CN101652342B - 遮蔽不适感感觉的有机化合物 - Google Patents
遮蔽不适感感觉的有机化合物 Download PDFInfo
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- CN101652342B CN101652342B CN200880010956.2A CN200880010956A CN101652342B CN 101652342 B CN101652342 B CN 101652342B CN 200880010956 A CN200880010956 A CN 200880010956A CN 101652342 B CN101652342 B CN 101652342B
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Abstract
揭示遮蔽消费品中不适感的化合物和遮蔽消费品中不适感的方法,包括人造甜料包括阿司帕坦、糖精、乙酰舒泛K(乙酰舒泛钾)、三氯蔗糖和环己基氨基磺酸盐;和包括甜菊糖、罗汉果提取物、甘草甜素、紫苏糖、柑桔苷双氢查耳酮、新橙皮苷双氢查耳酮、罗汉果苷V、悬钩子苷、悬钩子提取物和甜叶菊苷A产生的不适感。
Description
技术领域
揭示的是能够掩盖或遮蔽消费品中不希望的不适感以及在消费品中采用所述化合物遮蔽不适感的方法。
概论
提供如下:
(1)不适感遮蔽化合物,其选自一种或多种4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸、4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸、2-(3,4-二甲基环己基)乙酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸、1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸;
(E)-3-(1-(2,2,3-三甲基环戊-3-烯基)环丙基)丙烯酸、(E)-4-(2,2,3-三甲基环己-3-烯基)丁-2-烯酸、(E)-4-(2,2,3-三甲基环戊基)丁-3-烯酸、(E)-4-(2,2,3-三甲基环戊基)丁-2-烯酸、1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸、2,2-二甲基-4-(2,2,3-三甲基环戊基)丁酸、2-((1,4-二甲基二环[3.1.0]己-2-基)甲基)-1-甲基环丙酸、2-(1-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)丙酸、2-(1-((1-甲基二环[3.1.0]己-2-基)甲基)环丙基)乙酸、3,3-二甲基-4-(2,2,3-三甲基环戊基)丁酸,和4-(1-甲基二环[3.1.0]己-2-基)丁酸,(E)-1-(2-(1-甲基二环[3.1.0]己-2-基)乙烯基)环丙酸、(E)-1-(2-(7-甲基螺[2.4]庚-4-基)乙烯基)环丙酸、(E)-4-(1-甲基二环[3.1.0]己-2-基)丁-3-烯酸、(E)-4-(7-甲基螺[2.4]庚-6-烯-4-基)丁-2-烯酸、(E)-4-(7-甲基螺[2.4]庚-4-基)丁-3-烯酸、(E)-4-(7-甲基螺[2.4]庚-4-基)丁-2-烯酸、(E)-4-(8-甲基螺[2.5]辛-7-烯-4-基)丁-2-烯酸、1-(2-(7-甲基螺[2.4]庚-4-基)乙基)环丙酸、2-((6,7-二甲基螺[2.4]庚-4-基)甲基)-1-甲基环丙酸、2-(1-((1,4-二甲基二环[3.1.0]己-2-基)甲基)环丙基)丙酸、2-(1-((1-甲基二环[3.1.0]己-2-基)甲基)环丙基)乙酸、2-(1-((7-甲基螺[2.4]庚-4-基)甲基)环丙基)乙酸,和4-(7-甲基螺[2.4]庚-4-基)丁酸。
(2)本文所述的不适感遮蔽化合物,包括(1)中的,选自一种或多种4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸4-丙基环己酸,和2-(3,4-二甲基环己基)乙酸。
(3)香料组合物,其包含提供消费品成分的不适感且一种或多种本文列出的所述不适感遮蔽化合物,包括(1)和(2)中的那些。
(4)消费品,其包含
a)以足以产生不适感的浓度的一种或多种成分,和
b)本文列出的不适感遮蔽化合物,包括(1)和(2)中的那些。
(5)本文所述消费品,包括(4)中的那些,其中一种或多种产生不适感的成分选自甜料、人造甜料、饮料、口香糖、营养制品和药物的一种或多种。
(6)本文所述消费品,包括(4)中的那些,其中一种或多种产生不适感的成分是选自阿司帕坦、乙酰舒泛K、糖精、三氯蔗糖(sucralose)和环拉酸钠的一种或多种的人造甜料。
(7)本文所述消费品,包括(4)中的那些,其中一种或多种产生不适感的成分包含选自甜菊糖、罗汉果提取物(swingle extract)、甘草甜素(glyccerhizin)、紫苏糖、柑桔苷双氢查耳酮、新橙皮苷双氢查耳酮、罗汉果苷V、悬钩子苷、悬钩子提取物和甜叶菊苷A的一种或多种的甜料。
(8)本文所述消费品,包括(4)中的那些,其中一种或多种产生不适感的成分包含选自可可、咖啡、咖啡因、可可碱、哌嗪二酮类、维生素类、氨基酸类、维生素B、酪蛋白、大豆蛋白质、布洛芬、水杨酸、葡糖醛酸内酯(glucoronolactone)、对乙酰氨基酚、右美沙芬、柑桔苷、牛磺酸、大环内酯(包括bioxin和红霉素)、对乙酰氨基酚、乙酰水杨酸、西咪替丁、雷尼替丁、阿莫西林、对乙酰氨基酚、头孢菌素类、苦木、丙二醇、三醋汀、钾盐、锌盐、洛哌丁胺、柠檬碱、类黄酮、异黄酮(包括染料木素和大豆黄素)、多酚(包括儿茶素和表儿茶素),薄荷油、D-薄荷脑、水解的植物蛋白、苦肽类、防腐剂类(包括苯甲酸、山梨酸钾、聚山梨醇80、乳酸钠和乳酸钾、苯甲酸钠),枸橼酸、奎宁、尿素(包含于口香糖中)、精油类(包括百里香、鼠尾草、罗勒、薄荷)、美拉德反应产物(包括由吡咯烷/葡萄糖、丙氨酸/木糖、脯氨酸/蔗糖或丙氨酸/木糖制备的环胺类,例如哌嗪二酮),啤酒、蛇麻草、葎草酮、反式-异构葎草酮、蛇麻酮,和希鲁酮的一种或多种的消费品。
(10)遮蔽在消费品中的不适感的方法,包括将(a)以足够产生不适感的浓度的一种或多种产生不适感的成分,和(b)本文中所列的不适感遮蔽化合物的一种或多种化合物,包括(1)和(2)中的那些,与消费品混合。
(11)本文所描述的方法,包括(10)中的那些,其中所述一种或多种产生不适感的成分选自下组:甜料、人造甜料、饮料、口香糖、营养制品和药物。
(12)本文所描述的方法,包括(10)和(11)中的那些,其中所述产生不适感的成分包含一种或多种选自阿司帕坦、乙酰舒泛K、糖精、三氯蔗糖,和环拉酸钠的人造甜料。
(13)本文所描述的方法,包括(10)至(12)中的那些,其中所述产生不适感的成分包含一种或多种选自甜菊糖、罗汉果提取物、甘草甜素、紫苏糖、柑桔苷双氢查耳酮、新橙皮苷双氢查耳酮、罗汉果苷V、悬钩子苷、悬钩子提取物,和甜叶菊苷A的甜料。
(14)本文所描述的方法包括(10)至(13),其中所述产生不适感的成分包含一种或多种选自可可、咖啡、咖啡因、可可碱、哌嗪二酮类、维生素类、氨基酸类、维生素B、酪蛋白、大豆蛋白质、布洛芬、水杨酸、葡糖醛酸内酯(glucoronolactone),对乙酰氨基酚、右美沙芬、柑桔苷、牛磺酸、大环内酯(包括bioxin和红霉素),对乙酰氨基酚、乙酰水杨酸、西咪替丁、雷尼替丁、阿莫西林、对乙酰氨基酚、头孢菌素类、苦木、丙二醇、三醋汀、钾盐、锌盐、洛哌丁胺、柠檬碱、类黄酮、异黄酮(包括染料木素和大豆黄素),多酚(包括儿茶素和表儿茶素),薄荷油、D-薄荷脑、水解的植物蛋白、苦肽类、防腐剂类(包括苯甲酸、山梨酸钾、聚山梨醇80、乳酸钠和乳酸钾、苯甲酸钠),枸橼酸、奎宁、尿素(包含于口香糖中),精油类(包括百里香、鼠尾草、罗勒、薄荷),美拉德反应产物(包括由吡咯烷/葡萄糖、丙氨酸/木糖、脯氨酸/蔗糖或丙氨酸/木糖制备的环胺类,例如哌嗪二酮),啤酒、蛇麻草、葎草酮、反式-异构葎草酮、蛇麻酮,和希鲁酮。
详细说明
本文所提供的所述不适感遮蔽化合物包括以下不适感遮蔽化合物:4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸、4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸、2-(3,4-二甲基环己基)乙酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸,和1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸。
这些化合物的化学结构如下所示:
(包括(E)-4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸),和(Z)-4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸)
不希望受到理论束缚,在所述不适感遮蔽化合物的5-环或者6-环部分的1至3个环丙基基团和/或连接环到酸基团的连接段的存在具有增强遮蔽所述不适感的活性的倾向。根据某些具体实施方式,这些化合物特别有用于遮蔽苦味不适感的遮蔽活性。此外,5-环结构(环戊烷)倾向于比相关的6-环结构(环己烷)具有更高的活性。
根据某些具体实施方式,以下化合物组还可以在消费品中用于遮蔽不适感:
一种或多种化合物,其选自(E)-3-(1-(2,2,3-三甲基环戊-3-烯基)环丙基)丙烯酸、(E)-4-(2,2,3-三甲基环己-3-烯基)丁-2-烯酸、(E)-4-(2,2,3-三甲基环戊基)丁-3-烯酸、(E)-4-(2,2,3-三甲基环戊基)丁-2-烯酸、1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸、2,2-二甲基-4-(2,2,3-三甲基环戊基)丁酸、2-((1,4-二甲基二环[3.1.0]己-2-基)甲基)-1-甲基环丙酸、2-(1-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)丙酸、2-(1-((1-甲基二环[3.1.0]己-2-基)甲基)环丙基)乙酸、3,3-二甲基-4-(2,2,3-三甲基环戊基)丁酸,和4-(1-甲基二环[3.1.0]己-2-基)丁酸。
这些化合物的化学结构如下所示。
根据进一步的实施方式,以下化合物组还可以在消费品中用于遮蔽不适感:
(E)-1-(2-(1-甲基二环[3.1.0]己-2-基)乙烯基)环丙酸、(E)-1-(2-(7-甲基螺[2.4]庚-4-基)乙烯基)环丙酸、(E)-4-(1-甲基二环[3.1.0]己-2-基)丁-3-烯酸、(E)-4-(7-甲基螺[2.4]庚-6-烯-4-基)丁-2-烯酸、(E)-4-(7-甲基螺[2.4]庚-4-基)丁-3-烯酸、(E)-4-(7-甲基螺[2.4]庚-4-基)丁-2-烯酸、(E)-4-(8-甲基螺[2.5]辛-7-烯-4-基)丁-2-烯酸、1-(2-(7-甲基螺[2.4]庚-4-基)乙基)环丙酸、2-((6,7-二甲基螺[2.4]庚-4-基)甲基)-1-甲基环丙酸、2-(1-((1,4-二甲基二环[3.1.0]己-2-基)甲基)环丙基)丙酸、2-(1-((1-甲基二环[3.1.0]己-2-基)甲基)环丙基)乙酸、2-(1-((7-甲基螺[2.4]庚-4-基)甲基)环丙基)乙酸,和4-(7-甲基螺[2.4]庚-4-基)丁酸。
这些化合物的化学结构如下所示。
通过本领域熟知的方法或者如以下所示或者本文中的实施例可以简单地合成大多数化合物。
2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸的合成:
2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸可以类似于Ochiai等人1989,Journal of Organic Chemistry,54(20),4832-40所描述的合成途径由2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁醛一步法合成。
2-(3,4-二甲基环己基)乙酸的合成:
2-(3,4-二甲基环己基)乙酸可以如以下所示使用氢和氧化铂(H2/PtO2)作为催化剂类似于Gault等人(1958),Compt.rend.,246,123-5所描述的合成途径由2-(3,4-二甲苯基)乙酸合成。
1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸的合成:
所述化合物可以类似于Hart等人2003,Journal of OrganicChemistry 68(1),187-190所描述的合成途径使用氯化钌(III)和高碘酸钠由(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲醇(aka)起始来合成。由Givaudan,Vernier,瑞士商购可得。
其它化合物的合成描述于本文下述的实施例2a至2d。本领域技术人员将清楚可以类似地合成剩余的化合物。
采用浓度-应答分析进行受体筛选,并由结果采用函数f(x)=(a-d)/(1+(x/C)nh)+d进行非线性回归可以计算抑制浓度(IC)IC50值;其中a=最小信号,d=最大信号,nh=hill系数,C=IC50.且x=拮抗剂浓度。IC50是针对拮抗剂产生最大可能的抑制应答的50%的拮抗剂摩尔浓度。有效的拮抗剂具有低的IC50值。
当采用TAS2R44苦味受体进行测试,本文中所揭示的大多数不适感遮蔽化合物,且特别是,例如,4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸、4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸、2-(3,4-二甲基环己基)乙酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸,和1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸,具有范围为约0.1至20微摩尔的IC50。
对于大多数食品应用,希望0.05至10的低IC50[微摩尔],然而,10至25的IC50也行并且高于25取决于应用也是可以接受的。
各种食物成分(包括在食品中包含的天然成分或混入食品的添加剂包括香料成分)产生不希望的不适感。特别不希望的不适感是苦味不适感、金属味不适感、余味(lingering)、甘草-型和涩不适感。术语不适感指在消费品的消费后持久的品尝后的不适感。
另一具体实例是苦和/或金属和/或涩和/或“人造”不适感和/或倒胃口的甜不适感(与糖的“较清爽”的味道相反),其与许多人造甜料包括阿司帕坦,Ace K,糖精,三氯蔗糖,和环拉酸钠相关。有时这些人造甜料的不适感被概括描述为苦味不适感。
产生不适感的成分的其它实例是天然存在的甜料包括甜菊糖、罗汉果提取物、甘草甜素、紫苏糖、柑桔苷双氢查耳酮、新橙皮苷双氢查耳酮、罗汉果苷V、悬钩子苷、悬钩子提取物,和甜叶菊苷A。
产生不适感的成分的其它实例还包括可可、咖啡、咖啡因、可可碱、哌嗪二酮类、维生素类、氨基酸类、维生素B、酪蛋白、大豆蛋白质、布洛芬、水杨酸、葡糖醛酸内酯(glucoronolactone)、对乙酰氨基酚、右美沙芬、柑桔苷、牛磺酸、大环内酯(包括bioxin和红霉素)、对乙酰氨基酚、乙酰水杨酸、西咪替丁、雷尼替丁、阿莫西林、对乙酰氨基酚、头孢菌素类、苦木、丙二醇、三醋汀、钾、锌、洛哌丁胺、柠檬碱、类黄酮、异黄酮(包括染料木素和大豆黄素)、多酚(包括儿茶素和表儿茶素)、薄荷油、D-薄荷脑、水解的植物蛋白、苦肽类、防腐剂类(包括苯甲酸、山梨酸钾、聚山梨醇80、乳酸钠和乳酸钾、苯甲酸钠)、枸橼酸、奎宁、尿素(包含于口香糖中)、精油类(包括百里香、鼠尾草、罗勒、薄荷)、美拉德反应产物(包括由吡咯烷/葡萄糖、丙氨酸/木糖、脯氨酸/蔗糖或丙氨酸/木糖制备的环胺类、例如哌嗪二酮)、啤酒、蛇麻草、葎草酮、反式-异构葎草酮、蛇麻酮、希鲁酮。
不适感遮蔽剂的添加将遮蔽或掩盖所述不适感并使得它们不那么明显或不能感觉到。人造甜料将由此丧失它们的苦/金属味和/或它们的倒胃口的甜余味且替代以更象真的糖(蔗糖)的味道。
乙酰舒泛钾(AceK)6-甲基-1,2,3-氧杂噻嗪-4(3H)-酮2,2-二氧化物(一种N-磺酰胺)的钾盐。已知于乙酰舒泛K或AceK,或于各种商标名称包括和Sweet在欧盟,还已知于E编号(添加剂码)为E950。
三氯蔗糖是6-二氯-1,6-二脱氧-β-D-果糖基-呋喃糖基4-氯-4-脱氧-α-D-吡喃半乳糖苷的名称,其为氯代脱氧糖。也已知于商标名称在欧盟,也已知于E编号(添加剂码)为E955。三氯蔗糖具有不适感(也特指为“余味”),其为后遗的甘草-样的不适感,有时也描述为苦味。
所述不适感遮蔽剂可以加至消费品中以遮蔽存在于消费品中或加入这样的消费品中的成分的不希望的不适感。
用于加入消费品的香料组合物可以配制提供所述不适感遮蔽剂和用于加入消费品的产生不适感的成分和任选地食品级辅料。可替代地,将所述不适感遮蔽剂直接加入消费品中。
特别地,所述不适感遮蔽剂可以加入香料组合物或直接加入消费品中以遮蔽产生不适感的成分的不希望的不适感,所述产生不适感的成分包括加入这样的消费品中的天然和人造甜料。
消费品包括所有食品、食物添加剂、营养剂、药物和任何置于口中的产品包括口香糖、口腔卫生产品,和口腔保健产品包括但不限于谷类产品、稻米产品、木薯产品、西米产品、烘烤产品、点心产品、糕饼产品、面包产品、糖果产品、甜点产品、胶冻、口香糖、漱口水、牙线、香料处理的或香料包覆的秸杆,香的或香料包覆的食品/饮料容器、巧克力、冰激凌、蜜制品、糖浆产品、酵母产品、焙粉、盐和调料产品、味香产品、芥菜产品、醋料产品、酱油(调味品)、烟草产品、雪茄、香烟、加工食品、熟制水果和蔬菜产品、肉和肉制品、凝胶剂、果酱品、水果调料、蛋制品、乳和奶制品、酸奶、奶酪产品、金属氯化物和金属氯化物替代产品、乳替代产品、大豆产品、食用油和脂肪产品、药品、饮料、碳酸饮料、酒精饮料、啤酒、软饮料、矿物质水和充气水和其他非酒精饮料、水果饮料、果汁、咖啡、人造咖啡、茶、可可,包括配制成需要重构的,浓缩食品、植物提取液、肉提取物、调味品、营养剂、明胶、药物或非药物橡胶、片剂、锭剂、滴剂、乳液、酏剂、糖浆剂和其它用于制造饮料的制剂,以及它们的组合。
例如,在消费品中包含钾,可以加入所述遮蔽剂以抑制与钾相关的苦味和金属味不适感。
在咖啡和可可产品中,可以加入所述不适感遮蔽剂以抑制与在所述产品中存在的咖啡因、可可碱、和/或哌嗪二酮相关的苦味。
在奶酪产品中,特别是在酶改性的奶酪产品中,可以加入所述不适感遮蔽剂以抑制与存在于所述奶酪产品中的苦肽类相关的苦味。
在大豆产品中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的肽、异黄酮类诸如染料木素和大豆黄素相关的苦味和豆腥味。
在HVP(水解的植物蛋白)产品中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的苦肽类相关的苦味。
在用于强化食品中的功能成分中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的维生素和氨基酸相关的苦味。
在药物中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的活性物质或苦添加剂相关的苦味。
在包含溶剂的消费品中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的丙二醇、三醋汀或乙醇相关的苦味。
在柠檬产品中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的柑桔苷相关的苦味。
在营养品和草药中,可以加入所述不适感遮蔽剂以抑制与存在于所述产品中的活性物质或添加剂相关的苦味。
在包含多酚诸如儿茶素和表儿茶素的消费品中,可以加入所述不适感遮蔽剂以抑制与这些成分相关的苦味。
在包含防腐剂类诸如山梨酸钾、聚山梨醇80、乳酸钠和乳酸钾、苯甲酸钠的消费品中,可以加入所述不适感遮蔽剂以抑制与所述防腐剂相关的苦味。
在包含锌和其它矿物质增补剂的消费品中,可以加入所述不适感遮蔽剂以抑制与所述这些矿物质增补剂相关的苦味和金属味不适感。
在包含薄荷油或薄荷脑(例如D-薄荷脑)枸橼酸高于7%的消费品中,可以加入所述不适感遮蔽剂以抑制与该成分组合相关的苦味。
在包含奎宁的消费品中,可以加入所述不适感遮蔽剂以抑制与奎宁相关的苦味。
在包含人造甜料(例如阿司帕坦、糖精、乙酰舒泛K、三氯蔗糖、环己基氨基磺酸盐)的消费品例如饮料中,可以加入所述不适感遮蔽剂以抑制与人造甜料相关的苦味。
在口香糖中,特别是牙科口香糖中,可以加入所述不适感遮蔽剂以抑制与口香糖中包含的尿素相关的苦味。
在包含精油类(例如百里香、鼠尾草、罗勒、薄荷)的消费品中,可以加入所述不适感遮蔽剂以抑制与这些精油类相关的苦味。
在包含蔬菜或草药或它们的提取液的消费品中,可以加入所述不适感遮蔽剂以抑制与这些成分相关的苦味。
在包含美拉德反应产物(即由脯氨酸/蔗糖或丙氨酸/木糖制备的环胺,例如哌嗪二酮)的消费品中,可以加入所述不适感遮蔽剂以抑制与美拉德反应产物相关的苦味。
在啤酒和包含啤酒或蛇麻草的消费品中,可以加入所述不适感遮蔽剂以抑制与蛇麻草相关的苦味。
实施例
以下实施例进一步详细阐明所述不适感遮蔽化合物并说明采用所述不适感遮蔽化合物以遮蔽或掩盖消费品中的不适感的方法。所述实施例是说明性的而不应当构成对化合物、消费品或方法任何形式的限制。
实施例1
各种消费品的感官评价
6至10名对苦味敏感的组员的合议组测试本文中所描述的不适感遮蔽剂。
除非另有说明,组员被要求描述在具有0.001%(wt/wt)不适感遮蔽剂的产品和不具有不适感遮蔽剂的对照之间不适感和苦感的区别。
A)包含阿司帕坦/乙酰舒泛-K的能量饮料(能量饮料)
包含牛磺酸、乙酰舒泛K、阿司帕坦、三氯蔗糖、葡糖醛酸内酯、咖啡因、B-族维生素(烟酸、泛酸、B6、B12)、香料、蔗糖、葡萄糖、颜料的能量饮料。
发现包含所述不适感遮蔽剂的该样品相比对照是较少苦味的。
B)蔗糖/葡萄糖-增甜能量饮料
该能量饮料包含牛磺酸、葡糖醛酸内酯、咖啡因、B-组维生素(烟酸、泛酸、B6、B12)、香料、蔗糖、葡萄糖、颜料。
发现包含所述不适感遮蔽剂的该样品相比对照是较少不适感的、较少苦味的和较少涩味的。
C)冰镇的低糖咖啡
发现包含所述不适感遮蔽剂的该样品相比对照是较少苦味的和较少涩味的。
D)商售的香草味的营养饮料
香草味的营养饮料包含酪蛋白酸钙、大豆蛋白质分离物、酪蛋白酸钠、维生素和矿物质。
发现包含所述不适感遮蔽剂的该样品相比对照是较少白垩味的,具有降低的蛋白质/维生素引起的不适感感觉,且是较少涩味的。
E)糖精增甜的可乐软饮料
发现包含所述不适感遮蔽剂的该样品相比对照是较少苦味的和余味减少的。
F)包含洛哌丁胺的薄荷味的药物糖浆
该糖浆包含1mg洛哌丁胺盐酸化物每7.5ml的份额。所述不适感遮蔽剂以0.004%(wt/wt)的浓度使用。
发现包含所述不适感遮蔽剂的该样品是较少苦味的,特别是品尝后的后遗苦味降低了。
G)日用咳嗽糖浆
该日用咳嗽糖浆包含325mg对乙酰氨基酚、10mg右美沙芬HBr、5mg去氧肾上腺素HCl,每15ml的份额。
发现包含所述不适感遮蔽剂的该样品是较少苦味的。
H)黑巧克力
发现包含所述不适感遮蔽剂的该样品是较少苦味的。
I)烘烤巧克力(100%可可,未增甜的)
所述不适感遮蔽剂以0.002%(wt/wt)的浓度使用。
发现包含所述不适感遮蔽剂的该样品相比对照是较少金属味、较少苦味的,特别是生物碱/咖啡因样的苦味降低了,而保持了upfront、温暖、木质苦味。
J)蒸煮过度的咖啡
在燃烧器上酿制和煮咖啡3小时。所述不适感遮蔽剂以0.0005%(wt/wt)的浓度使用。
发现包含所述不适感遮蔽剂的该样品是较少苦味的。
K)阿司帕坦/乙酰舒泛-K增甜的淡味的无脂酸奶
该酸奶包含0.0193%(wt/wt)和0.0083%(wt/wt)乙酰舒泛-K。
所述不适感遮蔽剂以0.00175%(wt/wt)的浓度使用。
发现包含所述不适感遮蔽剂的该样品相比对照是较少不适感的。
L)阿司帕坦/乙酰舒泛-K增甜的可乐软饮料
所述不适感遮蔽剂以0.0063%(wt/wt)的浓度使用。
可乐软饮料 | %(重量) |
苯甲酸钠 | 0.026 |
阿司帕坦 | 0.043 |
乙酰舒泛-K | 0.017 |
咖啡因 | 0.011 |
磷酸(85%) | 0.043 |
枸橼酸(50%在水中稀释) | 0.017 |
焦糖色 | 0.085 |
水 | 加至100 |
发现包含所述不适感遮蔽剂的该样品相比对照是较少不适感的。
M)三氯蔗糖增甜的可乐软饮料
所述不适感遮蔽剂以0.0035%(wt/wt)的浓度使用。
三氯蔗糖可乐软饮料 | %(重量) |
苯甲酸钠 | 0.03 |
三氯蔗糖(25%在水中稀释) | 0.06 |
咖啡因 | 0.01 |
磷酸(85%) | 0.08 |
焦糖色 | 0.09 |
水 | 加至100 |
发现包含所述不适感遮蔽剂的该样品相比对照是较少不适感和较少苦味的。
实施例2a-2xy
不适感遮蔽化合物的合成
实施例2a
4-(2,2,3-三甲基环戊基)丁酸的合成:
4-(2,2,3-三甲基环戊基)丁酸以三个步骤合成;第一步骤,将2-(2,2,3-三甲基环戊-3-烯-1-基)乙醛(aka龙脑烯醛)反应生成4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸乙酯,在第二步骤中,将后者经历氢化过程以生成4-(2,2,3-三甲基环戊基)丁酸乙酯,和在第三步骤中,由后者在氢氧化钠(NaOH)和四氢呋喃(THF)的存在下形成4-(2,2,3-三甲基环戊基)丁酸。
步骤1(4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸乙酯的形成):
向直火干燥的250ml圆底烧瓶中加入龙脑烯醛(10.0g,65.7mmol)和甲基叔丁基醚(MTBE)(100ml)以获得溶液,并且将烧瓶在冰水浴中缓慢冷却至0℃。将(乙氧甲酰基亚甲基)三苯基-正膦(22.8g,66.0mmol)缓慢加入该溶液中。于0℃搅拌反应混合物20分钟然后于室温下搅拌约24小时。反应结束后,将反应混合物在真空中减少至其体积的一半并加入100ml己烷。将容纳反应混合物和己烷的所述烧瓶置于冰浴中30分钟。然后将该反应混合物滤过填料滤纸、硅藻土、硅石和砂子并洗涤三次,首先用己烷,然后用9∶1和然后用1∶1的己烷/MTBE。合并的洗脱物在真空中浓缩并经急骤柱色谱法(1∶8己烷/乙酸乙酯(AcOEt))纯化以获得呈油状的4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸乙酯(13.1g,89%)。NMR数据如下所示。
1H NMR(300MHz,CDCl3)δ6.92(dd,J=10.5,7.5Hz,1H),5.79(d,J=15.6Hz,1H),5.13(s,1H),4.13(m,2H),2.3(m,2H),2.1(m,1H),1.8(m,2H),1.52(s,3H),1.24(t,J=15,3H),0.91(s,3H),0.71(s,3H);13C NMR(75MHz,CDCl3)δ166.1,148.6,147.8,121.5,121.3,59.6,48.9,46.2,35.2,32.9,25.5,19.5,14.0,12.2;MS m/z 222。
步骤2-氢化过程:
向具有搅拌棒的三颈圆底烧瓶灌充氮气,加入Degussa型钯炭Pd/C(1.5g,10%Pd)作为催化剂。所述催化剂用蒸馏水(8ml)覆盖并且向反应烧瓶中加入于乙酸乙酯(AcOEt)(200ml)中的4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸乙酯/4-(2,2,3-三甲基环戊烯基)丁酸乙酯(10.0g,44.9mmol)。向所述烧瓶灌充氢气并且该反应在需要时再充气的氢气囊下进行。在室温下17h后,通过气体色谱和质谱仪(GCMS)发现该反应完成。将反应混合物滤经硅藻土塞。将所述有机层在真空中浓缩并经急骤柱色谱法AcOEt/己烷(梯度0至40%)纯化以获得呈无色油状的4-(2,2,3-三甲基环戊基)丁酸乙酯/乙基4-(2,2,3-三甲基环戊基)丁酸(7.48g,74%)。NMR数据如下所示。
1H NMR(300MHz,CDCl3)δ4.18(q,J=7.14,2H),2.34(m,2H),1.82(m,3H),1.56(m,5H),1.30(t,J=7.2,3H),0.(m,2H),0.99(s,3H),0.86(d,J=5.4,2H),0.52(s,3H);13C NMR(75MHz,CDCl3)δ173.8,60.1,50.6,45.2,42.2,34.8,30.1,30.0,28.1,25.6,24.3,14.3,14.2,13.8;MS m/z 226。
步骤3-皂化反应
将4-(2,2,3-三甲基环戊基)丁酸乙酯(5g,22mmol)加入于圆底烧瓶中的THF(25ml)中。然后将1N NaOH水溶液(25ml)加入烧瓶中并将反应混合物于110℃回流8h。反应结束后,用1N NaOH(25ml)稀释反应混合物并将水层用MTBE洗涤两次(50mlx2)。将水层用1.0N HCl水溶液处理直至达到pH约为3(例如2至4),然后用AcOEt萃取3次(50mlx3)。合并的AcOEt萃取液在真空中浓缩并经急骤柱色谱法(0-40%梯度)纯化以获得呈无色油状4-(2,2,3-三甲基环戊基)丁酸(3.82g,87%)。NMR数据如下所示。
1H NMR(300MHz,CDCl3)δ11.22(br s,1H),2.37(m,2H),1.75(m,3H),1.49(m,4H),1.17(m,3H),0.86(s,3H),0.84(d,J=6.9Hz,3H),0.52(s,3H);13C NMR(75MHz,CDCl3)δ179.9,50.6,45.2,42.2,34.4,30.1,30.0,28.1,25.0,24.0,14.3,13.8;MS m/z 198。
实施例2b
4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸的合成:
以两个步骤合成4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸;第一步骤如上所述将龙脑烯醛反应生成4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸乙酯,并在第二步骤中,由后者,在NaOH和THF的存在下形成4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸(见以下反应)。
将4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸乙酯(2.0g,9.0mmo l)加入于50ml圆底烧瓶中的THF(10ml)。然后将1N NaOH水溶液(10ml)加入烧瓶中并将该反应混合物于83℃回流19h。在反应结束后,用1N NaOH(10ml)稀释反应混合物并用MTBE洗涤水层两次(10mlx2)。所述水层用1.0N HCl水溶液处理直至达到pH约为3(例如2至4),然后用AcOEt萃取3次(10mlx3)。合并的AcOEt萃取液在真空中浓缩并经急骤柱色谱法用MTBE/己烷(5-20%梯度)纯化以获得呈粘稠油状4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸(1.58g,90%)。NMR数据如下所示。
1H NMR(300MHz,CDCl3)δ11.47(br.s,1H),7.15(m,1H),5.90(d,J=2.8Hz 1H),5.23(s,1H),2.39(m,3H),1.91(m,2H),1.62(s,3H),1.20(s,3H),0.827(s,3H);13C NMR(75MHz,CDCl3)δ171.3,152.2,148.3,121.9,120.9,49.1,46.9,35.4,33.4,25.8,19.7,12.5;MS m/z 194。
实施例2c
4-(2,2,6-三甲基环己基)丁酸的合成:
由2-(2,6,6-三甲基环己-1-烯基)乙醛起始以三步法合成4-(2,2,6-三甲基环己基)丁酸,类似于如上针对4-(2,2,3-三甲基环戊基)丁酸所描述的3-步骤过程,除了在步骤2中将AcOEt替换为甲醇(MeOH),如下所示。
第一步骤生成4-(2,6,6-三甲基环己-1-烯基)丁-2-烯酸(E)-乙酯,第二步骤生成4-(2,2,6-三甲基环己基)丁酸乙酯,第三步骤生成4-(2,2,6-三甲基环己基)丁酸。主要产物包含(E)-4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸),且在异构体混合物中(Z)-4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸)以浓度直至10%(w/w)存在。
实施例2d
3-(2,2,6-三甲基环己基)丙酸的合成
由2,6,6-三甲基环己-1-烯甲醛起始以三步法合成3-(2,2,6-三甲基环己基)丙酸,类似于以上针对4-(2,2,6-三甲基环己基)丁酸和4-(2,2,3-三甲基环戊基)丁酸所描述的3-步骤过程,如下所示。
第一步骤生成3-(2,6,6-三甲基环己-1-烯基)丙烯酸(E)-乙酯,第二步骤生成3-(2,2,6-三甲基环己基)丙酸乙酯,第三步骤生成产物3-(2,2,6-三甲基环己基)丙酸。
实施例3
用于确定IC 50的TAS 2R44苦味受体检测
1)人TAS2R44表达载体的产生
使用基因特异性引物经聚合酶链反应(PCR)扩增人TAS2R44的全长基因,所述引物覆盖描述于WO 2004/029087中的全部编码区。
基于下列质粒/表达载体之一:pcDNA3.1Zeo(Invitrogen),所述TAS2R44 cDNA被亚克隆入表达盒。这些载体在它们的多克隆位点内包含编码大鼠生长抑素受体亚型3(RSS标签)的前45个氨基酸的核苷酸序列以促进转基因(SEQ ID#4)靶向细胞表面,和编码单纯疱疹病毒(HSV)糖蛋白D表位(HSV表位在氨基末端向羧基末端的方向,HSV标签)核苷酸序列。(SEQ ID#3)用于促进免疫细胞化学检测。
所述TAS2R44构建体包含RSS标签、TAS2R44和HSV标签,其融合入框架以允许翻译成受体蛋白和所得的受体cDNA。
该转染表达载体被称为pcDNA3.1Zeo-TAS2R44(SEQ ID#1)并允许用于TAS2R44蛋白(SEQ ID#2)的表达。
2)稳定表达Gα16-味转导素44和TAS2R44的细胞系的产生
通过将pcDNA3.1Zeo-TAS2R44转染入HEK293T/Gα16-味转导素44细胞(两者均如上1中所述而形成)产生稳定表达人苦味受体(TAS2R44)的细胞系。宿主细胞系HEK-293T是由American Tissue CultureCollection(catalog #CRL-1573)商购可得的。
转染如下进行:
在0日,将HEK293T Gα16-味转导素44细胞在6-孔板中以每孔900,000细胞的密度接种并在选择性生长培养基(具有10%(v/v)热灭活的胎牛血清的DMEM、2mM L-谷氨酰胺、100units/ml青霉素、100μg/ml链霉素、200μg/ml G418和200μg/ml博莱霉素(zeocin))中生长过夜。
在第1日,用2ml无抗生素和无血清的生长培养基替换所述培养基。将10μl脂质体2000转染试剂溶解于250μl DMEM中并于室温下孵育5分钟。平行地,将4μg TAS2R44载体DNA溶解于250μlDMEM中。将这两种获得的溶液混合并于室温下孵育20分钟,之后将它们加至细胞培养基的细胞中。4小时后,用无抗生素、包含血清的生长培养基替换所述培养基。
所述细胞在加湿气氛(37℃,5%CO2)下孵育。24小时后,将所述细胞再置于选择性生长培养基中并进一步在加湿气氛(37℃,5%CO2)中孵育。
在培养(视需要替换培养基)2至4周后,选择耐博莱霉素的菌落并扩增。
所选择的菌落经成功测试用于TAS2R44的功能性表达。
3)Fluo-4钙检测
Fluo-4AM(Invitrogen)是细胞内钙动力学(浓度变化)的荧光指示剂并允许监测钙浓度的变化,特别是在暴露于激动剂后应答受体激活出现的钙浓度增加。
在0日,如描述于2)下的稳定表达Gα16-味转导素44和TAS2R44的HEK293T细胞系在无抗生素生长培养基(具有10%(v/v)热灭活的胎牛血清的标准DMEM,2mM L-谷氨酰胺具有10%(v/v)热灭活的胎牛血清的标准DMEM,2mM L-谷氨酰胺,100单位/ml青霉素,和100μg/ml链霉素)中以浓度为每孔15,000细胞接种入暗壁/透明底的96-孔板,用聚(乙烯亚胺)(0.005%v/v)覆盖并在加湿气氛(37℃,5%CO2)下孵育48小时。
在检测时,倾倒生长培养基并将细胞在加湿气氛(37℃,5%CO2)下进一步用50μl由在DMEM中的1.5μM氟-4AM和2.5μM丙磺舒(Sigma-Aldrich)组成的加样缓冲液孵育1小时。
之后,用每孔200μl检测缓冲液(130mM NaCl、5mM KCl、10mMHEPES、2mM CaCl2和5mM葡萄糖,pH 7.4)洗涤96-孔板5次,使用自动洗板机(BioTek)。该板进一步于室温下在黑暗中孵育30分钟以允许完成Fluo-4的反酯化作用。之后,用每孔200μl检测缓冲液洗涤该板5次并用每孔180μl检测缓冲液重构。
用于检测读取,将该板置于荧光成像阅读仪(Fluorometric ImagingPlate Reader)(FLIPR)(FLIPR-TETRATM,Molecular Devices)中,并通过加入20μl的10倍浓度的激动剂母液(加入180μl的检测缓冲液获得所希望的激动剂终浓度)引发受体的激活,所述母液用检测缓冲液制备。
在加入激动剂之前,持续监测荧光20秒以获得信号基线(平均以提供F0)并在加入激动剂后监测120秒。将信号的变化除以F0获得在表中指示的ΔF/F0,ΔF为在120秒内出现的最大信号减去最小信号(在加入激动剂后120秒内出现的)。
所有数据的采集来源于至少两个独立的试验,而每个试验重复3次。
进行浓度应答分析并且使用函数f(x)=(a-d)/(1+(x/C)nh)+d进行非线性回归计算IC50值;其中a=最小信号,d=最大信号,nh=hill系数,C=IC50,且x=拮抗剂浓度。IC50是针对拮抗剂产生最大可能的有效/抑制应答的50%的拮抗剂摩尔浓度。较有效的拮抗剂具有较低的IC50值。
所获得的钙信号被校正为仅表达G蛋白α亚基(Gα16-味转导素44)的细胞的应答并使用ΔF/F0(Fmax-Fmin/F0)标准化为刺激前的细胞荧光。
