CN104883904B - 口味改变组合物 - Google Patents
口味改变组合物 Download PDFInfo
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- CN104883904B CN104883904B CN201380067198.9A CN201380067198A CN104883904B CN 104883904 B CN104883904 B CN 104883904B CN 201380067198 A CN201380067198 A CN 201380067198A CN 104883904 B CN104883904 B CN 104883904B
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- acrylamide
- taste
- dimethoxyphenyl
- broth
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Abstract
本发明涉及一种式(I)的化合物作为与其它成分组合以赋予、增强、改善或改变已调味制品的浓厚味或鲜味口味的成分的用途，
该化合物为任一其立体异构体的形式或立体异构体的混合物的形式并且其中n为整数0～2；虚线表示碳‑碳单键或双键；并且R1～R4的每一个彼此独立时表示氢原子或表示R5或OR5基团，R5表示C1～C5或甚至C1～C3烷基；并且可选地R1～R4中的一个表示–OH；和/或R1与R2结合在一起和/或R3与R4结合在一起表示OCH2O基团，前提是结合在一起的所述基团是苯基上的邻位取代基。
Description
技术领域
本发明涉及口味领域。更具体地，本发明涉及某些肉桂酸衍生的酰胺作为矫味成分以赋予或增强称为浓厚味(kokumi)或鲜味(umami)的口味的应用。
本发明还涉及含有至少一种前述化合物的组合物或制品。
背景技术
已知各种肉桂酸衍生的酰胺天然存在于植物诸如花椒属冬凌草(Zanthoxylumrubescens)(芸香科)[Amides from Zanthoxylum Rubescens.Adesina,S.K.；Reisch,J.Phytochem.1989,3,839-842.]或胡椒科(Piperaceae)[Chemical constituents ofpeppers(Piper spp.)and application to food preservation:naturally occurringantioxidative compounds.Nakatani,N.；Inatani,R.；Ohta,H.；Nishioka,A.,Environ.Health Perspectives 1986,67,135-142]中。
由于香草酰胺诸如辣椒素或胡椒碱通常发现于胡椒或辣椒种中，因此它们一般具有辛辣的或热的味道。期望避免这种味道。US2003/0152682(Bayer Polymers LLC)和EP 1323 356(Symrise)公开了阿魏酸酰胺作为口腔卫生产品用的辛辣化合物或发热系统的用途。该文献中包括化合物反式-rubenamine，但是其没有描述或甚至暗示其具有鲜味。EP 2138 152(Henkel所有)描述了除了其它酰胺或辛辣化合物或清凉化合物之外还包括阿魏酸衍生的酰胺的漱口剂组合物。但是，这些文献均没有预期、报道或暗示本文所描述的化合物具有能够用于赋予或增强浓厚味或鲜味的感官特性。
在Winkel等的New Developments in Umami(Enhancing)Molecules,Chemistry&Biodiversity,Vol.5(2008),p1195-1203中，给出了已知的鲜味改变化合物的综述。但是，其没有暗示本发明的化合物。
浓厚味和鲜味现在在口味领域是确定的描述形式并且已知为补充、增强或改变食品的口味和/或芳香而它们本身不一定具有强烈的特征性口味或芳香。广泛的食品如汤、酱汁、风味小吃、准备好的饭菜、调味品等均需要深厚味和鲜味的存在。另外，发现它们往往补充或增强了具有咸味或盐味特性的食物并因此可能在需要降钠或盐的情况下是有用的。
鲜味是由存在于人类舌头上的专门受体细胞所感知到的五种基本口味之一。鲜味适用于咸味(savoriness)的感觉，并且特别地适用于检测肉类、奶酪及其它富含蛋白质的食物中常有的谷氨酸盐和/或核糖核苷酸。鲜味受体的行为解释了为什么含有谷氨酸单钠盐(MSG)的食物通常口味“更全面(fuller)”。但是一些消费者显然对MSG敏感并且可能由于对其的消费而遭受头痛或其它疾病。因此至少部分地替换掉MSG是可取的。
浓厚味被不同地描述为“美味”、“延绵”、“满口”、“口感”和“厚实”。其天然地存在于各种食品中，如乳酪，提供‘成熟的’奶酪味道；蔬菜调味料，特别是番茄；肉，其中其提供饱满度和更持久的味道；蛋黄酱和敷料，其中其能够圆润酸的香调；减脂食品，其中其提供与全脂产品类似的饱满度；香草和香料；和汤，特别是味噌汤。
US2006/057268报道了饱和的或不饱和的N-烷基酰胺及它们作为鲜味成分的应用。
需要提供具有鲜味或浓厚味特性的风味或口味增强成分。甚至更加需要提供具有鲜味和浓厚味特性的风味或口味增强成分。
发明内容
本文提供的是一种口味改变组合物，其用于赋予、增强、改善或改变已调味的制品的浓厚味或鲜味，包含一种以至少一种根据式(I)的化合物作为与其它成分组合的成分的混合物，
该式(I)的化合物为其任一其立体异构体或立体异构体的混合物的形式，并且其中
n为整数0～2；
虚线表示碳-碳单键或双键；并且
R1～R4的每一个彼此独立时，表示氢原子或表示R5或OR5基团，R5表示C1～C5或甚至C1～C3烷基；并且可选地，基团R1～R4中的一个表示–OH；和/或
在R1与R2结合在一起和/或R3与R4结合在一起时，表示OCH2O基团，前提是所述结合在一起的基团是苯基上的邻位取代基。
具体实施方式
一种口味改变组合物，其包含一种混合物，该混合物为下列(i)和(ii)的混合物：
(i)根据式(I)的化合物
该化合物为其任一其立体异构体或立体异构体的混合物的形式，并且其中
n为整数0～2；
虚线表示碳-碳单键或双键；并且
R1～R4的每一个彼此独立时，表示氢原子或表示R5或OR5基团，R5表示C1～C5烷基；并且可选地，基团R1～R4中的一个表示–OH；和/或
在R1与R2结合在一起和/或R3与R4结合在一起时，表示OCH2O基团，前提是所述结合在一起的基团是苯基上的邻位取代基；
(ii)调味料基料，其中该调味料基料选自于下列成分组成的组：
a)鲜味赋予成分；
b)酸；
c)盐；
d)甜味赋予化合物；和
e)甜味受体调节剂化合物，其选自于由下列物质组成的组：
它们的盐的一种。
在另一个方面，如上所示的，本文提供的是一种赋予、增强、改善或改变已调味制品的口味特性或口感的方法，该方法包含向所述制品中添加上述的口味改变组合物。
在特定的实施方式中，式I的化合物在所述口味改变组合物中所占的量为约0.1～70％。
在另一实施方式中，所述鲜味赋予成分在所述口味改变组合物中所占的量为约5～99重量％。根据本发明的特定的实施方式，所述调味料基料不包含另一种鲜味赋予调味料成分，诸如MSG(谷氨酸单钠)和核糖核苷酸[共混物，例如50-50w/w的IMP(单磷酸肌苷)和GMP(单磷酸鸟苷)]，例如以95/5～90/10的MSG/核糖核苷酸w/w比率。
在另一个实施方式中，所述酸在所述口味改变组合物中所占的量为约0.1～15重量％。
在另一个实施方式中，所述盐在所述口味改变组合物中所占的量为约5～99重量％。
在另一个实施方式中，所述甜味赋予化合物所占的量为约0.2～99重量％。
在另一个实施方式中，上述的甜味受体调节剂化合物所占的量为约0.2至至多约99重量％。
上述口味改变组合物可以被用作风味或口味增强成分，例如用于赋予或增强风味制品的浓厚味或鲜味。
在本发明的上下文中，“式(I)的化合物的应用”包括含有化合物(I)并且能够有利地作为活性成分用于调味料工业中的任何组合物的应用。
为了清楚起见，表述“任一其立体异构体”或类似是指本领域技术人员所理解的通常含义，即本发明的化合物可以是纯的对映体(如具有手性)或非对映体(例如，构象E或Z的双键)。
为了清楚起见，表述“其中虚线表示碳-碳单键或双键”或类似是指本领域技术人员所理解的通常含义，即由所述虚线连接的碳原子之间的整个键(实线和虚线)为碳-碳单键或双键。
本发明的一个优点是所述化合物赋予产品以鲜味和/或浓厚味而不会不利地影响产品的风味概况。
根据本发明的一个特定的实施方式，所述化合物(I)选自于下列化合物的组，其中：
n为0或1；
虚线表示碳-碳单键或双键；且
R1～R4的每一个彼此独立地表示氢原子或表示R5或OR5基团，R5表示C1～C5或甚至C1～C3烷基。
根据本发明的一个特定的实施方式，所述化合物(I)选自于其中R1和R2均表示甲氧基且n为1的化合物的组。
根据任一本发明的上述实施方式，所述虚线表示碳-碳双键。
根据本发明的特定的实施方式，所述化合物(I)为式(II)的化合物：
该化合物为其任一立体异构体的形式或立体异构体的混合物的形式，并且其中的R3或R4每一个彼此独立地表示氢原子或表示R5或OR5基团，R5表示C1～C5或甚至C1～C3烷基。
根据任一本发明的上述实施方式，R3表示氢原子或表示R5或OR5基团，且R4表示R5或OR5基团，R5表示C1～C5或甚至C1～C3烷基。
根据任一本发明的上述实施方式，R3表示氢原子或表示R5基团，且R4表示R5或OR5基团，R5表示C1～C5或甚至C1～C3烷基。
根据任一本发明的上述实施方式,R3表示氢原子或表示R5基团，且R4表示R5，R5表示C1～C5或甚至C1～C3烷基。
根据任一本发明的上述实施方式，R5表示甲基、乙基、丙基或异丙基。
式(II)的化合物也是新的化合物，其中：
R3表示氢原子或表示C1～C5或甚至C1-3烷基或OR6基团，R6表示C1～C5或甚至C2-3烷基；和
R4表示C1～C5或甚至C1-3烷基或OR6基团，R6表示C1～C5或甚至C1-3烷基；
因此它们代表了本发明的另一方面。
根据任一本发明的上述实施方式，所述新的化合物是其中R3表示氢原子或C1-3烷基且R4表示C1-3烷基或OR6基团，R6表示C1～C3烷基的那些。
根据任一本发明的上述实施方式，所述化合物(I)或(II)是C19-25化合物或甚至C19-22化合物。
根据任一本发明的上述实施方式，化合物(I)或(II)的非芳香族碳-碳双键可以为构型Z或E或它们的混合物。根据任一本发明的上述实施方式，所述化合物(I)或(II)是E和Z立体异构体的混合物的形式，所述混合物包含至少50％w/w或至少80％w/w的立体异构体E，其余基本上为Z立体异构体。
根据本发明的特定的方面，所述化合物(I)选自于(E)-3-(3,4-二甲氧基苯基)-N-(4-甲氧基苯乙基)丙烯酰胺(在实施例中称为酰胺1)、(E)-3-(3,4-二甲氧基苯基)-N-(3-甲氧基苯乙基)丙烯酰胺(在实施例中称为酰胺4)、(E)-3-(3,4-二甲氧基苯基)-N-(3-乙氧基苯乙基)丙烯酰胺(在实施例中称为酰胺7)、(E)-3-(3,4-二甲氧基苯基)-N-(3-丙氧基苯乙基)丙烯酰胺(在实施例中称为酰胺8)、(E)-3-(3,4-二甲氧基苯基)-N-(4-异丙氧基-苯乙基)丙烯酰胺(在实施例中称为酰胺9)、(E)-3-(3,4-二甲氧基苯基)-N-(4-乙基苯乙基)丙烯酰胺(在实施例中称为酰胺10)、(E)-3-(3,4-二甲氧基苯基)-N-(3,4-二甲基苯乙基)丙烯酰胺(在实施例中称为酰胺11)、(E)-3-(3,4-二甲氧基苯基)-N-(4-异丙基苯乙基)丙烯酰胺(在实施例中称为酰胺12)或(E)-3-(3,4-二甲氧基苯基)-N-(3-甲基苯乙基)丙烯酰胺(在实施例中称为酰胺17)。
本发明的化合物可以单独使用或以混合物使用并且在非常低的水平下提供了强烈的浓厚味或鲜味。
如上所述，本发明涉及式(I)的化合物作为口味赋予或增强成分的应用，特别是赋予或增强浓厚味或鲜味。
根据本发明的特定的实施方式，所述化合物(I)用于赋予或增强浓厚味或鲜味以及增强风味的盐味和/或咸味的感知。
根据本发明的特定实施方式，此类应用非常受调香师赞赏，以赋予或增强咸味风味(例如牛肉、鸡肉、猪肉和海鲜)中的浓厚味或鲜味。令人惊讶的是，在海鲜应用中，如鱼糜、或海鲜肉汤或风味小吃，还发现式(I)的化合物增强了甜度的感知以及风味的持久性。相反，在牛肉风味中，发现式(I)的化合物增强了脂肪和牛脂香调的感知。此外，我们发现所述化合物能够增加肉类产品的多汁性。
另一方面，本发明提供一种口味改变组合物，其包含：
i)作为口味-赋予或改变成分的至少一种上述式(I)的化合物；
ii)至少一种从调味料载体和调味料基料所组成的组中选出的成分；
iii)可选的至少一种调味料佐剂。
“调味料载体”在此我们指的是从调味料的角度实际上是中性的材料，只要其不显著改变调味成分的感官特性。所述载体可以是液体或固体。
适合的液体载体包括例如含水体系、乳化体系，即溶剂和表面活性剂体系，或通常用于调味料的溶剂。通常用于调味料的溶剂的特性和类型的详细描述不能穷尽。适合的溶剂包括例如水、丙二醇、甘油三乙酸酯、柠檬酸三乙酯、苄醇、乙醇、植物油或萜类。
适合的固体载体包括例如吸收胶或聚合物、或甚至包封材料。此类材料的例子可以包含成壁和增塑材料，如单糖、二糖或三糖、天然或改性淀粉、水解胶体、纤维素衍生物、聚醋酸乙烯酯、聚乙烯醇、蛋白质或果胶、或在参考文献例如H.Scherz,Hydrokolloids:Stabilisatoren,Dickungs-und Gehermittel in Lebensmittel,Band 2derSchriftenreihe Lebensmittelchemie,
Behr's VerlagGmbH&Co.,Hamburg,1996中列举的材料。包封是本领域技术人员公知的方法，并且可以用如喷雾干燥、凝聚、挤出、团聚等的技术来实施。
“调味料基料”在此我们指的是一种组合物，其包含至少一种调味成分。
所述调味成分不是式(I)的化合物。另外，“调味成分”在此是指一种化合物，其用于调味制剂或组合物以给予快感。换句话说，被认为是调味成分的此成分必须被本领域技术人员公认为能够以积极或令人愉悦的方式赋予或改变组合物的口味，而不仅仅是具有口味。
存在于基料中的调味助成分的特性和类型在此不保证更详细的描述，技术人员基于其常识和根据预期的用途或应用以及期望的感官效果能够对其进行选择。概括来说，这些调味助成分属于不同的化学分类，如醇类、醛类、酮类、酯类、醚类、醋酸酯类、腈类、萜类化合物、含氮或含硫杂环化合物和精油，并且所述加香助成分可以是天然的或人工合成的。在任何情况下，许多的这些助成分列于参考文献如S.Arctander的著作,Perfume andFlavor Chemicals,1969,Montclair,New Jersey,USA，或其更新的版本或类似性质的其他著作中，以及调味料领域内丰富的专利文献中。也可理解为所述助成分还可以是已知的以受控的方式释放各种类型的调味化合物的化合物。
根据本发明的特定实施方式，所述调味料基料包含另一种鲜味赋予调味料成分，如MSG(谷氨酸单钠)和核糖核苷酸[共混物，例如50-50w/w的IMP(单磷酸肌苷)和GMP(单磷酸鸟苷)]，例如以95/5～90/10的MSG/核糖核苷酸w/w比率。或者，为本领域技术人员所熟知的富含前述那些化合物的成分。
本文中进一步提供的是一种口味改变组合物，其包含式I的化合物与调味料基料的混合物，其中所述混合物经过配制以添加至食品中以提供经调味的制品。在另一个特定的实施方式中，提供基本上不存在食品的所述口味改变组合物混合物。在进一步特定的实施方式中，所述口味改变组合物包含低于2％、特别是低于1％、更特别是低于0.5％、且更特别是低于0.1％的食品。在特定的实施方式中，提供不存在食品的所述口味改变组合物混合物。
在另一个实施方式中，所述混合物为干燥粉末。
在另一个实施方式中，经调味的制品以约1～100ppm的量、更特别地约10～25ppm的量包含式I的化合物，其中所述经调味的制品进一步包含调味料基料，其中所述调味料基料包含：
a)甜味赋予化合物，其量为约0.05～1000ppm，特别为约0.1～500ppm。在特定的实施方式中，所述甜味赋予化合物选自于由下列物质组成的组：甜叶菊提取物、甜叶菊提取物的糖基化衍生物(例如但不限于，美国专利7,807,206中描述的且通过引用并入本文的甜叶菊的反式葡糖基化的甜糖苷混合物)、糖类(例如但不限于蔗糖、葡萄糖、果糖高果糖玉米糖浆和玉米糖浆)、三氯蔗糖、D-色氨酸、NHDC、多元醇(糖醇，例如但不限于山梨糖醇、木糖醇、和甘露醇、木糖、阿拉伯糖、鼠李糖和乳糖)、甜菊糖苷、莱鲍迪苷A、索马甜、罗汉果甜甙(例如但不限于存在于罗汉果提取物中的那些)、摩尔林、纽甜、阿斯巴甜、安赛蜜钾、糖精、甘草酸单铵、环己氨基磺酸钙、环己基氨基磺酸钠、糖精钠、糖精钾、糖精铵和糖精钙；
b)鲜味赋予成分，其量为约1～约2000ppm，更具体地为约50～约200ppm。在特定的实施方式中，当鲜味赋予成分是核糖核酸时，其在鸡肉汤中不以300ppm提供。在另一实施方式中，所述鲜味赋予成分选自于由下列成分组成的组：谷氨酸、MSG、核糖核甘酸、以及为谷氨酸、MSG、核糖核苷酸的来源的成分(如酵母提取物)、水解蛋白(例如但不限于蔬菜、玉米、小麦面筋)、发酵配料、香菇粉、番茄粉、酶改性奶酪、奶酪粉、鱼提取物、发酵的鱼、蚝油、辣酱油、和酱油；
c)盐，其量为约100～约10,000ppm。在特定的实施方式中，所述盐选自于由下列成分组成的组：氯化钠、氯化钾、海盐、氯化镁、氯化钙、硫酸镁、硫酸钙和以及富含至少一种上述盐的阳离子和阴离子的源；
d)酸，其量为约1ppm～约2000ppm，更具体地为约50～约200ppm。在特定的实施方式中，所述酸选自于由下列成分组成的组：酒石酸、柠檬酸、琥珀酸、鞣酸、苹果酸、磷酸、乳酸、乙酸、抗坏血酸、和琥珀酸二钠、和乳酸钠；
e)从由下列成分组成的组中选择的化合物，其量为约0.1ppm～约200ppm，特别地为约0.1～约20ppm，更特别地为约1～约15ppm：
它们的盐之一。
“调味料佐剂”在此我们指的是一种成分，其能赋予附加的益处如颜色、特定的抗光性、化学稳定性等。通常用于调味基料中的佐剂的特性和类型的详细描述不能穷尽。无论如何，此类佐剂为本领域的技术人员所熟知，但必需提及的是所述成分为本领域技术人员所熟知。
除了包含至少一种式(I)的化合物、至少一种调味料载体、至少一种调味料基料和可选的至少一种调味料佐剂的调味组合物外，一种由至少一种式(I)的化合物和至少一种调味料载体组成的本发明组合物也代表了本发明的一个特定的实施方式。
在特定的实施方式中，组合使用多于一种的式(I)化合物，因为发现这样可以获得协同增强的浓厚味或鲜味。另外，还发现成分的组合可能提供所需的浓厚味或鲜味而不赋予不期望的风味香调。
另外，式(I)的化合物能够有利地被掺入到已调味的制品中以积极地赋予或改变所述制品的浓厚味或鲜味口味。因此，在又另一方面，本发明提供一种已调味的制品，其包含：
i)作为口味-赋予或改变成分的至少一种如上定义的式(I)的化合物，该化合物可选地作为调味组合物的一部分而存在；和
ii)食品基料。
适合的食品基料(例如食物或饮料)可以是油炸的或非油炸的、以及冷冻的或非冷冻的、低脂的或非低脂的、腌制的、制糊的(battered)、冷藏的、脱水的、速溶的、罐装的、重构的、干馏的或防腐的。所述食品基料的典型例子包括：
·调味料或调味品(seasonings or condiment)，如储料(stock)、咸味方料、粉末混合物(powder mix)、调味油、调味汁[例如调味品(relish)、烤肉酱、敷料(dressing)、肉汁或甜和/或酸酱]、沙拉酱或蛋黄酱；
·肉类产品，如家禽、牛肉或猪肉类产品，海鲜，鱼糜或鱼香肠；
·汤，如清汤、奶油汤、鸡肉或牛肉汤或西红柿或芦笋汤；
·碳水化合物类产品，如方便面、米饭、面食、土豆片或炸土豆、面条、比萨、玉米饼、卷饼；
·乳制品或脂肪产品，如糊膏、乳酪、常规或低脂肪的人造黄油、黄油/人造黄油混合物、黄油、花生酱、起酥油、加工的或调味的干酪；
·咸味产品，如小吃、饼干(例如碎片或薯片)或蛋制品、马铃薯/玉米片、微波爆米花、坚果、咸面包圈、年糕、大米饼干等；
·模仿产品，如奶制品(如由油、脂肪和增稠剂制成的重整奶酪)或海鲜或肉类(如素肉替代品、素汉堡)类似物；或
·宠物或动物食品。
式(I)的化合物能够应用于其中的特定的食品(包括具有如海鲜、牛肉、鸡肉、蔬菜、奶酪、脂肪、牛脂和/或骨髓等的头香的那些)是重要的。
为了清楚起见，需要提及的是，此处的“食品(foodstuff)”我们指的是可食用的产品，例如食物或饮料。因此，根据本发明的已调味制品包含一种或多种式(I)的化合物以及可选的对应于期望可食用产品的口味和风味概况的益处剂，例如咸味方料。
食品或饮料的组分的性质和类型在此不保证更详细的描述，本领域技术人员基于其常识并根据所述产品的性质能够对它们进行选择。
根据任一上述本发明的实施方式，本发明所述的口味-改变组合物和已调味制品包含作为口味赋予或改变成分的式(II)的化合物，其中R3表示氢原子或表示R5基团，并且R4表示R5或OR5基团，R5表示C1～C3烷基。根据任一上述本发明的实施方式，R5表示甲基、乙基、丙基或异丙基。
能够将本发明的化合物掺入至各种上述制品或组合物的比例在一个宽的数值范围内变化。这些数值取决于待调味的制品的特性和期望的感官效果，以及当本发明的化合物与通常用于本领域的调味助成分、溶剂或添加剂混合时，还依赖于给定基料中的助成分的特性。
对于调味组合物而言，本发明的化合物的典型浓度基于其掺入的调味组合物的重量，约为0.05％～30％，更优选0.1％～20％，最优选0.1％～10％。当将这些化合物掺入到已调味制品中时，其浓度可以比上述数值更低，例如相对于制品重量的百分比，按重量计约为0.5ppm～300ppm，更优选5ppm～75ppm，最优选8～50ppm。
在这些水平下，通常将口味描述为鲜味样、持久的、甜的和缠绵的。
还预期了本文所公开的组合物的附加实施方式及其用途，其中所述组合物由或基本上由所列举的组份组成。
实施例
现在将通过下述实施例的方式进一步详细说明本发明，其中的缩写具有本领域内的通常含义，NMR波谱数据是在CDCl3中用400MHz仪器对1H进行记录且用100或125MHz仪器对13C进行记录的，化学位移δ以TMS为基准，单位为ppm，且耦合常数J单位为Hz。
实施例1
根据本发明所述的化合物的制备
用氯甲酸乙酯合成酰胺的一般工序：
将酸(E)-3-(3,4-二甲氧基苯基)丙烯酸(典型地为33mmol)和DIEA(二异丙基乙基胺,2当量)稀释于200mL的EtOAc和50mL的二氯甲烷中。将溶液冷却至15℃并且逐滴加入氯甲酸乙酯(1摩尔当量)。将反应搅拌1小时，然后加入起始胺(1摩尔当量，在EtOAc中稀释2-3倍)。在室温下搅拌反应过夜。用5％KHSO4水溶液、盐水、5％NaHCO3水溶液、盐水洗涤，然后用Na2SO4干燥，并且在高真空下蒸发3小时。通过快速柱色谱(硅胶；环己烷/EtOAc，2:8)或通过在EtOAc中重结晶对粗产物进行纯化。纯产物的产率为50～80％。
酰胺1：
(E)-3-(3,4-二甲氧基苯基)-N-(4-甲氧基苯乙基)丙烯酰胺
化学式：C20H23NO4
起始胺：2-(4-甲氧基苯基)乙胺
1H NMR:2.82(t,J＝7.0,2H),3.61(～q,J＝7.0,5.9,2H),3.78(s,3H),3.86(s,3H),3.88(s,3H),5.87(t,J＝5.9,1H),6.24(d,J＝15.5,1H),6.81(d,J＝8.3,1H),6.84(d,J＝8.6,2H),6.98(d,J＝2.0,1H),7.05(dd,J＝8.3,2.0,1H),7.13(d,J＝8.6,2H),7.55(d,J＝15.5,1H).
13C NMR:34.8(t),41.0(t),55.2(q),55.8(q),55.9(q),109.7(d),111.1(d),114.1(d),118.6(d),121.9(d),127.8(s),129.7(d),130.9(s),140.7(d),149.1(s),150.5(s),158.3(s),166.2(s).
酰胺2：
(E)-3-(3,4-二甲氧基苯基)-N-苯乙基丙烯酰胺
化学式：C19H21NO3
起始胺：2-苯基乙胺
1H NMR:2.89(t,J＝6.8,2H),3.66(～q,J＝6.8,5.5,2H),3.87(s,3H),3.89(s,3H),5.72(t,J＝5.5,1H),6.21(d,J＝15.5,1H),6.83(d,J＝8.3,1H),6.99(d,J＝2.0,1H),7.06(dd,J＝8.3,2.0,1H),7.20-7.26(m,3H),7.30-7.34(m,2H),7.56.(d,J＝15.5,1H).
13C NMR:35.7(t),40.8(t),55.9(q),55.9(q),109.7(d),111.1(d),118.5(d),121.9(d),126.5(d),127.8(s),128.7(d),128.8(d),139.0(s),140.9(d),149.1(s),150.6(s),166.1(s).
酰胺3：
(E)-N-(3,4-二甲氧基苯乙基)-3-(3,4-二甲氧基苯基)丙烯酰胺
化学式：C21H25NO5
起始胺：2-(3,4-二甲氧基苯基)乙胺
1H NMR:2.84(t,J＝6.9,2H),3.63(～q,J＝6.9,6.0,2H),3.86(s,6H),3.87(s,3H),3.89(s,3H),5.79(t,J＝6.0,1H),6.23(d,J＝15.5,1H),6.75(～d,J＝8.0,1H),6.77(d,J＝2.0,1H),6.81(d,J＝8.0,1H),6.83(d,J＝8.0,1H),6.99(d,J＝2.0,1H),7.06(dd,J＝8.3,2.0,1H),7.56(d,J＝15.5,1H).
13C NMR:35.2(t),40.9(t),55.86(q),55.88(q),55.93(2q),109.6(d),111.1(d),111.4(d),112.0(d),118.5(d),120.7(d),122.0(d),127.8(s),131.4(s),140.9(d),147.7(s),149.1(s),149.1(s),150.6(s),166.1(s)；
酰胺4：
(E)-3-(3,4-二甲氧基苯基)-N-(3-甲氧基苯乙基)丙烯酰胺
化学式：C20H23NO4
起始胺：2-(3-甲氧基苯基)乙胺
1H NMR:2.86(t,J＝6.9,2H),3.65(～q,J＝7.0,5.7,2H),3.79(s,3H),3.87(s,3H),3.89(s,3H),5.76(t,J＝5.7,1H),6.22(d,J＝15.5,1H),6.76-6.82(m,3H),6.83(d,J＝8.4,1H),6.99(d,J＝2.0,1H),7.05(dd,J＝8.4,2.0,1H),7.23(dt,J＝7.5,1.0,1H),7.56(d,J＝15.5,1H).
13C NMR:35.7(t),40.6(t),55.2(q),55.8(q),55.9(q),109.7(d),111.1(d),111.9(d),114.5(d),118.6(d),121.1(d),121.9(d),127.8(s),129.7(d),140.6(s),140.8(d),149.1(s),150.6(s),159.8(s),166.2(s).
酰胺5：
(E)-3-(3,4-二甲氧基苯基)-N-(2-甲氧基苯乙基)丙烯酰胺
化学式：C20H23NO4
起始胺：2-(2-甲氧基苯基)乙胺
1H NMR:2.90(t,J＝6.8,2H),3.62(～q,J＝6.8,5.6,2H),3.84(s,3H),3.87(s,3H),3.88(s,3H),5.91(t,J＝5.6,1H),6.22(d,J＝15.5,1H),6.82(d,J＝8.3,1H),6.87(～dd,J＝8.4,1.0,1H),6.91(dd,J＝7.5,1.0,1H),6.99(d,J＝1.9,1H),7.05(dd,J＝8.3,1.9,1H),7.15(dd,J＝7.5,1.8,1H),7.22(dt,J＝7.5,1.8,1H),7.53(d,J＝15.5,1H).
13C NMR:30.3(t),39.8(t),55.3(q),55.8(q),55.9(q),109.7(d),110.4(d),111.1(d),118.9(d),120.7(d),121.8(d),127.4(s),127.9(d),127.9(s),130.6(d),140.4(d),149.1(s),150.5(s),157.6(s),166.1(s).
酰胺6：
(E)-N-(3,5-二甲氧基苯乙基)-3-(3,4-二甲氧基苯基)丙烯酰胺
化学式：C21H25NO5
起始胺：2-(3,5-二甲氧基苯基)乙胺
1H NMR:2.82(t,J＝6.9,2H),3.64(～q,J＝6.9,5.7,2H),3.76(s,3H),3.87(s,3H),3.88(s,3H),5.85(t,J＝5.7,1H),6.24(d,J＝15.7,1H),6.34(t,J＝2.2,1H),6.38(d,J＝2.2,1H),6.82(d,J＝8.3,1H),6.99(d,J＝2.0,1H),7.05(dd,J＝8.3,2.0,1H),7.55(d,J＝15.7,1H).
