MX2012013954A - 1-hidroxi-octahidroazulenos como fragancias. - Google Patents
1-hidroxi-octahidroazulenos como fragancias.Info
- Publication number
- MX2012013954A MX2012013954A MX2012013954A MX2012013954A MX2012013954A MX 2012013954 A MX2012013954 A MX 2012013954A MX 2012013954 A MX2012013954 A MX 2012013954A MX 2012013954 A MX2012013954 A MX 2012013954A MX 2012013954 A MX2012013954 A MX 2012013954A
- Authority
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- Mexico
- Prior art keywords
- carbon
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- formula
- Prior art date
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 14
- SSKPLWCMVWTKGA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,7-octahydroazulen-1-ol Chemical class C1CCCC=C2C(O)CCC21 SSKPLWCMVWTKGA-UHFFFAOYSA-N 0.000 title 1
- 108010029541 Laccase Proteins 0.000 claims abstract description 23
- 239000000796 flavoring agent Substances 0.000 claims abstract description 21
- 235000019634 flavors Nutrition 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 30
- 239000001738 pogostemon cablin oil Substances 0.000 claims description 22
- 239000003921 oil Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- GGHMUJBZYLPWFD-UHFFFAOYSA-N patchoulialcohol Chemical compound C1CC2(C)C3(O)CCC(C)C2CC1C3(C)C GGHMUJBZYLPWFD-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 235000011751 Pogostemon cablin Nutrition 0.000 claims description 7
- GGHMUJBZYLPWFD-MYYUVRNCSA-N Patchouli alcohol Natural products O[C@@]12C(C)(C)[C@H]3C[C@H]([C@H](C)CC1)[C@]2(C)CC3 GGHMUJBZYLPWFD-MYYUVRNCSA-N 0.000 claims description 5
- 241000222666 Boerhavia diffusa Species 0.000 claims 1
- 239000004615 ingredient Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 19
- -1 ethanol) Chemical compound 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- NUWMTBMCSQWPDG-SDDRHHMPSA-N Rotundone Chemical compound C1([C@H](CC[C@H](C2)C(C)=C)C)=C2[C@@H](C)CC1=O NUWMTBMCSQWPDG-SDDRHHMPSA-N 0.000 description 9
- NUWMTBMCSQWPDG-UHFFFAOYSA-N Rotundone Natural products C1C(C(C)=C)CCC(C)C2=C1C(C)CC2=O NUWMTBMCSQWPDG-UHFFFAOYSA-N 0.000 description 9
- 230000005587 bubbling Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 description 7
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 6
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- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 6
- 244000061176 Nicotiana tabacum Species 0.000 description 6
- 240000002505 Pogostemon cablin Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- NVEQFIOZRFFVFW-RGCMKSIDSA-N caryophyllene oxide Chemical compound C=C1CC[C@H]2O[C@]2(C)CC[C@H]2C(C)(C)C[C@@H]21 NVEQFIOZRFFVFW-RGCMKSIDSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 description 6
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- 238000004821 distillation Methods 0.000 description 5
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- FMAMZCDLBGIMFZ-CRWXNKLISA-N (1s,3s,3as,5r)-3,8-dimethyl-5-prop-1-en-2-yl-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol Chemical compound C1C[C@@H](C(C)=C)C[C@H]2[C@@H](C)C[C@H](O)C2=C1C FMAMZCDLBGIMFZ-CRWXNKLISA-N 0.000 description 4
- PYNOUJREBZBBTE-FMSGJZPZSA-N (1s,3s,5r,8s)-3,8-dimethyl-5-prop-1-en-2-yl-1,2,3,4,5,6,7,8-octahydroazulen-1-ol Chemical compound C1([C@H](CC[C@H](C2)C(C)=C)C)=C2[C@@H](C)C[C@@H]1O PYNOUJREBZBBTE-FMSGJZPZSA-N 0.000 description 4
- CKTOECQMCPFOEU-XQQFMLRXSA-N (3s,3as,5r)-3,8-dimethyl-5-prop-1-en-2-yl-3,3a,4,5,6,7-hexahydro-2h-azulen-1-one Chemical compound C1C[C@@H](C(C)=C)C[C@H]2[C@@H](C)CC(=O)C2=C1C CKTOECQMCPFOEU-XQQFMLRXSA-N 0.000 description 4
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 4
- 235000002566 Capsicum Nutrition 0.000 description 4
- 239000006002 Pepper Substances 0.000 description 4
- 235000016761 Piper aduncum Nutrition 0.000 description 4
- 240000003889 Piper guineense Species 0.000 description 4
- 235000017804 Piper guineense Nutrition 0.000 description 4
- 235000008184 Piper nigrum Nutrition 0.000 description 4
- 244000235659 Rubus idaeus Species 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- YXCPDVDLUQEPKX-UHFFFAOYSA-N 2h-azulen-1-one Chemical compound C1=CC=CC=C2C(=O)CC=C21 YXCPDVDLUQEPKX-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 description 3
- 239000007836 KH2PO4 Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 3
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 description 3
- RSYBQKUNBFFNDO-UHFFFAOYSA-N caryophyllene oxide Natural products CC1(C)CC2C(=C)CCC3OC3(C)CCC12C RSYBQKUNBFFNDO-UHFFFAOYSA-N 0.000 description 3
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 3
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- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 3
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 3
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- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
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- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229960003598 promazine Drugs 0.000 description 1
- XCWPXUNHSPOFGV-UHFFFAOYSA-N prop-2-enyl 2-(3-methylbutoxy)acetate Chemical compound CC(C)CCOCC(=O)OCC=C XCWPXUNHSPOFGV-UHFFFAOYSA-N 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000001290 saussurea lappa clarke root oil Substances 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-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
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
-
- 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
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
-
- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/34—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (5.3.0.) system, e.g. azulenols
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10167739A EP2402301A1 (en) | 2010-06-29 | 2010-06-29 | 1-hydroxy-octahydroazulenes as fragrances |
| PCT/EP2011/060862 WO2012001018A1 (en) | 2010-06-29 | 2011-06-28 | 1-hydroxy-octahydroazulenes as fragrances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2012013954A true MX2012013954A (es) | 2013-01-24 |
Family
ID=43066824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2012013954A MX2012013954A (es) | 2010-06-29 | 2011-06-28 | 1-hidroxi-octahidroazulenos como fragancias. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8883468B2 (enExample) |
| EP (2) | EP2402301A1 (enExample) |
| JP (1) | JP5758000B2 (enExample) |
| CN (1) | CN102958885B (enExample) |
| BR (1) | BR112012033493B1 (enExample) |
| DK (1) | DK2588436T3 (enExample) |
| ES (1) | ES2574727T3 (enExample) |
| MX (1) | MX2012013954A (enExample) |
| SG (1) | SG185732A1 (enExample) |
| WO (1) | WO2012001018A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201300073D0 (en) * | 2013-01-03 | 2013-02-20 | Givaudan Sa | Process |
| JP6262171B2 (ja) * | 2015-04-09 | 2018-01-17 | 長谷川香料株式会社 | 果実香味増強剤 |
| JP6262170B2 (ja) * | 2015-04-09 | 2018-01-17 | 長谷川香料株式会社 | 柑橘香味増強剤 |
| JP6522551B2 (ja) * | 2016-06-10 | 2019-05-29 | 長谷川香料株式会社 | （−）−ロタンドンの製造方法 |
| US11028034B2 (en) * | 2017-02-27 | 2021-06-08 | Symrise Ag | Method for producing rotundone-containing mixtures |
| EP3495489A1 (en) | 2017-12-05 | 2019-06-12 | Givaudan SA | Production of guaiene and rotundone |
| GB201720211D0 (en) | 2017-12-05 | 2018-01-17 | Givaudan Sa | Improvements in or relating to organic compounds |
| GB201902566D0 (en) | 2019-02-26 | 2019-04-10 | Givaudan Finance Sa | Improvements in or relating to organic compounds |
| US20220136015A1 (en) * | 2019-03-01 | 2022-05-05 | T. Hasegawa Co., Ltd. | Method for producing oxygen adduct of sesquiterpene,compound and composition |
| CN110373395B (zh) * | 2019-06-05 | 2021-03-26 | 中国农业科学院北京畜牧兽医研究所 | 提高漆酶对真菌毒素降解率的薰衣草介体及其应用 |
| JP6868086B1 (ja) * | 2019-12-18 | 2021-05-12 | 小川香料株式会社 | ロタンドンを有効成分とする香味発現増強剤 |
| GB202115380D0 (en) | 2021-10-26 | 2021-12-08 | Givaudan Sa | Organic compounds |
| GB202401544D0 (en) * | 2024-02-06 | 2024-03-20 | Givaudan Sa | Process |
| WO2025176279A1 (en) | 2024-02-19 | 2025-08-28 | Symrise Ag | Process for the refinement of essential oils by treatment with nitric and acetic acid |
| CN118374316B (zh) * | 2024-06-26 | 2024-08-23 | 中国林业科学研究院木材工业研究所 | 一种分级预处理提取沉香精油和沉香油的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0477444A (ja) * | 1990-07-17 | 1992-03-11 | Shiono Koryo Kk | 新規グアイアー１（１０），１１―ジエン誘導体およびそれを含有する香料組成物 |
| JP2661506B2 (ja) | 1993-06-18 | 1997-10-08 | 日本電気株式会社 | 復調回路 |
-
2010
- 2010-06-29 EP EP10167739A patent/EP2402301A1/en not_active Withdrawn
-
2011
- 2011-06-28 CN CN201180029245.1A patent/CN102958885B/zh active Active
- 2011-06-28 SG SG2012086328A patent/SG185732A1/en unknown
- 2011-06-28 MX MX2012013954A patent/MX2012013954A/es active IP Right Grant
- 2011-06-28 WO PCT/EP2011/060862 patent/WO2012001018A1/en not_active Ceased
- 2011-06-28 JP JP2013517258A patent/JP5758000B2/ja active Active
- 2011-06-28 EP EP11728628.6A patent/EP2588436B1/en active Active
- 2011-06-28 BR BR112012033493-0A patent/BR112012033493B1/pt active IP Right Grant
- 2011-06-28 ES ES11728628.6T patent/ES2574727T3/es active Active
- 2011-06-28 DK DK11728628.6T patent/DK2588436T3/en active
- 2011-06-28 US US13/703,761 patent/US8883468B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5758000B2 (ja) | 2015-08-05 |
| CN102958885A (zh) | 2013-03-06 |
| EP2588436B1 (en) | 2016-03-09 |
| US20130089904A1 (en) | 2013-04-11 |
| CN102958885B (zh) | 2015-07-01 |
| SG185732A1 (en) | 2013-01-30 |
| JP2013534927A (ja) | 2013-09-09 |
| EP2402301A1 (en) | 2012-01-04 |
| DK2588436T3 (en) | 2016-06-20 |
| BR112012033493B1 (pt) | 2020-02-11 |
| US8883468B2 (en) | 2014-11-11 |
| ES2574727T3 (es) | 2016-06-21 |
| BR112012033493A2 (pt) | 2016-11-29 |
| WO2012001018A1 (en) | 2012-01-05 |
| EP2588436A1 (en) | 2013-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |