JP4038282B2 - 付臭性組成物 - Google Patents
付臭性組成物 Download PDFInfo
- Publication number
- JP4038282B2 JP4038282B2 JP28683998A JP28683998A JP4038282B2 JP 4038282 B2 JP4038282 B2 JP 4038282B2 JP 28683998 A JP28683998 A JP 28683998A JP 28683998 A JP28683998 A JP 28683998A JP 4038282 B2 JP4038282 B2 JP 4038282B2
- Authority
- JP
- Japan
- Prior art keywords
- musk
- mol
- compound
- methyl
- solution
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 40
- 239000003205 fragrance Substances 0.000 claims description 25
- NUSRNVWNTPMBJA-UHFFFAOYSA-N 13-methyl-1-oxacyclopentadec-10-en-2-one Chemical compound CC1CCOC(=O)CCCCCCCC=CC1 NUSRNVWNTPMBJA-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- 150000001875 compounds Chemical class 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 241000402754 Erythranthe moschata Species 0.000 description 23
- 239000012043 crude product Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 17
- 238000010626 work up procedure Methods 0.000 description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 239000002537 cosmetic Substances 0.000 description 8
- 150000002596 lactones Chemical group 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- -1 Polymethylene Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 6
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XFGDAPQOKJYPQP-UHFFFAOYSA-N 1-chloropropane-1,2-diol Chemical compound CC(O)C(O)Cl XFGDAPQOKJYPQP-UHFFFAOYSA-N 0.000 description 4
- 238000007239 Wittig reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000011097 chromatography purification Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- NUSRNVWNTPMBJA-VURMDHGXSA-N (10z)-13-methyl-1-oxacyclopentadec-10-en-2-one Chemical compound CC1CCOC(=O)CCCCCCC\C=C/C1 NUSRNVWNTPMBJA-VURMDHGXSA-N 0.000 description 3
- IFNXWGYZEYSBEW-UHFFFAOYSA-N 10-methyl-oxacyclopentadecan-2-one Chemical compound CC1CCCCCCCC(=O)OCCCCC1 IFNXWGYZEYSBEW-UHFFFAOYSA-N 0.000 description 3
- JUWYRPZTZSWLCY-UHFFFAOYSA-N 5-carboxypentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCC(=O)O)C1=CC=CC=C1 JUWYRPZTZSWLCY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002678 macrocyclic compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- MJBVGUVEKHRPDM-HYXAFXHYSA-N (11z)-1-oxacycloheptadec-11-en-2-one Chemical compound O=C1CCCCCCCC\C=C/CCCCCO1 MJBVGUVEKHRPDM-HYXAFXHYSA-N 0.000 description 2
- BXXMZAVKTPVXLU-CLFYSBASSA-N (5z)-1-oxacyclohexadec-5-en-2-one Chemical compound O=C1CC\C=C/CCCCCCCCCCO1 BXXMZAVKTPVXLU-CLFYSBASSA-N 0.000 description 2
- USYAGNRXEGBFEX-XQRVVYSFSA-N (6z)-1-oxacyclopentadec-6-en-2-one Chemical compound O=C1CCC\C=C/CCCCCCCCO1 USYAGNRXEGBFEX-XQRVVYSFSA-N 0.000 description 2
- LFCDRJNMQLWVDK-NTMALXAHSA-N (6z)-4-methyl-1-oxacyclohexadec-6-en-2-one Chemical compound CC1C\C=C/CCCCCCCCCOC(=O)C1 LFCDRJNMQLWVDK-NTMALXAHSA-N 0.000 description 2