13C NMR:36.0(t),40.5(t),55.3(q),55.8(q),55.9(q),98.4(d),106.8(d),109.7(d),111.1(d),118.6(d),122.0(d),127.8(s),140.8(d),141.3(s),149.1(s),150.6(s),161.0(s),166.2(s).
酰胺7：
(E)-3-(3,4-二甲氧基苯基)-N-(3-乙氧基苯乙基)丙烯酰胺
化学式：C21H25NO4
起始胺：2-(3-乙氧基苯基)乙胺
1H NMR:1.40(t,J＝7.0,3H),2.85(t,J＝6.9,2H),3.65(～q,J＝6.9,5.6,2H),3.88(s,3H),3.89(s,3H),4.02(q,J＝7.0,2H),5.70(t,J＝5.6,1H),6.21(d,J＝15.4,1H),6.76-6.81(m,3H),6.83(d,J＝8.3,1H),7.00(d,J＝2.0,1H),7.06(dd,J＝8.3,2.0,1H),7.20-7.25(m,1H),7.55(d,J＝15.4,1H).
13C NMR:14.9(q),35.7(t),40.6(t),55.9(q),55.9(q),63.4(t),109.7(d),111.1(d),112.4(d),115.1(d),118.6(d),121.0(d),122.0(d),127.8(s),129.7(d),140.5(s),140.8(d),149.1(s),150.6(s),159.2(s),166.1(s).
酰胺8：
(E)-3-(3,4-二甲氧基苯基)-N-(3-丙氧基苯乙基)丙烯酰胺
化学式：C22H27NO4
起始胺：2-(3-丙氧基苯基)乙胺
1H NMR:1.01(t,J＝7.4,3H),1.79(～hex,J＝7.4,6.5,2H),2.85(t,J＝6.9,2H),3.65(～q,J＝6.9,5.7,2H),3.87(s,3H),3.88(s,3H),3.90(t,J＝6.5,2H),5.70(t,J＝5.7,1H),6.22(d,J＝15.5,1H),6.76-6.81(m,3H),6.82(d,J＝8.4,1H),6.99(d,J＝1.9,1H),7.05(dd,J＝8.4,2.0,1H),7.19-7.23(m,1H),7.55(d,J＝15.4,1H).
13C NMR:10.5(q),22.6(t),35.7(t),40.6(t),55.8(q),55.9(q),69.5(t),109.7(d),111.1(d),112.5(d),115.1(d),118.6(d),120.9(d),122.0(d),127.8(s),129.6(d),140.5(s),140.8(d),149.1(s),150.6(s),159.4(s),166.1(s).
酰胺9：
(E)-3-(3,4-二甲氧基苯基)-N-(4-异丙氧基苯乙基)丙烯酰胺
化学式：C22H27NO4
起始胺：2-(4-异丙氧基苯基)乙胺
1H NMR:1.32(d,J＝6.1,6H),2.81(t,J＝6.9,2H),3.61(～q,J＝6.9,5.8,2H),3.87(s,3H),3.88(s,3H),4.51(hept,J＝6.1,1H),5.80(t,J＝5.8,1H),6.23(d,J＝15.5,1H),6.81-6.85(m,3H),6.99(d,J＝2.0,1H),7.05(dd,J＝8.4,2.0,1H),7.11(～d,J＝8.6,2H),7.55(d,J＝15.5,1H).
13C NMR:22.1(q),34.8(t),40.9(t),55.8(q),55.9(q),69.9(d),109.7(d),111.1(d),116.1(d),118.6(d),121.9(d),127.8(s),129.7(d),130.7(s),140.8(d),149.1(s),150.5(s),156.6(s),166.1(s).
酰胺10：
(E)-3-(3,4-二甲氧基苯基)-N-(4-乙基苯乙基)丙烯酰胺
化学式：C21H25NO3
起始胺：2-(4-乙基苯基)乙胺
1H NMR:1.23(t,J＝7.6,3H),2.63(q,J＝7.6,2H),2.85(t,J＝6.8,2H),3.64(～q,J＝6.8,5.6,2H),3.87(s,3H),3.89(s,3H),5.73(t,J＝5.6,1H),6.22(d,J＝15.6,1H),6.81-6.85(m,3H),6.83(d,J＝8.4,1H),6.99(d,J＝2.0,1H),7.06(dd,J＝8.4,2.0,1H),7.15(宽s,4H),7.55(d,J＝15.6,1H).
13C NMR:15.6(q),28.4(t),35.3(t),40.8(t),55.8(q),55.9(q),109.7(d),111.1(d),118.7(d),121.9(d),127.8(s),128.1(d),128.7(d),136.1(s),140.7(d),142.4(s),149.1(s),150.5(s),166.1(s).
酰胺11：
(E)-3-(3,4-二甲氧基苯基)-N-(3,4-二甲基苯乙基)丙烯酰胺
化学式：C21H25NO3
起始原料：2-(3,4-二甲基苯基)乙胺
1H NMR:2.24(宽s,6H),2.82(t,J＝7.1,2H),3.63(～q,J＝7.1,5.5,2H),3.87(s,3H),3.88(s,3H),5.75(t,J＝5.5,1H),6.22(d,J＝15.6,1H),6.82(d,J＝8.4,1H),6.95(dd,J＝7.7,1.8,1H),6.98-7.00(m,2H),7.04-7.08(m,2H),7.55(d,J＝15.6,1H).
13C NMR:19.3(q),19.8(q),35.2(t),40.8(t),55.9(q),55.9(q),109.7(d),111.1(d),118.6(d),121.9(d),126.1(d),127.9(s),129.9(d),130.1(d),134.7(s),136.2(s),136.8(s),140.7(d),149.1(s),150.6(s),166.1(s).
酰胺12：
(E)-3-(3,4-二甲氧基苯基)-N-(4-异丙基苯乙基)丙烯酰胺
化学式：C22H27NO3
起始原料：2-(4-异丙基苯基)乙胺
1H NMR:1.25(t,J＝7.0,3H),2.85(t,J＝6.9,2H),2.89(七重峰,J＝7.0,1H),3.65(～q,J＝6.9,5.4,2H),3.88(s,3H),3.89(s,3H),5.71(t,J＝5.4,1H),6.22(d,J＝15.6,1H),6.83(d,J＝8.4,1H),7.00(d,J＝2.0,1H),7.06(dd,J＝8.4,2.0,1H),7.14-7.19(m,4H),7.56(d,J＝15.6,1H).
13C NMR:24.0(q),33.7(d),35.3(t),40.8(t),55.9(q),55.9(q),109.7(d),111.1(d),118.6(d),121.9(d),126.7(d),127.9(s),128.7(d),136.2(s),140.8(d),147.1(s),149.1(s),150.6(s),166.1(s).
酰胺13：
(E)-3-(苯并[d][1,3]二氧杂环戊烯-5-基)-N-(3,4-二甲氧基苯乙基)丙烯酰胺
化学式：C20H21NO5
起始胺：2-(3,4-二甲氧基苯基)乙胺
起始酸：(E)-3-(苯并[d][1,3]二氧杂环戊烯-5-基)丙烯酸
1H NMR:2.83(t,J＝7.1,2H),3.62(～q,J＝7.1,5.9,2H),3.858(s,3H),3.862(s,3H),5.70(t,J＝5.9,1H),5.98(s,2H),6.16(d,J＝15.6,1H),6.74-6.83(m,4H),6.96-6.97(m,2H),7.56(d,J＝15.6,1H).
13C NMR:35.2(t),40.9(t),55.9(q),55.9(q),101.4(t),106.3(d),108.5(d),111.4(d),112.0(d),118.6(d),120.7(d),123.8(d),129.2(s),131.4(s),140.8(d),147.7(s),148.2(s),149.0(s),149.1(s),166.0(s).
酰胺14：
(E)-N-(3,4-二甲氧基苯乙基)-3-(4-甲氧基苯基)丙烯酰胺
化学式：C20H23NO4
起始胺：2-(3,4-二甲氧基苯基)乙胺
起始酸：(E)-3-(4-甲氧基苯基)丙烯酸
1H NMR:2.83(t,J＝6.9,2H),3.62(～q,J＝6.9,5.7,2H),3.80(s,3H),3.83(s,3H),3.84(s,3H),5.97(t,J＝5.7,1H),6.25(d,J＝15.6,1H),6.73-6.81(m,3H),6.84(d,J＝8.8,2H),7.40(d,J＝8.8,2H),7.57(d,J＝15.6,1H).
13C NMR:35.3(t),41.0(t),55.3(q),55.8(q),55.9(q),111.4(d),112.0(d),114.2(d),118.4(d),120.7(d),127.5(s),129.3(d),131.5(s),140.5(d),147.7(s),149.0(s),160.8(s),166.3(s).
酰胺15：
(E)-N-(3,4-二甲氧基苯乙基)-3-(4-羟基-3-甲氧基苯基)丙烯酰胺
化学式：C20H23NO5
起始胺：2-(3,4-二甲氧基苯基)乙胺
起始酸：(E)-3-(4-乙酰氧基-3-甲氧基苯基)丙烯酸。偶联后，在MeOH/5％Na2CO3水溶液(1:1)中进行脱保护步骤。
1H NMR:2.83(t,J＝6.9,2H),3.63(～q,J＝6.9,5.7,2H),3.86(s,3H),3.87(s,3H),3.90(s,3H),5.63(t,J＝5.7,1H),6.17(d,J＝15.4,1H),6.74(～d,J＝1.9,1H),6.76(～dd,J＝8.0,1.9,1H),6.82(d,J＝8.0,1H),6.89(d,J＝8.0,1H),6.96(d,J＝1.9,1H),7.03(dd,J＝8.2,1.9,1H),7.52(d,J＝15.4,1H).未看到可替换的OH。
13C NMR:35.2(t),40.9(t),55.9(q),56.0(q),109.6(d),111.4(d),112.0(d),114.7(d),118.0(d),120.7(d),122.2(d),127.3(s),131.4(s),141.2(d),146.7(s),147.4(s),147.7(s),149.1(s),166.3(s).
酰胺16：
(E)-3-(3,4-二甲氧基苯基)-N-(4-甲氧基苄基)丙烯酰胺
化学式：C19H21NO4
起始胺：(4-甲氧基苯基)甲胺
起始酸：(E)-3-(3,4-二甲氧基苯基)丙烯酸
1H NMR:3.79(s,3H),3.87(s,3H),3.89(s,3H),4.49(d,J＝5.7,2H),5.93(t,J＝5.7,1H),6.29(d,J＝15.5,1H),6.83(d,J＝8.4,1H),6.86(～d,J＝8.7,2H),7.00(d,J＝2.0,1H),7.06(dd,J＝8.4,2.0,1H),7.24(～d,J＝8.7,2H),7.59(d,J＝15.5,1H).
13C NMR:43.3(t),55.3(q),55.8(q),55.9(q),109.7(d),111.1(d),114.1(d),118.4(d),121.9(d),127.8(s),129.3(d),130.4(s),141.1(d),149.1(s),150.6(s),159.1(s),165.9(s).
酰胺17：
(E)-3-(3,4-二甲氧基苯基)-N-(3-甲基苯乙基)丙烯酰胺
化学式：C20H23NO3
起始胺：2-(3-甲基苯基)乙胺
起始酸：(E)-3-(3,4-二甲氧基苯基)丙烯酸
1H NMR:2.34(s,3H),2.85(t,J＝7.1,2H),3.65(～q,J＝7.1,5.4,2H),3.88(s,3H),3.89(s,3H),5.67(t,J＝5.4,1H),6.21(d,J＝15.5,1H),6.83(d,J＝8.3,1H),7.00(d,J＝2.0,1H),7.02-7.07(m,4H),7.21(～d,J＝7.5,1H),7.55(d,J＝15.5,1H).
13C NMR:21.4(q),35.6(t),40.7(t),55.9(q),55.9(q),109.7(d),111.1(d),118.6(d),121.9(d)，125.8(d)，127.3(d)，127.8(s)，128.6(d)，129.6(d)，138.3(s)，138.8(s)，140.8(d)，149.1(s)，150.6(s)，166.1(s).
实施例2
根据本发明所述的化合物的鲜味效果的评价(在水中)
a)纯酰胺在纯水中
与0.05％谷氨酸单钠(MSG)比较，在矿泉水中以20ppm评价了酰胺。经过训练的组员(5-10)给出鲜味口味强度记录。计算相对鲜味强度(RUI)如下：
RUI＝(酰胺的鲜味强度)/(MSG的鲜味强度)*10
下表给出了获自所有组员的记录的平均值。
| 酰胺N° | 1 | 2 | 3 | 4 | 5 | 6 | 7 |
| RUI | 5.6 | 3.8 | 3.3 | 10.2 | 3.2 | 3.7 | 9.8 |
| 酰胺N° | 8 | 9 | 10 | 11 | 12 | 14 | 17 |
| RUI | 9.9 | 6.5 | 11.5 | 13.3 | 5.9 | 3.8 | 12.1 |
b)在麦芽糖糊精和MSG的存在下
以10％w/w将酰胺1、3、4和8混合并稀释于麦芽糖糊精中。
然后将每个混合物加入到含有500ppm的MSG的水溶液中以获得20～100ppm浓度范围的酰胺，如下表所示：
| Sol 1 | Sol 2 | Sol 3 | Sol 4 | Sol 5 | Sol 6 | Sol 7 | |
| MSG | 500 | 500 | 500 | 500 | 500 | 500 | 500 |
| 酰胺1 | - | - | - | - | 20 | - | - |
| 酰胺3 | - | 20 | 35 | 50 | - | - | - |
| 酰胺4 | - | - | - | - | - | 20 | - |
| 酰胺8 | - | - | - | - | - | - | 20 |
以及：
| Sol 8 | Sol 9 | Sol 10 | Sol 11 | Sol 12 | Sol 13 | |
| MSG | 500 | 500 | 500 | 500 | 500 | 500 |
| 酰胺7 | 20 | - | - | - | - | - |
| 酰胺9 | - | 20 | - | - | - | - |
| 酰胺10 | - | - | 20 | - | - | - |
| 酰胺11 | - | - | - | 20 | - | - |
| 酰胺12 | - | - | - | - | 20 | - |
| 酰胺17 | - | - | - | - | - | 20 |
Sol＝溶液
由15～20位经训练的组员组成的评议组在-5至5标度内对样品的口味性质进行评价(-5表示无鲜味效果且5表示极强的鲜味效果，0为含有0.05％的谷氨酸单钠的参照鲜味溶液的鲜味强度)。
样品是在使用和未使用鼻夹以专注于口味来进行评价的。
实施例3
根据本发明所述的化合物的鲜味的评价(在应用中)
1)酰胺1和3在牛肉汤中的评价
制备了含有下列成分的牛肉储液：
| 成分％w/w | |
| 麦芽糖糊精 | 52 |
| 洋葱粉 | 1.5 |
| 盐 | 32.7 |
| 白胡椒 | 0.1 |
| 酵母提取物 | 3.8 |
| 棕榈油 | 7.6 |
| 焦糖色素 | 0.7 |
| 牛肉调味料 | 1.5 |
将10g牛肉储液倒入到500ml沸水中。以表1所示的剂量将MSG和酰胺1和3加入到该牛肉汤中。
表1：成分(ppm)
| 肉/汤1 | 肉汤2 | 肉汤3 | 肉汤4 | |
| MSG | - | 700 | - | - |
| 酰胺1 | - | - | - | 25 |
| 酰胺3 | - | - | 50 | - |
将肉汤提供给5位受训的组员进行盲测。要求他们基于0～10的标度对样品的口味性质进行评分(0表示无鲜味效果且10表示极强的鲜味效果)。结果报道于下文中：
表2：各肉汤的均值和描述形式
| 鲜味强度 | 评述 | |
| 肉汤1 | 2.1 | 酵母味、洋葱似的、牛肉脂肪、淡而无味 |
| 肉汤2 | 5.1 | 比较咸、圆润、鲜味、洋葱似的、多汁、脂肪 |
