CN1277189A - 风味化合物 - Google Patents
风味化合物 Download PDFInfo
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- CN1277189A CN1277189A CN00117660A CN00117660A CN1277189A CN 1277189 A CN1277189 A CN 1277189A CN 00117660 A CN00117660 A CN 00117660A CN 00117660 A CN00117660 A CN 00117660A CN 1277189 A CN1277189 A CN 1277189A
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- 239000000796 flavoring agent Substances 0.000 title claims abstract description 94
- 235000019634 flavors Nutrition 0.000 claims abstract description 89
- 235000013305 food Nutrition 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 235000013361 beverage Nutrition 0.000 abstract description 11
- RFMHFOPFUZZBAD-UHFFFAOYSA-N 2-methyl-3-sulfanylbutan-1-ol Chemical compound CC(S)C(C)CO RFMHFOPFUZZBAD-UHFFFAOYSA-N 0.000 abstract 1
- PSALIMFZUGITJC-UHFFFAOYSA-N 3-methyl-3-sulfanylhexan-1-ol Chemical compound CCCC(C)(S)CCO PSALIMFZUGITJC-UHFFFAOYSA-N 0.000 abstract 1
- 235000013372 meat Nutrition 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 235000014347 soups Nutrition 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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- 206010036590 Premature baby Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
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- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- 150000004702 methyl esters Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 2
- 240000006108 Allium ampeloprasum Species 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 240000001890 Ribes hudsonianum Species 0.000 description 2
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 2
- 235000001466 Ribes nigrum Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 235000013622 meat product Nutrition 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000014860 sensory perception of taste Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-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
- 235000013311 vegetables Nutrition 0.000 description 2
- 235000020097 white wine Nutrition 0.000 description 2
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 1
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-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
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000013730 Passiflora edulis f flavicarpa Nutrition 0.000 description 1
- 240000004520 Passiflora ligularis Species 0.000 description 1
