CN105592719B - 有机化合物 - Google Patents
有机化合物 Download PDFInfo
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- CN105592719B CN105592719B CN201380080020.8A CN201380080020A CN105592719B CN 105592719 B CN105592719 B CN 105592719B CN 201380080020 A CN201380080020 A CN 201380080020A CN 105592719 B CN105592719 B CN 105592719B
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- C07C233/45—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 carboxyl groups
- C07C233/46—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—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 carboxyl 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 a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- 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
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- C07C233/46—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/49—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 carboxyl 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 a carbon atom of an acyclic unsaturated carbon skeleton
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Abstract
本公开涉及香味改进和用于改进香味的式(I)的化合物,其中R1选自C6‑C13烷基和C9‑C13烯基,且R2选自‑CH2‑苯基、‑CH2‑1H‑吲哚、‑CH2‑苯酚和‑CH2‑咪唑。
Description
本公开涉及香味改进和用于改进香味的化合物。
向可食用产品即口服摄入(例如食品、糖食和饮料)或吐出(例如牙膏和漱口液)的产品中添加香味是长久确立的实践。香味可以通过添加其它香味成分得以改变,这通常属于普通香料工作者的范围。
更近来,期望通过添加自身并非标准香味成分的材料改进香味,即它们不具有适合于作为香味成分的期望的味道(如果有的话),但可以在以极低浓度使用时以一定期望的方式改进香味。它们的一些实例包括:
-香味加强剂。它们强化香味或香味的一些方面。例如,可以将甜味加强剂加入到可食用产品中以便以减少的糖含量提供相同的甜味水平。强化咸味是这类加强的另一个种类。这在生产健康和膳食食品中已经成为极为重要的,其中期望盐和/或糖的水平降低。
-异味掩蔽剂。众所周知一些期望的香味成分存在还提供不期望的异味的缺陷。一个实例是有时与一些高强度甜味剂相关的“金属”异味。掩蔽剂可以阻断这些异味并且能够实现完全期望的香味效果,而没有缺陷。
-口感加强剂。尽管没有严格的香味特征,但是口感可以从可食用组合物中显著地添加或减去。不期望的口感对于另外期望的香味组合物而言可能是严重的缺陷。
工业上另一种期望在于在大量生产的可食用组合物、尤其是食品和饮料中更完整地生成捕获天然、真实香味的香味。例如,通常期望形成尽可能接近新鲜压榨的橙汁的橙子加香的饮料味道。一般公知,在制备商品橙子加香的饮料的过程中,更多的真实橙子香味不可避免地丧失。这在各种大量生产的食品和饮料中是确切的。
目前已经发现,向包含香料的可食用组合物中添加一些化合物可以以上述举出的方式中的一种或多种理想地改进其中的香味,导致组合物对于消费者更具有吸引力。因此,提供改进包含至少一种香味辅助成分的可食用组合物的味道的方法,所述方法包括将改进香味比例的式(I)的化合物或其可食用盐掺入其中,
其中
R1选自C6-C13烷基和C9-C13烯基,且
R2选自-CH2-苯基、-CH2-1H-吲哚、-CH2-苯酚和-CH2-咪唑。
除非另有指示,否则本文涉及的式(I)的化合物的“烷基”是指直链和支链C6-C13烷基,优选C9-C13;例如C10或C11烷基;
“烯基”是指直链和支链C9-C13烯基,包括C10、C11和C12烯基,其包含1或2个双键,所述双键可以为顺式-或反式-构型。
可食用盐包括典型地用于食品和饮料工业的那些盐,且包括氯化物、硫酸盐、磷酸盐、葡糖酸盐、钠、柠檬酸盐、碳酸盐、乙酸盐和乳酸盐。
在一个实施方案中,R1选自C9、C10和C13直链烷基和C9、C10和C13直链烯基,例如R1选自壬基、十一-4-烯-基、十一烷基、十三-4-烯基、十三烷基。
另外的非限制性实例是选自(Z)-2-(十二-5-烯酰氨基)-3-苯基丙酸(实施例1)、(Z)-2-(十二-5-烯酰氨基)-3-(4-羟基苯基)丙酸(实施例2)、2-(十二烷酰氨基)-3-苯基丙酸(实施例3)、2-(十二烷酰氨基)-3-(1H-吲哚-3-基)丙酸(实施例4)、2-(十二烷酰氨基)-3-(4-羟基苯基)丙酸(实施例5)、(Z)-2-(十二-5-烯酰氨基)-3-(1H-吲哚-3-基)丙酸(实施例6)和3-(1H-吲哚-3-基)-2-十四烷酰氨基丙酸(实施例7)的式(I)的化合物。
