UHFFFAOYSA-N hex-3-enyl 4-hydroxydecanoate Chemical compound CCCCCCC(O)CCC(=O)OCCC=CCC RBBLRYOHDSHTKL-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229960003500 triclosan Drugs 0.000 description 4
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 4
- BUIQYRMXTZBRTB-UHFFFAOYSA-N 2,6-dimethylheptan-2-yl 4-oxodecanoate Chemical compound CCCCCCC(=O)CCC(=O)OC(C)(C)CCCC(C)C BUIQYRMXTZBRTB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 3
- SWXKLOXBUBQJQN-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 4-hydroxynonanoate Chemical compound CCCCCC(O)CCC(=O)OCC=C(C)CCC=C(C)C SWXKLOXBUBQJQN-UHFFFAOYSA-N 0.000 description 3
- RJDHDCLWRJEPEJ-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 4-hydroxyundecanoate Chemical compound CCCCCCCC(O)CCC(=O)OCC=C(C)CCC=C(C)C RJDHDCLWRJEPEJ-UHFFFAOYSA-N 0.000 description 3
- QQAVZEYXLCYOKO-UHFFFAOYSA-N 4-Hydroxycapric acid Chemical compound CCCCCCC(O)CCC(O)=O QQAVZEYXLCYOKO-UHFFFAOYSA-N 0.000 description 3
- KRGVTRNRRGDYON-UHFFFAOYSA-N 4-oxoundecanoyl chloride Chemical compound CCCCCCCC(=O)CCC(Cl)=O KRGVTRNRRGDYON-UHFFFAOYSA-N 0.000 description 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- JGNPMRZXWSYRPI-UHFFFAOYSA-N [1-(3,7-dimethylocta-2,6-dienoxy)-1-oxoundecan-4-yl] benzoate Chemical compound CC(C)=CCCC(C)=CCOC(=O)CCC(CCCCCCC)OC(=O)C1=CC=CC=C1 JGNPMRZXWSYRPI-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 3
- GJFQZYHSFMMUOK-UHFFFAOYSA-N hex-3-enyl 4-hydroxynonanoate Chemical compound CCCCCC(O)CCC(=O)OCCC=CCC GJFQZYHSFMMUOK-UHFFFAOYSA-N 0.000 description 3
- JOVQDKYEUSPVHU-UHFFFAOYSA-N hex-3-enyl 4-oxodecanoate Chemical compound CCCCCCC(=O)CCC(=O)OCCC=CCC JOVQDKYEUSPVHU-UHFFFAOYSA-N 0.000 description 3
- BEJDQQMKQCEZFV-UHFFFAOYSA-N hex-3-enyl 4-oxononanoate Chemical compound CCCCCC(=O)CCC(=O)OCCC=CCC BEJDQQMKQCEZFV-UHFFFAOYSA-N 0.000 description 3
- SLGWLOYQWMFQBC-UHFFFAOYSA-N hex-3-enyl 4-oxoundecanoate Chemical compound CCCCCCCC(=O)CCC(=O)OCCC=CCC SLGWLOYQWMFQBC-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 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
- JHEPBQHNVNUAFL-AATRIKPKSA-N (e)-hex-1-en-1-ol Chemical compound CCCC\C=C\O JHEPBQHNVNUAFL-AATRIKPKSA-N 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- AYJXHIDNNLJQDT-UHFFFAOYSA-N 2,6,6-Trimethyl-2-cyclohexene-1,4-dione Chemical compound CC1=CC(=O)CC(C)(C)C1=O AYJXHIDNNLJQDT-UHFFFAOYSA-N 0.000 description 2
- HGDVHRITTGWMJK-UHFFFAOYSA-N 2,6-dimethylheptan-2-ol Chemical compound CC(C)CCCC(C)(C)O HGDVHRITTGWMJK-UHFFFAOYSA-N 0.000 description 2
- GMTKKOJWCRJLFA-UHFFFAOYSA-N 2,6-dimethylheptan-2-yl 4-hydroxydecanoate Chemical compound CCCCCCC(O)CCC(=O)OC(C)(C)CCCC(C)C GMTKKOJWCRJLFA-UHFFFAOYSA-N 0.000 description 2
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 description 2
- VGECIEOJXLMWGO-UHFFFAOYSA-N 2-hexylcyclopent-2-en-1-one Chemical compound CCCCCCC1=CCCC1=O VGECIEOJXLMWGO-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- RRSAEHIIUDIBBP-UHFFFAOYSA-N 3,7-dimethyloct-6-enyl 4-hydroxydecanoate Chemical compound CCCCCCC(O)CCC(=O)OCCC(C)CCC=C(C)C RRSAEHIIUDIBBP-UHFFFAOYSA-N 0.000 description 2
- MXQLKIWCJNLACB-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 4-(2-phenylethoxycarbonyloxy)undecanoate Chemical compound CC(C)=CCCC(C)=CCOC(=O)CCC(CCCCCCC)OC(=O)OCCC1=CC=CC=C1 MXQLKIWCJNLACB-UHFFFAOYSA-N 0.000 description 2
- BDSYJWYMYJLOGP-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienyl 4-hex-3-enoxycarbonyloxyundecanoate Chemical compound CCC=CCCOC(=O)OC(CCCCCCC)CCC(=O)OCC=C(C)CCC=C(C)C BDSYJWYMYJLOGP-UHFFFAOYSA-N 0.000 description 2
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 2
- UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 2
