CN114786499A - 味道改良成分 - Google Patents
味道改良成分 Download PDFInfo
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- CN114786499A CN114786499A CN202080086724.6A CN202080086724A CN114786499A CN 114786499 A CN114786499 A CN 114786499A CN 202080086724 A CN202080086724 A CN 202080086724A CN 114786499 A CN114786499 A CN 114786499A
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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Landscapes
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- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
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- Inorganic Chemistry (AREA)
- Microbiology (AREA)
- Seasonings (AREA)
- Dairy Products (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Non-Alcoholic Beverages (AREA)
- Confectionery (AREA)
- General Preparation And Processing Of Foods (AREA)
Abstract
提供了在具有约20%或更低的脂肪含量的消费品中提供改善的口感的方法。该方法包括向消费品组合物基料中添加基于消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物的步骤,而无需任何后续加热。所述阿马道里化合物为葡萄糖与脯氨酸的反应产物。
Description
技术领域
本公开内容涉及使用味道改良成分改善消费品(consumable)的口感的方法。更具体地,本公开内容涉及使用作为葡萄糖和氨基酸的反应产物的阿马道里(Amadori)化合物改善含有脂肪或低脂的消费品的口感的方法,其中所述消费品为食品和饮料。甚至更具体地,本公开涉及包含阿马道里味道改良成分的香料组合物和消费品以及阿马道里味道改良成分在消费品中的用途,例如用于改善消费品的口感。
背景
广泛使用用于改变消费品(即口服用于摄取或吐出的产品,诸如食品、饮料、糖食、口腔护理产品等)的味道的化合物。它们本身不向消费品添加香味,但它们提供期望的辅助益处,如增强的口感,或掩蔽其他成分的不期望的特征,如与在膳食产品中替代糖使用的一些甜味剂相关的苦味余味。期望的口感通常以光滑感(无粗糙度和磨损)和奶油感为典型。
持续需要提供味道改良成分,所述味道改良成分补充其中掺入它们的消费品的香味,以便强调所述组合物的香味和口感,而不是发挥其自身特定的味道特征;并且因此使其适用于广泛范围的食品和饮料类别的非常广泛的用途。
因此,需要提供用于含有脂肪或低脂的消费品的化合物,其改善口感,同时保持或增强此类可食用组合物的期望的感官特性。
概述
在一个示例性实施方案中,在具有约20%或更低的脂肪含量的消费品中提供改善的口感的方法包括以下步骤:向消费品组合物基料中添加基于消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物,而不进行任何后续加热。
在另一个示例性实施方案中,消费品组合物包含具有约20%或更低的脂肪含量的消费品基料以及基于消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物。
在另一个示例性实施方案中,乳制品消费品组合物包含消费品基料和基于所述消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物,其中所述阿马道里化合物补充所述消费品组合物的口感特征。
通过阅读本公开内容,具体实施方案的这些和其他特征、方面和优点对于本领域技术人员将变得显而易见。
详细描述
以下文本阐述了本公开的许多不同实施方案的广泛描述。本说明书应被解释为仅是示例性的,并且并不描述每个可能的实施方案,因为描述每个可能的实施方案即使不是不可能也是不切实际的。应当理解,本文所述的任何特征、特性、组分、组合物、成分、产品、步骤或方法可以全部或部分地被删除、组合或替代本文所述的任何其他特征、特性、组分、组合物、成分、产品、步骤或方法。可以使用现有技术或在本申请的申请日之后开发的技术来实施许多替代实施方案,这些替代实施方案仍然落入权利要求的范围内。本文引用的所有出版物和专利均通过引用并入本文。
不期望的口感可能严重不利于另外期望加香的含脂肪或低脂的消费品。如本文所用,“口感”是指由食品、饮料或成分在口腔中产生的物理感觉,包括但不限于厚重度、稠度、粘度、湿润度、光滑感、成膜度、干燥度和/或口腔涂覆感。令人遗憾地,期望的效果通常是脂肪食品(诸如乳制品)的特征,出于健康和饮食原因,许多人应减少其摄入。目前已经令人意外地发现,通过将阿马道里化合物掺入消费品组合物中可以改善不期望的口感特性,其中阿马道里化合物以基于消费品组合物的总重约十亿分之0.02至约百万分之25的量存在。
在一个实施方案中,公开了在具有约20%或更低的脂肪含量的消费品中提供改善的口感的方法,该方法包括向消费品组合物基料中添加基于消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物的步骤。令人惊讶地,已经发现,包含以一定浓度存在的葡萄糖与脯氨酸的阿马道里反应产物改善了具有约20%或更低的脂肪含量的消费品的总体口感。
在另一个实施方案中,已发现包含以一定浓度存在的葡萄糖与脯氨酸的阿马道里反应产物改善了具有大于约20%的脂肪含量的消费品的总体口感。
还发现以一定浓度存在的葡萄糖与脯氨酸的阿马道里反应产物也增强了其他口感特征,例如奶油感、脂肪感和质地感(body)。
阿马道里化合物(也称作阿马道里产物)通过众所周知的阿马道里重排反应形成,其中醛糖通过酸或碱异构化,然后与胺反应以在席夫碱中间体重排后形成阿马道里化合物(参见M.Amadori,Atti Accad.Naz.Lincei 2(6),337(1925);The Merck Index(第14版),pg.ONR-3,(2006))。下面的反应方案显示了己糖与氨之间反应以形成阿马道里化合物。
尽管制备阿马道里化合物(产物)的方法在本领域中是众所周知的,但它们的用途在本领域中鲜为人知。阿马道里化合物被视为本身没有益处,而是用作形成高级终产物(AEP)的中间体化合物,其中阿马道里化合物处于脱水、碎片化或羟醛缩合下。这些AEP通常在食品工业中作为香料具有益处。一个这样的实例为阿马道里化合物的热解以产生具有焦糖气味的化合物。Mills等人,“Amadori Compounds as Nonvolatile Flavor Precursorsin Processed Foods”,Agric.Food Chem.,第17卷,第48期,723-727页(1969年7月-8月)。
根据某些实施方案,通过葡萄糖与氨基酸的反应形成阿马道里化合物,其中氨基酸选自组氨酸、异亮氨酸、甲硫氨酸、脯氨酸和丝氨酸。在一个实施方案中,由葡萄糖与脯氨酸的反应形成的阿马道里化合物可以表示为N-(1-脱氧-D-果糖-1-基)-L-脯氨酸:
类似地,葡萄糖与其他天然存在的氨基酸的反应可以表示为:
·N-(1-脱氧-D-果糖-1-基)-L-组氨酸;
·N-(1-脱氧-D-果糖-1-基)-L-异亮氨酸;
·N-(1-脱氧-D-果糖-1-基)-L-甲硫氨酸;
在另一个实施方案中,通过葡萄糖和丝氨酸反应形成的阿马道里化合物可以表示为N-(1-脱氧-D-果糖-1-基)-L-丝氨酸:
本申请中所述的阿马道里化合物的上述结构也预期包括其盐形式和带电荷形式。此外,尽管上述阿马道里化合物描述了D-葡萄糖,但来自L-葡萄糖的阿马道里化合物也被视为本公开内容的组成部分。