- NVIPUOMWGQAOIT-RQOWECAXSA-N (Z)-7-Hexadecen-1,16-olide Chemical compound O=C1CCCCC\C=C/CCCCCCCCO1 NVIPUOMWGQAOIT-RQOWECAXSA-N 0.000 description 2
- IUYYZXLVJWARRG-NTMALXAHSA-N (z)-15-bromo-3-methylpentadec-5-enoic acid Chemical compound OC(=O)CC(C)C\C=C/CCCCCCCCCBr IUYYZXLVJWARRG-NTMALXAHSA-N 0.000 description 2
- JRVIFIREWVQSDU-UHFFFAOYSA-N 10-bromodecanal Chemical compound BrCCCCCCCCCC=O JRVIFIREWVQSDU-UHFFFAOYSA-N 0.000 description 2
- WNFYJWNAWIJMEL-UHFFFAOYSA-N 10-carboxydecyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCC(=O)O)C1=CC=CC=C1 WNFYJWNAWIJMEL-UHFFFAOYSA-N 0.000 description 2
- CWNWZHGYIJPAJF-UHFFFAOYSA-N 10-methyl-1-oxacyclopentadec-9-en-2-one Chemical compound CC1=CCCCCCCC(=O)OCCCCC1 CWNWZHGYIJPAJF-UHFFFAOYSA-N 0.000 description 2
- AMBKQXOKMUHKGV-UHFFFAOYSA-N 14-hydroxy-7-methyltetradec-6-enoic acid Chemical compound OC(=O)CCCCC=C(C)CCCCCCCO AMBKQXOKMUHKGV-UHFFFAOYSA-N 0.000 description 2
- LFRBTEIFKVKTES-UHFFFAOYSA-N 14-hydroxy-8,12-dimethyltetradec-7-enoic acid Chemical compound OCCC(C)CCCC(C)=CCCCCCC(O)=O LFRBTEIFKVKTES-UHFFFAOYSA-N 0.000 description 2
- WSFGIUKXIGESIV-UHFFFAOYSA-N 14-hydroxy-9-methyltetradec-8-enoic acid Chemical compound CC(CCCCCO)=CCCCCCCC(O)=O WSFGIUKXIGESIV-UHFFFAOYSA-N 0.000 description 2
- VCEBDMAAUOHLIO-UHFFFAOYSA-N 15-methyl-1-oxacycloheptadec-12-en-2-one Chemical compound CC1CCOC(=O)CCCCCCCCCC=CC1 VCEBDMAAUOHLIO-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-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
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- IASRMNRQZIRYHM-UHFFFAOYSA-N 6-carboxyhexyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCC(=O)O)C1=CC=CC=C1 IASRMNRQZIRYHM-UHFFFAOYSA-N 0.000 description 2
- FZBHOQVRBBGPHF-UHFFFAOYSA-N 7-carboxyheptyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCC(=O)O)C1=CC=CC=C1 FZBHOQVRBBGPHF-UHFFFAOYSA-N 0.000 description 2
- VCVZNXWGDGXMLY-UHFFFAOYSA-N 7-methyl-1-oxacyclohexadec-6-en-2-one Chemical compound CC1=CCCCC(=O)OCCCCCCCCC1 VCVZNXWGDGXMLY-UHFFFAOYSA-N 0.000 description 2
- KPSRRRHHYOTMEU-UHFFFAOYSA-N 8-carboxyoctyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCC(=O)O)C1=CC=CC=C1 KPSRRRHHYOTMEU-UHFFFAOYSA-N 0.000 description 2
- WDCLUMRMLMFXCD-UHFFFAOYSA-N 9,13-dimethyl-1-oxacyclopentadec-8-en-2-one Chemical compound CC1CCCC(C)=CCCCCCC(=O)OCC1 WDCLUMRMLMFXCD-UHFFFAOYSA-N 0.000 description 2
- JEFWDMFCGYSDHL-UHFFFAOYSA-N 9,13-dimethyl-oxacyclopentadecan-2-one Chemical compound CC1CCCCCCC(=O)OCCC(C)CCC1 JEFWDMFCGYSDHL-UHFFFAOYSA-N 0.000 description 2
- HQVHZUJAAKTDQH-UHFFFAOYSA-N 9-hydroxynonan-2-one Chemical compound CC(=O)CCCCCCCO HQVHZUJAAKTDQH-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QILMAYXCYBTEDM-IWQZZHSRSA-N Isoambrettolide Chemical compound O=C1CCCCCCC\C=C/CCCCCCO1 QILMAYXCYBTEDM-IWQZZHSRSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000019568 aromas Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 125000000686 lactone group Chemical group 0.000 description 2
- 238000007273 lactonization reaction Methods 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- OYMOMDQCVLFYGQ-UHFFFAOYSA-N methyl 14-hydroxy-7-methylpentadec-6-enoate Chemical compound COC(=O)CCCCC=C(C)CCCCCCC(C)O OYMOMDQCVLFYGQ-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000001738 pogostemon cablin oil Substances 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 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
- QILMAYXCYBTEDM-HNQUOIGGSA-N (10e)-1-oxacycloheptadec-10-en-2-one Chemical compound O=C1CCCCCCC\C=C\CCCCCCO1 QILMAYXCYBTEDM-HNQUOIGGSA-N 0.000 description 1
- ZYXGECMFJMLZNA-SOFGYWHQSA-N (12e)-1-oxacyclohexadec-12-en-2-one Chemical compound O=C1CCCCCCCCC\C=C\CCCO1 ZYXGECMFJMLZNA-SOFGYWHQSA-N 0.000 description 1
- KFHHBWJZXNKNGE-ALCCZGGFSA-N (12z)-1-oxacycloheptadec-12-en-2-one Chemical compound O=C1CCCCCCCCC\C=C/CCCCO1 KFHHBWJZXNKNGE-ALCCZGGFSA-N 0.000 description 1
- XWCWYOGCIDZQFF-CLFYSBASSA-N (13z)-1-oxacycloheptadec-13-en-2-one Chemical compound O=C1CCCCCCCCCC\C=C/CCCO1 XWCWYOGCIDZQFF-CLFYSBASSA-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
- PEIGDAJJNZNVBO-UHFFFAOYSA-N (3-methyl-5-oxopentyl) acetate Chemical compound O=CCC(C)CCOC(C)=O PEIGDAJJNZNVBO-UHFFFAOYSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- GYAOTYXYOKZNEJ-UHFFFAOYSA-N (4-carboxy-3-methylbutyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC(C)CC(O)=O)C1=CC=CC=C1 GYAOTYXYOKZNEJ-UHFFFAOYSA-N 0.000 description 1
- ICQIZCGGONTBTM-UHFFFAOYSA-N (5-acetyloxy-3-methylpentyl) acetate Chemical compound CC(=O)OCCC(C)CCOC(C)=O ICQIZCGGONTBTM-UHFFFAOYSA-N 0.000 description 1
- HMHWFDWPYUEHTN-UHFFFAOYSA-N (5-hydroxy-3-methylpentyl) acetate Chemical compound OCCC(C)CCOC(C)=O HMHWFDWPYUEHTN-UHFFFAOYSA-N 0.000 description 1
- HMWPDRYGIBLSHB-XQRVVYSFSA-N (7z)-1-oxacycloheptadec-7-en-2-one Chemical compound O=C1CCCC\C=C/CCCCCCCCCO1 HMWPDRYGIBLSHB-XQRVVYSFSA-N 0.000 description 1
- AWJGKZUXZITPIZ-KAMYIIQDSA-N (7z)-8-methyl-1-oxacyclopentadec-7-en-2-one Chemical compound C\C1=C\CCCCC(=O)OCCCCCCC1 AWJGKZUXZITPIZ-KAMYIIQDSA-N 0.000 description 1
- KFGBSCFOJPHENY-UPHRSURJSA-N (9z)-1-oxacycloheptadec-9-en-2-one Chemical compound O=C1CCCCCC\C=C/CCCCCCCO1 KFGBSCFOJPHENY-UPHRSURJSA-N 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
- HKVHXCLQVGBOBY-CLFYSBASSA-N (z)-15-bromopentadec-4-enoic acid Chemical compound OC(=O)CC\C=C/CCCCCCCCCCBr HKVHXCLQVGBOBY-CLFYSBASSA-N 0.000 description 1
- GPTUUMAGTKZYRF-IWQZZHSRSA-N (z)-16-bromohexadec-9-enoic acid Chemical compound OC(=O)CCCCCCC\C=C/CCCCCCBr GPTUUMAGTKZYRF-IWQZZHSRSA-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