可以通过已知方法、使用商购的原料、试剂和溶剂制备式(I)的化合物。例如,可以通过使相应的氨基酸与相应的羧酸卤化物例如氯化物在碱性条件下在水性条件下例如水/THF溶剂系统中反应制备式(I)的化合物。可以通过给该反应混合物施加加热改善收率和反应时间。或者,可以通过使相应的羧酸与相应的氨基酸在二噁烷中在DCC(二环己基碳二亚胺)和1-羟基吡咯烷-2,5-二酮的存在下反应制备式(I)的化合物。
如上文所述的式(I)的化合物将显著的感官特征传递给添加它们的可食用产品,尤其是甜味可食用产品。具体地,它们给包含它们的可食用产品传递高度强烈的、真实的和协调的香味和圆和与丰满感。
这种发现更令人惊奇的方面是考虑到,当申请人品尝稀水溶液形式的化合物时,它们展示出令人失望的、微弱的脂肪味道特性。照此,它们显然十分不适用于香味用品。仅它们与香味辅助成分的组合及其使用水平的甚重选择能够发现这些化合物的显著的感官特性。其对可食用产品的效果十分罕见的方面在于它们实际上补充、提升或加强入它们的食品或饮料的基本或真实的香味和口感特征。因此,本发明的化合物应用于食品和饮料工业以及健康和保健中的广泛用品。
因此,在另一个方面,提供赋予可食用组合物香味和/或口感或改善其味道和/或口感的方法,该方法包括向所述组合物中添加本文定义的式(I)的化合物。
当将式(I)的化合物掺入包含一种或多种香味辅助成分的可食用组合物中时,观察到显著的感官效应。
因此,在另一个实施方案中,提供可食用组合物,其包含可食用组合物基料、至少一种香味辅助成分和改进香味比例的如本文所定义的式(I)的化合物。
所谓“香味辅助成分”是指能够以积极或令人愉快的方式给可食用组合物贡献或传递或改变味道的成分,例如糖类、脂肪、盐(例如氯化钠)、MSG(谷氨酸一钠)、钙离子、磷酸根离子、有机酸、蛋白质、嘌呤类、香料及其混合物。香味辅助成分还可以包括咸味促味剂、鲜味促味剂和调味的香味化合物。
所谓“味道”是指通过口腔感觉到的那些感觉,包括咸味、甜味、酸味、苦味和鲜味。
香味辅助成分的非限制性实例包括:NaCl、KCl、MSG、鸟苷一磷酸(GMP)、肌苷一磷酸(IMP)、核糖核苷酸类例如肌苷酸二钠、鸟苷酸二钠、N-(2-羟基乙基)-乳酰胺、N-乳酰基-GMP、N-乳酰基酪胺、γ氨基丁酸、烯丙基半胱氨酸、1-(2-羟基-4-甲氧基苯基)-3-(吡啶-2-基)丙-1-酮、精氨酸、氯化钾、氯化铵、琥珀酸、N-(2-甲氧基-4-甲基苄基)-N'-(2-(吡啶-2-基)乙基)草酰胺、N-(庚-4-基)苯并(D)(1,3)间二氧杂环戊烯-5-甲酰胺、N-(2,4-二甲氧基苄基)-N'-(2-(吡啶-2-基)乙基)草酰胺、N-(2-甲氧基-4-甲基苄基)-N'-2(2-(5-甲基吡啶-2-基)乙基)草酰胺、环丙基-E,Z-2,6-壬二烯酰胺。
在一个具体的实施方案中,糖类以占可食用组合物总重0.001%-90%、更具体地为0.001%-50%、仍然更具体地为0.001%-20%的量存在。
例如,糖类(例如甜味剂,例如蔗糖、高果糖玉米糖浆、果糖和葡萄糖;高强度无营养甜味剂,例如阿司帕坦、乙酰舒泛钾、三氯蔗糖、环己氨磺酸类、糖精Na+、纽甜、莱鲍迪甙A和/或其它基于甜叶菊的甜味剂)在饮料中可以占可食用组合物总重的至多20%。
通常存在于饮料中的甜味剂浓度的实例是:
碳酸软饮料:<1%-15%甜味剂;不充气饮料(无酒精):<1%-15%甜味剂;果汁饮料;<1%-15%甜味剂;粉状软饮料:<1%-20%甜味剂;液体浓缩物:<1%-20%甜味剂;酒精性饮料:<1%-40%甜味剂;功能性饮料:<1%-20%甜味剂;基于咖啡的饮料:<1%-15%甜味剂;和基于茶的饮料:<1%-15%甜味剂。
在一个具体的实施方案中,脂肪以占可食用组合物总重0.001%-100%、更具体地为0.001%-80%、更具体地为0.001%-30%、仍然更具体地为0.001%-5%的量存在。
在一个具体的实施方案中,盐(例如氯化钠)以占可食用组合物总重0.001%-20%、更具体地为0.001%-5%的量存在。
在一个具体的实施方案中,MSG以占可食用组合物总重0.001%-2%的量存在。
在一个具体的实施方案中,钙以占可食用组合物总重0.001%-50%、更具体地为0.001%-20%、仍然更具体地为0.001%-1%的量存在。
在一个具体的实施方案中,有机酸以占可食用组合物总重0.001%-10%、更具体地为0.001%-7%的量存在。有机酸的类型包括柠檬酸、苹果酸、酒石酸、富马酸、乳酸、乙酸和琥珀酸。包含有机酸的可食用产品的类型包括饮料,例如碳酸软饮料、不充气饮料、果汁、粉状软饮料、液体浓缩物、酒精性饮料和功能性饮料。
在一个具体的实施方案中,磷的存在量至多占可食用组合物重量的0.5%。典型地,磷作为磷酸盐或磷酸存在。
在一个具体的实施方案中,嘌呤类的存在量至多占可食用组合物重量的0.5%。术语“嘌呤类”包括核糖核苷酸,例如IMP和GMP。
在一个具体的实施方案中,香料的存在量至多占可食用组合物重量的15%,例如其用量为0.01-15%重量(例如零食中占10-15%重量,调味食品中占0.1-0.5%重量,甜品和乳制品中占0.01-0.1%重量)。
所有形式的香料均可以用于本发明的组合物,包括、但不限于天然香料、人造香料、香料调味品、作料等。香料包括合成香味油和加香香料和/或油、来源于植物、叶、花、果实等的油性树脂、精油、蒸馏物和提取物和包含上述成分的至少一种的组合。
