CN1267018C - 风味和香料组合物 - Google Patents
风味和香料组合物 Download PDFInfo
- Publication number
- CN1267018C CN1267018C CNB028113314A CN02811331A CN1267018C CN 1267018 C CN1267018 C CN 1267018C CN B028113314 A CNB028113314 A CN B028113314A CN 02811331 A CN02811331 A CN 02811331A CN 1267018 C CN1267018 C CN 1267018C
- Authority
- CN
- China
- Prior art keywords
- sulfydryl
- compound
- hydrogen
- formula
- methyl
- 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
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- 239000000796 flavoring agent Substances 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 235000019634 flavors Nutrition 0.000 title claims abstract description 33
- 239000003205 fragrance Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- -1 methylidene, ethyl Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- JDERTPFOJMSORC-UHFFFAOYSA-N 1-diphenylphosphanylethanethiol Chemical compound C=1C=CC=CC=1P(C(S)C)C1=CC=CC=C1 JDERTPFOJMSORC-UHFFFAOYSA-N 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 235000013361 beverage Nutrition 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000036541 health Effects 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000007970 thio esters Chemical class 0.000 claims description 4
- WKTSFRBEJWLNKI-UHFFFAOYSA-N 1-phenylpropane-1-thiol Chemical compound CCC(S)C1=CC=CC=C1 WKTSFRBEJWLNKI-UHFFFAOYSA-N 0.000 claims description 3
- 230000037123 dental health Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- AZPXVXMDTDJETJ-UHFFFAOYSA-N 1-phenylbutane-1-thiol Chemical compound CCCC(S)C1=CC=CC=C1 AZPXVXMDTDJETJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000000606 toothpaste Substances 0.000 claims description 2
- 229940034610 toothpaste Drugs 0.000 claims description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 235000013355 food flavoring agent Nutrition 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 235000019640 taste Nutrition 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- ZMRFRBHYXOQLDK-UHFFFAOYSA-N 2-phenylethanethiol Chemical compound SCCC1=CC=CC=C1 ZMRFRBHYXOQLDK-UHFFFAOYSA-N 0.000 description 7
- 241000675108 Citrus tangerina Species 0.000 description 7
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 7
- 235000014214 soft drink Nutrition 0.000 description 7
- 235000013599 spices Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 235000008504 concentrate Nutrition 0.000 description 6
- 235000021438 curry Nutrition 0.000 description 6
- 239000010502 orange oil Substances 0.000 description 6
- QZZBJCFNHPYNKO-UHFFFAOYSA-N 1-Phenylethane-1-thiol Chemical compound CC(S)C1=CC=CC=C1 QZZBJCFNHPYNKO-UHFFFAOYSA-N 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 235000010234 sodium benzoate Nutrition 0.000 description 3
- 239000004299 sodium benzoate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 229920001285 xanthan gum Polymers 0.000 description 3
- JDERTPFOJMSORC-LBPRGKRZSA-N C[C@@H](P(C1=CC=CC=C1)C2=CC=CC=C2)S Chemical compound C[C@@H](P(C1=CC=CC=C1)C2=CC=CC=C2)S JDERTPFOJMSORC-LBPRGKRZSA-N 0.000 description 2
- 235000019501 Lemon oil Nutrition 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- CEYULKASIQJZGP-UHFFFAOYSA-L disodium;2-(carboxymethyl)-2-hydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O CEYULKASIQJZGP-UHFFFAOYSA-L 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000008216 herbs Nutrition 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000010501 lemon oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- CNJYZHYDDJHXGK-UHFFFAOYSA-N s-(1-phenylethyl) ethanethioate Chemical compound CC(=O)SC(C)C1=CC=CC=C1 CNJYZHYDDJHXGK-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000003756 stirring Methods 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
