CN103814012A - 吡啶衍生物及其作为鲜味促味剂的用途 - Google Patents
吡啶衍生物及其作为鲜味促味剂的用途 Download PDFInfo
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- CN103814012A CN103814012A CN201280046005.7A CN201280046005A CN103814012A CN 103814012 A CN103814012 A CN 103814012A CN 201280046005 A CN201280046005 A CN 201280046005A CN 103814012 A CN103814012 A CN 103814012A
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- A—HUMAN NECESSITIES
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- 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
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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Abstract
式(1)的化合物及其作为鲜味促味剂的用途；其中R1选自Me、Et、Pr或iPr；R2选自H或Me；或R1和R2与芳族环碳原子一起形成5或6元环。
Description
本说明书涉及新分子及其在生成、增强或改变鲜味风味中的用途。
鲜味是一般与亚洲烹饪相关的风味感觉。此外，改进的鲜味有助于使得低盐产品更可口。鲜味风在传统上通过向食品中添加谷氨酸一钠(MSG)实现。然而，在食品中存在MSG并非普遍可接受的，且对使用较低比例的MSG实现鲜味的关注超过一般的情况。
目前已经发现了这样的化合物，尽管其具有相对低的极性和由此其相对低的水溶性，但是在放入口腔中时，仍然保留强烈鲜味印象。通过使用这些化合物，能够在使用少量MSG乃至不使用MSG的食品和饮料中生成可接受的鲜味印象。
在一个方面中，提供了式(1)的化合物
其中
R1选自Me、Et、Pr或iPr，
R2选自H或Me，
或R1和R2与芳族环碳原子一起形成5或6元环。
本文所用的Me是甲基，Et是乙基，Pr是丙基，iPr是异丙基。
在本发明的另一个方面中提供了式(I)的化合物，其选自：
2-[(2,3-二氢-1H-茚基-5-基)氧基]-N-(吡啶-2-基甲基)乙酰胺；
2-[(5,6,7,8-四氢萘-2基)氧基]-N-(吡啶-2-基甲基)乙酰胺；
2-(4-甲基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(4-乙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(4-丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(4-异丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(3,4-二甲基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(3-甲基,4-乙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(3-甲基,4-丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；和
2-(3-甲基,4-异丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺。
在一个具体的实施方案中，式(1)的化合物是2-[(2,3-二氢-1H-茚基-5-基)氧基]-N-(吡啶-2-基甲基)乙酰胺，其表示为下式：
在另一个具体的实施方案中，式(1)的化合物是2-(4-乙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺：
在另一个具体的实施方案中，式(1)的化合物是2-(4-异丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺：
在另一个方面中，式(1)的化合物是2-(3,4-二甲基苯氧基)-N-(吡啶-2-基甲基)乙酰胺：
在本发明的另一个具体的实施方案中提供了式(I)的化合物，条件是它不是选自如下化合物的一种或多种：
2-[(2,3-二氢-1H-茚基-5-基)氧基]-N-(吡啶-2-基甲基)乙酰胺；
2-(4-乙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(4-异丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；
2-(3,4-二甲基苯氧基)-N-(吡啶-2-基甲基)乙酰胺；和
2-(3-甲基,4-异丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺。
可以通过本领域众所周知的方法制备式(1)的化合物。一种这样的方法包括：首先通过使适合的醇与溴乙酸乙酯在碱性催化剂的存在下反应制备醚键，然后通过使所述酯与适合的胺反应形成酰胺键。当直接从反应体系中除去乙醇时，后面的步骤可以得到改善。
式(1)的化合物的合成在如下举出的实施例中更详细地解释。
式(1)的化合物甚至可以在非常低应用水平时提供强烈鲜味印象。照此，它们可以向食品、饮料和口腔护理产品中添加味道，使得它们显然适合于作为这些用品中的香料成分。
因此，在另一个方面中提供了包含式(1)的化合物的消费组合物。
在另一个方面中提供了赋予、增强、改善或改变消费组合物味道的方法，该方法包括向所述组合物中添加式(1)的化合物。
该消费组合物可以由式(1)的化合物组成，或者其可以包含式(1)的化合物与一种或多种另外的成分。
所述一种或多种另外的成分可以选自载体材料、香味基料或任意其他用于香味制剂的配料。
本文所用的载体材料是指可以有助于式(1)的化合物或任意其他可以包含在消费组合物中的香味成分的配制的物质。这种载体材料可以用于包封影响它们从消费组合物中释放的速率或防止它们受到周围介质影响的物质。它们是中性的或实际上从味道观点来看是中性的，即该物质不会显著地改变香味组合物的味道。
作为载体材料，可以举出的是胶囊、溶剂、表面活性剂、吸附剂、树胶、聚合物等。
本文所用的术语“香味基料”是指包含至少一种不同于式(1)的化合物的香味共同成分的组合物。
此外，所述的共同成分可以用于施加香气或味道或它们两者。例如，如果这种共同成分被视为香味成分，则其必须被本领域技术人员公认为能够生成、改变或增强香味品质。
香料共同成分的具体实例可以包括、但不限于天然香料、人造香料、香料调味品、作料等。典型的香味成分包括合成的香料油和调味的芳香物质和/或油、油性树脂、精油、来源于植物、叶、花、果实等的蒸馏物和提取物和包含至少一种上述成分的组合。
典型的香料油包括留兰香油、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、肉豆蔻油、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。增香剂递送的另外的典型香精包括牛奶香精、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；和蔬菜材料例如洋葱香精、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。
香味共同成分的具体实例是还传递鲜味印象的成分。
可用于本申请的其他鲜味化合物的具体实例是式(2)的化合物(包括其盐)：
其中
R1选自H、甲基或乙基；
R2选自H、OH、氟、C1-C4直链或支链烷基、或C1-C6烷氧基，其中烷基是直链或支链的，或包含C3-C5环烷基部分或由C3-C5环烷基部分组成；
R3选自H或甲氧基；
或R2和R3一起形成它们所连接的苯基碳原子之间的桥连部分-O-CH2-O-；
R4选自OH或甲氧基；且
R5和R6独立地选自H或甲基；
选择R1、R2、R3、R4、R5和R6，使得
(i)当R2和R3一起形成它们所连接的苯基碳原子之间的桥连部分-O-CH2-O-时，R1、R5、R6是H，且R4是OH；且
(ii)当R4是OH且R1-R3是H时，R5或R6中的至少一个是甲基。
在一个具体的实施方案中，R2选自H、OH、氟、甲基或C1-C6烷氧基，其中烷基是直链或支链的，或包含C3-C5环烷基部分或由C3-C5环烷基部分组成。
在另一个具体的实施方案中，R2选自甲基、甲氧基或异丁氧基，R3是H，R4是OH，且R5和R6是H。
这种化合物描述在UK专利申请No.0913804中。这种化合物的具体的非限制性实例包括：
1-(2-羟基-4,5-二甲基苯基)-3-(吡啶-2-基)丙-1-酮；
1-(2-羟基-4-甲基苯基)-3-(吡啶-2-基)丙-1-酮；
1-(2-羟基-4-甲氧基苯基)-3-(吡啶-2-基)丙-1-酮；和
1-(2-羟基-4-异丁氧基苯基)-3-(吡啶-2-基)丙-1-酮。
适合的化合物的其他非限制性实例包括：
N1-(2-甲氧基-4-甲基苄基)-N2-(2-吡啶-2-基-乙基)草酰胺；
N1-(2,4-二甲氧基苄基)-N2-(2-吡啶-2-基-乙基)草酰胺；
N1-(2-甲氧基-3-甲基苄基)-N2-(2-(-5甲基)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(3,7-二甲基-2,6-辛二烯-1-基)环丙基甲酰胺；和
环丙烷甲酸2-异丙基-5-甲基-环己基酰胺。
可以与式(1)的化合物一起使用的赋予和增强鲜味的化合物的其他非限制性实例包括MSG(谷氨酸一钠)、IMP(肌苷一磷酸)、GMP(鸟苷一磷酸)和描述在EP1642886、WO2005/015158、EP1312268、WO2003/088768、EP1291342和WO2006/003107中的那些。MSG的典型剂量水平为0.05%－0.2%。IMP/GMP的典型剂量水平为10－100ppm。
本文所用的术语“添加剂”是指影响组合物性能而不是其愉悦性能的成分。例如，添加剂可以是作为加工组合物助剂起作用的成分或它可以改善所述组合物的操作性或贮存。它还可以是提供另外的有益性的成分，例如给组合物传递颜色或质地。它还可以是给组合物中包含的一种或多种成分传递耐光性或化学稳定性的成分。常用于香味组合物的添加剂的性质和类型的详细描述不能穷尽，但所述成分是本领域技术人员众所周知的。添加剂的实例包括溶剂和共溶剂；表面活性剂和乳化剂；粘度和流变调节剂；增稠剂和胶凝剂；防腐材料；色素、染料和着色物质；增充剂、填充剂和强化剂；防止热和光的有害作用的稳定剂、增量剂、酸化剂、缓冲剂和抗氧化剂。
消费品成分的性质和类型并不能成为本文更详细描述的依据，在任何情况下，都不可能穷尽，本领域技术人员能够基于其一般知识并且根据所述组合物的性质和期望的效果选择它们。
消费组合物还可以包括任意固体或液体组合物，消费该组合物是为了至少一种营养和愉悦或预以保持在口腔中一定时间期限，然后弃去。广泛的一般清单包括、但不限于所有类型的食品、糖食、烘烤食品、甜点、乳制品和饮料以及口腔护理产品。
式(1)的化合物可以掺入不同消费组合物中的比例在宽范围数值内改变。这些数值依赖于所调味的组合物的性质和期望的器官感觉效应以及与本领域常用的香味共同成分、溶剂或添加剂混合的指定香味基料中共同成分的性质。
所述比例可以在宽限内改变，典型地为消费组合物重量的0.1ppm－10ppm，更具体地为0.5ppm－5ppm。然而，这些仅是有用比例中的一般表示，香料领域技术人员可以为特定效果使用这些范围以外的比例。
为了进一步示例本发明的实施方案及其优点，给出了如下具体的实施例和对比例，应理解它们仅作为示例，而不以任何方式起限定作用。
实施例1
2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺的合成：
搅拌2,3-二氢-1H-茚-5-醇(25g，186mmol)、2-溴乙酸乙酯(31.1g，186mmol)和碳酸钾(25.8g，186mmol)在丙酮(80ml)中的混合物，回流加热4小时。冷却后，通过过滤除去固体，用250mL冰/水稀释滤液，用100mL MBTE萃取3次。合并醚萃取物，依次用氢氧化钠和水洗涤，然后用硫酸镁干燥。过滤后，在60℃温度/20mbar下减压除去溶剂。
通过使用Kugelrohr蒸馏减压除去剩余的挥发性物质(原料)，直到最高温度140℃/7mbar，得到11g中间体化合物。
在20mL梨形烧瓶中，将2-(2,3-二氢-1H-茚-5-基氧基)乙酸乙酯(2g，9.08mmol)和吡啶-2-基甲胺(2g，18.49mmol)在120℃搅拌几小时，同时蒸馏出乙醇。使用Kugelrohr仪器。
用乙醚/戊烷使粗产物结晶，过滤，干燥，得到2g标题化合物，纯度>95%。
1H-NMR，在氯仿-d中：2.02-2.10(2H，五重峰，C18)，2.80-2.92(4H，m，C17，19)，4.51-4.55(2H，s，C11)，4.65-4.70(2H，d，C7)，6.72-6.77(1H，m，C15)，6.82-6.85(1H，s，C21)，7.12-7.15(1H，d，C14)，7.23-7.27(1H，m，C4)，7.31-7.34(1H，d，C3)，7.67-7.73(1H，t，C5)，7.74-7.83(1H，bs，-NH-)，8.55-8.59(1H，d，C6)。
实施例2
制备两种溶液：
A-0.3%NaCl和0.05%MSG的溶液，
B-0.3%NaCl和1ppm的2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺的溶液。
由年龄在30－60岁的2位女性和3位男性组成的专业小组品尝样品。小组成员同意两种溶液均品尝出鲜味。他们还同意溶液B的鲜味稍强，具有多汁液感和甜味并且具有更加逗留不去的回想。
实施例3
制备两种溶液：
A-0.5%NaCl、0.15%MSG和0.025%核苷酸混合物的溶液，
B-0.5%NaCl、0.05%MSG、0.010%核苷酸混合物和2ppm的2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺的溶液。
由年龄在30－60岁的2位女性和3位男性组成的专业小组品尝样品。小组成员同意两种溶液均具有等同的鲜味强度。
实施例4
制备三种溶液：
A-0.5%NaCl和0.002%核苷酸混合物的溶液，
B-0.5%NaCl、0.002%核苷酸混合物和10ppm的2-(4-乙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺的溶液，
C-0.5%NaCl、0.002%核苷酸混合物和10ppm的2-(4-异丙基苯氧基)-N-(吡啶-2-基甲基)乙酰胺的溶液。
由年龄在30－60岁的2位女性和2位男性组成的专业小组品尝样品。小组成员同意溶液B和C具有的鲜味强度高于溶液A。
实施例5
由9.4g氯化钠、1g谷氨酸一钠、0.08g核苷酸(ex酵母)、32g番茄粉(ex Spreda)、25.1g葡萄糖、21g淀粉(
5ex NationalStarch)、5g棕榈脂肪粉、3g酵母粉、1g洋葱粉、0.15g胡萝卜粉、0.05g白胡椒粉、0.3g芹菜提取物粉、0.05g月桂叶粉和1.85g蔗糖制备番茄汤混合物。
将25g充分混合的成分加入到250g沸水中，搅拌至完全溶解。
将参比汤与一批包含2ppm的2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺的相同的汤比较。
一个香料专家小组(2位男性，2位女性)品尝所述的汤，并且同意测试汤更具有鲜味，并且品尝出比基料汤更综合的味道。
实施例6
制备普通的马铃薯片。
1份用1.2%氯化钠(样品A)调味。
1份用1.2%氯化钠和0.3%谷氨酸一钠(样品B)调味。
1份用1.2%氯化钠和5ppm2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺(样品C)调味。
由年龄在30－60岁的20位女性组成的专业感觉小组品尝样品A、B和C。
小组同意样品C优于另外两种样品。
将样品A描述为具有咸味，样品B为咸味和鲜味，样品C为咸味、咸味、长久、风味极佳。
实施例7
用自来水将
酱油稀释10倍。取1份基料酱油作为参比。向另一份(称作样品A)中加入1.5ppm的2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺。向第三份(称作样品B)中加入0.5ppm的2-(2,3-二氢-1H-茚-5-基氧基)-N-(吡啶-2-基甲基)乙酰胺和1ppm的1-(2-羟基-4-甲氧基苯基)-3-(吡啶-2-基)丙-1-酮。
一个香料专家小组(2位男性，2位女性)品尝稀释的酱油并且同意样品A和样品B更具有鲜味且甜味稍多。样品A和B都比基料酱油具有更综合味道，而样品B明显优于样品A。
尽管通过上述描述和前述实施例详细描述了实施方案，但是这些实施例的目的仅在于示例，应理解，本领域技术人员可以在不脱离本说明书精神和范围的情况下进行改变和变型。应理解上述实施方案不仅是可选的，而且是可以合并的。
Claims (7)
1.式(1)的化合物
其中
R1选自Me、Et、Pr或iPr；
R2选自H或Me；
或R1和R2与芳族环碳原子一起形成5或6元环。
2.权利要求1的化合物，具有下式：
3.消费组合物，包含权利要求1或权利要求2的化合物。
4.赋予、增强、改善或改变消费组合物味道的方法，该方法包括向所述组合物中添加式(1)的化合物。
5.权利要求3的消费组合物，该组合物还包含至少一种式(2)的化合物和/或其盐：
其中
R1选自H、甲基或乙基；
R2选自H、OH、氟、C1-C4直链或支链烷基、或C1-C6烷氧基，其中烷基是直链或支链的，或包含C3-C5环烷基部分或由C3-C5环烷基部分组成；
R3选自H或甲氧基；
或R2和R3一起形成它们所连接的苯基碳原子之间的桥连部分-O-CH2-O-；
R4选自OH或甲氧基；且
R5和R6独立地选自H或甲基；
选择R1、R2、R3、R4、R5和R6，使得
(i)当R2和R3一起形成它们所连接的苯基碳原子之间的桥连部分-O-CH2-O-时，R1、R5、R6是H，且R4是OH；且
(ii)当R4是OH且R1-R3是H时，R5或R6中的至少一个是甲基。
6.权利要求3或权利要求5的消费组合物，其中式(1)的化合物的存在程度为所述消费组合物重量的0.1ppm－10ppm。
7.权利要求3或权利要求5的消费组合物，其中式(1)的化合物的存在程度为所述消费组合物重量的0.5ppm－5ppm。
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| PCT/EP2012/068495 WO2013041599A1 (en) | 2011-09-21 | 2012-09-20 | Pyridine derivates and their use as umami tastants |
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| EP3019034B1 (en) | 2013-07-01 | 2018-10-31 | Givaudan SA | Organic compounds |
| JP6352227B2 (ja) * | 2015-09-15 | 2018-07-04 | 長谷川香料株式会社 | ２−（３−ベンジルオキシプロピル）ピリジンを含有する乳化組成物および粉末組成物 |
| JP6436890B2 (ja) * | 2015-10-20 | 2018-12-12 | 長谷川香料株式会社 | ピリジン誘導体を有効成分とする香味変調剤 |
| JP5805902B1 (ja) * | 2015-04-15 | 2015-11-10 | 長谷川香料株式会社 | 香味変調剤 |
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| CN107529803A (zh) * | 2015-04-15 | 2018-01-02 | 长谷川香料株式会社 | 以吡啶衍生物或其盐作为有效成分的香味调制剂 |
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| JP6180034B2 (ja) | 2017-08-16 |
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| CN103814012B (zh) | 2016-03-23 |
| EP2758374A1 (en) | 2014-07-30 |
| WO2013041599A1 (en) | 2013-03-28 |
| US20140342073A1 (en) | 2014-11-20 |
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