香味油包括留兰香油、肉桂油、冬青油(水杨酸甲酯)、胡椒薄荷油、日本薄荷油、丁香油、桂花油、八角茴香油、桉叶油、百里香油、香柏叶油、肉豆蔻油、多香果、鼠尾草油、肉豆蔻、苦杏仁油和桂皮油;有用的增香剂包括人造、天然和合成水果香料,例如香草和柑橘油,包括柠檬、橙、白柠檬、葡萄柚、yazu、史达橘(sudachi)和水果香精包括苹果、梨、桃、葡萄、蓝莓、草莓、覆盆子、樱桃、李子、洋李、葡萄干、可乐、瓜拉那、橙花油、菠萝、杏子、香蕉、甜瓜、杏子、ume、樱桃、覆盆子、黑莓、热带水果、芒果、山竹果、石榴、番木瓜等。
香味组合物递送的另外的示例性香精包括牛奶香精、黄油香精、干酪香精、奶油香精和酸奶香精;香草香精;茶或咖啡香精例如绿茶香精、乌龙茶香精、茶香精、可可香精、巧克力香精和咖啡香精;薄荷香精例如薄荷香精、留兰香香精和日本薄荷香精;香辣香精例如阿魏香精、香旱芹香精、大茴香香精、当归属香精、小茴香香精、多香果香精、肉桂香精、黄春菊香精、芥茉香精、小豆蔻香精、葛缕子香精、小茴香子香精、丁香香精、胡椒香精、芫荽子香精、黄樟香精、香旱芹菜香精、川花椒香精、紫苏香精、杜松子香精、姜香精、八角茴芹香精、辣根香精、百里香香精、龙艾香精、莳萝子香精、辣椒香精、肉豆蔻香精、罗勒香精、马郁兰香精、迷迭香香精、月桂叶香精和绿芥末(日本辣根)香精;坚果香精例如杏仁香精、榛子香精、坚果香精、花生香精、美洲山核桃香精、阿月浑子香精和胡桃香精;酒精香精例如葡萄酒香精、威士忌酒香精、白兰地酒香精、甜酒香精、杜松子酒香精和利口酒香精;花香精;和蔬菜香精例如洋葱香精、大蒜香精、甘蓝香精、胡萝卜香精、芹菜香精、香茹香精和蕃茄香精。
在一些实施方案中,所述香味组合物包括醛类和酯类,例如可以使用乙酸肉桂酯、肉桂醛、柠檬醛二乙基缩醛、乙酸二氢香芹酯、丁子香酚49甲酸酯、对-甲基茴香醇(amisol)等。醛香料的另外的实例包括乙醛(苹果)、苯甲醛(樱桃,杏仁)、茴香醛(甘草,大茴香)、肉桂醛(肉桂)、柠檬醛即α-柠檬醛(柠檬,白柠檬)、橙花醛即β-柠檬醛(柠檬,白柠檬)、癸醛(橙,柠檬)、乙基香草醛(香草,奶油)、天芥菜即胡椒醛(香草,奶油)、香草醛(香草,奶油)、α-戊基肉桂醛(辛香水果香精)、丁醛(黄油,干酪)、戊醛(黄油,干酪)、香茅醛(改性剂,许多类型)、癸醛(柑橘类水果)、醛C-8(柑橘类水果)、醛C-9(柑橘类水果)、醛C-12(柑橘类水果)、2-乙基丁醛(浆果类)、己烯醛即反式-2(浆果类)、甲苯醛(樱桃,杏仁)、藜芦醛(香草)、2,6-二甲基-5-庚烯醛即甜瓜醛(甜瓜)、2,6-二甲基辛醛(青香果实)和2-十二碳烯醛(柑橘,橘子)等。
其它香料的另外的实例可以在National Academy of Sciences的“ChemicalsUsed in Food Processing”,1274卷,63-258页中找到。
在制备可食用组合物的过程中,式(I)的化合物可以以任意物理形式使用。可以以净形式、储备溶液的形式使用它们;可以以乳液形式使用它们;或可以以粉末形式使用它们。如果式(I)的化合物以粉末形式呈现,则可以通过分散蒸发法、例如喷雾干燥法生产粉末形式。液体制品可以包括包含式(I)的化合物的溶液、混悬液或乳液。液体制品可以包含其它成分,例如适合于香味组合物的载体材料和/或助剂。
在另一个实施方案中,可以将式(I)的化合物与香味辅助成分混合,特别是与香料混合,然后掺入可食用组合物基料。
因此,在另一个方面,提供香味组合物,其包含如本文所定义的式(I)的化合物和至少一种香味辅助成分、特别是香料和任选的适合于香味组合物的载体材料和/或助剂。
载体材料可以用于将式(I)的化合物或包含式(I)的化合物的组合物、特别是香味组合物包封或俘获在基质中。载体材料的作用可以仅在于加工助剂或填充剂的作用,或可以用于屏蔽或防止其它成分受到湿气或氧或任意其它攻击性介质的影响。载体材料还可以在消费时作为控制香味从可食用产品中释放的用品起作用。
载体材料可以包括单糖、二糖或三糖、天然或改性淀粉、水胶体、纤维素衍生物、聚乙酸乙烯酯、聚乙烯醇、蛋白质或果胶。具体的载体材料的实例包括蔗糖、葡萄糖、乳糖、左旋糖、果糖、麦芽糖、核糖、右旋糖、异麦芽酮糖醇(isomalt)、山梨糖醇、甘露糖醇、木糖醇、乳糖醇、麦芽糖醇、戊糖醇(pentatol)、阿拉伯糖、戊糖、木糖、半乳糖、麦芽糖糊精、糊精、化学修饰的淀粉、氢化淀粉水解物、琥珀酰化或水解淀粉、琼脂、角叉菜胶、阿拉伯树胶、金合欢树胶(gum accacia)、黄蓍胶、藻酸盐、甲基纤维素、羧甲基纤维素、羟乙基纤维素、羟丙基甲基纤维素、其衍生物和混合物。当然,本领域技术人员可以理解,所引述的材料作为实例并入本文且不解释为限制本发明。
所谓“香味助剂”是指能够将额外添加的有益性例如颜色、耐光性、化学稳定剂等赋予给本发明组合物的成分。适合的助剂包括溶剂(包括水、醇、乙醇、三醋精、油、脂肪、植物油和miglyol)、粘合剂、稀释剂、崩解剂、润滑剂、着色剂、防腐剂、抗氧化剂、乳化剂、稳定剂、消结块剂等。在一个具体的实施方案中,所述香味组合物包含抗氧化剂。所述抗氧化剂可以包括维生素C、维生素E、迷迭香提取物、叔丁基对甲氧酚、丁羟茴醚(BHA)和丁羟甲苯(BHT)。
用于香味组合物的这种载体材料或助剂的实例可以在例如“Perfume andFlavour Materials of Natural Origin”,S.Arctander,Ed.,Elizabeth,N.J.,1960;“Perfume and Flavour Chemicals”,S.Arctander,Ed.,I&II卷,Allured PublishingCorporation,Carol Stream,USA,1994;“Flavourings”,E.Ziegler和H.Ziegler(ed.),Wiley-VCH Weinheim,1998和“CTFA Cosmetic Ingredient Handbook”,J.M.Nikitakis(ed.),第1版,The Cosmetic,Toiletry and Fragrance Association,Inc.,Washington,1988中找到。
香味组合物的其它适合的和期望的成分描述在标准教科书例如“Handbook ofIndustrial Chemical Additives”,ed.M.和I.Ash,第2版,(Synapse 2000)中。
本发明的香味组合物可以以任意适合的物理形式提供。例如,它们可以是在适用于可食用产品的水性液体或有机液体中的油、乳液或分散液形式或固体形式,例如粉末。
如果以粉末组合物形式提供所述香味组合物,则可以通过本领域一般公知的分散蒸发技术例如喷雾干燥制备它们。
因此,在本发明的另一个实施方案中,提供了形成粉末组合物的方法,所述方法包括下列步骤:提供包含式(I)的化合物和一种或多种任选的成分的液体组合物,所述任选的成分选自至少一种香味辅助成分、载体材料和助剂;和分散蒸发所述液体组合物,以形成粉末组合物。
按照这种方式,可以将式(I)的化合物或包含所述化合物的香味组合物制成粉末形式。
用于制备粉末的液体组合物可以是溶液、乳液、分散液或淤浆的形式。所述液体可以包含水和/或有机液体,例如对用于可食用产品可接受的乙醇、甘油、三醋精、miglyol(MCT)。
可以根据本领域中用于工业化规模生产粉末的方法和设备制备本发明的粉末组合物。特别适合的方法是喷雾干燥。喷雾干燥技术和设备是本领域众所周知的且无需在本文中详细讨论。描述在US2005/0031769和US2013/0022728中的喷雾干燥技术、设备和方法以及那些对比文件中所述的那些技术、设备和方法适合于生产本发明的粉末组合物,并且将这些文献完整地引入本文参考。
如上文所述,可以将式(I)的化合物或包含这类化合物的香味组合物掺入可食用产品,且包含这类式(I)的化合物的可食用组合物或香味组合物构成本发明的另外的方面。
术语“可食用组合物”是指受试者、典型地通过口腔消费(尽管消费可以通过非口腔的方式进行,例如吸入)的产品,其至少一个目的在于享乐、营养或健康和保健有益性。可食用产品可以以任意形式存在,包括、但不限于液体、固体、半固体、片剂、胶囊、锭剂、条状物、粉末、凝胶、树胶、糊剂、淤浆、糖浆、气雾剂和喷雾剂。该术语还指,例如膳食和营养补充剂。可食用产品包括在弃去前置于口腔中一定时间期限、不吞咽的组合物。可以将其在消费前置于口腔中,或将其保留在口腔中一定时间期限,然后弃去。如上文所定义的可食用组合物包括这样的组合物,其味道以本文所述的方式通过添加式(I)的化合物改变。
广泛地说,可食用组合物包括、但不限于所有种类的食品、糖食产品、烘烤制品、甜品、风味产品、发酵产品、乳制品、饮料和口腔护理产品。
在一个具体的实施方案中,术语“可食用产品”是指由受试者、典型地通过口腔消费的产品(不过,消费可以通过非口腔方式例如吸入进行),目的之一在于享乐或营养。
在一个更具体的实施方案中,术语“可食用产品”是指由受试者、典型地通过口腔消费的目的在于享乐的产品(不过,消费可以通过非口腔方式例如吸入进行)。更具体地,该术语是指食品和饮料。
示例性食品包括、但不限于速冻小吃、甜和风味极佳的小吃、水果小吃、油煎土豆片/炸土豆片、膨化休闲食品、玉蜀黍饼/玉米片、爆玉米花、椒盐卷饼、坚果、其它甜和风味极佳的点心、小吃、低脂肪小饼干、早餐棒、能量棒、水果棒、其它小吃、膳食替代品、减肥产品、恢复性饮料、即食餐、罐头即食餐、冷冻即食食品、干燥好的饭、冷冻即食餐、混合方便饭、速冻比萨、冷冻比萨、汤、汤品罐头、汤粉、速溶汤粉、冷汤、超高温汤、冷冻汤、意面、罐装意面、干意面、冷冻/新鲜意面、面条、阳春面、方便面、杯装/碗装方便面、袋装方便面、油醋汁凉面、方便面、干燥食品、什锦点心、酱油、调料和调味品、草药和香料调味品、糊状食品、果酱和蜜饯、蜂蜜、巧克力酱、基于坚果的酱和基于发酵的粉酱。
示例性糖食产品包括、但不限于口香糖(包括糖化口香糖、无糖口香糖、功能性口香糖和泡泡糖)、夹心糖食、巧克力和其它巧克力糖食、含药糖食、脆性硬糖、片剂、软果糕、薄荷糖、标准薄荷糖、强力薄荷糖、软糖、硬糖、硬糖果、呼吸和其它口腔护理膜或条、拐杖糖、棒糖、粘糖、果冻、乳脂软糖、焦糖、硬和脆松糖、乳脂糖、太妃糖、甘草、胶糖、橡皮糖、豆形胶质软糖、奶油杏仁糖、微晶糖膏、一种或多种上述的组合和掺入上述一种或多种的可食用香味组合物。
示例性烘烤制品包括、但不限于夹心饼干(alfajores)、面包、包装/工业化面包、散装的/手工面包、面粉糕饼、蛋糕、包装/工业化蛋糕、散装的/手工蛋糕、饼干、巧克力糖皮饼干、三明治饼干、有馅饼干、加调味料的饼干和薄脆饼干、面包替代品。
示例性甜品包括、但不限于早点用谷物片、可即食(“rte”)谷物、家庭早点用谷物片、薄片、早餐食品、其它可即食谷物、儿童早点用谷物片、热谷物。
示例性的风味产品包括、但不限于含盐零食(马铃薯片、薄脆、坚果、炸玉米粉圆饼、椒盐卷饼、干酪零食、玉米零食、马铃薯零食、可即食爆玉米花、可微波烹饪的爆玉米花(microwaveable popcorn)、猪肉皮、坚果、薄脆饼干、薄脆零食、早点用谷物片、肉类、肉冻、腌肉(火腿、咸猪肉)、午餐/早餐肉(热狗、冷吃的肉片、香肠)、番茄产品、人造黄油、花生酱、汤(清汤、罐装汤、奶油、即食汤、UHT)、罐装蔬菜、面酱。
示例性的乳制品包括、但不限于干酪、干酪调味品、基于干酪的产品、冰淇淋、兴消费的冰淇淋、单份牛奶冰淇淋、单份水冰淇淋、一包多件包装的牛奶冰淇淋、一包多件包装的水冰淇淋、带回家的冰淇淋、带回家的牛奶冰淇淋、冰淇淋甜点、散装冰淇淋、带回家的水冰淇淋、冷冻酸奶、手工冰淇淋、乳制品、乳品、新鲜/巴氏灭菌牛奶、全脂新鲜/巴氏灭菌牛奶、半脱脂新鲜/巴氏灭菌牛奶、保存期较长的/超高温奶、全脂保存期较长的/超高温奶、半脱脂保存期较长的/超高温奶、无脂保存期较长的/超高温奶、羊奶、炼乳/脱水奶、纯炼乳/脱水奶、加味的、功能性和其它炼乳、香味奶饮料、只有调味乳饮料乳制品、含果汁的香味奶饮料、豆浆、酸乳饮料、发酵奶饮料、咖啡白化剂、奶粉、香味奶粉饮料、奶油、酸奶、纯/天然酸奶、加味酸奶、加水果的酸奶、益生菌酸奶、饮用酸奶、定期饮用酸奶、益生菌饮用酸奶、冷冻点心和耐储存点心、基于乳品的点心、基于大豆的点心。
示例性饮料包括、但不限于调味的水、软饮料、果汁饮料、基于咖啡的饮料、基于茶的饮料、基于果汁的饮料(包括水果和蔬菜)、基于奶的饮料、胶冻饮料、碳酸或非碳酸饮料、粉末饮料、酒精或非酒精性饮料。
示例性的发酵食品包括、但不限于干酪和干酪产品、肉和肉制品、大豆和大豆制品、鱼和鱼制品、谷物和谷物制品、水果和水果制品。
式(I)的化合物在添加到香味组合物和/或可食用组合物中时可以改进可食用组合物的味道和/或口感的短暂特性的任意方面。
可以将式(I)的化合物或包含它们的香味组合物以广泛携带量加入到可食用产品中。用量取决于所加香的可食用组合物的性质和期望的效果以及存在于所述组合物中的成分的性质。为了得到归因于存在的式(I)的化合物的显著的有益效果,香味组合物应当以这样的用量使用,使得式(I)的化合物的存在量为占可食用组合物总重的每十亿份中1份至每百万份中10份。尽管可以使用高于它的用量,但是有益效果明显相当低且不期望的异味可能逐步变得明显。
当以1-100ppb的水平使用式(I)的化合物时,可以在包含盐或酒精或清凉化合物的可食用产品中实现有意义的感官效果,例如咸、酒精或清凉加强效果。
当以100-250ppb的水平使用式(I)的化合物时,可以在包含鲜味促味剂的可食用产品中实现有意义的感官效果,例如鲜味加强效果。
当以250-500ppb的水平使用式(I)的化合物时,可以在可食用产品中实现有意义的感官效果,特别是口感加强效果。
当以500-1000ppb的水平使用式(I)的化合物时,可以在包含脂肪的可食用产品中实现有意义的感官效果,例如脂肪加强效果。
特别有利的是将式(I)的化合物掺入在高温条件下例如烘烤、油煎形成或通过热处理例如巴氏消毒或UHT条件下加工的可食用产品。在高制备或加工温度下,挥发性香味成分可能丧失或被降解,结果是香味强度可能下降且基本和真实的香味特征可能减少。这类可食用产品包括乳制品、零食、烘焙食品、粉状软饮料和类似干燥混合物等、脂肪和作料、蛋黄酱、调味品、汤和肉汤和饮料。
本发明的一种特别优选类型的可食用组合物是粉状软饮料和类似的干燥混合物用品。干燥混合物用品是本领域公知的且包括预期在消费前再溶解的粉末形式的产品。它们包括汤粉、粉状蛋糕混合料、粉状巧克力饮料、速溶咖啡、调味品和方坦糖(fonds)等。
通过分散蒸发法例如喷雾干燥形成的干粉代表将香味油品质的香味递送给可食用产品的极为便利的载体。
本发明可食用组合物的另一种特别优选的种类是快餐食品。快餐食品是食品工业领域普通技术人员众所周知类型的产品。这些产品如上所述且包括、但不限于椒盐卷饼、玉米片、马铃薯片、膨化制品、挤出产品、玉米粉圆饼片等。更具体地,本发明涉及低脂肪快餐食品组合物。低脂肪快餐食品组合物包含低于30%重量的脂肪,更具体地为5-25%重量的脂肪。
在快餐食品组合物中减少脂肪的问题在于味道和质地缺失。脂肪以这样的方式起重要作用,即生面团在加工过程中的行为且显著地影响方便食品的质量、香味和质地。当零食产品中的脂肪含量下降或被其它成分(例如不可消化的脂肪、蛋白质、纤维、树胶)替代时,不良感官效应(例如口腔涂抹、干燥、缺乏脆性和缺乏香味)增加。不良感官效应导致产品的适口性下降。
在设计香味组合物的过程中已经花费了相当的努力来克服与低脂肪快餐食品相关的问题。可以将香料作为干粉和/或液体形式(例如基于油、基于水)的局部涂料涂布于快餐食品上。另一种方法在于向生面团中添加香料。
尽管采取这些不同方法来改善消费者对快餐食品且特别是低脂肪快餐食品的吸引力和适口性,但是仍然需要改进的低脂肪快餐食品,其上涂布有全脂快餐食品的视觉吸引力、香味和质地的涂料。
可以将式(I)的化合物或包含它们的香味组合物掺入快餐食品以赋予有效的香味和具有显著的圆和与丰满感的口感。此外,甚至可以在低脂肪快餐食品中实现所述味道和口感效应。
因此,本发明在其另一个方面中提供了包含如上所述的香味组合物的快餐食品。在本发明的一个具体的实施方案中,所述快餐食品具有的脂肪含量占该快餐食品总重的约40%重量或以下,更具体地为约30%重量或以下,仍然更具体地为25%重量或以下,更具体地为约10%重量或以下,仍然更具体地为约5%重量或以下,仍然更具体地为约3%重量或以下。
快餐食品的实例如上所述且包括通过烤箱烘烤、挤出或油煎加工和由马铃薯和/或玉米和/或不同谷物例如稻米或小麦加工的产品。
本发明的另一种特别优选类型的可食用组合物是酒精性饮料。
申请人令人惊讶地发现,掺入酒精性饮料的式(I)的化合物具有增加该饮料酒精影响的作用。
因此,本发明在其另一个方面中提供了包含式(I)的化合物的酒精性饮料。
在本发明的另一个方面中提供了在酒精性饮料中产生增强的酒精影响的方法,通过将式(I)的化合物掺入所述饮料来进行。
可以将式(I)的化合物以1ppb-1ppm的量掺入所述酒精性饮料。
另一类可食用产品是通过口服摄取的片剂、胶囊、粉末、多颗粒等形式的产品。这种化合物可以包括药物剂型或营养品剂型。
一类人存在吞咽片剂或胶囊、粉末、多颗粒等困难的问题。该问题在一些消费者类型中特别显著,例如儿童和极老的老年人或虚弱的人。申请人令人惊讶地发现,式(I)的化合物在摄入口腔中时产生显著的分泌唾液效应。将所述化合物掺入这些形式,特别是作为所述剂型周围包衣衣料的组成部分可以使得消费者的吞咽过程便利,特别是儿童和老年人或虚弱的人。
因此,本发明在其另一个方面中提供了可口服施用的剂型,特别是包含式(I)的化合物的片剂、胶囊、粉末或多颗粒形式。
另一种优选类型的可食用组合物是烘烤制品。可以局部或在生面团中掺入式(I)的化合物。掺入1ppb-1ppm水平的式(I)的化合物使得烘烤制品干燥程度较低且更具有多汁性。