- MKZHVQSYPRGNAH-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)but-1-enyl 4-hydroxyundecanoate Chemical compound CCCCCCCC(O)CCC(=O)OC=CC(C)C1=CC=CC(C(C)C)=C1 MKZHVQSYPRGNAH-UHFFFAOYSA-N 0.000 description 2
- GMFMSOANCBJHLV-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)but-1-enyl 4-oxoundecanoate Chemical compound CCCCCCCC(=O)CCC(=O)OC=CC(C)C1=CC=CC(C(C)C)=C1 GMFMSOANCBJHLV-UHFFFAOYSA-N 0.000 description 2
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 description 2
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 2
- YFXHYHIJRNUIGB-UHFFFAOYSA-N 4-hex-3-enoxy-4-oxobutanoic acid Chemical compound CCC=CCCOC(=O)CCC(O)=O YFXHYHIJRNUIGB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
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- KBBZXUDOYKCRBE-UHFFFAOYSA-N n-dodecyl-4-hydroxyundecanamide Chemical compound CCCCCCCCCCCCNC(=O)CCC(O)CCCCCCC KBBZXUDOYKCRBE-UHFFFAOYSA-N 0.000 description 1
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
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- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 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
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 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 1
- WGPCZPLRVAWXPW-UHFFFAOYSA-N xi-Dihydro-5-octyl-2(3H)-furanone Chemical compound CCCCCCCCC1CCC(=O)O1 WGPCZPLRVAWXPW-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
- A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- 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
- 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
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- 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
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810337.0 | 1998-04-20 | ||
| EP98810337 | 1998-04-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000053613A true JP2000053613A (ja) | 2000-02-22 |
| JP2000053613A5 JP2000053613A5 (enExample) | 2006-05-25 |
Family
ID=8236042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11111199A Pending JP2000053613A (ja) | 1998-04-20 | 1999-04-19 | 保護されたヒドロキシ基を有する化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6437150B1 (enExample) |
| EP (2) | EP0952142B1 (enExample) |
| JP (1) | JP2000053613A (enExample) |
| DE (1) | DE69933608T2 (enExample) |
| ES (1) | ES2273468T3 (enExample) |
| SG (1) | SG75160A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006523244A (ja) * | 2003-04-14 | 2006-10-12 | ジボダン エス エー | フレグランスとして有用なカルバメート類 |
| JP2020510048A (ja) * | 2017-03-29 | 2020-04-02 | クリューバー リュブリケーション ミュンヘン ソシエタス ヨーロピア ウント コンパニー コマンディートゲゼルシャフトＫｌｕｅｂｅｒ Ｌｕｂｒｉｃａｔｉｏｎ Ｍｕｅｎｃｈｅｎ ＳＥ ＆ Ｃｏ．ＫＧ | 新規エステル化合物、それらの製造方法ならびにそれらの使用 |
| JP2023553779A (ja) * | 2021-11-18 | 2023-12-26 | ケーティー アンド ジー コーポレイション | 新規な香味剤を含む喫煙物品｛ｓｍｏｋｉｎｇ ａｒｔｉｃｌｅ ｃｏｍｐｒｉｓｉｎｇ ｎｅｗ ｆｌａｖｏｒｉｎｇ ａｇｅｎｔ｝ |
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| KR102766839B1 (ko) * | 2021-11-18 | 2025-02-14 | 주식회사 케이티앤지 | 열에 의해 향미 성분이 방출되는 벽지 조성물 및 벽지 |
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| JP2006523244A (ja) * | 2003-04-14 | 2006-10-12 | ジボダン エス エー | フレグランスとして有用なカルバメート類 |
| JP2020510048A (ja) * | 2017-03-29 | 2020-04-02 | クリューバー リュブリケーション ミュンヘン ソシエタス ヨーロピア ウント コンパニー コマンディートゲゼルシャフトＫｌｕｅｂｅｒ Ｌｕｂｒｉｃａｔｉｏｎ Ｍｕｅｎｃｈｅｎ ＳＥ ＆ Ｃｏ．ＫＧ | 新規エステル化合物、それらの製造方法ならびにそれらの使用 |
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Also Published As
| Publication number | Publication date |
|---|---|
| SG75160A1 (en) | 2000-09-19 |
| US20020193269A1 (en) | 2002-12-19 |
| EP1760067A3 (en) | 2007-05-30 |
| US6627763B2 (en) | 2003-09-30 |
| ES2273468T3 (es) | 2007-05-01 |
| EP1760067A2 (en) | 2007-03-07 |
| EP0952142A1 (en) | 1999-10-27 |
| DE69933608D1 (de) | 2006-11-30 |
| EP0952142B1 (en) | 2006-10-18 |
| US6437150B1 (en) | 2002-08-20 |
| DE69933608T2 (de) | 2007-08-23 |
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