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- SDOFMBGMRVAJNF-KVTDHHQDSA-N (2r,3r,4r,5r)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-KVTDHHQDSA-N 0.000 description 1
- WAPNOHKVXSQRPX-SSDOTTSWSA-N (R)-1-phenylethanol Chemical compound C[C@@H](O)C1=CC=CC=C1 WAPNOHKVXSQRPX-SSDOTTSWSA-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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- 239000001278 2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol Substances 0.000 description 1
- SJWKGDGUQTWDRV-UHFFFAOYSA-N 2-Propenyl heptanoate Chemical compound CCCCCCC(=O)OCC=C SJWKGDGUQTWDRV-UHFFFAOYSA-N 0.000 description 1
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 description 1
- YFEHVRMRZKALIR-UHFFFAOYSA-N 4-hydroxy-2h-furan-5-one Chemical compound OC1=CCOC1=O YFEHVRMRZKALIR-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 244000137282 Agathosma betulina Species 0.000 description 1
- 235000013388 Agathosma crenulata Nutrition 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- GDZGRGIDVIVRIK-UHFFFAOYSA-N C[O-].OS(=O)=O.[Na+] Chemical compound C[O-].OS(=O)=O.[Na+] GDZGRGIDVIVRIK-UHFFFAOYSA-N 0.000 description 1
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- 241000266847 Mephitidae Species 0.000 description 1
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- ZSBOMYJPSRFZAL-JLHYYAGUSA-N [(2e)-3,7-dimethylocta-2,6-dienyl] butanoate Chemical compound CCCC(=O)OC\C=C(/C)CCC=C(C)C ZSBOMYJPSRFZAL-JLHYYAGUSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
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- 239000001722 capsicum frutescens oleoresin Substances 0.000 description 1
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- 230000002688 persistence Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000001894 piper nigrum l. oleoresin black Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- GAICOFHJBGCHLA-UHFFFAOYSA-N s-(1-phenylethyl) butanethioate Chemical compound CCCC(=O)SC(C)C1=CC=CC=C1 GAICOFHJBGCHLA-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229930000308 sinensal Natural products 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000013975 turmeric oleoresin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23L27/204—Aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/10—Thiols having mercapto groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/20—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
Description
实施例 | R1 | R2(a) | R6 | R7 |
1 | 甲基 | H | H | H |
2 | 乙基 | H | H | H |
3 | 正丁基 | H | H | H |
4 | 甲基 | H | H | 甲基 |
5 | 甲基 | H | H | 甲氧基 |
6 | 甲基 | H | 甲基 | H |
7 | 甲基 | 甲基 | H | H |
8 | 甲基 | A | H | H |
9 | 乙基 | A | H | H |
10 | 正丁基 | A | H | H |
11 | 甲基 | A | H | 甲基 |
12 | 甲基 | A | H | 甲氧基 |
13 | 甲基 | B | H | H |
14 | 甲基 | C | H | H |
15 | 甲基 | D | H | H |
16 | 甲基 | A | 甲基 | H |
17 | 甲基 | E | H | H |
实施例 | |
1H-NMRMS | 74-7.2(m,5H),42(quintet,1H),20(d,1H),17(d,3H)138(M+),121,105,91,77 |
21H-NMRMS | 73-72(m,5H),39(quin tet,1H),2.0-19(m,3H),09(t,3H)152(M+),123,119,103,91,77 |
31H-NMRMS | 73-72(m,5H),4.0(quartet,1H),2.0-19(m,3H),1.4-1.3(m,4H),09(t,3H)180(M+),147,123,105,91,77 |
41H-NMRMS | 73(d,2H),7.1(d,2H),4.2(quintet,1H),23(s,3H),20(d,1H),17(d,3H)152(M+),135,119,103,91,77 |
51H-NMRMS | 73(d,2H),68(d,2H),43(quintet,1H),3.8(s,3H),20(d,1H),1.7(d,3H)168(M+),151,135,120,105,91,77 |