- MKEIDVFLAWJKMY-UHFFFAOYSA-N 1,7-dioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCCCCO1 MKEIDVFLAWJKMY-UHFFFAOYSA-N 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
- 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
- ITXAKAYTXBTIFX-UHFFFAOYSA-N 1-hydroxyundecan-2-one Chemical compound CCCCCCCCCC(=O)CO ITXAKAYTXBTIFX-UHFFFAOYSA-N 0.000 description 1
- XWCWYOGCIDZQFF-UHFFFAOYSA-N 1-oxacycloheptadec-13-en-2-one Chemical compound O=C1CCCCCCCCCCC=CCCCO1 XWCWYOGCIDZQFF-UHFFFAOYSA-N 0.000 description 1
- AITOWGRDMYKLTB-UHFFFAOYSA-N 1-oxacycloheptadec-6-en-2-one Chemical compound O=C1CCCC=CCCCCCCCCCCO1 AITOWGRDMYKLTB-UHFFFAOYSA-N 0.000 description 1
- MTTKFVBUVGIIIF-UHFFFAOYSA-N 1-oxacyclohexadec-11-en-2-one Chemical compound O=C1CCCCCCCCC=CCCCCO1 MTTKFVBUVGIIIF-UHFFFAOYSA-N 0.000 description 1
- TXIFFCXBKFWXFJ-UHFFFAOYSA-N 11-bromoundecanal Chemical compound BrCCCCCCCCCCC=O TXIFFCXBKFWXFJ-UHFFFAOYSA-N 0.000 description 1
- KUJPLLZKKCBLDR-UHFFFAOYSA-N 11-carboxyundecyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCC(=O)O)C1=CC=CC=C1 KUJPLLZKKCBLDR-UHFFFAOYSA-N 0.000 description 1
- KXMAQDRCOQTPEP-UHFFFAOYSA-N 14-hydroxy-7-methylpentadec-6-enoic acid Chemical compound CC(O)CCCCCCC(C)=CCCCCC(O)=O KXMAQDRCOQTPEP-UHFFFAOYSA-N 0.000 description 1
- UFZKGJDPVUFUBL-UHFFFAOYSA-N 16-chlorohexadec-12-enoic acid Chemical compound OC(=O)CCCCCCCCCCC=CCCCCl UFZKGJDPVUFUBL-UHFFFAOYSA-N 0.000 description 1
- 150000007548 17-membered macrocycles Chemical class 0.000 description 1
- HMWPDRYGIBLSHB-UHFFFAOYSA-N 17-oxacycloheptadec-6-en-1-one Chemical compound O=C1CCCCC=CCCCCCCCCCO1 HMWPDRYGIBLSHB-UHFFFAOYSA-N 0.000 description 1
- ORHSGDMSYGKJJY-UHFFFAOYSA-N 2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound CC1CCC(C2(C)C)C2C11COC(C)(C)OC1 ORHSGDMSYGKJJY-UHFFFAOYSA-N 0.000 description 1
- NKVJKVMGJABKHV-UHFFFAOYSA-N 3-carboxypropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC(=O)O)C1=CC=CC=C1 NKVJKVMGJABKHV-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
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- CQXDPVRLSFREOB-UHFFFAOYSA-N 4-methyl-oxacyclohexadecan-2-one Chemical compound CC1CCCCCCCCCCCCOC(=O)C1 CQXDPVRLSFREOB-UHFFFAOYSA-N 0.000 description 1
- IIRRBSSXLQFMDU-UHFFFAOYSA-N 6-methylpentadec-5-enoic acid Chemical compound CCCCCCCCCC(C)=CCCCC(O)=O IIRRBSSXLQFMDU-UHFFFAOYSA-N 0.000 description 1
- UXHBEJHWPUSRJH-UHFFFAOYSA-N 7-bromoheptanal Chemical compound BrCCCCCCC=O UXHBEJHWPUSRJH-UHFFFAOYSA-N 0.000 description 1
- GHBTZUIMOPVXAV-UHFFFAOYSA-N 7-hydroxyheptan-2-one Chemical compound CC(=O)CCCCCO GHBTZUIMOPVXAV-UHFFFAOYSA-N 0.000 description 1
- WJHJXCAQXYKVHX-UHFFFAOYSA-N 7-methyl-oxacyclohexadecan-2-one Chemical compound CC1CCCCCCCCCOC(=O)CCCC1 WJHJXCAQXYKVHX-UHFFFAOYSA-N 0.000 description 1
- DETKMHVWNMOSRN-UHFFFAOYSA-N 8-bromooctanal Chemical compound BrCCCCCCCC=O DETKMHVWNMOSRN-UHFFFAOYSA-N 0.000 description 1