其它优选类型的可食用产品是有热量的或无热量的饮料,其包含碳水化合物甜味剂,例如蔗糖、高果糖玉米糖浆、果糖和葡萄糖;或高强度无营养甜味剂,例如阿斯巴甜、乙酰舒泛钾、三氯蔗糖、环己氨基磺酸盐、糖精钠、纽甜、莱鲍迪甙A和/或其它基于甜叶菊的甜味剂;以及其它任选的成分,例如果汁、有机酸例如柠檬酸、醇和功能性成分。
掺入1ppb-10ppm水平的式(I)的化合物给包含低于1%且至多为约20%水平的甜味剂的所述饮料赋予上等的甜味和暗示为糖的口感。
其它优选的可食用产品是风味组合物,特别是为基于大豆的或基于鱼肉的那些组合物。
在包含5-40%盐的基于大豆的组合物(例如大豆酱油)或基于鱼肉的组合物(例如鱼肉调味料)中掺入1ppb-10ppm水平,发现这些组合物显示逗留不去和丰富的强烈鲜味。
另一种优选的可食用组合物是混浊状饮料组合物。
一些饮料例如果汁具有相对较高的浊度且由此具有不透明的外观。通常期望饮料具有相对高的浊度,这可能期望给具有低果汁含量的饮料提供天然的外观,或可能的原因与掩蔽沉降或“清脆声响(ringing)”(其中在贮存期间香味或色素油升至容器表面)相关。混浊状饮料通常借助于混浊剂形成。混浊剂通常以乳液形式提供,或混浊剂可以是粉状饮料的组成部分,在重构时,形成乳液,从而为饮料提供持久的混浊。
式(I)的化合物除其显著的感官特征外还可以赋予混浊剂和包含它们的饮料组合物稳定性。
其它优选的可食用产品是通过熟化方法形成的那些组合物。在食品加工过程中,对于食品而言频繁出现需要在充分确定条件下保持延长时间期限的需求,以得到具有必不可少和公认的品质的食品。用于该过程的常用术语是熟化。熟化是一些类型的干酪、肉类、大豆酱油和葡萄酒以及啤酒香肠、泡菜、印尼豆豉和豆腐加工中众所周知的。还存在因特定原因进行的具体步骤(例如除去水或除去异味),它们对食品产生有益作用。其实例是精炼巧克力和干燥面条、蔬菜和水果。改善食品质量的转化通过化学转化、酶催化的转化或发酵转化诱导。所有这些转化均为缓慢的且由此是昂贵的;它们也不完全可预期或可控。
式(I)的化合物在其添加到掺入它们的可食用产品的真实味道特征方面具有显著特性,可以将式(I)的化合物在熟化过程中添加到可食用产品中,以便减少贮存时间,而不会对熟化产品的味道品质产生不良影响。
因此,本发明在另一个方面中提供了熟化产品的方法,所述产品选自干酪、肉类、大豆酱油和葡萄酒、啤酒、香肠、泡菜、印尼豆豉和豆腐,该方法包括在式(I)的化合物的存在下熟化所述产品的步骤。
本发明在另一个方面中提供了精炼巧克力的方法,该方法包括将式(I)的化合物或包含它的香味组合物添加到巧克力中的步骤。
现在参照下列非限制性实施例进一步描述本发明。这些实施例仅由于示例目的,但是应当理解,本领域技术人员可以进行改变和变型。
实施例1:(Z)-2-(十二-5-烯酰氨基)-3-苯基丙酸(GR-72-7877)
向冷却的(-15℃)苯丙氨酸甲酯HCl(1.20g,5.55mmol)在二氯甲烷中的混合物中缓慢地各自加入无水(100ml)三乙胺(0.7ml,5.04mmol)和(Z)-十二-5-烯酸(1.00g,5.04mmol)。在5分钟内滴加二环己基碳二亚胺(1.04g,5.04mmol)在二氯甲烷(10ml)中的溶液。搅拌该反应体系,同时将其自身温热至室温,持续搅拌16小时。过滤后,用碳酸氢钠溶液(10%)、盐酸(1N)、水和盐水洗涤液体滤液。将有机层用硫酸钠干燥,真空浓缩,得到粗固体残余物(2g),用80g硅胶柱进行色谱。用己烷和乙酸乙酯作为洗脱液。回收酰氨基甲酯中间体,为无色液体0.83g。缓慢地加入氢氧化钠(37%,1.00g,9.23mmol),将该反应体系在室温搅拌16小时。用水(50ml)和乙酸乙酯(20ml)稀释该反应体系,用盐酸(浓,0.8ml)酸化至pH3。用乙酸乙酯各30ml将该混合物萃取3次。用水(20ml)和盐水(20ml)洗涤合并的萃取物;用硫酸钠干燥,真空浓缩。回收氨基酸,为白色固体0.71g(2mmol,86%收率)。
表征合成的化合物。
1H NMR(300MHz,DMSO-d6)δppm 0.80-0.91(m,3H),1.20-1.33(m,8H),1.37-1.50(m,2H),1.82-1.99(m,4H),2.00-2.10(m,2H),2.84(dd,J=13.75,9.80Hz,1H),3.05(dd,J=13.85,4.80Hz,1H),4.42(ddd,J=9.70,8.19,4.71Hz,1H),5.15-5.43(m,2H),7.04-7.36(m,5H),8.10(d,J=8.29Hz,1H),12.62(s,1H)。
13C NMR(75MHz,DMSO-d6)δppm 173.14,171.94,137.74,129.99,129.05,129.00,128.04,128.04,126.28,53.23,36.71,34.61,31.11,29.05,28.26,26.55,26.13,25.30,22.04,13.91.MS-APCI[M+H]+:m/z 346.3。
实施例2:(Z)-2-(十二-5-烯酰氨基)-3-(4-羟基苯基)丙酸(GR-72-7888)
根据实施例1的相同方法,由(Z)-十二-5-烯酸和酪氨酸制备(Z)-2-(十二-5-烯酰氨基)-3-(4-羟基苯基)丙酸,收率为68%。
1H NMR(300MHz,DMSO-d6)δppm 0.81-0.91(m,3H),1.20-1.34(m,8H),1.45(五重峰,J=7.44Hz,2H),1.86-2.01(m,4H),2.02-2.11(m,2H),2.72(dd,J=13.85,9.51Hz,1H),2.91(dd,J=13.75,4.90Hz,1H),4.25-4.39(m,1H),5.13-5.45(m,2H),6.51-6.74(m,2H),6.88-7.11(m,2H),8.02(d,J=7.91Hz,1H),9.17(br.s.,1H),12.55(br.s.,1H)。