| 肉汤3 | 3.1 | 口感，咸，稠度的(body) |
| 肉汤4 | 3.9 | 鲜味、圆润 |
2)酰胺1在鸡肉汤中的评价
制备了含有下列成分的鸡肉储液：
| 成分％w/w | |
| 鸡肉粉 | 2.5 |
| 麦芽糊精 | 32.2 |
| 大蒜粉 | 0.5 |
| 棕榈油 | 5 |
| 白胡椒粉 | 0.3 |
| 酵母提取物 | 10 |
| 洋葱粉 | 3.25 |
| 烤洋葱粉 | 2 |
| 姜黄 | 0.25 |
| 盐 | 35 |
| 鸡脂肪 | 5 |
| 鸡肉调味料 | 4 |
将10g鸡肉储液倒入到500ml沸水中。以表3所示的剂量将MSG和酰胺1加入到该鸡肉汤中。
表3：成分(ppm)
| 肉汤1 | 肉汤2 | 肉汤3 | |
| MSG | - | 500 | - |
| 酰胺1 | - | - | 20 |
如前所述的，将所述肉汤提供给5位受训的组员进行盲测。结果如下文所示：
表4：各肉汤的均值及描述形式
| 鲜味强度 | 评述 | |
| 肉汤1 | 3.5 | 淡而无味、咸 |
| 肉汤2 | 6.4 | 鲜味、口感、甜、令人愉快的 |
| 肉汤3 | 6.3 | 鲜味 |
3)酰胺1和4在猪肉调味料中的评价
如上所述，由5位受训的组员以20ppm在猪肉调味料中进行盲测来评价酰胺1和4。结果如下文所示：
表5：各肉汤的均值及描述形式
| 鲜味强度 | 评述 | |
| 猪肉调味料 | 4.5 | 肉香、猪肉、动物香、脂肪、口感、均衡、好 |
| 猪肉调味料+酰胺1 | 6 | 更具鲜味、更肉香的、增加的猪肉香调、甘草香调、略清凉、脂肪 |
| 猪肉调味料+酰胺4 | 7 | 更具鲜味、丰富强烈的肉香和猪肉香调、脂肪 |
4)酰胺1、4、8、11、12在含有MSG和核糖核苷酸的鸡肉汤中的评价
制备了含有下列成分的鸡肉汤：
| 成分％w/w | |
| 盐 | 27 |
| MSG | 10 |
| 核糖核苷酸 | 0.03 |
| 糖 | 4 |
| 植物油 | 2 |
| 鸡脂肪 | 2 |
| 白胡椒粉 | 0.1 |
| 酵母粉 | 1.5 |
| 酱油粉 | 0.5 |
| 鸡肉粉 | 4 |
| 麦芽糊精 | 35.77 |
| 玉米淀粉 | 5 |
| 小麦粉 | 3 |
| 蛋粉 | 4 |
| 鸡肉调味料 | 1.1 |
将1g鸡肉汤倒入到100ml沸水中。以表6所示的剂量向该鸡肉汤中加入酰胺1、4、8、11、12。
表6：成分(ppm)
如上所述，将肉汤提供给5位受训的组员进行盲测。结果如下文所示：
表7：各肉汤的均值及描述形式
| 鲜味强度 | 评述 | |
| 肉汤1 | 5.3 | 白肉、圆润、无异味 |
| 肉汤2 | 6.3 | 甜、肉香、均衡、非常圆润、全面 |
| 肉汤3 | 6.3 | 缓慢的构建、口感、甜、鲜味、无异味、圆润、非常均衡 |
| 肉汤4 | 6.7 | 强烈的鲜味、甜、延绵、甜以及鲜味 |
| 肉汤5 | 6.7 | 白肉、微涩的、很全面、圆润、持久、无异味 |
| 肉汤6 | 6 | 口感、无异味、鲜味、甜、非常均衡、微涩的 |
5)酰胺1和3在腌鸡肉中的评价
制备了含有下列成分的腌泡汁：
| 成分％w/w | |
| 水 | 90 |
| 盐 | 4 |
| Hamine磷酸盐 | 1 |
| 鸡白肉调味料 | 5 |
以下文所示的剂量向该腌泡汁中加入MSG、酰胺1和3：
以下列量将腌泡汁和鸡肉加入到塑料袋中：
在真空下将样品滚动(tumble)25分钟，然后在蒸汽炉中进行烹调直到肉温到达75℃。然后将样品冷冻，并且在评价之前在炉中80℃下再加热20分钟。
将腌鸡肉样品提供给5位受训的组员如上所述进行盲测。结果如下所示：
表8：各腌鸡肉的均值和描述形式
| 鲜味强度 | 评述 | |
| 腌鸡肉1 | 1.3 | 干 |
| 腌鸡肉2 | 4 | 强、干净、令人愉快的后味、多汁 |
| 腌鸡肉3 | 4.9 | 非常相似于MSG、肉香、圆润的、肉汤的(brothy)、均衡、甜、全面 |
| 腌鸡肉4 | 3 | 干净、令人愉快的、强烈的冲击力、增强鸡肉多汁、甜 |
6)酰胺1和3在鱼糜中的评价
以％w/w使用下列成分制备了鱼糜：
| 成分％w/w | |
| 冷冻鱼糜基料 | 39.8 |
| 盐 | 1.19 |
| 原生小麦淀粉 | 4.98 |
| 马铃薯淀粉 | 4.98 |
| 葵花油 | 4.98 |
| 蛋白 | 6.97 |
| 冰 | 36.6 |
| 蟹提取物 | 0.5 |
首先将干成分(盐、淀粉)放入到碗切碎机中。加入冰混合物直到均匀。然后加入鱼糜基料并且混合3分钟。搅拌的同时加入油，然后加入蛋白。
以如下所示的剂量向鱼糜制剂中加入MSG和酰胺1和3：
| 鱼糜1 | 鱼糜2 | 鱼糜3 | 鱼糜4 | |
| MSG | - | 5000ppm | - | - |
| 酰胺1 | - | - | 50ppm | - |
| 酰胺3 | - | - | - | 50ppm |
将4份鱼糜放入烹调袋中并且在蒸汽炉中在90℃下烹调45分钟。然后快速地将样品冷却。
将鱼糜样品提供给5位受训的组员如上所述进行盲测。结果如下所示：
表9：各鱼糜的均值及描述形式
| 鲜味强度 | 评述 | |
| 鱼糜1 | 2.2 | 淡而无味的、蛋味、略带胺味、非真正的鱼腥味 |
| 鱼糜2 | 5.3 | 甜、鲜味、圆润、甜、咸 |
| 鱼糜3 | 3.2 | 略甜、鲜味、多汁、圆润、鱼腥、蟹 |
| 鱼糜4 | 3.7 | 蟹、略带胺味、甜、鱼腥、牡蛎、蟹、多汁 |
实施例4
称量谷氨酸单钠(MSG)、酰胺1、一种成分[自于美国专利号7,807,206的葡糖基化的甜叶菊糖苷类(含有莱鲍迪苷A和甜菊糖苷)、海盐、琥珀酸、酵母提取物、水解玉米蛋白质、或水解小麦面筋]和酰胺与所述成分的共混物，并且根据每个实验中所示的剂量向每个样品中加入热矿泉水。
将每个样品冷却并且由5位受训的组员进行随机品尝。
对于每个样品，在1～10的范围内对鲜味强度进行评分(1表示无鲜味效果，而10表示非常强烈的鲜味效果)。并且在1～10的范围内对“喜爱”进行评分(如果样品不被喜爱，则评为1，而如果非常喜爱，则评为10)。并且要求组员描述样品。
表10：酰胺1&菊糖基化的甜菊糖苷
表11：酰胺1与海盐
| 样品 | 鲜味 | 喜爱 | 组员的评述 |
| MSG@0.04％ | 5.8 | 6.8 | 立即起效，鲜味，均衡，干净 |
| 酰胺1@20ppm | 3.3 | 3.8 | 鲜味，干净，持久 |
| 海盐@0.03％ | 1.0 | 1.4 | 涩的，空，弱 |
| 酰胺1@20ppm+海盐@0.03％ | 4.1 | 5.0 | 鲜味，缓慢构建，延绵的，持久 |
表12：酰胺1与琥珀酸(36ppm)
表13：酰胺1与酵母提取物(60ppm)
表14：酰胺1与酵母提取物(175ppm)
表15：酰胺1与酵母提取物(10ppm)
表16：酰胺1与水解的玉米蛋白(ppm)
表17：酰胺1与水解的玉米蛋白(320ppm)
表18：酰胺1与水解的小麦面筋(320ppm)
表19：酰胺1与水解的小麦面筋(100ppm)
在某些情况下，所述组合可以提供比每种单独的组分更加优异的鲜味口味的提高。在其它情况下，所述组合相比于每种单独的组分更加优选。
Claims (11)
1.一种口味改变组合物，其包含一种下列(i)和(ii)的混合物：
(i)用于赋予或增强浓厚味或鲜味的化合物，该化合物选自于(E)-3-(3,4-二甲氧基苯基)-N-(4-甲氧基苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基-苯基)-N-(3-甲氧基苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基苯基)-N-(3-乙氧基-苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基苯基)-N-(3-丙氧基苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基苯基)-N-(4-异丙氧基苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基苯基)-N-(4-乙基苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基苯基)-N-(3,4-二甲基苯乙基)丙烯酰胺、(E)-3-(3,4-二甲氧基苯基)-N-(4-异丙基-苯乙基)丙烯酰胺或(E)-3-(3,4-二甲氧基苯基)-N-(3-甲基苯乙基)丙烯酰胺；和