- AWJGKZUXZITPIZ-UHFFFAOYSA-N 8-methyl-1-oxacyclopentadec-7-en-2-one Chemical compound CC1=CCCCCC(=O)OCCCCCCC1 AWJGKZUXZITPIZ-UHFFFAOYSA-N 0.000 description 1
- YNWWJGZENANFOC-UHFFFAOYSA-N 9-hydroxydecan-2-one Chemical compound CC(O)CCCCCCC(C)=O YNWWJGZENANFOC-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- JFHRZFXGTBFINI-UHFFFAOYSA-N CC(CCCCCCCO)=CCCCCC Chemical compound CC(CCCCCCCO)=CCCCCC JFHRZFXGTBFINI-UHFFFAOYSA-N 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 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
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- VJYFMQREUJXCQV-UHFFFAOYSA-N Limonene aldehyde Chemical compound O=CCC(C)C1CCC(C)=CC1 VJYFMQREUJXCQV-UHFFFAOYSA-N 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- SUAUILGSCPYJCS-UHFFFAOYSA-N Musk ambrette Chemical compound COC1=C([N+]([O-])=O)C(C)=C([N+]([O-])=O)C=C1C(C)(C)C SUAUILGSCPYJCS-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- GPCOYPLKJNMTJX-UHFFFAOYSA-N acetyl 3-methyl-5-oxopentanoate Chemical compound O=CCC(C)CC(=O)OC(C)=O GPCOYPLKJNMTJX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 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
- 238000004458 analytical method Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical class CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ODGMPRNNVXITJQ-UHFFFAOYSA-N ethyl 6-acetyloxyhexanoate Chemical compound CCOC(=O)CCCCCOC(C)=O ODGMPRNNVXITJQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-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
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- SIYAUEFISWYMHE-UHFFFAOYSA-N methyl 14-hydroxy-7-methyltetradec-6-enoate Chemical compound COC(=O)CCCCC=C(C)CCCCCCCO SIYAUEFISWYMHE-UHFFFAOYSA-N 0.000 description 1
- MMRFTCPPIOEGLJ-UHFFFAOYSA-N methyl 16-hydroxy-14-methylhexadec-11-enoate Chemical compound COC(=O)CCCCCCCCCC=CCC(C)CCO MMRFTCPPIOEGLJ-UHFFFAOYSA-N 0.000 description 1
- CEGLUAJHVSSTTB-UHFFFAOYSA-N methyl 16-hydroxyhexadec-11-enoate Chemical compound COC(=O)CCCCCCCCCC=CCCCCO CEGLUAJHVSSTTB-UHFFFAOYSA-N 0.000 description 1
- KRFVOPIKLNHWEE-UHFFFAOYSA-N methyl 6-methylpentadec-5-enoate Chemical compound CCCCCCCCCC(C)=CCCCC(=O)OC KRFVOPIKLNHWEE-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- CELWCAITJAEQNL-UHFFFAOYSA-N oxan-2-ol Chemical compound OC1CCCCO1 CELWCAITJAEQNL-UHFFFAOYSA-N 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-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
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH19972362/97 | 1997-10-09 | ||
| CH236297 | 1997-10-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11193395A JPH11193395A (ja) | 1999-07-21 |
| JPH11193395A5 JPH11193395A5 (enExample) | 2005-10-27 |
| JP4038282B2 true JP4038282B2 (ja) | 2008-01-23 |
Family