13C NMR(75MHz,DMSO-d6)δppm 173.27,171.94,155.82,130.02,129.89,129.89,129.05,127.70,114.86,114.86,53.64,35.99,34.61,31.11,29.06,28.26,26.55,26.18,25.32,22.04,13.91.MS-APCI[M+H]+:m/z 362.1。
实施例3:2-(十二烷酰氨基)-3-苯基丙酸(GR-72-7558)
根据实施例1的相同方法,由十二烷酰氯和苯丙氨酸制备2-(十二烷酰氨基)-3-苯基丙酸,收率为88%。
1H NMR(600MHz,DMSO-d6)δppm 0.85(t,J=6.87Hz,3H,H-C(12))0.99-1.30(m,16H,H-C(4,5,6,7,8,9,10,11)1.36(五重峰,J=7.30Hz,2H,H-C(3))2.01(t,J=7.22Hz,2H,H-C(2)))2.83(dd,J=13.75,9.62Hz,1H,H-C(15))3.06(dd,J=13.75,4.47Hz,1H,H-C(15))4.38(ddd,J=9.45,8.25,4.64Hz,1H,H-C(14))7.08-7.29(m,5H,H-C(17,18,19,20,21))7.98(d,J=8.25Hz,1H,H-N(22))。
13C NMR(150MHz,DMSO-d6)δppm 13.95(C(12)),22.11(C(11)),28.28-29.18(C(4,5,6,7,8,9)31.31(C(10)),35.20(C(2)),36.95(C(15)),53.71(C(14)),126.10(C((19)),127.94(C(18,20))129.13(C(17,21)),138.16C(16)),171.91(C(1)),173.49(C(13))。
实施例4:2-(十二烷酰氨基)-3-(1H-吲哚-3-基)丙酸(GR-72-7557)
根据实施例1的相同方法,由十二烷酰氯和色氨酸制备2-(十二烷酰氨基)-3-(1H-吲哚-3-基)丙酸,收率为76%。
1H NMR(600MHz,DMSO-d6)δppm 0.79-0.92(m,3H,H-C(12))1.05-1.32(m,16H,H-C(4,5,6,7,8,9,10,11)1.40(五重峰,J=7.05Hz,2H,H-C(3))1.95-2.13(m,2H,H-C(2))2.99(dd,J=14.43,8.94Hz,1H,H-C(15))3.15(dd,J=14.61,4.98Hz,1H,H-C(15))4.47(td,J=8.42,5.16Hz,1H,H-C(14))6.93-7.00(t,J=7.39Hz,1H,H-C(19))7.05(t,J=7.39Hz,1H,H-C(20)7.12(d,J=2.41Hz,1H,H-C(23))7.32(d,J=7.56Hz,1H,H-C(21))7.52(d,J=7.56Hz,1H,H-C(18))8.06(d,J=7.90Hz,1H,H-N(25))。
13C NMR(150MHz,DMSO-d6)δppm 13.97(C(12)),22.13(C(11)),26.91-29.25(C(4,5,6,7,8,9,15),31.33(C(10)),35.12(C(2)),52.86(C(14)),110.04(C(16)),111.35(C(21)),118.17(C(18)),118.29(C(19)),120.86(C(20)),123.50(C(23)),127.22(C(17)),136.10(C(22)),172.24(C(1)),173.61(C(13))。
实施例5:2-(十二烷酰氨基)-3-(4-羟基苯基)丙酸(GR-72-7732)
根据实施例1的相同方法,由十二烷酰氯和酪氨酸制备2-(十二烷酰氨基)-3-(4-羟基苯基)丙酸,收率为5%。
1H NMR(600MHz,DMSO-d6)δppm 0.85(t,J=6.70Hz,3H,H-C(12))1.09-1.31(m,16H)1.35-1.43(m,2H,H-C(3))1.98-2.06((t,J=7.22Hz,2H,H-C(2))2.71(dd,J=13.92,9.79Hz,1H,H-C15))2.91(dd,J=13.92,4.64Hz,1H,H-C(15)4.31(td,J=8.76,4.81Hz,1H,H-C(14))6.63(d,J=8.59Hz,2H,H-C(18,20)6.95-7.02(d,J=8.59Hz,2H,H-C(17,21))8.00(d,J=8.25Hz,1H,H-N(22))
13C NMR(150MHz,DMSO-d6)δppm 13.97(C(12)),22.13(C(11)),25.22(C(3)),28.35-29.17C((4,5,6,7,8,9))31.33(C(10)),35.11(C(2)),36.07(C(15)),53.71(C(14)),114.88C((18,20)),127.80(C(16)),129.96(C(17,21))155.86(C(19)),172.14(C(1)),173.40(C(13))。
实施例6:(Z)-2-(十二-5-烯酰氨基)-3-(1H-吲哚-3-基)丙酸-GR72-7759
根据实施例1的相同方法,由(Z)-十二-5-烯酸和色氨酸制备(Z)-2-(十二-5-烯酰氨基)-3-(1H-吲哚-3-基)丙酸,收率为10%。