- 235000013744 Passiflora ligularis Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- NIONDZDPPYHYKY-UHFFFAOYSA-N Z-hexenoic acid Natural products CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
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- XAPCMTMQBXLDBB-UHFFFAOYSA-N hexyl butyrate Chemical compound CCCCCCOC(=O)CCC XAPCMTMQBXLDBB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000007823 ocimene derivatives Chemical class 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke 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
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C323/12—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 being acyclic and saturated
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
Abstract
本发明公开了3-巯基-2-甲基丁-1-醇和3-巯基-3-甲基己-1-醇及其立体异构体、风味组合物,以及用这些化合物中的至少一种增味的食品或饮料。
Description
本发明涉及新的3-巯基-链烷醇,即3-巯基-2-甲基丁-1-醇和3-巯基-3-甲基己-1-醇和其立体异构体、风味组合物,以及用这些化合物中的至少一种增味的食品或饮料,还涉及3-巯基-2-甲基-丁-1-醇的两种非对映异构体的制备方法。
在食品和饮料工业中,风味剂在食品和饮料制品的鉴别中起着关键作用。在本文中术语风味包括风味、香味和/或味觉,以下文中,所有这些术语均可相互替换。
几种巯基-烷-1-醇化合物已被确认为是食品制品中的风味剂。如此,3-巯基-己-1-醇已在下述水果及饮料中得到确认:黄色西番莲果(西番莲f.flavicarpa)(K.-H.Engel,R.Tressel,《农业食品化学杂志》(J.Agric.Food Chem)1991,39,2249)、白葡萄酒(Sauvignon blancwine)(T.Tominaga,A.Furrer,R.Henry,D.Dubourdieu,风味香精杂志(Flavour Fragrance J.)1988,13,159;P.Werkhoff,M.Güntert,G.Krammer,H.Sommer,J.Kaulen,《农业食品化学杂志》1998,46,1076)以及红波尔多葡萄酒(P.Bouchilloux,P.Darriet,R.Henry,V.Lavigne-Cruège,D.Dubourdieu,《农业食品化学杂志》1998,46,3095),其通常描述具有西番莲果和葡萄柚特征。
3-巯基-3-甲基-丁-1-醇还在焙炒咖啡中(W.Holscher,O.G.Vitzthum,H.Steinhart,《农业食品化学杂志》1992,40,655)及在Sauvignon blanc白葡萄酒中(T.Tominaga,A.Furrer,R.Henry,D.Dubourdieu,风味香精杂志1988,13,159)中被发现。由Holscher等人描述其风味为类似甜汤味。
3-巯基-2-甲基-丙-1-醇已在红波尔多葡萄酒(P.Bouchilloux,P.Darriet,R.Henry,V.Lavigne-Cruège,D.Dubourdieu,《农业食品化学杂志》1998,46,3095)中得到确认,其被描述为类似肉汤,有汗味(sweat-like)。
德国专利2316456描述了γ-巯基-醇类和其甲酸酯及乙酸酯作为重要的增香剂和调味剂,可用于制备和改进各种风味组合物。这些化合物被描述为具有弱的类似未成熟的洋葱味、硫磺味和汗味,具有很宽的味觉临界值。
本发明的目的是提供新的用作风味组分和/或作为风味增强剂的3-巯基-烷-1-醇。
令人惊奇地发现,2类新的巯基链烷醇具有非常令人感兴趣的风味性质,其强烈地依赖于化合物的绝对和相对构型,所述的新巯基链烷醇,即下式I的3-巯基-2-甲基-丁-1-醇及式II的3-巯基-3-甲基-己-1-醇及其所有可能的立体异构体
相对构型:异型(unlike)
和式IV的(l)-3-巯基-2-甲基-丁-1-醇
相对构型:同型(like)
业已发现,式III的(u)-3-巯基-2-甲基-丁-1-醇对映异构体显示出强烈的洋葱样香味,并具有令人惊奇的4pg/l空气的极低的嗅觉阈值。由于这种极强的芳香味,式III的(u)-3-巯基-2-甲基-丁-1-醇成为有价值的风味成分,甚至在水中浓度低于0.01ppb时,这些化合物的风味也可被辨别出。业已发现,式III的对映异构体可用来以0.1-1ppb的浓度增强食品特别是肉类制品的肉味、清炖肉的味道,并以1-100ppb的浓度赋予食品,特别是汤品以烹调过的蔬菜和肉的香味。
还发现,式IV的(l)-3-巯基-2-甲基-丁-1-醇对映异构体显示出草本味、类似洋葱的香味、韭葱味、象气体的味道(gassy),与式III的对映异构体相比,具有相当高的阈值,约400pg/l空气。令人惊奇地,发现这种化合物可以10ppb-50ppm、优选100ppb-5ppm的浓度用来增强食品中常规天然的外来水果的水果香味。
式III和式IV的化合物并不限于任何特定的异构体;所有可能的对映异构体和所有的混合物均包含在本发明的范围之内。
还发现,3-巯基-3-甲基-己-1-醇的两种对映异构体具有相当不同的嗅觉性质,(S)-异构体显示出草本味、乡土和未成熟(green)的风味;而(R)-异构体则显示出葡萄柚/西番莲果、黑茶藨子和类似洋葱的风味。这两种对映异构体均显示出极强的香味,甚至在水中浓度低至0.1ppb时还如此,因而是有价值的风味成分。(S)-3-巯基-3-甲基-己-1-醇可用来增强食品的风味,特别是赋予肉产品的肉味、清蒸肉的风味特征;赋予汤品以蒸煮过的蔬菜和肉味特性。赋予这些风味特性的风味剂的所需用量取决于欲改善风味的食品,并且是本领域技术人员所公知的。通常,浓度范围为0.1ppb-1ppm,优选1ppb-100ppb。(R)-3-巯基-3-甲基-己-1-醇可用来增强食品常规天然的外来水果风味的水果特征,其浓度范围为10ppb-50ppm,优选100ppb-5ppm。
根据所需的最终食品或饮料的风味性质,3-巯基-3-甲基-1-己-1-醇可以对映异构体纯的形式或其混合物的形式使用。
本发明的3-巯基-链烷醇可用于各种产品如食品、饮料、口香糖、口腔卫生制品及药品,但特别适用于对风味食品和饮料进行增香。本发明的3-巯基-烷-1-醇可直接加入到产品中,或者优选以风味组合物的形式加入到产品中,所述风味组合物包含本领域技术人员公知的添加剂。本发明的3-巯基-烷-1-醇也可用于风味组合物中以增强或改善现有的风味以提供特殊的风味。于是,可将其单独掺入风味组合物中或与其它风味成分如酯、醛、酮、醇、内酯、杂环化合物如呋喃、吡啶、吡嗪以及其它含硫化合物如硫醇、硫化物、二硫化物等组合掺入。这些组分可按照本领域中常规制备风味剂所采用的比例掺入,本领域的技术人员均非常清楚如何使用这些组分。
优选按照本发明采用载体材料来制备风味组合物,所述载体材料如阿拉伯胶或麦芽糖糊精,或溶剂如乙醇、丙二醇、水或甘油三乙酸酯,特别是得到乳液。通过采用载体材料或溶剂可或获得风味组合物所需的物理形式。当载体材料形成乳液时,风味组合物可进一步包含乳化剂如脂肪酸的单和二甘油酯等。本发明的风味组合物可为喷雾干燥形式、液体形式、胶囊形式、乳液形式或其它形式。
本发明的3-巯基-烷-1-醇可以单独使用或与其它本领域技术人员公知的风味成分组合使用。因此,风味组合物可包含一种或多种本发明的化合物。一种或多种的这些化合物的总含量优选为0.01ppb-50ppm,优选1ppb-5ppm,这取决于所需增香的产品。
本发明的另一个目的是提供式I的3-巯基-2-甲基-丁-1-醇2种非对映异构体,即式III的(u)-3-巯基-2-甲基-丁-1-醇和式IV的(l)-3-巯基-2-甲基-丁-1-醇的立体有择合成方法。用于制备(u)-3-巯基-2-甲基-丁-1-醇的方法包括:当归酸甲酯与苄基硫醇的缩合,将形成的酯用氢化铝锂还原,随后用钠/液氨进行脱苄基化反应。采用该方法可获得非对映异构体纯度>6∶1的(u)-3-巯基-2-甲基-丁-1-醇。这种异构体富集产物可直接用作风味剂以增强食品的风味特性,或者其也可通过色谱进行纯化,得到非对映异构纯的(u)-3-巯基-2-甲基-丁-1-醇,用作下文所述的风味剂。
相对构型:异型
用于制备(l)-3-巯基-2-甲基-丁-1-醇的方法包括:惕各酸甲酯与苄基硫醇的缩合,将形成的酯用氢化铝锂还原,随后用钠/液氨进行脱苄基化反应。采用该方法可获得非对映异构体纯度>30∶1的(l)-3-巯基-2-甲基-丁-1-醇。这种异构体富集产物可用直接作风味剂以增强食品的风味特性,或者其也可通过色谱进行纯化,得到非对映异构纯的(l)-3-巯基-2-甲基-丁-1-醇,用作下文所述的风味剂。
相对构型:同型
下述说明具体实施方案的实施例用于进一步描述本发明,这些实施例用于进一步解释本发明,并非限制本发明。
实施例1
制备(外消旋)-3-巯基-3-甲基-己-1-醇(a)(外消旋)-3-甲基-2-己酸乙酯
将NaH(35.5g,0.8mol,60%油分散液)用己烷洗涤2次,并将其悬浮于THF(450ml)中。将悬浮液升温至35℃,并在搅拌下加入膦酰基乙酸三乙酯(triethyl phosphonoacetate)(222.2g,0.98mol),使内部温度仍保持在35-45℃。然后,在大约30分钟内加入2-戊酮(100g,1.16mol),并保持温度为40-45℃,继续搅拌1小时。将反应混合物冷却至室温,分液。将下层溶于400ml水中,并用己烷(150ml)萃取三次。将上层与己烷层合并,用硫酸钠干燥,真空浓缩,得到172.4g的浅黄色油状物。减压蒸馏(42毫巴,92℃),得到119.4g(77%)的(外消旋)-3-甲基-2-己酸乙酯。
NMR(CDCl3):0.93(t,CH3),1.27(t,CH3),1.50(m,CH2,异构体B),1.51(m,CH2,
异构体A),1.89(d,CH3,异构体B),2.10(d,CH2,异构体A),2.16,
(d,CH3,异构体A),2.60(dd,CH2,异构体B),4.11(q,CH2,异构体
B),4.12(q,CH2,异构体A),5.67(q,CH)ppm.
MS: 156(26,M+),128(32),111(100),95(38),82(49),69(63),55(87),
41(66),29(66).
IR(纯): 2962m,2936m,2874w,1718s,1649s,1218s,1149s,1106m,
1040m.(b)(外消旋)-3-苄硫基-3-甲基-己酸乙酯
将在哌啶(100ml)中的苄基硫醇(62.1g,0.5mol)和来自步骤(a)的(外消旋)-3-甲基-2-己酸乙酯(78.1g,0.5mol)的混合物加热回流直至反应完全(48小时),冷却至室温。然后,将过量的哌啶减压蒸馏出来(0.04毫巴,26-33℃)。残余物为(外消旋)-3-苄硫基-3-甲基-己酸乙酯(96.5g,68%),具有较好的纯度,可直接用于下一步骤中。
NMR(CDCl3):0.90(t,CH3),1.29(t,CH3),1.43(s,CH3),1.40-1.65(m,2CH2),
2.61(s,CH2),3.75(s,CH2),4.16(q,CH2),7.15-7.38(m,5芳族.H)
ppm.
MS: 280(3,M+),235(1),157(17),122(27),91(100),83(59),45(36),
29(51).
IR(纯): 2960m,2933m,2872w,1732s,1453m,1198m.(c)(外消旋)-3-苄硫基-3-甲基-己-1-醇
在0℃下,向LiAlH4(6.8g,0.18mol)于乙醚(200ml)的悬浮液中缓慢加入来自步骤(b)的(外消旋)-3-苄硫基-3-甲基-己酸乙酯,加入过程在搅拌下进行,以使温度不超过10℃。继续搅拌1小时,在冷却下依次缓慢加入丙酮及饱和氯化铵溶液(400ml)。将反应混合物用乙醚(200ml)萃取三次,合并后的有机相用硫酸钠干燥,真空浓缩,得到40.8g的浅黄色油状物。在高真空下(0.05毫巴/150℃)干燥后,得到32.5g(75%)的(外消旋)-3-苄硫基-3-甲基-己-1-醇,为浅黄色油状物。
NMR(CDCl3):0.90(t,CH3),1.30(s,CH3),1.35-1.60(m,2CH2),1.85(m,CH2),
2.40(br.,OH),3.73(s,CH3),3.82(td,CH2),7.15-7.38(m,5芳族.
H)ppm.
MS: 238(4,M+),114(13),97(40),91(89),55(100),41(28).
IR(纯): 3357br,2957s,2931s,2871m,1453m,1042m.(d)(外消旋)-3-巯基-3-甲基-己-1-醇
在-78℃下,向来自步骤(c)的(外消旋)-3-苄硫基-3-甲基-己-1-醇的乙醚(200ml)溶液中加入来自气体钢瓶的氨气(约200ml)。然后,加入钠片(约4.0g)直至反应混合物保持蓝色超过20分钟。将该蓝色的混合物过夜并升温至室温,加入乙醇直至蓝色消失。然后,将混合物用约2.7M的盐酸酸化,并用乙醚(150ml)萃取三次。合并后的有机层用硫酸钠干燥,真空浓缩。将粗产物在减压(40毫巴/130℃)下蒸馏,得到11.2g(73%)的(外消旋)-3-巯基-3-甲基-己-1-醇,为无色油状物。主要风味:西番莲果、黑茶藨子、未成熟风味NMR(CDCl3):0.94(t,CH3),1.37(s,CH3),1.38-1.62(m,2CH2),1.70(s,SH),
1.88(m,CH2),2.30(br.,OH),3.82(td,CH2)ppm.MS: 148(1,M+),114(12),97(25),71(37),55(100),41(68).IR(纯): 3346br,2959s,2932s,2872m,1456m,1046m.
实施例2
制备(S)-3-巯基-3-甲基-己-1-醇(a)(外消旋)-3,5-二硝基-苯甲酸3-巯基-3-甲基-己基酯
向(外消旋)-3-巯基-3-甲基-己-1-醇(5.0g,34mmol)的四氯化碳(20ml)溶液中分批加入3,5-二硝基苯甲酰氯(8.6g,37mmol)。将混合物搅拌72小时,然后加入饱和碳酸氢钠溶液(10ml),分离出有机层,用盐水洗涤(15ml),硫酸镁干燥,真空浓缩。将残余物用快速色谱纯化(硅胶,己烷/乙酸乙酯4∶1),得到9.8g(84%)的(外消旋)-3,5-二硝基-苯甲酸3-巯基-3-甲基-己基酯。NMR(CDCl3): 0.97(t,CH3),1.44(s,CH3),1.40-1.72(m,2CH2),1.68(s,SH),
2.12(m,CH2),4.67(t,CH2),9.15(d,2H),9.24(t,1H)ppm.MS: 342(5,M+),309(2),195(9),103(12),97(95),87(25),55(100),
41(21).IR(纯): 3101m,2961m,2933m,1732s,1629m,1547s,1463m,1345s,
1279s,1168s.(b)(1S,3S)-3,5-二硝基-苯甲酸3-甲基-3-(4,7,7-三甲基-3-氧代-2-氧杂-双环[2.2.1]庚烷-1-羰基硫基)-己基酯
在搅拌下,向来自步骤(a)的(外消旋)-3,5-二硝基-苯甲酸3-巯基-3-甲基-己基酯(9.8g,28.6mmol)和吡啶(2.5g,31.5mmol)的四氯化碳(80ml)溶液中加入(-)-莰烷酰氯(6.82g,31.5mmol)。将混合物在回流温度下加热48小时。再加入(-)-莰烷酰氯(1.86g,0.3当量)和吡啶(0.68g,0.3当量),再在回流温度下搅拌16小时。将混合物冷却至室温,加入饱和碳酸氢钠溶液(50ml),分液。有机层用饱和碳酸氢钠溶液(40ml)和水(40ml)洗涤,硫酸镁干燥,真空浓缩,得到16.0g的黄色油状物。粗产物进行色谱纯化(硅胶,己烷/乙酸乙酯4∶1),得到10.0g的橙色油状物。在冰箱中用乙醚进行重结晶,得到1.84g的非对映异构纯的(1S,3S)-3,5-二硝基-苯甲酸3-甲基-3-(4,7,7-三甲基-3-氧代-2-氧杂-双环[2.2.1]庚烷-1-羰基硫基)-己基酯。用CH3CN生长的晶体的X射线研究表明C-3的绝对构型为S。NMR(CDCl3): 0.99(s,CH3),1.05(s,CH3),1.10,(s,CH3),1.21(t,CH3),1.35-2.05
(m,7H),1.57(s,CH3),2.42-2.55(m,3H),4.58(t,CH2),9.15(d,
2H),9.23(t,1H)ppm.MS: 522(0.1,M+),492(0.5),309(15),214(3),195(3),55(62).IR(纯): 3104m,2965s,2934m,2874m,1795s,1734s,1659s,1547s,1463m,
1345s,1279s,1166s.(c)(S)-3-巯基-3-甲基-3-己-1-醇
向LiAlH4(0.28g,7.5mmol)于乙醚(10ml)的悬浮液中缓慢加入来自步骤(b)的(1S,3S)-3,5-二硝基-苯甲酸3-甲基-3-(4,7,7-三甲基-3-氧代-2-氧杂-双环[2.2.1]庚烷-1-羰基硫基)-己基酯(1.3g)的THF(10ml)溶液。将反应混合物在室温下搅拌过夜,用水(20ml)使反应停止,用硅藻土过滤。分离出有机层,用硫酸镁干燥,真空浓缩。将残余物蒸馏(球对球短程蒸馏(bulb to bulb),0.06托,最高190℃),得到100mg(27%)的(S)-3-巯基-3-甲基-己-1-醇,为无色油状物。
NMR(CDCl3): 0.94(t,CH3),1.37(s,CH3),1.38-1.62(m,2 CH2),1.70(s,SH),
1.88(m,CH2),2.30(br.,OH),3.82(t,CH2)ppm.
[α]D 22: -2.5(c=0.8,CHCl3)主要风味:草本味、乡土味、未成熟味
实施例3
制备(l)-3-巯基-2-甲基-丁-1-醇(外消旋)(a)(l)-3-苄基硫烷基-2-甲基-丁酸甲酯
在搅拌及0℃下,向正丁基锂(13.0ml,1.6M己烷溶液)的THF(500ml)溶液中加入苄基硫醇(236ml,2.0mol)。然后,加入惕各酸甲酯(23.6g,0.2mol)的THF(500ml)溶液。将反应混合物升温至室温并继续搅拌3.5小时。用200ml的5%氢氧化钠溶液使反应混合物停止反应,分离出有机层,用硫酸镁干燥。真空蒸出THF和苄基硫醇(旋转蒸发仪,10毫巴/60℃),将残余物进行蒸馏(0.1毫巴,110-118℃),得到40.8g(85.7%)的(l)-3-苄硫基-2-甲基-丁酸甲酯,为无色油状物,其非对映异构纯度为98∶2(NMR)。
NMR(CDCl3): 1.22(d,CH3),1.28(d,CH3),2.57(m,CH),2.96(m,CH),3.64(s,
CH3),3.72(s,CH2),7.15-7.35(m,5芳族.H)ppm.
MS: 238(3,M+),151(3),147(15),123(27),91(100),59(18).
IR(纯): 3028w,2977m,2950m,1736s,1495m,1453s,1200m.(b)(l)-3-苄硫基-2-甲基-丁-1-醇
在0℃下,向LiAlH4(4.78g,126mmol)于乙醚(150ml)的悬浮液中缓慢加入来自步骤(a)的(l)-3-苄硫基-2-甲基-丁酸甲酯(20.0g,84mmol)的乙醚(100ml)溶液。将反应混合物升温至室温,继续搅拌5小时。然后,缓慢加入水,直至观察不到有氢气释出。将反应混合物用硅藻土过滤,有机层用硫酸镁干燥,真空浓缩。粗产物在减压下蒸馏(0.05托/110℃),得到15.5g(87%)的(l)-3-苄硫基-2-甲基-丁-1-醇。
NMR(CDCl3): 0.89(d,CH3),1.29(d,CH3),1.60(t,OH),1.87(m,CH),2.84(qd,
CH),3.37-3.68(m,CH2),3.74(d,CH2),7.18-7.38(m,5芳族.H)
ppm.
MS: 210(6,M+),151(7),123(9),91(100),45(17),31(8).
IR(纯): 3381br,3028w,2961s,2921s,2875s,1494m,1452s,1029s.(c)(l)-3-巯基-2-甲基-丁-1-醇
将来自钢瓶的约200ml的氨气冷凝(condensed)到-78℃的冷烧瓶中,加入小片的钠直至蓝色持续出现。然后,在搅拌下,分小批加入(l)-3-苄硫基-2-甲基-丁-1-醇(3.47g,64mmol)。在反应混合物变为无色后,再加入钠,直至再次持续出现蓝色。继续在-78℃下搅拌1小时,然后用饱和氯化铵溶液使反应停止,直至其变为无色,用2N盐酸(100ml)酸化,并用乙醚萃取。合并后的有机层用硫酸镁干燥,真空浓缩。粗产物于减压下在10cm的Vigreux柱上蒸馏(0.15托/60℃),得到5.8g(86%)的(l)-3-巯基-2-甲基-丁-1-醇,为无色油状物,其非对映异构纯度为40∶1(NMR)。NMR(CDCl3): 0.90(d,CH3),1.28(d,SH),1.37(d,CH3),1.72(s,OH),1.86(m,
CH),3.28(m,CH),3.60(m,CH2)ppm.MS: 120(12,M+),102(3),86(55),71(60),61(89),45(89),41(100),
31(83).IR(纯): 3356br,2964s,2926s,2876s,1450m,1379m,1039s.主要风味:草本味、类似洋葱味、韭葱味、象气体的风味
实施例4
制备(u)-3-巯基-2-甲基-丁-1-醇(外消旋)(a)(u)-3-苄硫基-2-甲基-丁酸甲酯
在0℃下,向正丁基锂(13.0ml,1.6M己烷溶液)的THF(500ml)溶液中加入苄基硫醇(236ml,2.0mol)。然后,加入当归酸甲酯(23.6g,0.2mol)的THF(500ml)溶液。将反应混合物在0℃下搅拌3.5小时。用200ml的5%氢氧化钠溶液使反应混合物停止反应,分离出有机层,用硫酸镁干燥。真空蒸出THF和苄基硫醇(旋转蒸发仪,10毫巴/60℃),将残余物进行蒸馏(0.1毫巴,104-130℃),得到28.2g(59%)的(u)-3-苄硫基-2-甲基-丁酸甲酯,为无色油状物,其非对映异构纯度为9∶1(NMR)。NMR(CDCl3): 1.18(d,CH3),1.20(d,CH3),2.65(m,CH),3.03(m,CH),3.66(s,
CH3),3.72(s,CH2),7.15-7.35(m,5芳族.H)ppm.MS: 238(3,M+),151(2),147(12),123(22),91(100).IR(纯): 3029w,2975m,1736s,1495m,1453s,1199m.(b)(u)-3-苄硫基-2-甲基-丁-1-醇
在0℃下,向LiAlH4(4.78g,126mmol)于乙醚(150ml)的悬浮液中缓慢加入(u)-3-苄硫基-2-甲基-丁酸甲酯(20.0g,84mmol)的乙醚(100ml)溶液。将反应混合物升温至室温,并继续搅拌5小时。然后,缓慢加入水,直至观察不到有氢气释出。将反应混合物用硅藻土过滤,有机层用硫酸镁干燥,真空浓缩。粗产物在减压下蒸馏(0.05托/110℃),得到14.7g(83%)的(u)-3-苄硫基-2-甲基-丁-1-醇,其非对映异构纯度为6.5∶1(NMR)。NMR(CDCl3): 0.95(d,CH3),1.22(d,CH3),1.73(t,OH),1.86(m,CH),2.78(m,
CH),3.53(m,CH2),3.74(d,CH2),7.18-7.38(m,5芳族.H)ppm.MS: 210(6,M+),151(7),123(9),91(100),45(17).IR(纯): 3377br,3028w,2963s,2923s,2875s,1494m,1452s,1029s.(c)(u)-3-巯基-2-甲基-丁-1-醇
将约200ml的氨气冷凝到-78℃的冷烧瓶中,加入小片的钠直至蓝色持续出现。然后,在搅拌下,分小批加入来自步骤(b)的(u)-3-苄硫基-2-甲基-丁-1-醇(3.47g,64mmol)。在反应混合物变为无色后,再加入钠,直至再次持续出现蓝色。继续在-78℃下搅拌1小时,然后用饱和氯化铵溶液使反应停止,直至其变为无色,用2N盐酸(100ml)酸化,并用乙醚萃取。合并后的有机层用硫酸镁干燥,真空浓缩。粗产物于减压下在10cm的Vigreux柱上蒸馏(0.06托/47℃),得到3.0g(62%)的(u)-3-巯基-2-甲基-丁-1-醇,为无色油状物,其非对映异构纯度为6.5∶1。NMR(CDCl3): 1.00(d,CH3),1.35(d,CH3),1.51(d,SH),1.78(m,CH),1.97(br,
OH),3.08(m,CH),3.65(d,CH2).MS: 120(13,M+),102(4),86(58),71(62),61(90),45(79),41(100),
31(76).IR(纯): 3353br,2965s,2928s,2876s,1449m,1379m,1034s.主要风味:强烈的类似洋葱味、肉汤特性
实施例5食品风味实验
制备具有下述组成(重量份数)的肉基(meat base):
水 10
HVP 30
盐酸硫胺素 10
烟提取物 50
总计 100
采用这种肉基制备下述肉汤:
肉汤A(对照):
原料:无脂肉汤
向其中加入肉基 100ppm
肉汤B
原料:无脂肉汤
向其中加入肉基 100ppm
(外消旋)-(u)-3-巯基-2-甲基-丁-1-醇 1ppb
肉汤C
原料:无脂肉汤
向其中加入肉基 100ppm
(R)-3-巯基-3-甲基-己-1-醇 1ppb
在盲鉴实验(blind test)中由评价小组的6名风味专家对肉汤A和B进行比较。该小组评价认为:肉汤B具有更浓郁、更具肉汤的香味,增加了肉香和脂肪香。
在盲鉴实验中由评价小组的6名风味专家对肉汤A和C进行比较。该小组评价认为:肉汤C具有更浓郁、更新鲜的风味,更具肉汤的香味,增加了鸡肉、脂肪和洋葱的风味。
因此,在两个实验中,本发明的风味组分均分别增加了肉汤或肉味特征。
实施例6饮料风味实验
采用下述成分(重量份)制备具有西番莲果风味的风味组合物A和B:
成分 A B
丁酸己酯 96 96
己酸乙酯 82 82
顺-3-己醇 86 86
沉香醇 31 31
己醛 9 9
柠檬醛 11 11
2-辛烯酸甲酯 34 34
糠醇(Furonol) 48 48
己酸 68 68
橙油 247 207
罗勒烯 69 69
2-甲基-庚酸 27 27
2-己烯酸 137 137
乙酸顺-3-己烯酯 55 55(外消旋)-3-巯基-3-甲基-己-1-醇 - 40
总计 1000 1000
以每100ml饮料2滴向标准不充气饮料中加入西番莲果风味组合物A和B(约200mg/l),所述标准不充气饮料由具有下述组成的饮料浆液通过1+5稀释制得(重量份数):
成分
糖浆,65Bx 1033
苯甲酸钠 1
柠檬酸三钠 2
无水柠檬酸,50%w/w水中 30
水,冷却加至1000ml
在盲鉴实验中由评价小组的6名风味专家对所制备的包含风味组合物A的西番莲果味饮料AA和包含风味组合物B并包含本发明的化合物(即:(外消旋)-3-巯基-3-甲基-己-1-醇)约5ppm的西番莲果味饮料BB进行比较。该小组评价认为,西番莲果味饮料BB比西番莲果味饮料AA具有更圆润(rounded off)的西番莲果风味,具有典型的外来水果特征,具有更为新鲜、新奇及果味特征。
通过说明性的实施方案和实施方式说明并描述了本发明,但本领域的技术人员可以在不背离本发明的范围和实质的前提下作出各种改进和变化。因而,本发明并不限于这些说明性的实施方案和实施方式。
Claims (17)
1.下式I和II的3-巯基-烷-1-醇和其立体异构体
6.根据权利要求1-5任一项的化合物作为风味剂的用途。
7.一种风味组合物,它包含至少一种根据权利要求1-5的化合物。
8.根据权利要求7的风味组合物,它包含权利要求2的化合物的立体异构体。
9.根据权利要求8的风味组合物,它包含权利要求3的化合物的立体异构体或其混合物。
10.根据权利要求8的风味组合物,它包含权利要求4的化合物的立体异构体或其混合物。
11.根据权利要求7的风味组合物,它包含权利要求5的化合物的立体异构体。
12.根据权利要求11的风味组合物,它包含(外消旋)-3-巯基-3-甲基-己-1-醇。
13.根据权利要求11的风味组合物,它包含(S)-3-巯基-3-甲基-己-1-醇。
14.根据权利要求11的风味组合物,它包含(R)-3-巯基-3-甲基-己-1-醇。
15.根据权利要求7-14任一项的风味组合物,它总共包含的一种或多种所述化合物的量为约0.01ppb-50ppm。
16.根据权利要求15的风味组合物,它总共包含的一种或多种所述化合物的量为约1ppb-5ppm。
17.一种食品或饮料,它包含根据权利要求7-16任一项的风味组合物。
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EP1553411B1 (en) | 2002-10-04 | 2012-04-04 | Kao Corporation | Body odor assessment method |
US20080300314A1 (en) * | 2003-11-21 | 2008-12-04 | Givaudan Sa | Cooling Compounds |
DE102004031589A1 (de) * | 2004-06-30 | 2006-02-16 | Symrise Gmbh & Co. Kg | Verwendung von 3-Mercapto-3-methyl-hexan-1-ol als Malodor-Standard |
WO2006079236A1 (en) * | 2005-01-25 | 2006-08-03 | Givaudan Sa | Encapsulation method for compounds |
WO2006119660A1 (en) * | 2005-05-11 | 2006-11-16 | Givaudan Sa | Encapsulation method |
US9452982B2 (en) * | 2005-08-15 | 2016-09-27 | Givaudan, S.A. | Pyridinyl cyclohexanecarboxamide cooling compounds |
EP1919441A1 (en) * | 2005-08-22 | 2008-05-14 | Givaudan SA | Substituted bicyclo [2.2.2]oct/5-ene compounds and their use as cooling agents |
EP1940791B1 (en) * | 2005-10-25 | 2009-09-16 | Givaudan SA | Organic compounds |
EP1996535A2 (en) * | 2006-03-15 | 2008-12-03 | Givaudan SA | Para-substituted 2-alkoxyphenol compounds |
EP2158031B1 (en) * | 2007-05-08 | 2011-08-03 | Givaudan SA | Wax encapsulation |
ATE540667T1 (de) | 2007-06-13 | 2012-01-15 | Givaudan Sa | Verbindungen mit kühlender wirkung |
US7880011B2 (en) | 2007-07-23 | 2011-02-01 | Givandan, S.A. | Amide addition reaction |
US20100297038A1 (en) * | 2008-01-17 | 2010-11-25 | Givaudan S.A. | Benzimidazole Derivatives And Their Use As Cooling Agents |
JP6859419B1 (ja) * | 2019-11-15 | 2021-04-14 | 長谷川香料株式会社 | 3−メルカプト−3−メチルペンチル アセテートおよび香味付与剤 |
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US4053656A (en) | 1973-04-04 | 1977-10-11 | Polak's Frutal Works B.V. | Mercapto alcohols and mercaptoalkyl esters |
US3892878A (en) | 1973-04-25 | 1975-07-01 | Int Flavors & Fragrances Inc | Flavoring with sulfur containing compounds |
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