ID=4232025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28683998A Expired - Lifetime JP4038282B2 (ja) | 1997-10-09 | 1998-10-08 | 付臭性組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6255276B1 (enExample) |
| EP (1) | EP0908455B1 (enExample) |
| JP (1) | JP4038282B2 (enExample) |
| AU (1) | AU748249B2 (enExample) |
| BR (1) | BR9803887A (enExample) |
| CA (1) | CA2249843A1 (enExample) |
| DE (1) | DE59804713D1 (enExample) |
| ES (1) | ES2179409T3 (enExample) |
| SG (1) | SG78320A1 (enExample) |
| ZA (1) | ZA989210B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1481049A1 (en) * | 2002-02-23 | 2004-12-01 | Symrise GmbH & Co. KG | Malodor counteracting composition |
| CN1874749A (zh) * | 2003-11-04 | 2006-12-06 | 宝洁公司 | 包含残留谐香剂的芳香剂 |
| CN1976914B (zh) * | 2004-04-30 | 2012-07-04 | 曾田香料株式会社 | 11-甲基-13-十三内酯、12-甲基-14-十四内酯以及13-甲基-15-十五内酯,包含它们的香料组合物、以及包含它们的化合物的制造方法 |
| GB0506263D0 (en) * | 2005-03-29 | 2005-05-04 | Givaudan Sa | Skin lightening methods, composition and products |
| US7485668B2 (en) | 2005-04-14 | 2009-02-03 | International Flavors & Fragrances Inc. | Cyclopropanated macrocyclic ketones and lactones |
| DE502007003130D1 (de) * | 2007-01-02 | 2010-04-29 | Symrise Gmbh & Co Kg | Mischungen mit 3-(4-Methyl-cyclohex-3-enyl)-butyraldehyd und 2,6-Dimethyl-7-octen-2-ol |
| GB0718806D0 (en) * | 2007-09-27 | 2007-11-07 | Givaudan Sa | Organic compounds |
| KR101438368B1 (ko) * | 2007-11-19 | 2014-09-12 | (주)아모레퍼시픽 | 인삼꽃의 향취를 재현한 향료 조성물 |
| JP5474360B2 (ja) * | 2009-01-13 | 2014-04-16 | 花王株式会社 | 新規大環状ラクトン |
| BR112012004809A2 (pt) * | 2009-09-02 | 2016-03-15 | Takasago Perfumery Co Ltd | 7,10,13-ciclohexadecatrien-16-olídeo e composição de sabor ou de fragância, fragância ou produto cosméticos, produto alimentar ou bebida ou produto de toalete compreendendo o mesmo |
| JP2012211099A (ja) * | 2011-03-31 | 2012-11-01 | Takasago Internatl Corp | 香粧品用香料組成物 |
| EP2662098B1 (de) | 2012-05-10 | 2018-10-24 | Symrise AG | Verwendung bestimmter Verbindungen zum Verändern von Gerüchen |
| EP2895470B1 (de) * | 2012-09-14 | 2020-02-12 | Symrise AG | Ungesättigte lactone als riechstoffe |
| JP6189773B2 (ja) | 2013-03-19 | 2017-08-30 | 花王株式会社 | 13−メチル−9−シクロペンタデセン−15−オリド |
| GB201404468D0 (en) * | 2014-03-13 | 2014-04-30 | Givaudan Sa | Process |
| EP2966158B2 (de) | 2014-07-07 | 2024-03-13 | Symrise AG | Isomerenmischungen von ungesättigten makrocyclischen Moschusverbindungen |
| EP3237372B1 (en) * | 2014-12-26 | 2021-01-20 | Kao Corporation | Method for producing omega-hydroxy fatty acid ester and precursor compound thereof |
| EP3303315A1 (de) * | 2015-05-29 | 2018-04-11 | Basf Se | Verfahren zur herstellung cyclischer ester |
| JP2017122101A (ja) * | 2017-02-17 | 2017-07-13 | シムライズ アーゲー | 香気物質としての不飽和ラクトン |
| EP3778843A4 (en) * | 2018-04-02 | 2021-12-22 | Kao Corporation | MUSK-TYPE COMPOSITION |
| EP3561029A1 (en) | 2018-04-27 | 2019-10-30 | Basf Se | Esters and ethers of 3-methyl-pentan-diol and unsaturated derivates thereof and their use as aroma chemical |
| FR3108608A1 (fr) * | 2020-03-27 | 2021-10-01 | Global Bioenergies | Oléfines ramifiées fonctionnalisées et leur procédé de préparation |
| KR102679049B1 (ko) * | 2021-08-23 | 2024-07-01 | 주식회사 엘지생활건강 | 살냄새 향취를 구현한 향료 조성물 |
| WO2024022574A1 (en) * | 2022-07-26 | 2024-02-01 | Symrise Ag | Biotechnological production of macrocyclic lactones |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2234551A (en) * | 1941-03-11 | Preparation of lactones | ||
| GB490044A (en) | 1937-01-04 | 1938-08-04 | Givaudan & Cie Sa | Improvements in or relating to the preparation of lactones |
| NL188920B (enExample) | 1954-07-02 | 1956-10-15 | Honeywell Information Systems Inc. Te Waltham, Massachusetts, Ver. St. V. Am. | |
| US3681395A (en) * | 1970-03-11 | 1972-08-01 | Int Flavors & Fragrances Inc | Preparation of ambrettolide |
| US4014902A (en) * | 1976-06-09 | 1977-03-29 | International Flavors & Fragrances Inc. | Intermediate in the process for the preparation of trans-Δ9 -isoambrettolide |
| US4541950A (en) * | 1983-07-18 | 1985-09-17 | International Flavors & Fragrances Inc. | Use of macrocyclic lactone in augmenting or enhancing aroma or taste of consumable materials |
| CA1221105A (en) * | 1983-09-16 | 1987-04-28 | Alfred H. Dougan | Omega halogenated fatty acids |
| EP0424787B1 (fr) * | 1989-10-27 | 1996-10-02 | Firmenich Sa | Utilisation de lactones macrocycliques insaturées à titre d'ingrédients parfumants |
| US5266559A (en) | 1989-10-27 | 1993-11-30 | Firmenich S.A. | Use of unsaturated macrocyclic lactones as perfuming ingredients |
| JPH08190076A (ja) * | 1995-01-11 | 1996-07-23 | Canon Inc | 画像形成装置 |
| US5792740A (en) * | 1996-03-08 | 1998-08-11 | Firmenich Sa | Fragrant macrocyclic lactones |
| US5726328A (en) * | 1996-07-09 | 1998-03-10 | V. Mane Fils S.A. | Preparation of cis-isoambrettolides and their use as a fragrance |
-
1998
- 1998-10-05 EP EP98118789A patent/EP0908455B1/de not_active Expired - Lifetime
- 1998-10-05 ES ES98118789T patent/ES2179409T3/es not_active Expired - Lifetime
- 1998-10-05 DE DE59804713T patent/DE59804713D1/de not_active Expired - Lifetime
- 1998-10-07 AU AU88358/98A patent/AU748249B2/en not_active Ceased
- 1998-10-08 CA CA002249843A patent/CA2249843A1/en not_active Abandoned
- 1998-10-08 JP JP28683998A patent/JP4038282B2/ja not_active Expired - Lifetime
- 1998-10-08 ZA ZA989210A patent/ZA989210B/xx unknown
- 1998-10-08 SG SG1998004139A patent/SG78320A1/en unknown
- 1998-10-09 BR BR9803887-7A patent/BR9803887A/pt active IP Right Grant
-
2000
- 2000-02-16 US US09/504,471 patent/US6255276B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU8835898A (en) | 1999-05-06 |
| SG78320A1 (en) | 2001-02-20 |