(ii)调味料基料；
其中所述调味料基料选自于由下列成分组成的组：
a)鲜味赋予成分；
b)酸；
c)盐；
d)甜味赋予化合物；和
e)从由下列化合物组成的组中选择的化合物：
2.根据权利要求1所述的组合物，其中所述调味料基料包含另一种鲜味赋予调味料成分。
3.一种已调味的制品，包含：
i)权利要求1或2所述的组合物；和
ii)食品基料，其中权利要求1中定义的用于赋予或增强浓厚味或鲜味的化合物的量为1～100ppm并且其中所述调味料基料选自于由下列成分组成的组：
a)至少1～2000ppm的鲜味赋予成分，但是当所述鲜味赋予成分为核糖核苷酸时，其在鸡肉汤中的量不为300ppm；
b)至少1～500ppm的酸；
c)至少100～10,000ppm的盐；和
d)至少0.1～1000ppm的甜味赋予化合物；和
e)至少0.1ppm至至多200ppm的选自于由下列化合物组成的组中的化合物：
4.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为调味料或调味品、肉类产品、汤、碳水化合物类产品、乳制品或脂肪产品、咸味产品、模仿产品、或宠物食品。
5.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为动物食品。
6.根据权利要求3所述的已调味的制品，其特征在于所述食品基料选自于由下列成分组成的组：
a)储料、咸味方料、粉末混合物、调味油、调味汁、沙拉酱或蛋黄酱；
b)家禽、牛肉或猪肉类产品，海鲜，鱼糜或鱼香肠；
c)清汤、奶油汤、鸡肉汤、牛肉汤、西红柿汤或芦笋汤；
d)米饭、面食、土豆片或炸土豆；
e)糊膏、乳酪、常规或低脂肪的人造黄油、黄油/人造黄油混合物、黄油、花生酱、起酥油、加工的干酪；
f)饼干或蛋制品、马铃薯/玉米片、微波爆米花、坚果、咸面包圈、年糕；或
g)素肉替代品或素汉堡。
7.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为方便面、面条、比萨、玉米饼或卷饼。
8.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为调味的干酪。
9.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为由油、脂肪和增稠剂制成的重整奶酪。
10.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为小吃。
11.根据权利要求3所述的已调味的制品，其特征在于所述食品基料为大米饼干。
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| BR112021008782A2 (pt) * | 2019-03-28 | 2021-11-03 | Firmenich S/A | Sistema de sabor |
| US20220304352A1 (en) * | 2019-08-15 | 2022-09-29 | Firmenich Sa | Taste-modifying compounds and uses thereof |
| BR112022004348A2 (pt) | 2019-09-30 | 2022-05-31 | Givaudan Sa | Aperfeiçoamentos em ou relacionados a compostos orgânicos |
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| CN101779124A (zh) * | 2007-06-08 | 2010-07-14 | 西诺米克斯公司 | 对感化性受体及与其相关的配体进行的调节 |
| CN102171197A (zh) * | 2008-07-31 | 2011-08-31 | 西诺米克斯公司 | 制备增甜剂的方法和中间体 |
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| KR20000056307A (ko) * | 1999-02-19 | 2000-09-15 | 강해진 | 초피차 |
| EP1323356B1 (de) | 2001-12-27 | 2006-03-15 | Symrise GmbH & Co. KG | Verwendung von Ferulasäureamiden als Aromastoffe |
| NZ619746A (en) * | 2003-08-06 | 2014-05-30 | Senomyx Inc | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US7427421B2 (en) | 2004-09-10 | 2008-09-23 | International Flavors & Fragrances Inc. | Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions |
| US7807206B2 (en) | 2005-10-11 | 2010-10-05 | Purecircle Sdn Bhd | Sweetner and use |
| US8076491B2 (en) * | 2007-08-21 | 2011-12-13 | Senomyx, Inc. | Compounds that inhibit (block) bitter taste in composition and use thereof |
| DE102008029665A1 (de) | 2008-06-24 | 2009-12-31 | Henkel Ag & Co. Kgaa | Perlend-prickelnde Mundwässerzubereitungen |
| ES2433004T3 (es) * | 2011-05-31 | 2013-12-05 | Symrise Ag | Amidas de ácido cinámico como sustancias saporíferas especiadas |
| WO2013000673A1 (en) * | 2011-06-30 | 2013-01-03 | Firmenich Sa | Taste modifying product |
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2013
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- 2013-12-12 EP EP13817901.5A patent/EP2934182B1/en active Active
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- 2013-12-12 US US14/654,832 patent/US20160205979A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101779124A (zh) * | 2007-06-08 | 2010-07-14 | 西诺米克斯公司 | 对感化性受体及与其相关的配体进行的调节 |
| CN102171197A (zh) * | 2008-07-31 | 2011-08-31 | 西诺米克斯公司 | 制备增甜剂的方法和中间体 |
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| US20160205979A1 (en) | 2016-07-21 |
| CN104883904A (zh) | 2015-09-02 |
| US11224243B2 (en) | 2022-01-18 |
| EP2934182A1 (en) | 2015-10-28 |
| US20190029300A1 (en) | 2019-01-31 |
| WO2014095564A1 (en) | 2014-06-26 |
| EP2934182B1 (en) | 2021-07-28 |
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