为了获得归因于包含葡萄糖与脯氨酸的阿马道里反应产物的存在的显著有益效果,基于消费品组合物的总重,反应产物应以十亿分之0.02至百万分之25的量使用。尽管可以使用高于该量的量,但有益效果相当地较不明显,并且不期望的异味(off-note)可能变得越来越明显。
根据某些实施方案,存在于消费品组合物中的葡萄糖与脯氨酸的阿马道里反应产物的量可以为约0.02ppb至约25ppm的浓度。根据某些实施方案,存在于消费品中的葡萄糖与脯氨酸的阿马道里反应产物的量可以为约0.1ppb至约10ppm的浓度。根据某些实施方案,存在于消费品中的葡萄糖与脯氨酸的阿马道里反应产物的量可以为约0.25ppb至约1ppm的浓度。根据某些实施方案,存在于消费品中的葡萄糖与脯氨酸的阿马道里反应产物的量可以为约0.5ppb至约250ppb的浓度。
当表示为“ppb”或“ppm”时,浓度是基于消费品的总重按重量计十亿分之几或百万分之几,如情况所示。应当理解,当在本公开内容中描述值的范围时,旨在将该范围内的任何和每个值(包括端点)视为已经被公开。例如,葡萄糖与脯氨酸的阿马道里反应产物的“100ppm至1000ppm的范围”应被解读为指示沿着100至1000之间的连续区间的每个和每一个可能的数值。应当理解,本发明人认识到并理解,该范围内的任何和所有值应被认为已被指定,并且本发明人拥有整个范围和该范围内的所有值。
在本公开中,与数值结合使用的术语“约”包括所述值并且具有上下文所规定的含义。例如,它至少包括与特定值的测量相关的误差程度。本领域普通技术人员本领域可以理解,术语“约”在本文中用于表示所述值的“约”的量在本公开内容的组合物和/或方法中产生期望程度的有效性。本领域普通技术人员将进一步理解,在一个实施方案中,关于任何成分的百分比、量或数量的值的“约”的界限和边界可以通过改变该值、确定对于每个值的组合物或方法的有效性并确定产生具有根据本公开内容的期望有效性程度的组合物或方法的值的范围来确定。
冠词“一个/种(a)”、“一个/种(an)”和“所述(the)”在本文中用于指示该冠词的语法对象的一个或多于一个(即,至少一个)。作为实例,“一种化合物”是指一种化合物或多于一种化合物。
味道改良成分的最终形式可以根据本领域众所周知的方法来选择,并且将取决于特定的食品应用。对于液体食品,味道改良成分可以以其液体形式使用而无需进一步加工。对于干燥应用,可以使用喷雾干燥的浓缩的味道改良成分。可以将味道改良成分直接添加到食品中,或者可以作为用于加香或调味食品的香料组合物的组成部分来提供。
所述消费品组合物可以包括基料。如本文所用,术语“基料”是指消费品所必需的所有成分,葡萄糖与脯氨酸的味道改良的阿马道里反应产物除外。根据消费品或添加剂的性质和用途的不同,这些自然将在性质和比例上不同,但它们都是本领域众所周知的,并且可以以本领域公认的比例使用。因此,用于每种可以设想到的目的的这种基料的配制在本领域的普通技术人员的范围内。
非限制性地并且仅作为示例的方式,适合的基料可以包括防结块剂、消泡剂、抗氧化剂、粘合剂、着色剂、稀释剂、崩解剂、乳化剂、包封剂或制剂、酶、脂肪、增味剂、矫味剂、树胶、多糖、防腐剂、蛋白质、增溶剂、溶剂、稳定剂、糖衍生物、表面活性剂、甜味剂、维生素、蜡等。可以使用的溶剂为本领域技术人员已知的,并且包括例如水、乙醇、乙二醇、丙二醇、甘油和三醋精。包封剂和树胶包括麦芽糖糊精、阿拉伯树胶、海藻酸盐、明胶、改性淀粉、其他多糖和蛋白质。
用于香料化合物的赋形剂、载体、稀释剂或溶剂的实例可以在如下文献中找到,例如:“Perfume and Flavour Materials of Natural Origin”,S.Arctander,Ed.,Elizabeth,N.J.,1960;“Perfume and Flavour Chemicals”中,S.Arctander,Ed.,第I&II卷,Allured Publishing Corporation,Carol Stream,USA,1994;“Flavourings”,E.Ziegler和H.Ziegler(ed.),Wiley-VCH Weinheim,1998,和“CTFA Cosmetic IngredientHandbook”,J.M.Nikitakis(ed.),第1版,The Cosmetic,Toiletry and FragranceAssociation,Inc.,Washington,1988。
根据某些实施方案,葡萄糖与脯氨酸的阿马道里反应产物可以作为味道改良组合物的组成部分添加到消费品中,其中所述组合物包含至少一种特征香料。葡萄糖与脯氨酸的阿马道里反应产物可以直接添加到消费品中或与消费品的某些成分预混合。适合的特征香料的非限制性实例包括天然香料、人造香料、香料调味品、作料等。这些包括合成香味油和调味芳香剂和/或油、油性树脂、香精和馏出物及其组合。术语“特征香味”是指在个体食用(consumption)时被个体感知为占主导地位的香味。
香味油包括留兰香油、肉桂油、冬青油(水杨酸甲酯)、薄荷油、日本薄荷油、丁香油、月桂油、茴香油、桉树油、百里香油、雪松叶油、肉豆蔻油、多香果(allspice)、鼠尾草油、肉豆蔻衣(mace)、苦杏仁油和肉桂油;有用的矫味剂包括人造的、天然的和合成的水果香料,例如香草,和柑桔油,包括柠檬、橙子、酸橙、葡萄柚、日本柚子(yuzu)、酢橘(sudachi),和水果香精,包括苹果、梨、桃、葡萄、覆盆子、黑莓、醋栗、蓝莓、草莓、樱桃、李子、西梅、葡萄干、可乐、瓜拉那、橙花油、菠萝、杏、香蕉、甜瓜、杏、樱桃、热带水果、芒果、山竹、石榴、番木瓜等。
由特征香料赋予的另外的示例性香味可以包括牛奶香味、黄油香味、奶酪香味、奶油香味和酸奶香味、香草香味、茶或咖啡香味,例如绿茶香味、乌龙茶香味、茶香味、可可香味、巧克力香味和咖啡香味;薄荷香味,例如胡椒薄荷香味、留兰香香味和日本薄荷香味;辛辣香味,例如阿魏香味、香旱芹香味、大茴香香味、当归香味、茴香香味、多香果香味、肉桂香味、甘菊香味、芥末香味、小豆蔻香味、香菜香味、孜然香味、丁香香味、胡椒香味、芫荽香味、黄樟香味、开胃的(savory)香味、川花椒(Zanthoxyli Fructus)香味、紫苏香味、杜松子香味、姜香味、八角茴香香味、辣根香味、百里香香味、龙蒿香味、莳萝香味、辣椒香味、肉豆蔻香味、罗勒香味、马郁兰香味、迷迭香香味、月桂叶香味和山葵(日本辣根)香味;坚果香味,如杏仁香味、榛子香味、澳洲坚果香味、花生香味、山核桃香味、开心果香味和胡桃香味;花香味;以及蔬菜香味,例如洋葱香味、大蒜香味、卷心菜香味、胡萝卜香味、芹菜香味、蘑菇香味和番茄香味。
通常,可以使用任何特征香料或食品添加剂,例如由National Academy ofSciences在“Chemicals Used in Food Processing”,出版号1274,63-258页中所述的那些。
可以存在辅助成分以提供其他益处,例如增强的稳定性、易于掺入消费品或添加剂中以及增强的营养价值。这类辅助成分的非限制性典型实例包括稳定剂、乳化剂、防腐剂、树胶、淀粉、糊精、维生素和矿物质、功能性成分、盐、抗氧化剂和多不饱和脂肪酸。具体实例为可用于喷雾干燥方法的乳化剂和载体。这些的非限制性实例为改性淀粉,例如CapsulTM和麦芽糖糊精。
添加剂可以为单一成分或成分的共混物,或者可以将其包封在任意适合的包封剂中,例如上述那些。添加剂可以通过任意适合的方法制备,例如喷雾干燥、挤压和流化床干燥。
阿马道里反应产物可用于多种消费品或应用,并且不限于任何特定的物理模式或产品形式。根据本公开内容,术语“消费品”是指用于受试者出于享受、营养或健康和保健益处目的中的至少一种而典型地经由口腔(尽管可经由非口服手段诸如吸入进行食用)食用的产品。消费品可以以任何形式存在,包括但不限于液体、固体、半固体、片剂、胶囊、锭剂、条带、粉末、凝胶、树胶、糊剂、浆料、溶液、混悬液、糖浆、气雾剂和喷雾剂。该术语还指例如膳食和营养以及健康和保健补充剂。消费品包括在丢弃而不吞咽之前在口腔内放置一段时间期限的组合物。可以在食用之前将其放入口中,或者可以在丢弃之前将其保持在口腔中一段时间期限。已经发现,与乳制品和低脂乳制品结合,特别增强了阿马道里反应产物的口感改善效果。
广泛地,消费品包括但不限于所有种类的食品、糖果产品、烘焙产品、甜味产品、开胃产品、发酵产品、乳制品、非乳制品、饮料、营养物质和药物。
消费品的非限制性实例包括:湿/液体汤,无论浓度或容器如何,包括冷冻汤。出于该定义的目的,汤是指由肉、家禽、鱼、蔬菜、谷物、水果和其他成分制备的食品,在液体中烹饪,其可以包括一些或所有这些成分的可见碎片。它可以是清澈的(作为肉汤)或浓稠的(作为杂烩)、光滑的、泥状的或大块的、即食的(ready-to-serve)、半浓缩的或浓缩的,并且可以热或冷供应,作为膳食的第一道菜或作为主菜或作为餐间小吃(像饮料一样啜饮),汤可以用作制备其他膳食组分的成分,并且可以从肉汤(清炖肉汤)到调味汁(基于奶油或奶酪的汤);脱水和烹饪食品,包括烹饪辅助产品,例如:粉末、颗粒、糊剂、浓缩液体产品,包括浓缩肉羹、肉羹和肉羹样产品(压制方块、片剂或粉末或颗粒形式),其作为成品或作为产品、调味汁和烹饪混合物内的成分单独销售(无论技术如何);膳食溶液产品,例如:脱水和冷冻干燥汤,包括脱水汤混合物、脱水速溶汤、脱水即煮汤、现成菜肴的脱水或环境制备物、膳食和单份主菜,包括意大利面、马铃薯和米饭菜肴;膳食装饰产品,例如:调味品、腌泡汁、色拉调料、色拉浇料、蘸料、面包屑、面糊混合物、贮存稳定涂抹料、烧烤酱汁、液体烹饪混合物、浓缩物、调味汁或调味汁混合物,包括用于色拉的烹饪混合物,作为成品或作为产品内的成分出售,无论是脱水的、液体的还是冷冻的;饮料,包括饮料混合物和浓缩物,包括但不限于酒精和非酒精即饮和干粉饮料、碳酸和非碳酸饮料,例如苏打水、果汁或蔬菜汁、酒精和非酒精饮料、茶如绿茶和红茶、酒如红酒;糖食产品,例如蛋糕、曲奇、派、糖果、口香糖、明胶剂、冰淇淋、冰冻果子露、布丁、果酱、果冻、色拉调味汁和其他调味品、谷类食品和其他早餐食品、罐装水果和水果酱等。
根据某些实施方案,葡萄糖与氨基酸的阿马道里反应产物用于改善低脂乳制品(例如牛奶或酸奶)的口感。根据某些实施方案,葡萄糖与脯氨酸的阿马道里反应产物用于改善低脂乳制品(例如牛奶或酸奶)的口感。
示例性乳制品包括但不限于奶酪、奶酪酱、基于奶酪的产品、冰淇淋、冲动型冰淇淋(impulse ice cream)、单份乳制品冰淇淋、单份水冰淇淋、多包装乳制品冰淇淋、多包装水冰淇淋、家用冰淇淋、家用乳制品冰淇淋、冰淇淋甜点、散装冰淇淋、家用水冰淇淋、冷冻酸奶、手工冰淇淋、牛奶、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、长期保存/超高温牛奶、全脂长期保存/超高温牛奶、半脱脂长期保存/超高温牛奶、无脂长期保存/超高温牛奶、山羊奶、炼乳/淡炼乳、纯炼乳/淡炼乳、加香的、功能性和其他炼乳、加香牛奶饮料、仅乳制品加香的牛奶饮料、含果汁的加香牛奶饮料、豆奶、酸牛奶饮料、发酵乳饮料、咖啡增白剂、奶粉、加香奶粉饮料、奶油、酸奶、纯/天然酸奶、加香酸奶、果味酸奶、益生菌酸奶、饮用酸奶、常规饮用酸奶、益生菌饮用酸奶、冷藏和贮存稳定的甜点、基于乳制品的甜点和基于大豆的甜点。
减少乳制品中脂肪的问题在于味道和质地的损失。随着乳制品中的脂肪含量降低或被其他成分(例如,不易消化的脂肪、蛋白质、纤维、树胶)替代,不利的感官影响(例如,口腔涂覆感、干燥、缺乏脆性和缺乏香味)增加。不利的感官影响导致产品具有降低的可口性。根据本公开内容,乳制品具有基于消费品的总重按重量计约40%或更低、更特别地约20%或更低、仍更特别地15%或更低、在又一个实施方案中10%或更低、并且在另一个实施方案中5%或更低的脂肪含量。
实施例
以下实施例仅出于示例的目的给出,并且不应被解释为对本发明的限制,因为在不脱离本公开内容的精神和范围的情况下,本发明的许多变化是可能的。
实施例1
在本实施例中,由葡萄糖与脯氨酸反应得到的阿马道里化合物由N-(1-脱氧-D-果糖-1-基)-L-脯氨酸(Fru-Pro)制备。
在室温下将5g糖(27.8mmol)和5g脯氨酸(38.1mmol)的混合物加入到1:1MeOH:DMF(100ml:100ml)的溶液中。将该混合物在85℃下搅拌3小时。然后向该混合物中加入1.15g丙二酸(11.05mmol),将得到的混合物在90℃下加热2小时,直至反应的颜色为浅棕色。将浅棕色混合物过滤以除去未溶解的组分,并真空浓缩以除去大部分溶剂。通过在~30℃下加入冷丙酮沉淀出阿马道里化合物。在离心和CI8快速柱纯化后,得到4.14g(92%纯度)的白色固体。
类似地,可以使用甲硫氨酸替代脯氨酸如上所述制备Fru-Met;可以使用异亮氨酸替代脯氨酸如上所述制备Fru-Ileu;并且可以使用组氨酸替代脯氨酸如上所述制备Fru-His。
NMR数据
Fru-Pro
1H NMR(300MHz,D2O)δppm 1.86-2.13(m,3H),2.14-2.39(m,1H),3.18-4.08(m,10H)。
13C NMR(75MHz,D2O,主要异构体)δppm 23.35,28.27,46.08,57.36,63.74,68.90,69.90,69.97,71.44,95.64,173.84。
Fru-Met
1H NMR(600MHz,D2O)δppm 2.09-2.16(m,1H),2.18-2.30(m,2H),2.58-2.74(m,1H),3.28-3.44(m,1H),3.74-3.81(m,1H),3.81-3.94(m,1H),3.98-4.08(m,1H)。
13C NMR(151MHz,D2O)δppm 16.95,31.63,31.90,55.53,62.28,66.76,71.78,72.20,72.76,98.21,175.78。
Fru-Ileu
1H NMR(300MHz,D2O)δppm 0.81-0.92(m,6H),1.19-1.29(m,1H),1.39-1.50(m,1H),1.91(br m,1H),3.20-3.22(m,2H),3.56-3.95(m,6H)。
13C NMR(75MHz,D2O,主要异构体)δppm 11.21,14.07,25.86,25.99,35.79,52.35,63.87,67.76,68.89,69.34,70.12,95.26,172.08。
Fru-His
1H NMR(600MHz,D2O)δppm 3.00-3.36(m,3H),3.46-4.03(m,5H),4.77-4.82(m,1H),4.87-5.05(m,1H),7.10-7.23(m,1H),8.06(s,1H)。
13C NMR(151MHz,D2O)δppm 30.20,55.45,65.35,65.86,71.83,72.31,72.71,98.96,119.42,134.29,137.99,178.04。
在另一个实施例中,通过葡萄糖和丝氨酸反应形成的阿马道里化合物可以表示为N-(1-脱氧-D-果糖-1-基)-L-丝氨酸(Fru-Ser):
将在200mL二氯甲烷中的草酰氯(Oxyalchloride)(6.64g,52.3mmol)冷却至-78℃(丙酮/干冰),通过加压滴液漏斗向该搅拌溶液中滴加在20mL二氯甲烷中的12ml(77mmol)DMSO。完成后,将该混合物在-78℃下搅拌15min,然后再次使用加压滴液漏斗滴加在80mL二氯甲烷中的乙酰基保护的糖(20g,77mmol),将该混合物在-78℃下搅拌17min,然后通过加压滴液漏斗滴加三乙胺(53.6mL,77mmol),在-78℃下连续搅拌17min,然后将该混合物温热至室温,加入水,将该混合物用二氯甲烷萃取3X,合并有机层,用1N HCl 2X、5%Na2CO3 2X、水2X和饱和NaCl洗涤。用硫酸钠干燥,过滤并浓缩滤液。通过快速色谱法使用硅胶柱用EtOAc/己烷(梯度:5%,10%,15%,20%EtOAc在己烷中的溶液至100%EtOAc)纯化,得到10g透明油状化合物A。照此使用。
在室温下,向A(2.55g,9.88mmol)和苄基保护的丝氨酸(1.76g,9.0mmol)在50mLMeOH中的溶液中加入1M氰基硼氢化钠溶液(10mL,9.0mmol),将该混合物在相同温度下搅拌2小时,旋转蒸发掉大部分MeOH。向该混合物中加入饱和NaCl,用EtOAc萃取3X。合并有机层,真空浓缩并经硫酸钠干燥。进行硅胶色谱,用5%MeOH在CH2Cl2中的溶液洗脱,得到3g化合物B的白色固体。
化合物B:1H NMR(300MHz,CD3OD-d6,δppm)1.32(s,3H),1.36(s,3H),1.42(s,3H),1.53(s,3H),3.35(s,2H),3.44(s,2H),3.72-3.76(d,d,J=12.9,Hz,1H),3.87-4.06(m,4H),4.25-4.27(d,J=6.2Hz,1H),4.31-4.32(d,J=2.4Hz,1H),4.58(s,2H),4.63-4.66(d,d,J=2.7,8.1Hz,1H),7.27-7.39(m,5H)。
在室温下向B(3g,6.86mmol)在甲醇(50mL)中的溶液中加入Pd/C,将该溶液脱气,在氢气气囊中搅拌4天。过滤固体;真空除去溶剂。进行硅胶色谱,用5%MeOH在CH2Cl2中的溶液洗脱,得到1.15g化合物B的白色固体,将其溶于2N HCl(2ml)。将圆底烧瓶置于旋转蒸发器上,并将该溶液在室温下真空(~30mmHg)浓缩。将得到的油状残余物溶于水中并真空浓缩。将该操作重复两次,得到粗阿马道里丝氨酸化合物C。将该粗物质用C18柱纯化以得到0.32g白色固体化合物C。
Fru-Ser
1H NMR(300MHz,D2O)δppm 3.20-3.37(m,2H),3.63-4.00(m,8H)。
13C NMR(75MHz,D2O,主要异构体)δppm 52.39,59.04,63.89,68.88,69.33,70.32,95.26,171.14。
制备具有和不具有阿马道里化合物的以下制品,并由专家品尝者(5-7名)品尝并进行比较。阿马道里化合物被掺入消费品中,而不需要额外的加热。
香草加香牛奶
基料:半全脂乳(Half full milk);5%糖;0.1%香草醛;20ppm Fru-Pro:略微更饱满,更丰富(相比于基料),更饱满如脂肪,更甜。
基料:2%乳脂肪;4%糖;0.2%香草提取物;0.1ppb Fru-Pro:更甜的残留感(linger),更多的粉末感,更多的脂肪质地感,饱满和奶油感,更多的乳制品冲击感(impact),更奶油样的口感,轻微的蜡质口感。
基料:2%乳脂肪;4%糖;0.2%香草提取物;1ppb Fru-Pro:更甜,增加饱满度,更奶油样口感,更乳制品感,轻微蜡质口感。
基料:2%脂乳;4%糖;0.15%香草香精;6ppm Fru-Pro:更甜,更丰富的奶油感,略微更甜,多汁感,轻微金属感和口干感。
巧克力加香牛奶
基料:2%乳脂肪;5%糖;2%可可粉;0.05%卡拉胶;0.1ppb Fru-Pro:奶油感,饱满,更丰富的巧克力感,轻微的蜡质,更多的可可冲击感。
基料:2%乳脂肪;5%糖;2%可可粉;0.05%卡拉胶;1ppb Fru-Pro:更多的巧克力残留感,更多的巧克力感,更复杂,饱满的口感,更甜的印象,更稠,蜡质,轻微的刺痛感(tangle)。
基料:2%脂乳;5%糖;2%可可粉;0.05%卡拉胶;10ppm Fru-Pro:更丰富,更多的质地感,更真实的巧克力轮廓感(profile),苦味略微增加。
杏仁牛奶
基料:商购的增甜香草杏仁乳;2ppb Fru-Pro:更奶油感,更强的香草香味,更多的质地感,更奶油样口感;更甜和更咸。
草莓加香酸奶
基料:1.7%脂肪;4%糖;草莓香料0.1%;1ppb Fru-Pro:几乎没有注意到任何效果。
基料:1.7%脂肪;4%糖;草莓香料0.1%;10ppb Fru-Pro:更甜,更奶油感,更丰富的口感,更多果味。
基料:1.7%脂肪;4%糖;草莓香料0.1%;100ppb Fru-Pro:类似于10ppb。
原味低脂酸奶
基料:1.5%脂肪;5%糖;5ppm Fru-Pro:较不酸,更甜,奶油感。
基料:1.5%脂肪;5%糖;10ppm Fru-Pro:增加的前期甜味,较不酸。
基料:1.5%脂肪;5%糖;25ppm Fru-Pro:金属感残留感,增加的整体和前期甜味。
冰淇淋
基料:14.31%重搅打奶油;77.60%全脂奶;8%蔗糖;0.009%香草醛;10ppb Fru-Pro:更奶油感、更甜、稍微更多的质地感和嘴圆润效果(mouth round effect)、稍微更具乳脂肪味道。
奶油馅料(Filling)
基料:66.4%蔗糖;32%棕榈油;0.2%盐;0.4%香草提取物;1%水;10ppb Fru-Pro:更多脂肪和奶油感,更甜和更咸,更具黄油的轮廓感。
奶酪酱
基料:33.46%麦芽糖糊精10DE;29.00%淀粉Ultrasphere 2000;10.00%切达奶酪(白色);9.00%脱脂乳粉;6.20%乳清;5.00%卡诺拉油起酥油粉(canola shorteningpowder);4.25%盐,40目;0.35%酵母提取物粉末;0.10%柠檬酸;0.10%乳酸;2.54%奶酪香料。