| US6255276B1 (en) | 2001-07-03 |
| ES2179409T3 (es) | 2003-01-16 |
| EP0908455A1 (de) | 1999-04-14 |
| DE59804713D1 (de) | 2002-08-14 |
| BR9803887A (pt) | 2000-03-28 |
| JPH11193395A (ja) | 1999-07-21 |
| AU748249B2 (en) | 2002-05-30 |
| EP0908455B1 (de) | 2002-07-10 |
| CA2249843A1 (en) | 1999-04-09 |
| ZA989210B (en) | 1999-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4038282B2 (ja) | 付臭性組成物 | |
| JPS6133005B2 (enExample) | ||
| JP5479466B2 (ja) | 匂い物質として適するイソロンギホラニル誘導体 | |
| EP0746552B1 (en) | Tetrahydrofurans and tetrahydropyrans | |
| SG194518A1 (en) | Terpene alcohols for use in fragrance compositions and perfumed products | |
| RU2482108C2 (ru) | Замещенные октан(ен)нитрилы, способ их получения и их применение в парфюмерии | |
| JPH05246917A (ja) | 新規有香物質 | |
| JP2610309B2 (ja) | 新規香料 | |
| CN101945985B (zh) | 有机化合物 | |
| MX2009001378A (es) | Derivados de ciclopentano/ciclopenteno aldehido o cetona y su uso como odorizantes. | |
| JPH06305999A (ja) | 着臭剤組成物 | |
| JP2010512347A (ja) | シクロヘキセニルブテノンおよびそれらを含むフレグランス組成物 | |
| EP1321508B1 (en) | Fragrance composition containing 3-(3-Hexenyl)-2-cyclopentenone | |
| JP4676880B2 (ja) | シクロオクト−(エン−)イル誘導体の香料としての使用 | |
| JPH05262757A (ja) | 環状イソロンギホラノン−ケタール類、その製法及び使用法 | |
| EP0882697B1 (fr) | Composés parfumants à odeur boisée, fruitée | |
| JP3574861B2 (ja) | 3−(3−へキセニル)−2−シクロペンテノンを含有する香料組成物 | |
| JP4859826B2 (ja) | フレグランス組成物の製造に好適な三置換フラン | |
| US5326748A (en) | Cyclic alcohols and their use as perfuming ingredients | |
| US6043210A (en) | Preparation of thiamacrolide compounds | |
| JP4751884B2 (ja) | 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 | |
| JPH01160936A (ja) | 新規な発香化合物 | |
| WO1980000839A1 (en) | Novel norcamphanyl-substituted pyrans,method for their synthesis and use thereof in perfumery | |
| JP2004527502A (ja) | 2,3,5,5−テトラメチルヘキサナール誘導体 | |
| MXPA98008318A (en) | Perfume compositions containing macrocic |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050830 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050830 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070614 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070626 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070914 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20070914 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20071030 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20071105 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101109 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111109 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111109 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121109 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121109 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131109 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |