ES2574727T3 - 1-Hidroxi-octahidroazulenos como fragancias - Google Patents
1-Hidroxi-octahidroazulenos como fragancias Download PDFInfo
- Publication number
- ES2574727T3 ES2574727T3 ES11728628.6T ES11728628T ES2574727T3 ES 2574727 T3 ES2574727 T3 ES 2574727T3 ES 11728628 T ES11728628 T ES 11728628T ES 2574727 T3 ES2574727 T3 ES 2574727T3
- Authority
- ES
- Spain
- Prior art keywords
- carbon
- bond
- dotted line
- line together
- formula
- 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.)
- Active
Links
- 239000003205 fragrance Substances 0.000 title claims description 23
- 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 description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 20
- 108010029541 Laccase Proteins 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- ADIDQIZBYUABQK-UHFFFAOYSA-N α-guaiene Chemical compound C1C(C(C)=C)CCC(C)C2=C1C(C)CC2 ADIDQIZBYUABQK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 72
- 239000000796 flavoring agent Substances 0.000 claims description 30
- 235000019634 flavors Nutrition 0.000 claims description 30
- 239000001738 pogostemon cablin oil Substances 0.000 claims description 19
- 239000003921 oil Substances 0.000 claims description 15
- GGHMUJBZYLPWFD-UHFFFAOYSA-N patchoulialcohol Chemical compound C1CC2(C)C3(O)CCC(C)C2CC1C3(C)C GGHMUJBZYLPWFD-UHFFFAOYSA-N 0.000 claims description 12
- 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
- 239000000047 product Substances 0.000 description 32
- 229910052799 carbon Inorganic materials 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- -1 for example Substances 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 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 12
- NUWMTBMCSQWPDG-UHFFFAOYSA-N Rotundone Natural products C1C(C(C)=C)CCC(C)C2=C1C(C)CC2=O NUWMTBMCSQWPDG-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- 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 8
- 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 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
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 7
- 244000061176 Nicotiana tabacum Species 0.000 description 7
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 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 6
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 6
- 235000002566 Capsicum Nutrition 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000006002 Pepper Substances 0.000 description 6
- 235000016761 Piper aduncum Nutrition 0.000 description 6
- 240000003889 Piper guineense Species 0.000 description 6
- 235000017804 Piper guineense Nutrition 0.000 description 6
- 235000008184 Piper nigrum Nutrition 0.000 description 6
- 235000011751 Pogostemon cablin Nutrition 0.000 description 6
- 240000002505 Pogostemon cablin Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000341 volatile oil Substances 0.000 description 6
- FMAMZCDLBGIMFZ-RFQIPJPRSA-N (1r,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-RFQIPJPRSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000007836 KH2PO4 Substances 0.000 description 4
- 244000235659 Rubus idaeus Species 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 4
- 235000019797 dipotassium phosphate Nutrition 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
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 4
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 4
- 235000019796 monopotassium phosphate Nutrition 0.000 description 4
- GGHMUJBZYLPWFD-CUZKYEQNSA-N patchouli alcohol Chemical compound C1C[C@]2(C)[C@@]3(O)CC[C@H](C)[C@@H]2C[C@@H]1C3(C)C GGHMUJBZYLPWFD-CUZKYEQNSA-N 0.000 description 4
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 4
- 238000000526 short-path distillation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PYNOUJREBZBBTE-CIQGVGRVSA-N (1r,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-CIQGVGRVSA-N 0.000 description 3
- 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 3
- 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 3
- YXCPDVDLUQEPKX-UHFFFAOYSA-N 2h-azulen-1-one Chemical compound C1=CC=CC=C2C(=O)CC=C21 YXCPDVDLUQEPKX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 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
- 238000004458 analytical method Methods 0.000 description 3
- 229910052681 coesite Inorganic materials 0.000 description 3
- 229910052906 cristobalite Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 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
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052682 stishovite Inorganic materials 0.000 description 3
- 229910052905 tridymite Inorganic materials 0.000 description 3
- 239000001069 triethyl citrate Substances 0.000 description 3
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 3
- 235000013769 triethyl citrate Nutrition 0.000 description 3
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 3
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 3
- 235000012141 vanillin Nutrition 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- RNLHVODSMDJCBR-SOFGYWHQSA-N (e)-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-SOFGYWHQSA-N 0.000 description 2
- DWWHYGIACVHWIZ-UHFFFAOYSA-N 1,5,11,11-tetramethyltricyclo[6.2.1.02,6]undec-2(6)-en-3-one Chemical compound C1C(C2(C)C)CCC2(C)C2=C1C(C)CC2=O DWWHYGIACVHWIZ-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 2
- IBHWREHFNDMRPR-UHFFFAOYSA-N 2,4,6-Trihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-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
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NVEQFIOZRFFVFW-UHFFFAOYSA-N Caryophyllene epoxide Chemical compound C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 description 2
- 241000675108 Citrus tangerina Species 0.000 description 2
- XURCUMFVQKJMJP-UHFFFAOYSA-N Dihydro-alpha-guaien Natural products C1C(C(C)C)CCC(C)C2=C1C(C)CC2 XURCUMFVQKJMJP-UHFFFAOYSA-N 0.000 description 2
- HZPKNSYIDSNZKW-UHFFFAOYSA-N Ethyl 2-methylpentanoate Chemical compound CCCC(C)C(=O)OCC HZPKNSYIDSNZKW-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000222418 Lentinus Species 0.000 description 2
- 241000234269 Liliales Species 0.000 description 2
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- 235000011034 Rubus glaucus Nutrition 0.000 description 2
- 235000009122 Rubus idaeus Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- OJOBTAOGJIWAGB-UHFFFAOYSA-N acetosyringone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1O OJOBTAOGJIWAGB-UHFFFAOYSA-N 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- ADIDQIZBYUABQK-RWMBFGLXSA-N alpha-guaiene Chemical compound C1([C@H](CC[C@H](C2)C(C)=C)C)=C2[C@@H](C)CC1 ADIDQIZBYUABQK-RWMBFGLXSA-N 0.000 description 2
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- XWEOGMYZFCHQNT-UHFFFAOYSA-N ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate Chemical compound CCOC(=O)CC1(C)OCCO1 XWEOGMYZFCHQNT-UHFFFAOYSA-N 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229940043353 maltol Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229930007790 rose oxide Natural products 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 229930000038 α-guaiene Natural products 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 1
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
- FAMPSKZZVDUYOS-HRGUGZIWSA-N (1E,4E,8E)-alpha-humulene Chemical compound C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1 FAMPSKZZVDUYOS-HRGUGZIWSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 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
- ZTOJFFHGPLIVKC-YAFCTCPESA-N (2e)-3-ethyl-2-[(z)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound S\1C2=CC(S(O)(=O)=O)=CC=C2N(CC)C/1=N/N=C1/SC2=CC(S(O)(=O)=O)=CC=C2N1CC ZTOJFFHGPLIVKC-YAFCTCPESA-N 0.000 description 1
- OEGPRYNGFWGMMV-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC OEGPRYNGFWGMMV-UHFFFAOYSA-N 0.000 description 1
- 229940098795 (3z)- 3-hexenyl acetate Drugs 0.000 description 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- NVIPUOMWGQAOIT-UHFFFAOYSA-N (E)-7-Hexadecen-16-olide Natural products O=C1CCCCCC=CCCCCCCCCO1 NVIPUOMWGQAOIT-UHFFFAOYSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-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
- DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 description 1
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- YQYKESUTYHZAGG-UHFFFAOYSA-N 1-(1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound C1CC(C(C)=O)(C)C(C)C2=C1CCCC2(C)C YQYKESUTYHZAGG-UHFFFAOYSA-N 0.000 description 1
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- YQYKESUTYHZAGG-BZNIZROVSA-N 1-[(1r,2s)-1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone Chemical compound C1([C@H]([C@@](CC2)(C)C(C)=O)C)=C2CCCC1(C)C YQYKESUTYHZAGG-BZNIZROVSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 229940082044 2,3-dihydroxybenzoic acid Drugs 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- DQBXTWHZXKRCSK-UHFFFAOYSA-N 3-methyl-5-(1,2,2-trimethylcyclopentyl)pentan-2-ol Chemical compound CC(O)C(C)CCC1(C)CCCC1(C)C DQBXTWHZXKRCSK-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- QWRGOHMKGNCVAC-UHFFFAOYSA-N 5,6,7-trimethylocta-2,5-dien-4-one Chemical compound CC=CC(=O)C(C)=C(C)C(C)C QWRGOHMKGNCVAC-UHFFFAOYSA-N 0.000 description 1
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 1
- HRRVLSKRYVIEPR-UHFFFAOYSA-N 6-hydroxy-5-nitroso-1H-pyrimidine-2,4-dione Chemical compound OC1=NC(O)=C(N=O)C(O)=N1 HRRVLSKRYVIEPR-UHFFFAOYSA-N 0.000 description 1
- AWAHFLZWCBUHMX-UHFFFAOYSA-N 7-(3-methylbutyl)-1,5-benzodioxepin-3-one Chemical compound O1CC(=O)COC2=CC(CCC(C)C)=CC=C21 AWAHFLZWCBUHMX-UHFFFAOYSA-N 0.000 description 1
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 1
- NVIPUOMWGQAOIT-DUXPYHPUSA-N 7-hexadecen-1,16-olide Chemical compound O=C1CCCCC\C=C\CCCCCCCCO1 NVIPUOMWGQAOIT-DUXPYHPUSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000271309 Aquilaria crassna Species 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 241000462056 Cestraeus plicatilis Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241000222680 Collybia Species 0.000 description 1
- 241000222511 Coprinus Species 0.000 description 1
- 241000222356 Coriolus Species 0.000 description 1
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 240000002943 Elettaria cardamomum Species 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 241000123326 Fomes Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 1
- 241000721662 Juniperus Species 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000205003 Methanothrix thermoacetophila Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 244000270834 Myristica fragrans Species 0.000 description 1
- 240000005125 Myrtus communis Species 0.000 description 1
- 235000013418 Myrtus communis Nutrition 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 241000221960 Neurospora Species 0.000 description 1
- 241000221961 Neurospora crassa Species 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- 241000222350 Pleurotus Species 0.000 description 1
- 241000221945 Podospora Species 0.000 description 1
- 241000222640 Polyporus Species 0.000 description 1
- 241000789035 Polyporus pinsitus Species 0.000 description 1
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- 235000011552 Rhamnus crocea Nutrition 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 244000178231 Rosmarinus officinalis Species 0.000 description 1
- 241001092459 Rubus Species 0.000 description 1
- 235000014548 Rubus moluccanus Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000222354 Trametes Species 0.000 description 1
- 241000759263 Ventia crocea Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- ZTOJFFHGPLIVKC-CLFAGFIQSA-N abts Chemical compound S/1C2=CC(S(O)(=O)=O)=CC=C2N(CC)C\1=N\N=C1/SC2=CC(S(O)(=O)=O)=CC=C2N1CC ZTOJFFHGPLIVKC-CLFAGFIQSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- JZQOJFLIJNRDHK-CMDGGOBGSA-N alpha-irone Chemical compound CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C JZQOJFLIJNRDHK-CMDGGOBGSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 235000005300 cardamomo Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000001359 coriandrum sativum l. oleoresin Substances 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- WTYGAUXICFETTC-UHFFFAOYSA-N cyclobarbital Chemical compound C=1CCCCC=1C1(CC)C(=O)NC(=O)NC1=O WTYGAUXICFETTC-UHFFFAOYSA-N 0.000 description 1
- 229960004138 cyclobarbital Drugs 0.000 description 1
- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000001567 elettaria cardamomum seed Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000001449 ethyl (2R)-2-methylpentanoate Substances 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- ZMXJAEGJWHJMGX-UHFFFAOYSA-N methyl syringate Chemical compound COC(=O)C1=CC(OC)=C(O)C(OC)=C1 ZMXJAEGJWHJMGX-UHFFFAOYSA-N 0.000 description 1
- YFBSBLHMAWUCJB-UHFFFAOYSA-N methyl syringate Natural products COc1cc(cc(OC)c1O)C(=O)OO YFBSBLHMAWUCJB-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 1
- 229940052490 naringin Drugs 0.000 description 1
- 229930019673 naringin Natural products 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- DSOXXQLCMAEPEZ-UHFFFAOYSA-N nona-2,6-dienenitrile Chemical compound CCC=CCCC=CC#N DSOXXQLCMAEPEZ-UHFFFAOYSA-N 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 229960003598 promazine Drugs 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000010671 sandalwood oil Substances 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-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
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 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)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Zoology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10167739A EP2402301A1 (en) | 2010-06-29 | 2010-06-29 | 1-hydroxy-octahydroazulenes as fragrances |
| EP10167739 | 2010-06-29 | ||
| PCT/EP2011/060862 WO2012001018A1 (en) | 2010-06-29 | 2011-06-28 | 1-hydroxy-octahydroazulenes as fragrances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2574727T3 true ES2574727T3 (es) | 2016-06-21 |
Family
ID=43066824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11728628.6T Active ES2574727T3 (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 |
| JP6947836B2 (ja) * | 2017-02-27 | 2021-10-13 | シムライズ アーゲー | ロタンドン含有混合物を生産するための方法 |
| 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 |
| JP7130110B2 (ja) * | 2019-03-01 | 2022-09-02 | 長谷川香料株式会社 | セスキテルペン酸素付加体の製造方法、化合物および組成物 |
| 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 EP EP11728628.6A patent/EP2588436B1/en active Active
- 2011-06-28 BR BR112012033493-0A patent/BR112012033493B1/pt active IP Right Grant
- 2011-06-28 JP JP2013517258A patent/JP5758000B2/ja active Active
- 2011-06-28 MX MX2012013954A patent/MX2012013954A/es active IP Right Grant
- 2011-06-28 DK DK11728628.6T patent/DK2588436T3/en active
- 2011-06-28 CN CN201180029245.1A patent/CN102958885B/zh active Active
- 2011-06-28 ES ES11728628.6T patent/ES2574727T3/es active Active
- 2011-06-28 WO PCT/EP2011/060862 patent/WO2012001018A1/en not_active Ceased
- 2011-06-28 SG SG2012086328A patent/SG185732A1/en unknown
- 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 |
| EP2588436A1 (en) | 2013-05-08 |
| JP2013534927A (ja) | 2013-09-09 |
| MX2012013954A (es) | 2013-01-24 |
| US8883468B2 (en) | 2014-11-11 |
| US20130089904A1 (en) | 2013-04-11 |
| BR112012033493B1 (pt) | 2020-02-11 |
| CN102958885B (zh) | 2015-07-01 |
| EP2588436B1 (en) | 2016-03-09 |
| EP2402301A1 (en) | 2012-01-04 |
| DK2588436T3 (en) | 2016-06-20 |
| BR112012033493A2 (pt) | 2016-11-29 |
| WO2012001018A1 (en) | 2012-01-05 |
| SG185732A1 (en) | 2013-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2574727T3 (es) | 1-Hidroxi-octahidroazulenos como fragancias | |
| CN106458959A (zh) | 新型混合物 | |
| CN105916970A (zh) | 粉质麝香气味剂大环 | |
| ES2593621T3 (es) | Alcoholes terapéuticos para su utilización en compuestos de fragancias y en productos perfumados | |
| ES3009463T3 (en) | Perfuming compositions | |
| CN113025426B (zh) | 作为加香成分的新戊酸1-异丙氧基-1-氧代丙-2-基酯 | |
| ES2370580T3 (es) | Compuestos éster ópticamente activos y su utilización en composiciones de perfume. | |
| ES2699240T3 (es) | Formulación de aroma y fragancia (IV) | |
| CN107848924B (zh) | 作为香料成分的2,4,7-三甲基辛-6-烯-1-醇 | |
| CN115651762B (zh) | 具有花香气味的醇 | |
| JP5897119B2 (ja) | アロマティックノートを有するペンタ／ヘキサメチル−３，４，５，８−テトラヒドロ−１（２ｈ）−ナフタレノン誘導体 | |
| JP2009509934A (ja) | ６−メトキシ−２，６−ジメチルオクタナールおよびフレグランス成分としてのこの使用 | |
| ES2659951T3 (es) | Formulación de aroma y fragancia (VI) | |
| US20160340285A1 (en) | Flavor and fragrance formulation (vii) | |
| ES2513790T3 (es) | Salicilato de 4-hepten-2-ilo y su utilización como ingrediente de fragancia | |
| US9468594B2 (en) | Flavor and fragrance formulation (II) | |
| CN103717723B (zh) | 紫罗兰叶增味剂 | |
| ES2354923T3 (es) | Nitrilos alfa, beta-insaturados utilizados como fragancias. | |
| JP2025508565A (ja) | 有機化合物 |