CN114466595A - 有机化合物中或与之相关的改进 - Google Patents
有机化合物中或与之相关的改进 Download PDFInfo
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- CN114466595A CN114466595A CN202080068280.3A CN202080068280A CN114466595A CN 114466595 A CN114466595 A CN 114466595A CN 202080068280 A CN202080068280 A CN 202080068280A CN 114466595 A CN114466595 A CN 114466595A
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- methylbut
- butyl
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- carbon
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- UYLFIIUIXMINML-UHFFFAOYSA-N n-(4-aminobutyl)-3-phenylprop-2-enamide Chemical compound NCCCCNC(=O)C=CC1=CC=CC=C1 UYLFIIUIXMINML-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- 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
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- 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
- A23L27/88—Taste or flavour enhancing agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/40—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- Seasonings (AREA)
Abstract
Description
本发明涉及鲜味香料及其产生方法。本发明涉及提供鲜味和美味(savouryflavor)的化合物,以及它们在组合物和消费品中的用途。
鲜味是通常与亚洲烹饪相关的香味感觉。它已被描述为美味或肉味,并且是肉汤和熟肉的特征。此外,改善的鲜味有助于使低盐产品更可口。传统上通过向食品中添加谷氨酸一钠(MSG)来实现鲜味。然而,据信一些消费者受到谷氨酸盐(特别是MSG)的不利影响,因此仍然需要不基于谷氨酸盐的化合物来代替或减少对这些化合物的依赖以改变消费品的鲜味和美味。
在US2012308703A1、WO2013000673A1或WO2014083202A1中已经报道了肉桂酸衍生物的酰胺和来自天然来源的芳族胺作为天然或天然相同的鲜味促味剂。WO2019063069A1中公开了包含此类酰胺和其他物质的香料组合物。可能产生三叉神经效应的特定类别的肉桂酰胺是最近公布的WO2019063069A1的主题。
现在已经令人惊讶地发现,某些腐胺双酰胺和酰胺酯类似物,即腐胺(丁-1,4-二胺)和4-氨基丁-1-醇的那些,其一方面具有例如肉桂酸、肉桂酸衍生物或4-甲氧基苯甲酸的部分,另一方面具有惕各酸((2E)-2-甲基丁-2-烯酸)的部分,其可以用作鲜味促味剂。
因此,在本发明的第一方面,提供了某些腐胺双酰胺和酰胺酯类似物作为成分以赋予、增强、改善或改变消费品组合物的鲜味的用途。
还提供了一种香料组合物,其包含香料成分和某些腐胺双酰胺或酰胺酯类似物。
还提供了具有鲜味的消费品组合物,所述鲜味至少部分地由其中存在的某些腐胺双酰胺或酰胺酯类似物提供。
在本发明的另一方面,提供了新的腐胺双酰胺和酰胺酯类似物。
在本发明的第一方面,提供了一种或多种式(I)的化合物作为赋予、增强、改善或改变消费品组合物的鲜味的成分的用途
且其中X、Y=-NH-或-O-,其中至少X或Y为-NH-,
所述化合物呈其立体异构体中的任一种或其混合物的形式,其中
波浪键表示相邻双键的未指定构型。
在本发明的一个实施方案中,提供了一种或多种式(II)的化合物作为赋予、增强、改善或改变消费品组合物的鲜味的成分的用途
所述化合物呈其立体异构体的任一种或其混合物的形式,其中
波浪键表示相邻双键的未指定构型。
式(II)的化合物是双酰胺并且相当于式(I)的化合物,其中X和Y为-NH-,并且其中一个碳-碳双键存在于C2上。
在本发明另一个实施方案中,提供了如上定义的式(I)的化合物的用途,其中所述化合物选自(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺、(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺、(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺、(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯、2-甲基丁-3-烯酸4-肉桂酰氨基丁酯和肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯。
在本发明的另一个实施方案中,提供了如上定义的式(I)的化合物的混合物的用途。更具体地,提供了比例为1:2的(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯和2-甲基丁-3-烯酸4-肉桂酰氨基丁酯的混合物的用途。
在本发明另一个实施例中,提供了如上定义的式(II)的化合物的用途,其中所述化合物选自(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺、(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺和(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺。
还提供了鲜味香料组合物,其包含一种或多种式(I)或式(II)的化合物和一种或多种其他香料成分。
式(I)或式(II)的化合物可以单独用作消费品组合物中的唯一香料成分,或与另外的香料成分组合以提供准备好添加到消费品组合物中的香料组合物。其他香料成分可包括其他鲜味促味剂和/或鲜味或美味增强剂,包括MSG。使用式(I)或式(II)的化合物允许显著降低MSG水平,并且在一些情况下完全消除MSG。
所述其他鲜味促味剂和/或所述鲜味或美味增强剂包括但不限于:L-Glu(谷氨酸、谷氨酸盐,例如以其盐的形式,如谷氨酸一钠、谷氨酸一钾、谷氨酸一铵、二谷氨酸钙、二谷氨酸镁)、L-Asp(L-天冬酰胺或其盐)、5'-核糖核苷酸或其盐,包括但不限于5'-核糖核苷酸钙、5'-核糖核苷酸二钠和5'-核糖核苷酸二钾(例如,肌苷酸、鸟苷酸、腺苷酸、肌苷酸盐、鸟苷酸盐和腺苷酸盐,包括鸟苷5'-单磷酸、肌苷5'-单磷酸和5'-腺苷酸及其盐,如鸟苷酸二钠、肌苷酸二钠、腺苷酸二钠;鸟苷酸二钾、肌苷酸二钾、腺苷酸二钾、鸟苷酸钙、肌苷酸钙、腺苷酸钙)、麦芽酚、乙基麦芽酚、甘氨酸、L-亮氨酸自溶或水解蛋白质(例如自溶酵母、水解酵母、水解植物蛋白)、Koji-Aji(一种富含核苷酸的酵母提取物,含有发酵小麦面筋和麦芽糊精,还含有Ajinomoto Food Ingredients生产的谷氨酸盐)和含有上述中的一种或多种的天然制剂或提取物,例如包括蔬菜(包括蘑菇、香菇、大豆、番茄、马铃薯、乳清、海带/海藻)、谷物、肉、鱼(例如贝类、鱼籽(masago))、牛奶、奶酪和蛋黄的提取物、浓汤或浓缩物,来自相关成分的新鲜或发酵、部分或完全水解形式(例如各种水解蛋白质)。
所述其他鲜味促味剂和/或所述鲜味或美味增强剂的具体实例包括英国专利申请号0913804和国际申请号PCT/EP2010/059916中描述的化合物。赋予鲜味香味和增强鲜味香味的化合物的其他非限制性实例包括EP1642886、WO2005/015158、EP1312268、WO2003/088768、EP1291342和WO2006/003107中所述的那些,所有这些参考文献通过引用并入本文。
除了其他鲜味促味剂和/或鲜味或美味增强剂之外,可以与式(I)或式(II)的化合物组合使用以提供香料组合物的其他香料成分可以选自天然香味剂、人造香味剂、香料、调味料等,合成香味油和香味芳香剂和/或油,油性树脂,精油,馏出物和源自植物、叶、花、果实等的提取物,通常,可以使用任何香味剂或食品添加剂,例如在National Academy ofSciences的Chemicals Used in Food Processing,出版物1274,第63-258页中所述的那些。该出版物通过引用并入本文。
式(I)或式(II)的化合物可以直接用于消费品组合物,或者它可以形成香料组合物、特别是鲜味香料组合物的一部分,其随后与消费品组合物混合。在一个具体实施方案中,基于香料组合物,式(I)或式(II)的化合物可以以约0.001至100%或0.01至10%,更优选0.1至10%,甚至更优选0.5至5%重量的量使用。
式(I)或式(II)的化合物可另外与一种或多种常用于香料组合物中的成分或赋形剂(例如本领域常用的载体材料和其它助剂)结合用于香料组合物中。用于香料组合物的合适赋形剂是本领域熟知的,并且包括例如但不限于溶剂(包括水、醇、乙醇、油、脂肪、植物油和miglyol)、粘合剂、稀释剂、崩解剂、润滑剂、调味剂、着色剂、防腐剂、抗氧化剂、乳化剂、稳定剂、增味剂、消结块剂等。
用于香料组合物的此类载体或稀释剂的实例可见于例如,"Perfume and FlavourMaterials of Natural Origin",S.Arctander,Ed.,Elizabeth,N.J.,1960;"Perfume andFlavour Chemicals",S.Arctander,Ed.,第I&II卷,Allured Publishing Corporation,Carol Stream,USA,1994;“Flavourings”,E.Ziegler和H.Ziegler(ed.),Wiley-VCHWeinheim,1998,和“CTFA Cosmetic Ingredient Handbook”,J.M.Nikitakis(ed.),第1版,The Cosmetic,Toiletry and Fragrance Association,Inc.,Washington,1988。
香料组合物的其他合适和期望的成分描述于标准教科书中,例如“Handbook ofIndustrial Chemical Additives”,ed.M.和I.Ash,第2版,(Synapse 2000)。
进一步提供了具有鲜味香料的消费品组合物,所述鲜味香料至少部分地由其中存在的式(I)或式(II)的化合物提供。
还提供了消费品组合物,其包含至少一种式(I)或式(II)的化合物,或包含一种或多种式(I)或式(II)的化合物的鲜味香料组合物;和产品基料。
在消费品组合物中使用的式(I)或式(II)的化合物的比例将取决于用途的性质和期望的效果。例如,MSG的部分替换所需的比例自然将低于完全MSG替换所需的比例。该比例可以在宽限度之间变化,典型地按消费品组合物的重量计在0.01ppm至10000ppm之间,更特别地在0.1ppm至1000ppm之间,仍更特别地在1ppm至500ppm之间或5-50ppm。然而,这些仅是有用比例的一般指示,并且熟练的调香师可以使用这些范围之外的比例用于特定效果。
“消费品组合物”是指被摄入口中以最终吐出或摄取的任何组合物。组合物可以是任何物理形式,固体、液体或气体。非限制性实例包括所有食品、食品添加剂、营养保健食品(nutraceuticals)、药物和放置在口中的任何产品,包括(但不限于)口香糖、口腔护理产品和口腔卫生产品,包括但不限于谷物产品、大米产品、木薯产品、西米产品、烘焙产品、饼干产品、糕点产品、面包产品、糖果产品、甜点产品、口香糖(gums)、口香糖(chewing gums)、调味剂或涂有调味剂的食品/饮料容器、酵母产品、发酵粉、盐和香料产品、小吃食品、咸鲜产品、芥末产品、醋产品、调味汁(调味品)、汤、调味料、即食餐、肉汁、坚果和坚果产品、加工食品、蔬菜产品、肉和肉制品、蛋制品、奶和乳制品、酸奶、奶酪产品、黄油和黄油替代产品、奶替代产品、大豆产品、食用油和脂肪产品、饮料、碳酸饮料、酒精饮料如啤酒、葡萄酒和烈酒、非酒精饮料如软饮料或其他调味制品,包括需要重构的形式,包括但不限于饮料粉末、乳基饮料粉末、无糖饮料粉末、饮料糖浆、饮料浓缩物、咖啡和茶、食物提取物、植物提取物、肉提取物、调味品、明胶、药物和非药物胶、片剂、锭剂、滴剂、乳剂、酏剂。糖浆和用于制作饮料的其他制品,以及它们的组合。
特别地,式(I)或式(II)的化合物适用于消费品组合物,其选自美味用品,包括小吃、汤、肉汤、调味汁、肉/蛋白质和即食餐等。
“产品基料”意指特定消费品组合物所需的所有通常的本领域公认的成分的组合。
在本发明的另一方面,提供了一种提供具有鲜味的消费品组合物的方法,所述方法包括将一种或多种式(I)或式(II)的化合物添加到所述消费品组合物中的步骤。
在本发明的另一方面,提供了式(I)的化合物
且其中X、Y=-NH-或-O-,其中至少X或Y为-NH-,
所述化合物呈其立体异构体的任一种或其混合物的形式,其中
波浪键表示相邻双键的未指定构型,
条件是所述化合物不为(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺。
在龙舌兰(Aglaia gracilis)的提取物中,已经发现了一类新的腐胺双酰胺(Inada等人,Phytochemistry 53,2000,1091-1095)。其中两种已被鉴定为肉桂酰胺,包括(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺。已经报道了它们的合成(Deterbeck等人,Tetrahedron,58(2002)6887-6893)。
特别地,式(I)的化合物选自(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺、(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺、(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯、2-甲基丁-3-烯酸4-肉桂酰氨基丁酯和肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯。
式(I)或式(II)的化合物可以使用本领域技术人员已知的直接合成方法和容易获得的起始材料获得。具体的反应条件在实施例中进一步描述。
现在通过以下描述特定实施方案的非限制性实施例进一步描述本发明。
实施例:
实施例1:(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺(Ia)的合成:
1a)(4-肉桂酰氨基丁基)氨基甲酸叔丁酯(1):
将肉桂酰氯(4.21g,25.3mmol)在二氯甲烷(50ml)中的溶液滴加到用冰浴冷却的(4-氨基丁基)氨基甲酸叔丁酯(5g,26.6mmol)和三乙胺(3.07g,30.4mmol)在二氯甲烷(200ml)中的溶液中。在室温搅拌2小时后,依次用1M HCl(2x100ml)、饱和NaHCO3(100ml)和H2O(100ml)洗涤该反应混合物。用MgSO4干燥有机相,过滤并浓缩。用MTBE/戊烷洗涤得到的固体,然后在40℃在真空烘箱内干燥。得到7.5g(93%)(4-肉桂酰氨基丁基)氨基甲酸叔丁酯(1),为白色粉末。
通过NMR分析,纯度>95%。
1H NMR(600MHz,DMSO-d6)δ=1.15-1.58(m,13H),2.82-3.00(m,2H),3.08-3.23(m,2H),6.55-6.70(m,1H),6.77-6.92(m,1H),7.29-7.47(m,4H),7.49-7.66(m,2H),8.03-8.32(m,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=26.74,27.26,28.44,38.61,39.65,77.52,122.48,127.63,129.10,129.54,135.11,138.55,155.77,164.96ppm。
1b)N-(4-氨基丁基)肉桂酰胺(2):
将TFA(4.84ml,62.8mmol)加入到(4-肉桂酰氨基丁基)氨基甲酸叔丁酯(1)(2g,6.28mmol)在二氯甲烷(100mL)中的溶液中。在室温下搅拌2小时后,在50℃减压(直至20mbar)除去挥发物。获得呈粘性黄色油状物的中间体N-(4-氨基丁基)肉桂酰胺(2,N-(4-氨基丁基)-3-苯基-丙-2-烯酰胺),其不经任何进一步纯化即用于下一步骤1c)中。
1c)(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺(Ia):
将中间体N-(4-氨基丁基)肉桂酰胺(2)溶于二氯甲烷中。向所得溶液中加入三乙胺(5.25ml,37.7mmol),同时在室温下搅拌。然后,滴加(E)-2-甲基丁-2-烯酰氯(1.043g,8.79mmol)在二氯甲烷(10mL)中的溶液。持续搅拌2小时,然后将溶液在室温下静置过夜。第二天,将溶液用二氯甲烷(100ml)稀释,然后依次用稀盐酸溶液(2×100ml)和饱和碳酸钾溶液(2×100ml)洗涤。分离有机层,用MgSO4干燥,过滤并浓缩。将获得的固体在真空烘箱中在50℃/20mbar下干燥。
1.5g(78%)的(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺(Ia),为白色固体。
纯度为约98%(通过NMR分析)。
1H NMR(600MHz,DMSO-d6)δ=1.33-1.51(m,4H),1.44(s,1H),1.45(s,1H),1.62-1.77(m,6H),1.68(s,1H),1.72(s,1H),2.96-3.25(m,4H),3.10(s,1H),3.17(s,1H),6.13-6.38(m,1H),6.29(s,1H),6.50-6.71(m,1H),6.61(s,1H),7.22-7.47(m,1H),7.34-7.43(m,2H),7.41(s,1H),7.50-7.64(m,2H),7.55(s,1H),7.69-7.80(m,1H),7.75(s,1H),8.01-8.36(m,1H),8.12(s,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=12.41,13.63,26.73,26.79,38.50,38.57,122.34,127.48,128.84,128.96,129.40,132.05,134.97,138.41,164.81,168.31ppm。
实施例2:(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺(1b)的合成
2a)(E)-(4-(2-甲基丁-2-烯酰氨基)丁基)氨基甲酸叔丁酯(3,N-Boc-N’-甲基巴豆酰基-腐胺):
将(E)-2-甲基丁-2-烯酰氯(3.19g,26.9mmol)滴加至用冰浴冷却的(4-氨基丁基)氨基甲酸叔丁酯(4.6g,24.43mmol)和三乙胺(5g,49.4mmol)在二氯甲烷(200mL)中的溶液中。将所得溶液在室温下搅拌2小时,然后依次用1M HCl(2x100ml)、饱和NaHCO3(100ml)和H2O(100ml)洗涤。用MgSO4干燥有机相,过滤并浓缩。将固体用戊烷洗涤,然后在40℃在真空烘箱中干燥。
得到6.1g(92%)的(E)-(4-(2-甲基丁-2-烯酰氨基)丁基)氨基甲酸叔丁酯(3),为灰白色固体。
通过NMR分析,纯度>95%。
2b)(E)-N-(4-氨基丁基)-2-甲基丁-2-烯酰胺(4,N-单-甲基巴豆酰基-腐胺):
将TFA(8.55ml,111mmol)滴加到(E)-(4-(2-甲基丁-2-烯酰氨基)丁基)氨基甲酸叔丁酯(3)(3g,11.10mmol)在二氯甲烷(50mL)中的溶液中,得到无色溶液。在室温下搅拌1小时后,将溶液在减压(直到20mbar)下在50℃浓缩。获得粘稠黄色油状的中间体(E)-N-(4-氨基丁基)-2-甲基丁-2-烯酰胺(4),其不经任何进一步纯化即用于下一步骤2c。
2c)(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺(1b):
将中间体(E)-N-(4-氨基丁基)-2-甲基丁-2-烯酰胺(4)溶于二氯甲烷(150mL)中。向所得溶液中加入三乙胺(13.47g,133mmol),同时在室温下搅拌。然后,滴加((E)-3-(4-甲氧基苯基)丙烯酰氯(2.62g,13.31mmol)在二氯甲烷(20ml)中的溶液,持续搅拌2小时,然后将溶液在室温下静置过夜,第二天,将溶液用二氯甲烷(100ml)稀释,依次用1M HCl(3x150ml)、饱和NaHCO3(2x150ml)和H2O(150ml)洗涤。用MgSO4干燥有机层,过滤并浓缩。得到3.3g黄白色固体,通过NMR分析,其具有约80%的纯度。
使用DCM/乙酸乙酯通过硅胶柱纯化,然后从乙醇中重结晶,得到1.5g(41%)的(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺(1b),为白色固体。
通过NMR分析,纯度>98%。
1H NMR(600MHz,DMSO-d6)δ=1.35-1.50(m,4H),1.43(s,1H),1.44(s,1H),1.60-1.77(m,6H),1.67(s,1H),1.72(s,1H),3.00-3.21(m,4H),3.10(s,1H),3.15(s,1H),3.70-3.85(m,3H),3.78(s,1H),6.17-6.36(m,1H),6.27(s,1H),6.41-6.56(m,1H),6.96(d,J=8.95Hz,2H),7.21-7.43(m,1H),7.43-7.56(m,2H),7.48(s,1H),7.60-7.82(m,1H),7.74(s,1H),7.89-8.17(m,1H),8.01(s,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=12.41,13.63,26.79,38.46,38.59,55.26,114.38,119.85,127.52,129.03,132.05,138.11,160.25,165.12,168.32ppm。
实施例3:(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺(1c)的合成
3a)将得自实施例2步骤2b)的中间体(E)-N-(4-氨基丁基)-2-甲基丁-2-烯酰胺(4)溶于二氯甲烷(150ml)中,在室温下搅拌的同时向所得溶液中加入三甲胺(4.04g,39.9mmol),然后滴加4-甲氧基苯甲酰氯(0.7g,4.10mmol)在二氯甲烷(20ml)中的溶液,持续搅拌2小时,然后将溶液在室温下静置过夜,第二天,将溶液用二氯甲烷(100ml)稀释,并依次用1M HCl(2x150ml)、饱和NaHCO3水溶液(2x150ml)和H2O(150ml)洗涤。用MgSO4干燥有机层,过滤并浓缩,得到浅黄色固体,将其从乙酸乙酯中重结晶,用***洗涤,在真空烘箱中在50℃下干燥。得到0.8g(79%)的(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺(1c),为白色粉末。
通过NMR分析,纯度>95%。
1H NMR(600MHz,DMSO-d6)δ=1.29-1.54(m,4H),1.61-1.74(m,6H),3.03-3.16(m,2H),3.18-3.28(m,2H),3.73-3.86(m,3H),5.82-6.50(m,1H),6.79-7.08(m,2H),7.59-7.92(m,3H),8.21-8.43(m,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=12.55,13.76,26.96,38.50,38.77,55.47,113.55,127.02,128.97,129.07,132.18,161.53,165.68,168.42ppm。
实施例4:(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯(Id)和2-甲基丁-3-烯酸4-肉桂酰氨基丁酯(Ie)(1:2)的混合物的合成
4a)N-(4-羟基丁基)肉桂酰胺(5)
在250mL圆底烧瓶中,提供在二氯甲烷(100mL)中的4-氨基丁-1-醇(3.21g,36.0mmol)和三乙胺(9.20mL,66.0mmol)。滴加在10mL二氯甲烷中的肉桂酰氯(5g,30.0mmol),同时用冰/水浴冷却。移除冷却浴,在室温下继续搅拌2小时。将反应混合物用二氯甲烷稀释,用稀盐酸溶液洗涤。分离有机层,用饱和碳酸氢钠溶液和盐水洗涤。将有机层干燥,蒸发,得到4.5g(67%)的N-(4-羟基丁基)肉桂酰胺(5),为油状物。
通过NMR分析,纯度>95%。
1H NMR(600MHz,DMSO-d6)δ=1.35-1.55(m,4H),3.09-3.25(m,2H),3.36-3.58(m,2H),4.43(t,1H),6.61-6.64(d,1H),7.32-7.43(m,4H),7.54-7.56(d,2H),8.11(br t,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=25.89,30.00,38.63,60.45,122.38,127.49,128.97,129.40,134.99,138.40,164.81ppm。
4b)(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯(Id)和2-甲基丁-3-烯酸4-肉桂酰氨基丁酯(Ie)
将N-(4-羟基丁基)肉桂酰胺(5)(1g,4.56mmol)溶于二氯甲烷(25mL)中。在搅拌下加入三乙胺(1.271mL,9.12mmol)。然后在搅拌下滴加(E)-2-甲基丁-2-烯酰氯(0.595g,5.02mmol)。放热反应开始回流。在室温下持续搅拌3小时。将反应混合物用***稀释,用稀盐酸溶液洗涤。分离有机层,用饱和碳酸氢钠溶液洗涤,干燥并浓缩。通过快速柱色谱法纯化残余物。洗脱液:二氯甲烷/甲醇,0-3%甲醇。
得到0.7g产物Id和Ie(51%),比例为1:2。
1H NMR(600MHz,DMSO-d6)δ=1.16-1.20(m,3H),1.45-1.56(m,3H),1.57-1.67(m,3H),1.74-1.78(m,3H),3.16-3.23(m,4H),4.03-4.07(m,2H),4.07-4.11(m,1H,)5.06-5.17(m,2H),5.84-5.92(m,1H),6.59-6.64(m,1H),6.74-6.81(m,1H),7.35-7.39(m,2H),7.39-7.41(m,2H),7.41-7.44(m,3H),7.53-7.59(m,3H),8.04-8.21(m,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=12.50,14.70,16.90,26.18,26.24,26.32,38.73,38.78,40.56,43.28,64.23,64.37,116.48,122.78,128.01,129.47,129.92,135.46,137.67,137.86,139.00,165.36,174.09ppm。
实施例5:肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯(If)的合成
5a)(E)-N-(4-羟基丁基)-2-甲基丁-2-烯酰胺(6)
将4-氨基丁-1-醇(3.01g,33.7mmol)溶于二氯甲烷(50mL)中。在搅拌下加入三乙胺(4.70mL,33.7mmol)。将溶液用冰/水浴冷却,滴加(E)-2-甲基丁-2-烯酰氯(2g,16.87mmol)。移除冷却浴,在室温下持续搅拌3小时。将反应混合物用二氯甲烷稀释,用稀盐酸溶液洗涤。分离有机层,用碳酸钾溶液洗涤,干燥并浓缩。通过快速柱色谱法纯化残余物。洗脱液DCM/甲醇,0-3%甲醇。得到1g油状物。
通过NMR分析,纯度>95%。
1H NMR(600MHz,DMSO-d6)δ=1.28-1.51(m,4H),1.62-1.70(d,3H),1.74(s,3H),3.00-3.13(m,2H),3.36-3.40(m,2H),4.30-4.36(t,1H),6.25-6.30(q,1H),7.59-7.86(brt,1H)ppm。
13C NMR(151MHz,DMSO-d6)δ=12.41,13.62,25.90,30.02,38.79,60.54,128.74,132.11,168.28ppm。
5b)肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯(If)
向(E)-N-(4-羟基丁基)-2-甲基丁-2-烯酰胺(6.1g,5.84mmol)中加入肉桂酰氯(0.973g,5.84mmol)。将反应混合物在60℃下搅拌3小时。然后将其在100℃下短时间加热。粗产物通过快速柱色谱纯化,洗脱液为含1%甲醇的DCM/甲醇,得到1.5g无色油状物。
1H NMR(600MHz,DMSO-d6)δ=1.39-1.77(m,10H),3.05-3.22(q,2H),4.08-4.21(t,2H),6.18-6.38(q,1H),6.59-6.71(d,1H),7.29-7.50(m,3H),7.62-7.82(m,4H)ppm。
13C NMR(151MHz,DMSO-d6)δ=12.54,13.75,25.88,30.86,38.53,63.98,118.24,128.34,128.54,129.08,130.63,132.17,134.18,144.62,165.43,168.48ppm。
实施例6:味道评估-与MSG比较
制备NaCl水溶液(0.5重量%)。向该基料中加入:
a)30ppm的化合物Ia(样品6a);
b)200ppm的MSG(样品6b,基准)。
两个样品6a和6b的味道已经由5名受过训练的小组成员评估。他们被要求将样品6a的强度评级为与样品6b的差异并描述总体效果。典型地,使用以下描述符来描述效果:鲜味、咸味、苦味、总体甜味。
样品6a的味道被描述为鲜味、肉汤味和持久味。苦味水平上的鲜味标记为略高于基准。总之,样品6a优于样品6b。
实施例7:味道评估-与其他衍生物的比较
制备NaCl水溶液(0.5重量%)。向该基料中加入:
a)20ppm的化合物Ia(样品7a);
b)20ppm的化合物Ib(样品7b);
c)20ppm的化合物Ic(样品7c)。
三个样品7a、7b和7c的味道已经由5名受过训练的小组成员评估。
与样品7a相比,样品7b的味道被描述为更具鲜味、更强且更持久、更甜,但具有异味、动物味、花香甜味。
样品7c的味道被描述为比样品7a更具鲜味和更清新的鲜味。
实施例8:酰胺酯类似物的味道评估
制备NaCl(0.5重量%)和MSG(0.05重量%)的水溶液。向该基料中加入:
a)20ppm的化合物(Id+Ie)的混合物,比例为1:2(样品8a);
b)20ppm的化合物If(样品8b)。
一组四个有经验的品尝者将样品8a和8b与纯基料进行比较。
一致地,该小组发现样品8a比基料更具鲜味。另外,感觉到一些苦味。
一致地,该小组发现样品8b比基料更具鲜味。品尝被描述为令人愉快的味道体验。
Claims (9)
3.权利要求1的一种或多种化合物的用途,其中所述一种或多种化合物为或选自(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺、(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺、(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺、(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯、2-甲基丁-3-烯酸4-肉桂酰氨基丁酯和肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯。
4.鲜味香料组合物,包含:
(i)一种或多种如权利要求1中所定义的式(I)的化合物;和
(ii)一种或多种另外的香料成分。
5.权利要求4的鲜味香料组合物,其中所述一种或多种式(I)的化合物为或选自(E)-N-(4-肉桂酰氨基丁基)-2-甲基丁-2-烯酰胺、(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺、(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺、(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯、2-甲基丁-3-烯酸4-肉桂酰氨基丁酯和肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯。
6.消费品组合物,包含:
(i)至少一种如权利要求1中所定义的式(I)的化合物或如权利要求4或5中所定义的鲜味香料组合物;以及
(ii)产品基料。
9.权利要求9的化合物,其选自(E)-N-(4-((E)-3-(4-甲氧基苯基)丙烯酰氨基)丁基)-2-甲基丁-2-烯酰胺、(E)-4-甲氧基-N-(4-(2-甲基丁-2-烯酰氨基)丁基)苯甲酰胺、(E)-2-甲基丁-2-烯酸4-肉桂酰氨基丁酯、2-甲基丁-3-烯酸4-肉桂酰氨基丁酯和肉桂酸4-((E)-2-甲基丁-2-烯酰氨基)丁酯。
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Title |
---|
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RICHARD DETTERBECK等: "Synthesis and structure elucidation of open-chained putrescine-bisamides from Aglaia species", 《TETRAHEDRON》, vol. 58, no. 34, pages 6889 * |
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