61H-NMRMS | 76(d,2H),7.3(t,2H),7.2(t,1H),2.3(s,1H),1.9(siglet,6H)152(M+),137,119,103,91,77 |
71H-NMRMS | 7.3-72(m,5H),39(quartet,1H),19(s,3H),1.6(d,3H)152(M+),137,121,105,91,77 |
81H-NMRMS | 7.4-7.2(m,5H),4.8(quartet,1H),2.3(s,3H),1.7(d,3H)180(M+),138,121,105,91,77 |
91H-NMRMS | 7.3-72(m,5H),45(t,1H),23(s,3H),2.0(quintet,2H),0.9(t,3H)194(M+),165,152,135,119,103,91,77 |
111H-NMRMS | 73(d,2H),71(d,2H),47(quartet,1H),2.3(s,3H),23(s,3H),1.6(d,3H)194(M+),151,135,119,103,91,77 |
121H-NMRMS | 71(d,2H),67(d,2H),4.6(quartet,1H),36(s,3H),2.1(s,3H),1.5(d,3H)210(M+),167,151,135,120,105,91,77 |
131H-NMRMS | 73-72(m,5H),47(quartet,1H),25(quartet,2H),17(d,3H),12(t,3H)194(M+),165,138,121,105,91,77 |
141H-NMRMS | 73-72(m,5H),4.8(quartet,1H),25(t,2H),1.7(m,5H),10(t,3H)208(M+),175,165,138,121,105,91,77 |
151H-NMRMS | 73-72(m,5H),47(quartet,1H),27(septlet,1H),17(d,3H),1.2(t,6H)208(M+),165,138,121,105,91,77 |
161H-NMRMS | 76(d,2H),7.3(t,2H),7.2(t,1H),22(s,3H),1.9(s,6H)194(M+),151,137,119,103,91,77 |
171H-NMRMS | 101(s,1H),74-73(m,5H),50(quartet,1H),1.7(d,3H)166(M+),135,121,105,91,77 |
Claims (12)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01113787A EP1264547A1 (en) | 2001-06-06 | 2001-06-06 | Flavour and fragrance compositions |
EP01113787.4 | 2001-06-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1512844A CN1512844A (zh) | 2004-07-14 |
CN1267018C true CN1267018C (zh) | 2006-08-02 |
Family
ID=8177652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028113314A Expired - Lifetime CN1267018C (zh) | 2001-06-06 | 2002-06-03 | 风味和香料组合物 |
Country Status (11)
Country | Link |
---|---|
US (1) | US7585535B2 (zh) |
EP (2) | EP1264547A1 (zh) |
JP (1) | JP4098232B2 (zh) |
KR (2) | KR100930751B1 (zh) |
CN (1) | CN1267018C (zh) |
AT (1) | ATE437578T1 (zh) |
BR (1) | BRPI0210160B1 (zh) |
DE (1) | DE60233128D1 (zh) |
ES (1) | ES2329663T3 (zh) |
MX (1) | MXPA03011128A (zh) |
WO (1) | WO2002098241A1 (zh) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0229453D0 (en) * | 2002-12-19 | 2003-01-22 | Givaudan Sa | Improvements in or related to organic compounds |
MXPA05012669A (es) * | 2003-05-20 | 2007-06-14 | Flexitral Inc | Alcoxi alquilosulfanil feniles. |
GB0906009D0 (en) * | 2009-04-07 | 2009-05-20 | Givaudan Sa | Organic compounds |
JP6180320B2 (ja) * | 2013-12-27 | 2017-08-16 | アサヒビール株式会社 | 発酵麦芽飲料 |
JP6294661B2 (ja) * | 2013-12-27 | 2018-03-14 | アサヒビール株式会社 | 発酵麦芽飲料 |
JP6742305B2 (ja) * | 2014-10-14 | 2020-08-19 | ジボダン エス エー | 悪臭低減組成物 |
WO2017033128A1 (en) | 2015-08-25 | 2017-03-02 | Novartis Ag | Biphenyl-substitued 4-amino-butyric acid derivatives and their use in the synthesis of nep inhibitors |
JP6979154B2 (ja) * | 2017-04-07 | 2021-12-08 | 曽田香料株式会社 | カレー風味食品およびカレー風味調味料 |
GB201707639D0 (en) | 2017-05-12 | 2017-06-28 | Givaudan Sa | Improvements in or relating to organic compounds |
CN109608373A (zh) * | 2018-12-26 | 2019-04-12 | 云南悦馨香料科技有限公司 | 一种对-孟-1-烯-8-硫醇的合成工艺方法 |
BR112021018863A2 (pt) * | 2019-04-24 | 2021-11-30 | Unilever Ip Holdings Bv | Composição de cuidados pessoais, composição pessoal, método de preservação de composições e uso de uma combinação |
WO2022117810A1 (en) * | 2020-12-04 | 2022-06-09 | Lucta, S.A. | A feed additive for increasing omega-3/omega-6 polyunsaturated fatty acids ratio in aquatic animals |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US396864A (en) * | 1889-01-29 | Die for making axle-nuts | ||
US3968264A (en) * | 1972-04-13 | 1976-07-06 | Firmenich & Cie | Flavoring agent |
AT323333B (de) | 1973-02-15 | 1975-07-10 | Hurka Wilhelm | Mit wirkstoffen getränkter träger |
US4277024A (en) | 1978-12-20 | 1981-07-07 | Donald Spector | Self-stick aroma-dispensing tab |
GB2055689A (en) | 1979-07-27 | 1981-03-11 | Cavon International Ltd | Face and hand cloth |
GB2235869A (en) | 1989-06-10 | 1991-03-20 | Bostik Ab | Disposable shoe-cleaning package |
GB2347644B (en) | 1999-03-06 | 2001-02-28 | Gerwyn Tudor Hodges | Sun screen wipe |
-
2001
- 2001-06-06 EP EP01113787A patent/EP1264547A1/en not_active Withdrawn
-
2002
- 2002-06-03 DE DE60233128T patent/DE60233128D1/de not_active Expired - Lifetime
- 2002-06-03 ES ES02732297T patent/ES2329663T3/es not_active Expired - Lifetime
- 2002-06-03 JP JP2003501290A patent/JP4098232B2/ja not_active Expired - Lifetime
- 2002-06-03 AT AT02732297T patent/ATE437578T1/de not_active IP Right Cessation
- 2002-06-03 US US10/479,453 patent/US7585535B2/en active Active
- 2002-06-03 CN CNB028113314A patent/CN1267018C/zh not_active Expired - Lifetime
- 2002-06-03 KR KR1020037016034A patent/KR100930751B1/ko active IP Right Grant
- 2002-06-03 WO PCT/CH2002/000288 patent/WO2002098241A1/en active Application Filing
- 2002-06-03 BR BRPI0210160A patent/BRPI0210160B1/pt not_active IP Right Cessation
- 2002-06-03 KR KR1020097011966A patent/KR100957887B1/ko active IP Right Grant
- 2002-06-03 MX MXPA03011128A patent/MXPA03011128A/es active IP Right Grant
- 2002-06-03 EP EP02732297A patent/EP1392132B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP1264547A1 (en) | 2002-12-11 |
DE60233128D1 (de) | 2009-09-10 |
JP4098232B2 (ja) | 2008-06-11 |
JP2004527639A (ja) | 2004-09-09 |
ATE437578T1 (de) | 2009-08-15 |
US7585535B2 (en) | 2009-09-08 |
ES2329663T3 (es) | 2009-11-30 |
US20040253362A1 (en) | 2004-12-16 |
EP1392132B1 (en) | 2009-07-29 |
KR20040010690A (ko) | 2004-01-31 |
CN1512844A (zh) | 2004-07-14 |
BRPI0210160B1 (pt) | 2015-11-10 |
EP1392132A1 (en) | 2004-03-03 |
KR100957887B1 (ko) | 2010-05-13 |
KR20090077022A (ko) | 2009-07-13 |
WO2002098241A1 (en) | 2002-12-12 |
KR100930751B1 (ko) | 2009-12-09 |
BR0210160A (pt) | 2004-08-03 |
MXPA03011128A (es) | 2004-03-19 |
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GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Food flavors & fragrances (Shanghai) Co., Ltd. Assignor: Givaudan S. A. Contract fulfillment period: 2007.1.1 to 2012.12.31 Contract record no.: 2009990001147 Denomination of invention: Flavour and fragrance composition Granted publication date: 20060802 License type: Exclusive license Record date: 20091014 |
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Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.1.1 TO 2012.12.31; CHANGE OF CONTRACT Name of requester: QIHUADUN EDIBLE ESSENCE SPICE( SHANGHAI ) CO., LTD Effective date: 20091014 |
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Address after: Swiss Wei Ernie Patentee after: Givaudan SA Address before: Swiss Wei Ernie Patentee before: Givaudan S. A. |
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Assignee: Food flavors & fragrances (Shanghai) Co., Ltd. Assignor: Givaudan S. A. Contract record no.: 2009990001147 Date of cancellation: 20100805 |
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Assignee: Food flavors & fragrances (Shanghai) Co., Ltd. Assignor: Givaudan SA Contract record no.: 2010990000596 Denomination of invention: Flavour and fragrance composition Granted publication date: 20060802 License type: Exclusive License Open date: 20040714 Record date: 20100805 |
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