CN101969791A - 调味方法 - Google Patents
调味方法 Download PDFInfo
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- CN101969791A CN101969791A CN2009801028073A CN200980102807A CN101969791A CN 101969791 A CN101969791 A CN 101969791A CN 2009801028073 A CN2009801028073 A CN 2009801028073A CN 200980102807 A CN200980102807 A CN 200980102807A CN 101969791 A CN101969791 A CN 101969791A
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- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000000796 flavoring agent Substances 0.000 claims abstract description 62
- 235000019634 flavors Nutrition 0.000 claims abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 235000009499 Vanilla fragrans Nutrition 0.000 claims abstract description 21
- 235000012036 Vanilla tahitensis Nutrition 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract description 4
- 244000263375 Vanilla tahitensis Species 0.000 claims abstract 3
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 41
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 41
- -1 normal-butyl Chemical group 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 23
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 16
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- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
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- OHPLLNOHNYTVPU-UHFFFAOYSA-N acetic acid;2-methylphenol Chemical class CC(O)=O.CC1=CC=CC=C1O OHPLLNOHNYTVPU-UHFFFAOYSA-N 0.000 description 7
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- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 5
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 240000006365 Vitis vinifera Species 0.000 description 4
- 235000014787 Vitis vinifera Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 235000019605 sweet taste sensations Nutrition 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- 244000299461 Theobroma cacao Species 0.000 description 3
- 235000013334 alcoholic beverage Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000019219 chocolate Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000008369 fruit flavor Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- DVCFNCQPOANJGU-UHFFFAOYSA-N oxolane-2-carbonyl chloride Chemical compound ClC(=O)C1CCCO1 DVCFNCQPOANJGU-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
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- FUSJIKIVYFVQHX-UHFFFAOYSA-N (2-methoxyphenyl) 2-hydroxypropanoate Chemical compound COC1=CC=CC=C1OC(=O)C(C)O FUSJIKIVYFVQHX-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 241001647745 Banksia Species 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- URZYOHKNDSYKEQ-UHFFFAOYSA-N butanedioic acid;2-methoxyphenol Chemical compound OC(=O)CCC(O)=O.COC1=CC=CC=C1O URZYOHKNDSYKEQ-UHFFFAOYSA-N 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
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- 235000021185 dessert Nutrition 0.000 description 1
- 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 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
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- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
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- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
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- 229940069338 potassium sorbate Drugs 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
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- 235000011888 snacks Nutrition 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
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- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 235000008939 whole milk 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
- A23L27/204—Aromatic compounds
-
- 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
- A23L27/205—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
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)
- Seasonings (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Confectionery (AREA)
- Medicinal Preparation (AREA)
- Dairy Products (AREA)
- Non-Alcoholic Beverages (AREA)
- Alcoholic Beverages (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
Abstract
在口服可接受的产品中提供希望的香草豆风味的方法,所述方法包括向产品基料中加入至少一种选自式I和式II化合物的化合物其中R′选自氢、甲基和-CHO,R选自氢、C1-C10直链烷基、C3-C10支链烷基、C2-C10直链烯基、C3-C10支链烯基、C1-C2羟基烷基、C1-C2烷基羧基、四氢呋喃基和式VII的基团
Description
本公开涉及香草豆风味的获得。
调味专家们长久以来一直都希望获得理想的香草豆风味。迄今为止,除了采用天然材料之外,其它方式都不可能获得这种风味。
现在发现可以提供这种理想的香草豆风味。因此,提供向口服可接受的产品提供香草豆风味的方法,所述方法包括向产品基料中加入至少一种选自式I和式II化合物的化合物
其中,R′选自氢、甲基和-CHO,R选自氢、C1-C10直链烷基、C3-C10支链烷基、C2-C10直链烯基、C3-C10支链烯基、C1-C10羟基烷基、C2-C10烷基羧基、四氢呋喃基和式VII的基团
R的具体例子包括氢、甲基、乙基、丙基、异丙基、正丁基、1-和2-甲基丙基、正戊基、1-,2-和3-甲基丁基、1-,2-,3-和4-甲基戊基、1-甲基丁-2-烯、羟基乙基、乙基羧基、2-四氢呋喃基和式VII的基团。
“产品基料”意指两种或多种物质的任意组合,所述物质与适当的风味成分结合以制备口服可接受的,即经口摄入用以咽下(例如食物或饮料)或吐出(例如漱口水)的产品。可以使用所属领域已知的所有标准物质,并且熟练技术人员在每种情况下能够选择适当的物质。
上述式I和式II的一些化合物是新物质。因此,还提供选自式III-VI化合物的化合物,其中R具有如下所示的值:
式I化合物可以采用所属领域已知的标准方法制备,并且熟练技术人员能够如此制备。例如,愈创木酚和对甲氧甲酚酯可以按照Parish R.C.和Stock L.M.在J.Org.Chem.,(1965)30(3),927-9中公开的方法来制备,香草醛和麦芽酚酯可以按照下列方法制备:
下表显示了赋予香草豆风味的化合物的特殊例子。表1包含了特别有效的化合物,表2是效果稍差的化合物,表3是效果更差的化合物。
表1
表2
表3
所述化合物可以用在任何口服可接受的产品中。因此,还提供一种包含产品基料的香草豆风味的口服可接受的产品,其中在产品基料中包括至少一种选自上述式I和式II化合物的化合物。
这种产品的例子包括但不限于下列产品:
饮料,包括软饮料和酒精饮料、茶、咖啡和果汁。
甜品,包括焙烤产品,例如蛋糕、小甜饼和饼干、馅饼、谷类食物、压块干粮;糖果,例如硬糖、口香糖、巧克力、软糖和凝胶剂。
奶制品,包括牛奶、冰激凌和酸乳酪。
开胃产品,包括点心、调味品、开胃奶油制品、土豆片小吃。
医用产品,例如糖浆、可咀嚼片。
洁齿剂,包括牙膏、牙粉、牙凝胶、漱口水和可食用膜。
现在参考下列实施例对所述方法做进一步描述。这些实施例描述了特殊的实施方案,但其并不意图以任何方式进行限制。
实施例1
愈创木酚乳酸酯的制备
向乳酸甲酯1(25g,9.6mmol)和DMF(50ml,2ml/g溶剂)的溶液中加入叔丁基二甲基甲硅烷基氯(43.4g,288.2mmol),之后加入咪唑(40.8g,144.2mmol)。室温下将反应搅拌过夜,之后用水淬灭。用乙酸乙酯(3×50ml)萃取混合物。用1N HCl、水和饱和NaCl洗涤合并的有机层、干燥(Na2SO4)、过滤并浓缩。粗物质用快速柱色谱法纯化,以100%的己烷洗脱,得到41.8g(80%)产物(“产物2”)。
0℃下向产物2(3g,13.8mmol)和THF(130ml)的混合物中加入1.13g(27.5mmol)溶于130ml水中的LiOH。RT下搅拌约4h后,真空除去THF。用EtOAc(2×50ml)洗涤所得的含水混合物。用饱和NaHCO3萃取EtOAc层。合并水层,用饱和KHSO4酸化至pH=5,之后用EtOAc萃取。合并所得的有机层、干燥并浓缩,得到2.49g(89%)产物,其为清澈的油(“产物3”)。产物3可以不经进一步纯化即使用。
0℃下在产物3(2.49g,12.2mmol)溶于50ml CH2Cl2而形成的溶液中处理DCC。搅拌混合物10分钟,之后在0℃下向反应混合物中加入愈创木酚(2.3g,18.5mmol)和DMAP(0.15g,1.2mmol)。室温下将反应搅拌过夜。向反应混合物中加入更多的二氯甲烷。之后用1NHCl和水洗涤反应混合物,在Na2SO4上干燥并真空浓缩。使用5%EtOAc/Hex在硅胶上纯化粗产物,得到1.74g(46%)产物(“产物4”)。
将产物4(1.74g,5.6mmol)溶解在20ml CH3CN 中,冷却至0℃,加入HF/Pyr(2ml),之后移去冰浴并在室温下搅拌反应2.5小时。向反应混合物中加入水并用EtOAc(3×50ml)进行反萃取,用水、盐水洗涤有机层,干燥并浓缩。经快速色谱法(20%EtOAc/Hex)得到0.93g(86%)终产物,其为清澈的油。
实施例2
愈创木酚琥珀酸酯的制备
将愈创木酚(2.23g,17.9mmol)、琥珀酸酐(2.7g,26.9mmol)和4-(二甲基氨基)吡啶(50mg,0.40mmol)溶解在10ml吡啶中并在室温下放置2天。加入50ml CH2Cl2,之后用1N HCl(3×50ml)、水、盐水洗涤所得的溶液,干燥(Na2SO4)并浓缩。经硅胶快速色谱法(20%EtOAc/Hex至100%EtOAc),得到1.47g(37%)为白色固体的终产物。
实施例3
2-甲氧基苯基四氢呋喃-2-甲酸酯的制备
室温下将2-四氢呋喃甲酸(16g,137.8mmol)溶解在70ml CH2Cl2中并用200ml 2M的草酰氯CH2Cl2溶液和0.2ml DMF处理。室温下搅拌反应2.5h。真空除去过量的草酰氯。室温下向愈创木酚(5g,40.3mmol)溶于50mL CH2Cl2所形成的溶液中加入新制备的四氢呋喃-2-羰基氯(8.1g,60.4mmol)和6.6ml(100.6mmol)吡啶。室温下搅拌所得混合物15分钟,用MeOH淬灭。将反应混合物倾入50mL 1N HCl中。用CH2Cl2(3×50mL)反萃取水层,合并有机层并用1N HCl、水、饱和NaCl洗涤,干燥(Na2SO4)并浓缩。在SiO2(20%EtOAc/Hex)上经快速色谱法纯化得到8.95g(63%)产物。
实施例4
香草醛丙酸酯的制备
室温下向香草醛(2.75g,18.1mmol)的CH2Cl2(30mL)溶液中加入丙基氯(3.7mL,27.1mmol)和吡啶(3.7mL,45.2mmol)。将所得混合物搅拌过夜。将反应混合物倾入1N HCl中,分离各层。水层用CH2Cl2(3×50mL)萃取,合并有机层。合并的CH2Cl2萃取物经H2O、饱和NaCl洗涤,用Na2SO4干燥,浓缩,经快速色谱法(20%EtOAc/Hex)纯化,得到2.06g(55%)香草醛丙酸酯。
实施例5
4-甲酰基-2-甲氧基苯基四氢呋喃-2-甲酸酯(香草醛2-四氢糠酸酯)的制备
室温下将2-四氢糠酸(16g,137.8mmol)溶解在70mL CH2Cl2中并用200mL 2M的草酰氯CH2Cl2溶液和0.2mL DMF处理。室温下搅拌反应2.5h。真空除去过量的草酰氯。室温下向香草醛(5g,32.9mmol)溶于50mL CH2Cl2所形成的溶液中加入新制备的四氢呋喃-2-羰基氯(6.6g,49.5mmol)和7mL(82.2mmol)吡啶。室温下搅拌所得混合物30分钟,之后回流2h并在室温下用MeOH淬灭。将反应混合物倾入1N HCl(50mL)中。水层用CH2Cl2(3×50mL)萃取,合并有机层并用1N HCl、H2O、饱和NaCl洗涤和干燥(Na2SO4)。真空除去溶剂,所得的油经SiO2色谱纯化得到3.2g(39%)希望的产物。
实施例6
带有香草风味的酒精饮料
将表4中所列的化合物以0.5或1ppm的浓度加入到下列酒精饮料基料中。
成分 | 量 |
水 | 852.78mL |
苯甲酸钠 | 0.25g |
山梨酸钾 | 0.15g |
柠檬酸钠 | 0.3g |
乙醇190标准强度 | 52.6mL |
香草调味剂V1*(5%) | 0.1g |
高果糖玉米糖浆-55 | 95mL |
*可商购自Givaudan Flavors Corp.的香草调味剂。
由三位香草调味专家评价风味特性。将所得组合物与初始饮料的芳香气味和味道特性进行比较,发现香草风味得到增强和/或改善。增强效果列于表4中。
表4
化合物 | 在饮料基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 润饰效果是多了一点褐色和油脂味、轻微烟熏味、略微加重的香草醛味,改进是一点微妙的改进。 |
香草醛四氢呋喃-2-甲酸酯 | 增强了褐色特征,得到一点更多的树脂香特性 |
香草醛丙酸酯 | 油脂味,油状,给出经高压萃取的印象。 |
愈创木酚四氢呋喃-2-甲酸酯 | 更多烟熏味和暗色,令人感兴趣的。 |
愈创木酚戊酸酯 | 豆香,果味润饰,增加了愈创木酚样芳香,但是更甜 |
愈创木酚辛酸酯 | 促进了芳香气味,口味是褐色略微加重、树脂香和略带酚味 |
香草醛巴豆酸酯 | 光滑,均衡,豆香,甜香草醛样香味,改善了整体风味 |
实施例7
带有香草风味的可乐饮料
将表5所列的化合物以0.5或1ppm的浓度加入到下列可乐饮料基料中。
成分 | 量 |
可乐糖浆基料 | 167g |
香草风味剂V2*(5%) | 0.01g |
苏打水(Schweppes) | 833g |
*可商购自Givaudan Flavors Corp.的香草风味剂。
由三位香草调味专家评价风味特性。将所得组合物与初始饮料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表5中:
表5
化合物 | 量(ppm) | 在可乐基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 0.5 | 略微更甜的尾香(ending),豆香,酚味,略微更甜 |
香草醛四氢呋喃-2-甲酸酯 | 0.51 | 口感更光滑,更甜与0.5ppm相同,给出中度光滑感,豆香 |
香草醛丙酸酯 | 0.5 | 美好的豆香,略微烟熏味,略微坚果味 |
愈创木酚四氢呋喃-2-甲酸酯 | 0.51 | 非常轻微的烟熏味,略微褐色豆香,酚味,略微药味 |
愈创木酚戊酸酯 | 0.51 | 豆香,酚味,药味,褐色特征略微加重,最后有一些甜味香质,难以形容的美好的背景特征 |
愈创木酚辛酸酯 | 0.5 | 略微变甜,非常轻微的油脂香/树脂香 |
香草醛巴豆酸酯 | 0.51 | 略微变甜消除了可乐中的不均衡性 |
实施例8
带有香草风味的小甜饼
将表6中所列的化合物以200ppm的浓度加入到小甜饼基料中。
成分 | 量 |
小甜饼基料 | 998g |
香草风味剂V1(5%) | 2g |
由三位香草调味专家评价风味特性。将所得组合物与小甜饼基料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表6中。
表6
化合物 | 在小甜饼基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 豆香,树脂香,油脂味,奶油味,香草样味,更甜 |
香草醛四氢呋喃-2-甲酸酯 | 奶油味更重,烘烤的,香草醛样味,有利于整体香质 |
愈创木酚四氢呋喃-2-甲酸酯 | 豆香,烟熏味,树脂香,酚味/愈创木酚样味 |
香草醛丙酸酯 | 烟熏味,香草香质,褐色 |
愈创木酚戊酸酯 | 更好的豆香香质,果味 |
愈创木酚辛酸酯 | 温和的香草味,光滑风味 |
香草醛巴豆酸酯 | 豆香,褐色的烘烤特征,奶油味,面团状 |
实施例9
带有香草风味的口香糖
将表7中所列的化合物以250ppm的浓度加入到下列口香糖基料中。
成分 | 量 |
口香糖基料 | 995g |
香草风味剂V1(5%) | 5g |
由三位香草调味专家评价风味特性。将所得组合物与口香糖基料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表7中。
表7
化合物 | 在口香糖基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 略微褐色,更甜,焦糖或可可粉样,好的风味 |
香草醛四氢呋喃-2-甲酸酯 | 树脂香,豆香,使风味具有好的改善 |
愈创木酚四氢呋喃-2-甲酸酯 | 美好的豆香,褐色,略微油脂味,树脂香 |
香草醛丙酸酯 | 豆香,树脂香,褐色,甜 |
愈创木酚辛酸酯 | 豆香更浓,褐色,树脂香,甜 |
实施例10
带有香草风味的牛奶
将表8中所列的化合物以20ppm的浓度加入到下列牛奶基料中。
成分 | 量 |
全脂奶 | 908.82g |
蔗糖 | 90.88g |
香草豆风味剂V1(5%) | 0.30g |
由三位香草调味专家评价风味特性。将所得组合物与牛奶基料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表8中。
表8
化合物 | 在牛奶基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 更甜,有争议的愈创木酚味,似朗姆酒的(rummy),烟熏味,豆香 |
香草醛四氢呋喃-2-甲酸酯 | 略微烟熏味,褐色,增强了豆香特征,更甜,有争议的愈创木酚味 |
香草醛丙酸酯 | 提高的干果味,奶油味,焦糖或太妃糖样,似朗姆酒的润饰 |
愈创木酚戊酸酯 | 软化的烟熏味特征,略微焦糖样,豆香,干果/葡萄干味,美好的气味 |
愈创木酚辛酸酯 | 豆香,木香,甜味略微增强,一点油脂味,树脂香,微妙改善 |
香草醛巴豆酸酯 | 似朗姆酒的,酒精味,提高的豆香/种子特征,甜味略微增强 |
实施例11
带有香草风味的酸乳酪
将表9中所列的化合物以20ppm的浓度加入到下列酸乳酪基料中。
成分 | 量 |
未加牛奶的酸乳酪 | 908.82g |
蔗糖 | 90.88g |
香草风味剂V2(5%) | 0.3g |
由三位香草调味专家评价风味特性。将所得组合物与酸乳酪基料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表9中。
表9
化合物 | 在酸乳酪基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 更甜,豆香,美好的气味,覆盖了参考物的一些酚类特征 |
香草醛四氢呋喃-2-甲酸酯 | 豆香,褐色更重,略微烟熏味 |
香草醛丙酸酯 | 豆香,褐色,几乎跟巧克力一样,压抑了参考物的酚类特征。略带焦糖样,葡萄干味,提高了甜味 |
愈创木酚四氢呋喃-2-甲酸酯 | 豆香,烟熏味,褐色,略带焦糖样,葡萄干味,甜 |
愈创木酚戊酸酯 | 烟熏味非常严重,似朗姆酒的,豆香,略带树脂香,褐色略微加重 |
愈创木酚辛酸酯 | 润饰效果为,具有美好的豆香特征,更甜,干果味 |
香草醛巴豆酸酯 | 褐色,香草醛味,豆香样,微甜的朗姆酒和葡萄干特征 |
实施例12
带有香草风味的止咳糖浆
将表10中所列的化合物以100ppm的浓度加入到下列止咳糖浆基料中。
成分 | 量 |
止咳糖浆 | 7.49g |
水 | 991.51g |
香草风味剂V1(5%) | 1g |
由三位香草调味专家评价风味特性。将所得组合物与止咳糖浆基料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表10中。
表10
化合物 | 在止咳糖浆中的风味特性描述 |
香草醛四氢呋喃-2-甲酸酯 | 甜,褐色,均衡的整体特性 |
香草醛丙酸酯 | 树脂香,油脂味,豆香,似朗姆酒的润饰 |
实施例13
带有香草风味的漱口水
将表11中所列的化合物以50ppm的浓度加入到下列漱口水基料中。
成分 | 量 |
薄荷风味漱口水 | 19.98g |
水 | 979.02g |
香草风味剂V1(5%) | 1g |
由三位香草调味专家评价风味特性。将所得组合物与漱口水基料的芳香气味和味道特性进行比较,香草风味得到增强和/或改善。增强效果列于表11中。
表11
化合物 | 在漱口水基料中的风味特性描述 |
甲氧甲酚乙酸酯 | 褐色略微加重,更甜,改善的豆香 |
香草醛四氢呋喃-2-甲酸酯 | 美好的豆香,甜,树脂香,略微似朗姆酒的,甜酯味 |
香草醛丙酸酯 | 改善的豆香,树脂香,略微似朗姆酒的 |
愈创木酚辛酸酯 | 豆香,微甜,面团状,均衡的 |
香草醛巴豆酸酯 | 油脂味口感 |
Claims (7)
2.根据权利要求1的方法,其中R选自氢、甲基、乙基、丙基、异丙基、正丁基、1-和2-甲基丙基、正戊基、1-,2-和3-甲基丁基、1-,2-,3-和4-甲基戊基、1-甲基丁-2-烯、羟基乙基、乙基羧基、2-四氢呋喃基和式VII的基团。
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US655208A (en) * | 1893-09-19 | 1900-08-07 | F Von Heyden Nachfolger Dr | Tar ester of fatty acids and process of making same. |
US2078205A (en) * | 1935-06-15 | 1937-04-20 | Sharp & Dohme Inc | Alkyl catechol ketones |
US4473588A (en) * | 1983-06-16 | 1984-09-25 | International Flavors & Fragrances Inc. | Flavoring with 2-methoxy-4-(2-methylpropenyl) phenyl ester of isobutyric acid |
US4533746A (en) * | 1983-06-16 | 1985-08-06 | International Flavors & Fragrances Inc. | 2-Methoxy-4-(2-methylpropenyl) phenyl ester of isobutyric acid, flavor use thereof and process for preparing same |
NL8403220A (nl) * | 1984-10-23 | 1986-05-16 | Naarden International Nv | Parfumcomposities en geparfumeerde produkten, die een of meer o-alkoxyfenolen als grondstof bevatten. |
US5137036A (en) * | 1990-08-10 | 1992-08-11 | Philip Morris Incorporated | Smoking compositions containing a vanillin-release additive |
US5120368A (en) * | 1990-08-10 | 1992-06-09 | Philip Morris Incorporated | Vanillin 5-hydroxyesters and smoking compositions containing a vanillin-release additive |
FR2691149B1 (fr) * | 1992-05-18 | 1994-07-08 | Adir | Nouveaux composes thiochromaniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
US5358930A (en) * | 1993-12-17 | 1994-10-25 | International Flavors & Fragrances Inc. | 2-ethoxy-4-formyl phenyl ester of propionic acid and use in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles |
DE19714826A1 (de) * | 1997-04-10 | 1998-10-15 | Haarmann & Reimer Gmbh | Ethylvanillinisobutyrat |
US5847398A (en) * | 1997-07-17 | 1998-12-08 | Imarad Imaging Systems Ltd. | Gamma-ray imaging with sub-pixel resolution |
US5847191A (en) * | 1997-07-29 | 1998-12-08 | E. I. Du Pont De Nemours And Company | Process for the hydrocyanation of monoolefins using bidentate phosphite ligands and zero-valent nickel |
US7282195B2 (en) * | 2003-04-10 | 2007-10-16 | Macdougald Ian T | Flavored sealants |
US20060045954A1 (en) * | 2004-09-01 | 2006-03-02 | Douglas Young | Vanilla flavoring compositions |
WO2008105652A1 (en) * | 2007-02-28 | 2008-09-04 | Givaudan Nederland Services B.V. | Flavour improving substances |
-
2009
- 2009-01-22 BR BRPI0906523A patent/BRPI0906523B1/pt active IP Right Grant
- 2009-01-22 WO PCT/CH2009/000026 patent/WO2009092176A2/en active Application Filing
- 2009-01-22 US US12/357,724 patent/US20090186138A1/en not_active Abandoned
- 2009-01-22 JP JP2010543352A patent/JP5999872B2/ja active Active
- 2009-01-22 CN CN2009801028073A patent/CN101969791B/zh active Active
- 2009-01-22 EP EP09704236.0A patent/EP2237683B1/en active Active
-
2013
- 2013-02-28 US US13/781,068 patent/US20130177688A1/en not_active Abandoned
-
2014
- 2014-12-01 JP JP2014243401A patent/JP2015107114A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP5999872B2 (ja) | 2016-09-28 |
JP2011510025A (ja) | 2011-03-31 |
WO2009092176A2 (en) | 2009-07-30 |
JP2015107114A (ja) | 2015-06-11 |
CN101969791B (zh) | 2013-10-30 |
EP2237683B1 (en) | 2015-11-11 |
US20090186138A1 (en) | 2009-07-23 |
BRPI0906523B1 (pt) | 2017-04-11 |
EP2237683A2 (en) | 2010-10-13 |
US20130177688A1 (en) | 2013-07-11 |
BRPI0906523A2 (pt) | 2015-07-14 |
WO2009092176A3 (en) | 2009-12-03 |
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