10ppm Fru-Pro:更浓,更具奶酪质(cheesier),光滑,更咸,更奶油感的口感,更清新的乳品味,丰富,轻微的金属感和涩味。
10ppm Fru-Met:更浓,奶酪质,鲜味,涩味,更清晰的奶酪味,咸味。
10ppm Fru-Ser:奶酪质,奶油感,浓郁,麻刺感,金属感,浓稠、光滑。
10ppm Fru-Ileu:轻微酸性,苦味,奶油感,增加的咸味。
10ppm Fru-His:更具奶酪质,微酸性,陈化,肉味,麻刺感,白垩感(chalky),口感增加,更奶油感。
尽管已经示例和描述了本发明的具体实施方案,但是对于本领域技术人员显而易见的是,在不脱离本发明的精神和范围的情况下,可以进行各种其他改变和变型。因此,预期在所附权利要求中覆盖在本发明范围内的所有这些改变和变型。
Claims (16)
1.在具有约20%或更低的脂肪含量的消费品中提供改善的口感的方法,该方法包含下列步骤:向消费品组合物基料中添加基于所述消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物,而无需任何后续加热,其中所述阿马道里化合物为葡萄糖与脯氨酸的反应产物。
2.根据权利要求1所述的方法,其中所述消费品中所述阿马道里化合物的量为约十亿分之0.1至百万分之10。
3.根据权利要求1所述的方法,其中脂肪含量为约10%或更低。
4.根据权利要求1所述的方法,其中脂肪含量为约5%或更低。
5.根据权利要求1所述的方法,其中所述阿马道里化合物为粉末。
6.根据权利要求1所述的方法,其中所述消费品为饮料。
7.根据权利要求1所述的方法,其中所述消费品为酸奶。
8.消费品组合物,包含具有约20%或更低的脂肪含量的消费品基料,以及基于所述消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物,其中所述阿马道里化合物为葡萄糖与脯氨酸的反应产物,并且其中所述阿马道里化合物补充该消费品组合物的口感特征。
9.根据权利要求8所述的消费品组合物,其中所述消费品中所述阿马道里化合物的量为约十亿分之0.1至百万分之10。
10.根据权利要求8所述的消费品组合物,其中脂肪含量为约10%或更低。
11.根据权利要求8所述的消费品组合物,其中脂肪含量为约5%或更低。
12.根据权利要求8所述的消费品组合物,其中所述阿马道里化合物为粉末。
13.根据权利要求8所述的消费品组合物,其中所述消费品为饮料。
14.根据权利要求8所述的消费品组合物,其中所述消费品为酸奶。
15.根据权利要求8所述的消费品组合物,还包含特征香料。
16.乳制品消费品组合物,包含消费品基料和基于该消费品组合物的总重约十亿分之0.02至约百万分之25的阿马道里化合物,其中所述阿马道里化合物为葡萄糖与脯氨酸的反应产物,并且其中所述阿马道里化合物补充该消费品组合物的口感特征。
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CN116715706A (zh) * | 2023-06-08 | 2023-09-08 | 安徽农业大学 | 一种延长茶氨酸体内半衰期的化学修饰方法 |
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JP2002194383A (ja) * | 2000-12-27 | 2002-07-10 | T Hasegawa Co Ltd | 新規フレーバーおよびその製造方法 |
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KR20220115612A (ko) | 2022-08-17 |
US20230024978A1 (en) | 2023-01-26 |
JP2023507366A (ja) | 2023-02-22 |
MX2022006310A (es) | 2022-06-22 |
BR112022010070A2 (pt) | 2022-08-30 |
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