CN113272273A - 味道改良化合物及其用途 - Google Patents
味道改良化合物及其用途 Download PDFInfo
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- CN113272273A CN113272273A CN202080007938.XA CN202080007938A CN113272273A CN 113272273 A CN113272273 A CN 113272273A CN 202080007938 A CN202080007938 A CN 202080007938A CN 113272273 A CN113272273 A CN 113272273A
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Abstract
本公开总体而言涉及用作味道改良剂的化合物,特别是用作用于增强鲜味的化合物,以及它们在各种可食用产品,例如食物和饮料产品中的用途。
Description
对相关申请的交叉引用
本申请要求于2019年8月15日提交的PCT申请No.PCT/CN2019/100810,于2019年10月22日提交的欧洲专利申请No.19204703.3的优先权,两者均以引用方式整体并入本文中,如同在此阐述一样。
技术领域
本公开总体而言涉及用作味道改良剂的化合物,特别是用作用于增强鲜味的化合物,以及它们在各种可食用产品,例如食物和饮料产品中的用途。
背景技术
风味改良剂(modifiers)是添加以补充、增强或改变已调味制品的原始风味的物质。风味定义为对味道、气味或香气和化学感觉因素的综合感知。风味的感知是口腔和鼻腔中受体的化学刺激的结果。基本味道是甜、酸、咸和苦。被描述为另一种基本味道的鲜味增强了风味概貌中其他成分和组分的味道效果。这些基本味道,包括鲜味在内,和某些三叉神经效果在颊腔中被感知。香气可能是食物在食用前散发出来的气味,或者是咀嚼和吞咽产品时感知到的风味。
可以将风味和/或香气改良剂添加到食品(包括饮料)、个人或家庭护理产品、药物制剂或其他组合物中,以通过增强所需的风味和/或香气或通过掩盖或消除不希望的性质来增加产品的接受度。风味改良剂可用于改变可摄入食物、营养食品和药品,以及口腔和个人护理产品(例如漱口水、牙膏、化妆品、香水等)或可能发现于房屋、企业等内部和周围的产品的味道和/或香气。
长期以来的目标是提高食物产品的品质并为这些产品提供新的和不同的风味和香气感觉。预期具有相对长保质期的食物的商业生产通常需要使用加工条件、储存条件和/或添加可能在食物组合物中产生不合需要的异味的成分。由于成分和制造成本高昂,典型的解决味道问题的方法通常无效。风味改良剂的使用可以消除或显著减少食物组合物中不希望的异味,并改善食物的总体味道感知和/或提供新颖和新奇的味道体验。因此,需要提供一种风味改良剂,其可为食物提供此类风味改善和新颖性,并优选以成本有效的方式贡献这些益处。
发明内容
在第一形态中,本公开提供了一种味道改良化合物,其为式(I)化合物或其盐:
其中
n是0至2的一个整数;
R1和R2独立地为氢原子、C1-5烷基、-O-(C1-5烷基)或-OH;
或者R1和R2在与相邻碳原子相连时可以可选地结合在一起以形成-OCH2O-基团;
R3是-COOH或-CH2OH;且
R4是无环饱和或不饱和烃,或取代有杂原子优选O、N或S原子的无环饱和或不饱和烃,或碳环或杂环基团;
其中双键处于E或Z构象。
在一些实施方案中,该化合物不是马尿酸,也不是CAS号为1643580-85-1、851669-61-9、851669-64-2、851668-86-5、851668-89-8和851668-91-2的化合物。
在第二形态中,本公开提供了一种味道改良化合物,其为式Ia化合物或其盐:
其中:
n是0至2的一个整数;且
R1和R2独立地为氢原子、C1-5烷基、-O-(C1-5烷基)或-OH;
或者R1和R2在与相邻碳原子相连时可以可选地结合在一起以形成-OCH2O-基团。
在第三形态中,本公开提供了一种味道改良化合物,其为式II化合物或其盐:
在第四形态中,本公开提供了一种味道改良化合物,其为式III化合物或其盐:
在第五形态中,本公开提供了一种味道改良化合物,其为式IV化合物或其盐:
在第六形态中,本公开提供了一种味道改良化合物,其为式V化合物或其盐:
在第七形态中,本公开提供了一种味道改良化合物,其为式Ib化合物或其盐:
其中:
R1是氨基酸的侧链,从由如下构成的群组中选出:丙氨酸(Ala)、天冬氨酸(Asp)、苯丙氨酸(Phe)、谷氨酸(Glu)、异亮氨酸(Ile)、赖氨酸(Lys)、亮氨酸(Leu)、天冬酰胺(Asn)、谷氨酰胺(Gln)、精氨酸(Arg)、缬氨酸(Val)、甘氨酸(Gly)、半胱氨酸(Cys)、茶氨酸、组氨酸(His)、甲硫氨酸(Met)、丝氨酸(Ser)、苏氨酸(Thr)、色氨酸(Trp)和酪氨酸(Tyr)。
在第八形态中,本公开提供了一种味道改良化合物,其为式VI化合物或其盐:
在第九形态中,本公开提供了一种味道改良化合物,其为式VII化合物或其盐:
在第十形态中,本公开提供了一种味道改良化合物,其为式XVI化合物或其盐:
在第十一形态中,本公开提供了第一至第十形态中任一形态的化合物用于增强已调味制品的鲜味的用途。在一些实施方案中,已调味制品包含鲜味成分。
在第十二形态中,本公开提供了第一至第十形态中任一形态的化合物用于增强已调味制品的咸味的用途。在一些实施方案中,已调味制品包含咸味成分。
在第十三形态中,本公开提供了增强已调味制品的鲜味的方法,包括向已调味制品引入第一至第十形态中任一形态的化合物。在一些实施方案中,已调味制品包含鲜味成分。
在第十四形态中,本公开提供增强已调味制品的咸味的方法,包括向已调味制品引入第一至第十形态中任一形态的化合物。在一些实施方案中,已调味制品包含咸味成分。
在第十五形态中,本公开提供了一种已调味制品,其包含第一至第十形态中任一形态的化合物。在一些实施方案中,已调味制品包含咸味成分、鲜味成分、或它们的组合。在一些实施方案中,已调味制品是食物产品或饮料产品。
附图说明
图1是柱状图,显示在使用和不使用鼻夹的受试者中,5ppm剂量的化合物II在0.25%的NaCl基料和0.05%的MSG基料溶液中增强了咸味和鲜味。
图2是柱状图,显示在使用和不使用鼻夹的受试者中,5ppm剂量的化合物III在0.25%的NaCl基料和0.05%的MSG基料溶液中增强了咸味和鲜味。
图3是柱状图,显示在使用和不使用鼻夹的受试者中,10ppm剂量的化合物IV在0.25%的NaCl基料和0.05%的MSG基料溶液中增强了咸味和鲜味。
图4是柱状图,显示在使用和不使用鼻夹的受试者中,20ppm剂量的化合物V增强了0.05%的MSG基料中的鲜味并掩盖了0.25%的KCl基料溶液中的KCl味道。
图5A和图5B显示柱状图,显示在使用和不使用鼻夹的受试者中,10ppm剂量的化合物VI在0.25%的NaCl基料和0.05%的MSG基料溶液中增强了咸味(图5A)和鲜味(图5B)。
具体实施方式
在一个形态中,本公开提供了一种味道改良化合物,其为式I化合物或其盐:
其中
n是0至2的一个整数;
R1和R2独立地为氢原子、C1-5烷基、-O-(C1-5烷基)或-OH;
或者R1和R2在与相邻碳原子相连时可以可选地结合在一起以形成-OCH2O-基团;
R3是-COOH或-CH2OH;且
R4是无环饱和或不饱和烃,或取代有杂原子优选O、N或S原子的无环饱和或不饱和烃,或碳环或杂环基团;
其中双键处于E或Z构象。
在一些实施方案中,该化合物不是马尿酸,也不是CAS号为1643580-85-1、851669-61-9、851669-64-2、851668-86-5、851668-89-8和851668-91-2的化合物。
在相关形态中,本公开提供了一种味道改良化合物,其为式Ia化合物或其盐:
其中:
n是0至2的一个整数;且
R1和R2独立地为氢原子、C1-5烷基、-O-(C1-5烷基)或-OH;
或者R1和R2在与相邻碳原子相连时可以可选地结合在一起以形成-OCH2O-基团。
本公开的味道改良化合物还包括以下化合物:
在另一形态中,本公开提供了一种味道改良化合物,其为式Ib化合物或其盐:
其中:
R1是氨基酸的侧链,从由如下构成的群组中选出:丙氨酸(Ala)、天冬氨酸(Asp)、苯丙氨酸(Phe)、谷氨酸(Glu)、异亮氨酸(Ile)、赖氨酸(Lys)、亮氨酸(Leu)、天冬酰胺(Asn)、谷氨酰胺(Gln)、精氨酸(Arg)、缬氨酸(Val)、甘氨酸(Gly)、半胱氨酸(Cys)、茶氨酸、组氨酸(His)、甲硫氨酸(Met)、丝氨酸(Ser)、苏氨酸(Thr)、色氨酸(Trp)和酪氨酸(Tyr)。
本公开的味道改良化合物还包括以下化合物:
味道改良化合物可以以任何合适的浓度包含在已调味制品中。在一些实施方案中,任何前述形态或其实施方案的味道改良化合物以0.1ppm至1000ppm、或5ppm至20ppm的浓度存在于已调味制品中。
如本文所用,“咸味成分”包括本领域已知的用于已调味制品的盐。咸味成分的非限制性例子包括氯化钠、氯化钾、氯化镁、氯化钙和类似的锂盐、钾盐、铵盐或其他碱土金属盐。
如本文所用,“鲜味成分”包括本领域已知的用于已调味制品的鲜味成分。鲜味成分的非限制性例子包括谷氨酸单钠(MSG)、核糖核苷酸、S336(FEMA4233)(Senomyx)、S807(FEMA4232)(Senomyx)、(E)-3-(3,4-二甲氧基苯基)-N-(4-甲氧基苯乙基)丙烯酰胺(Ericamide)(FEMA4877)(Firmenich)、鲁比胺(Rubemamine)(FEMA4310)、鲁森胺(Rubescenamine)(FEMA4773)(Fermenich)、香叶胺环丙烷羧酸酯(FEMA4267)。
在一些形态中,提供了包含根据本发明的化合物的已调味制品。
如本文所用,术语“已调味制品”包括但不限于各种食品、糖果点心(confectionery)产品、烘焙产品、甜食产品、美味(savory)产品、发酵产品、乳制品、饮料、口腔护理产品、营养食品和药品。
示例性食品包括但不限于冷藏零食(小吃)、甜味和美味/咸味零食、水果零食、薯片/脆片、膨化零食、玉米饼/玉米片、爆米花、椒盐脆饼、坚果、其他甜味和美味/咸味零食、零食棒、格兰诺拉麦片棒、早餐棒、能量棒、水果棒、其他零食棒、代餐产品、减肥产品、康复饮料、即食食品、罐装即食食品、冷冻即食食品、干燥即食食品、冷藏即食食品、晚餐混合品、肉类类似物、冷冻比萨、冷藏比萨、汤、罐头汤、脱水汤、速溶汤、冷藏汤、UHT汤、冷冻汤、面食(意大利面)、罐头面食、干面食、冷冻/新鲜的面食、面条、纯面、方便面、杯装/碗装方便面、袋装方便面、冷冻面、零食面、干制食品、甜点混合物、酱汁、调味汁(dressings)和调味品(condiments)、药草和香料、涂抹酱、果酱和蜜饯、蜂蜜、巧克力涂抹酱、坚果类涂抹酱和酵母类涂抹酱。
在一些形态中,基于已调味制品的总重量,本发明的化合物在添加至已调味制品时的浓度为例如约0.0001、0.0005、0.001、0.002、或0.003、或0.004、或0.005、或0.006、或0.007、或0.008、或0.009、或0.01、或0.02、或0.03、或0.04、或0.05、或0.06、或0.07、或0.08、或0.09、或0.1、或0.15、或0.2重量%。
在一些实施方案中,根据本文提出的一个形态的组合物可以以液体形式和/或干燥形式使用。当以后一种形式使用时,可以使用合适的干燥手段,例如将油喷雾干燥。或者,可以将该组合物吸收到水溶性材料上,例如纤维素、淀粉、糖、麦芽糊精、阿拉伯胶等,或者可以将其包封。制备这种干燥形式的技术是本领域公知的。
在一些形态中,根据本文提出的一个形态的组合物可以本领域公知的不同物理形式使用以提供初始的风味迸发和/或延长的风味感觉。不限于此,此类物理形式包括游离形式,例如喷雾干燥、粉末状、珠状形式、包封形式以及它们的混合形式。
在一个形态中,根据本文提出的一个形态的组合物可以是结晶、颗粒或粉末的形式。
示例性糖果点心产品包括但不限于口香糖(包括含糖胶糖、无糖胶糖、功能性胶糖和泡泡糖)、夹心糖果、巧克力和其他巧克力糖果、含药糖果、锭剂(lozenges)、片剂、颗粒(pastilles)、薄荷糖、标准薄荷糖、强力薄荷糖、耐嚼糖果、硬糖、熬制(boiled)糖、口气清新和其他口腔护理膜或条、拐杖糖、棒棒糖、软糖、果冻糖、粘糖、焦糖、硬和脆松糖、乳脂糖、太妃糖、甘草糖、明胶糖、橡皮糖、啫哩豆糖、牛轧糖、翻糖、上述一种或多种的组合,以及掺入上述一种或多种的食用风味组合物。
示例性烘焙产品包括但不限于面包、包装/工业面包、散装/手工面包、糕点、蛋糕、包装/工业蛋糕、散装/手工蛋糕、饼干、巧克力涂层饼干、夹心饼干、夹馅饼干、咸饼干和薄脆饼干、面包替代品。
示例性甜食产品包括但不限于早餐麦片、即食(“rte”)麦片、家庭早餐麦片、薄片、麦片、其他即食麦片、儿童早餐麦片、热麦片。
示例性的美味产品包括但不限于咸味零食(薯片、脆片、坚果、玉米粉圆饼、椒盐脆饼、奶酪零食、玉米零食、土豆零食、即食爆米花、可微波烹饪爆米花、猪皮、坚果、薄脆饼干、薄脆饼干零食、早餐麦片、肉类、肉冻、腌肉(火腿、培根)、午餐肉/早餐肉(热狗、冷切片、香肠)、番茄制品、人造黄油、花生酱、汤(清汤、罐装汤、奶油汤、速溶汤、超高温“UHT”汤)、罐装蔬菜和酱汁。
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,即食冰淇淋,单份奶制品冰淇淋,单份水冰淇淋,多包装奶制品冰淇淋,多包装水冰淇淋,家庭装冰淇淋,家庭装奶制品冰淇淋,冰淇淋甜点,散装冰淇淋,家庭装水冰淇淋,冷冻酸奶,手工冰淇淋,乳制品、牛奶,新鲜/巴氏灭菌奶,全脂新鲜/巴氏灭菌奶,半脱脂新鲜/巴氏杀菌奶,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/淡炼乳,纯炼乳/淡炼乳,调味的、功能性和其它炼乳,调味乳饮料,乳制品仅调味乳饮料,调味带果汁乳饮品,豆浆,酸奶饮料,发酵乳饮料,咖啡用奶精,奶粉,调味奶粉饮品,奶油、酸奶,原味/天然酸奶,调味酸奶,果冻酸奶,益生菌酸奶,饮用酸奶,常规饮用酸奶,益生菌饮用酸奶,冷冻和耐储存点心,基于乳品的点心,基于大豆的甜点。
示例性饮料包括但不限于调味水、软饮料、水果饮料、咖啡基饮料、茶基饮料、果汁基饮料(包括水果和蔬菜)、乳基饮料、胶冻饮料、碳酸或非碳酸饮料、粉状饮料、酒精或非酒精饮料,以及这些饮料的即饮液体制剂。
示例性发酵食品包括但不限于奶酪和奶酪产品、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。
实施例
本公开通过但不限于以下实施例来说明。
实施例1:化合物(II)的合成
将苯甲酰氯(1.00g,7.1mmol)加入到乙醇胺(0.48g,7.8mmol)和三乙胺(1.43g,14.1mmol)在20mL DCM中的混合物中。在室温(rt)下搅拌3小时后,向混合物中加入50mL水,然后用DCM萃取。水相在减压下干燥。然后将经浓缩的粗产物通过ODS纯化以提供白色固体(0.23g,19.2%)。
实施例2:化合物(III)的合成
将对羟基苯甲酸酯(4.00g,26.3mmol)和乙醇胺(1.61g,26.3mmol)加入到带有Dean-Stark的圆底烧瓶中。所得混合物在160℃下搅拌2.5小时。减压除去乙醇胺,然后通过硅胶纯化得到白色固体(0.27g,8.2%)。
实施例3:化合物(IV)的合成
将肉桂酰氯(1.00g,6.0mmol)加入到乙醇胺(0.40g,6.6mmol)和三甲胺(1.22g,12.0mmol)在25mL DCM中的混合物中。在室温下搅拌3小时后,向混合物中加入50mL水,然后用DCM萃取。有机相用盐水洗涤并用Na2SO4干燥。然后将经浓缩的粗产物通过硅胶纯化以提供白色固体(0.60g,52.3%)。
实施例4:化合物(V)的合成
将(E,E)-胡椒酰氯(0.50g,2.1mmol)在10ml二氯甲烷和三乙胺(0.59mL,4.2mmol)中稀释。添加乙醇胺(0.13g,2.1mmol)并将反应搅拌过夜。反应依次用5%KHSO4、5%NaHCO3和盐水洗涤。酰胺从EtOAc中重结晶。获得了43%的收率。
实施例5:感官测试
由25名受过训练的小组成员组成的小组评估了5、10或20ppm样品的味道特性(盐和/或鲜味,或KCl味道),等级为-5到5(-5表示强的掩蔽效果,5表示强的增强效果,0是含有0.25%的NaCl或0.25%的KCl或0.05%的MSG或1.5%鸡汤基料的参比水溶液的强度)。
鸡汤基料:
成分 | 剂量(%) |
NaCl | 0.36 |
KCl | 0.18 |
MSG | 0.315 |
核糖核苷酸 | 0.015 |
蔗糖 | 0.069 |
鸡油 | 0.03 |
大蒜粉 | 0.003 |
洋葱粉 | 0.009 |
酵母 | 0.042 |
鸡精 | 0.0075 |
白胡椒 | 0.0015 |
麦芽糊精 | 0.3255 |
玉米淀粉 | 0.12 |
苹果酸 | 0.0045 |
咖喱粉 | 0.0015 |
调味料1 | 0.0045 |
调味料2 | 0.003 |
调味料3 | 0.009 |
1)感官评价
剂量为5ppm的化合物II在0.05%的MSG基料中不使用鼻夹时增强了鲜味,不使用鼻夹时增强了咸味,并且在0.25%的NaCl基料中使用鼻夹时显著增强了咸味(99%的置信度水平)。图1。
剂量为5ppm的化合物III在0.05%的MSG基料中使用和不使用鼻夹时都增强了鲜味,并在0.25%的NaCl基料中使用和不使用鼻夹时都显著增强了咸味(至少99%的置信度水平)。图2。
剂量为10ppm的化合物IV在0.05%的MSG基料中使用和不使用鼻夹时都增强了鲜味,在不使用鼻夹时增强了咸味,并在0.25%的NaCl基料中使用鼻夹时显著增强了咸味(95%的置信度水平)。图3。
剂量为20ppm的化合物V在0.05%的MSG基料中使用和不使用鼻夹时都增强了鲜味,在0.25%的KCl基料中使用和不使用鼻夹时都增强了咸味并显著掩蔽了KCl味道(95%的置信度水平)。图4。
2)应用测试
基质 | 味道 | 化合物 | 不使用鼻夹 | 显著性水平 |
1.5%鸡汤基料 | 咸 | II | 0.61 | *** |
1.5%鸡汤基料 | 鲜 | II | 0.52 | * |
1.5%鸡汤基料 | 咸 | III | 0.4 | * |
1.5%鸡汤基料 | 鲜 | III | 0.51 | * |
5ppm的样品II和III在鸡汤中具有很强的咸味和鲜味增强效果。这些结果在至少95%的置信度水平(双尾配对学生测试)下是显著的。
实施例6:化合物VI至XVI的合成
将肉桂酰氯(11mmol)分成三份加入到圆底烧瓶中,该烧瓶中含有氨基酸组分(见下文)(10mmol)和氢氧化钠(40mmol)在100mL丙酮/水溶液(1:1)(w/w)中的混合物。将所得混合物在室温下搅拌2小时,然后将混合物加入到稀HCl水溶液(1mol/L)中以调节pH至2~3。在真空下除去丙酮并用Et2O萃取。将水相干燥,通过ODS或硅胶或结晶来纯化以提供最终产物。