1H NMR(600MHz,DMSO-d6)δppm 0.82-0.87(m,3H,H-C(12))1.19-1.30(m,8H,H-C(8,9,10,11)1.40-1.50(m,2H,2)1.88-1.97(m,4H,H-C(4,7))2.01-2.12(m,2H,H-C(2))2.98(dd,J=14.61,8.76Hz,1H,H-C(15))3.15(dd,J=14.78,5.15Hz,1H,H-C15))4.44(td,J=8.16,4.98Hz,1H,H-C(14))5.25-5.36(m,2H,H-C(5,6))6.94-6.98(t,J=6.87Hz,1H,H-C(20))7.03-7.07(t,J=6.87Hz,1H,H-C(21))7.11(d,J=2.06Hz,1H,H-C(17))7.31(d,J=7.90Hz,1H,H-C(19))7.52(d,J=7.90Hz,1H,H-C(22))8.03(d,J=7.56Hz,1H,H-N(24))。
13C NMR(150MHz,DMSO-d6)δppm 13.95(C(12)),22.08(C(11)),24.81-29.37(C(3,4,7,8,9,15),31.15(C(10)),34.68(C(2)),52.98(C(14)),110.13(C(16)),111.31(C(22)),118.19(C(19)),118.26(C(20)),120.84(C(21)),123.43(C(17)),127.25(C(18)),129.10C(5)),130.06(C(6)),136.05(C(23)),171.95(C(1)),173.58(C(13))。
实施例7:3-(1H-吲哚-3-基)-2-十四烷酰氨基丙酸
根据实施例1的相同方法,由肉豆蔻酰氯和色氨酸制备3-(1H-吲哚-3-基)-2-十四烷酰氨基丙酸,收率为19%。
1H NMR(600MHz,氯仿-d)δppm 0.88(t,J=7.05Hz,3H)1.09-1.36(m,21H)1.43-1.55(m,2H)2.07(t,J=7.73Hz,2H)3.22-3.41(m,2H)4.71-4.97(m,1H)6.11(d,J=7.56Hz,1H)6.97(s,1H)7.02-7.14(m,1H)7.18(t,J=7.56Hz,1H)7.26(s,1H)7.32(d,J=7.90Hz,1H)7.55(d,J=7.90Hz,1H)8.34(br.s.,1H)。
13C NMR(151MHz,氯仿-d)δppm 14.11(s,1C)22.68(s,1C)25.38(s,1C)27.03(s,1C)29.15(s,1C)29.28(s,1C)29.36(s,1C)29.45(s,1C)29.62(s,1C)29.65(s,1C)29.69(s,1C)31.91(s,1C)36.40(s,1C)53.37(s,1C)109.52(s,1C)111.40(s,1C)118.37(s,1C)119.70(s,1C)122.18(s,1C)123.20(s,1C)127.75(s,1C)136.08(s,1C)174.28(s,1C)175.17(s,1C)。
实施例8:牛肉汤
使用得自当地超市的汤粉块制备牛肉汤。由富有经验的品尝者小组评价饮品。
a)当将40ppb(Z)-2-(十二-5-烯酰氨基)-3-苯基丙酸加入到肉汤中时,小组同意品尝的汤比参比物具有更多的鲜味、稍多的甜味,且总体香味特性持续得比参比物更长。
b)当将40ppb(Z)-2-(十二-5-烯酰氨基)-3-(4-羟基苯基)丙酸加入到肉汤中时,小组同意品尝的汤比参比物具有稍多的鲜味、适度多的苦味和甜味。
实施例9:乳品
使用来自当地超市的牛奶饮品半脱脂乳制备牛奶饮料。
a)当将5ppm(Z)-2-(十二-5-烯酰氨基)-3-(1H-吲哚-3-基)丙酸加入到牛奶饮料中时,小组同意品尝的牛奶饮料比参比物具有适度增加奶油样感觉。
b)当将5ppm 3-(1H-吲哚-3-基)-2-十四烷酰氨基丙酸加入到乳品中时,小组同意牛奶饮料与参比物相比具有极似奶油样的余味且上部良好和适度干燥。
实施例10:鲜味基料香料
使用NaCl、MSG和核糖核苷酸类制备鲜味基料香料的水溶液。
a)当将50ppm 2-(十二烷酰氨基)-3-苯基丙酸加入到香料中时,小组同意品尝的基料比参比物具有更多的鲜味和浓稠感,具有众多的口感和良好的本体,并且提供更纯净的味道。
b)当将5ppm(Z)-2-(十二-5-烯酰氨基)-3-(1H-吲哚-3-基)丙酸加入到香料中时,小组同意品尝的基料比参比物具有更多的鲜味。
c)当将20ppm 2-(十二烷酰氨基)-3-(1H-吲哚-3-基)丙酸加入到香料中时,小组同意品尝的基料比参比物具有更多的脂肪样口感。
d)当将5ppm 3-(1H-吲哚-3-基)-2-十四烷酰氨基丙酸加入到基料中时,小组同意品尝的基料比参比物具有更多的鲜味。
实施例11:大豆酱油
通过稀释得自当地超市的大豆酱油制备大豆酱油。
a)当将5ppm 3-(1H-吲哚-3-基)-2-十四烷酰氨基丙酸加入到大豆酱油中时,小组同意酱油的味道比参比物具有更多的口感和丰富感。
Claims (5)
2.权利要求1的香味组合物,其中所述香味辅助成分选自:糖类、脂肪、氯化钠、谷氨酸一钠、钙离子、磷酸根离子、有机酸、蛋白质、嘌呤类、香料及其混合物。
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US10834950B2 (en) | 2020-11-17 |
EP3057447A1 (en) | 2016-08-24 |
US20160227824A1 (en) | 2016-08-11 |
EP3057447B1 (en) | 2017-12-06 |
CN105592719A (zh) | 2016-05-18 |
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