精氨酸为起始原料。收率:8.3%。
谷氨酰胺为起始原料。收率:15.3%。
天冬酰胺为起始原料。收率:30.9%。
甘氨酸为起始原料。收率:19.7%。
谷氨酸为起始原料。收率:34.2%。
丙氨酸作为起始原料。收率:29.8%。
天冬氨酸为起始原料。收率:26.0%。
亮氨酸为起始原料。收率:32.0%。
异亮氨酸为起始原料。收率:17.0%。
苯丙氨酸为起始原料。收率:25.8%。
茶氨酸为起始原料。收率:16.5%。
实施例7:感官测试
由25名受过训练的小组成员组成的小组评估了5ppm样品的味道特性(盐和/或鲜味),等级为-5到5(-5表示强的掩蔽效果,5表示强的增强效果,0是含有0.25%的NaCl或0.05%的MSG或1.5%鸡汤基料的参比水溶液的强度)。
1)感官评价
剂量为5ppm的化合物VI在0.25%的NaCl基料中使用鼻夹时显著增强了咸味强度,置信度水平为99%。化合物VI还在0.05%的MSG基料中不使用鼻夹时显著增强了鲜味强度,置信度水平为95%。图5。
2)应用测试
基质 | 味道 | 不使用鼻夹 | 显著性水平 |
1.5%鸡汤基料 | 咸 | 0.49 | ** |
1.5%鸡汤基料 | 鲜 | 0.66 | ** |
剂量为5ppm的化合物VI在鸡汤中具有很强的咸味和鲜味增强作用。这些影响在99%的置信度水平(双尾配对学生测试)下是显著的。
本文通篇所引用的出版物通过引用整体并入本文。尽管上面已经参考实施例和优选实施方案说明了本发明的各个形态,但是应当理解,本发明的范围并不由前述描述所限定,而是在专利法的原则下由适当解释的所附权利要求所限定。
Claims (13)
2.根据权利要求1所述的用途,其中该已调味制品包含咸味成分、鲜味成分、或它们的组合。
8.根据权利要求3至8中任一项所述的用途,其中该已调味制品包含咸味成分、鲜味成分、或它们的组合。
13.根据权利要求9至12中任一项所述的用途,其中该已调味制品包含咸味成分、鲜味成分、或它们的组合。
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- 2020-06-26 CN CN202080007938.XA patent/CN113272273B/zh active Active
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US20100129515A1 (en) * | 2005-07-29 | 2010-05-27 | Quest International Services B.V. | Flavour modulating substances |
CN102405079A (zh) * | 2009-02-13 | 2012-04-04 | 雀巢产品技术援助有限公司 | 包含n-苯基丙烯酰基氨基酸酰胺的产品及其用途 |
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US20170143022A1 (en) * | 2015-11-20 | 2017-05-25 | Senomyx, Inc. | Compositions Incorporating an Umami Flavor Agent |
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WO2021028106A2 (en) | 2021-02-18 |
WO2021028106A3 (en) | 2021-05-20 |
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