实施例4
确定不适感遮蔽剂的IC50,糖精
测试以下的不适感遮蔽剂:4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸、2-(3,4-二甲基环己基)乙酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸和1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸。
进行如描述于实施例3中的方法,使用糖精作为激动剂。将细胞暴露于恒定浓度(0.5mM)的糖精和一组不同浓度的不适感遮蔽剂中。如上描述于实施例3中地进行氟-4钙的检测并获得0.05至25范围内的IC50[微摩尔]。
这意味着所述不适感遮蔽剂抑制TAS2R44苦味受体的应答并将用于遮蔽苦味。
实施例5
确定不适感遮蔽剂的IC50,乙酰舒泛K
进行如描述于实施例4的方法,用乙酰舒泛K(0.8mM)替代糖精作为激动剂。确定IC50在相同的范围内。这意味着所述不适感遮蔽剂抑制TAS2R44苦味受体的应答并用于遮蔽苦味。
实施例6
确定不适感遮蔽剂的IC50,三氯蔗糖
进行如描述于实施例4的方法测试4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸,用三氯蔗糖(50mM)替代糖精作为激动剂。确定IC50在相同的范围内。这意味着所述不适感遮蔽剂抑制TAS2R44苦味受体的应答并用于遮蔽苦味。
实施例7
4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸的感觉评价
一组苦味敏感的个体(15)以1mM、3mM和7mM的浓度用三氯蔗糖在水中测试所述苦味遮蔽剂(13ppm),每种浓度重复两次。将所述样品对比无苦味遮蔽剂的阴性对照,并且在强制选择测试中,指示组员选择出较少苦味的样品。
所述苦味遮蔽剂被发现显著地降低苦味(22/30组员选择具有苦味遮蔽剂的样品作为较少苦味的)。
在构建体和本文所描述的方法中所采用的序列显示于以下列出的序列表中。
与说明性具体实施方式相关地如上描述化合物、消费品和方法,理解为也可以使用其它类似的具体实施方式或者可以对所描述的具体实施方式进行修改和增添以实施相同的功效而不偏离本发明范围和精神。另外,所有揭示的具体实施方式在替代方案中不是必要的,作为本发明的各种具体实施方式可以合并以提供希望的特征。本领域普通技术人员不偏离本发明范围和精神可以获得变化方案。因此,所述化合物、消费品和方法不应当被局限于任何单个的具体实施方式,而是根据所附权利要求的引述的宽度和范围构建。
Claims (14)
1.遮蔽消费品中不适感的方法,其中所述消费品为置于口中的产品;所述不适感是苦味不适感、金属味不适感、余味、甘草-型或涩不适感;所述方法包括:将(a)以足够产生不适感的浓度的一种或多种产生不适感的成分,和(b)一种或多种选自下组的不适感遮蔽化合物:4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸、4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸、2-(3,4-二甲基环己基)乙酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸、1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸,与消费品混合。
2.如权利要求1所述的方法,其中所述置于口中的产品选自食品、食物添加剂、营养剂、药物和口腔保健产品。
3.选自下列的一种或多种的不适感遮蔽化合物
4-(2,2,6-三甲基环己基)丁酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸、1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸、4-(2,2,3-三甲基环戊基)丁酸。
4.如权利要求3所述不适感遮蔽化合物,其选自下组:4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸和它们的混合物。
5.香料组合物,其包含产生不适感的消费品成分和选自下组的一种或多种不适感遮蔽化合物:4-(2,2,3-三甲基环戊-3-烯基)丁-2-烯酸、4-(2,2,3-三甲基环戊基)丁酸、4-(2,2,6-三甲基环己基)丁酸、3-(2,2,6-三甲基环己基)丙酸、2-(3,4-二甲基环己基)乙酸、2-甲基-4-(2,6,6-三甲基环己-2-烯基)丁酸、1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙酸。
6.消费品,其包含
a)足够产生不适感的浓度的一种或多种成分,和
b)如权利要求5中所定义的一种或多种不适感遮蔽化合物。
7.如权利要求6所述的消费品,其中所述一种或多种产生不适感的成分选自下组:甜料、饮料、口香糖、营养制品和药物。
8.如权利要求6所述的消费品,其中所述一种或多种产生不适感的成分包含选自下组的人造甜料:阿司帕坦、乙酰舒泛K、糖精、三氯蔗糖、环拉酸钠和它们的混合物。
9.如权利要求6所述的消费品,其中所述一种或多种产生不适感的成分包含选自下组的甜料:甜菊糖、罗汉果提取物、甘草甜素、紫苏糖、柑桔苷双氢查耳酮、新橙皮苷双氢查耳酮、罗汉果苷V、悬钩子苷、悬钩子提取物、甜叶菊苷A和它们的混合物。
10.如权利要求6所述的消费品,其中所述一种或多种产生不适感的成分包含选自下组的消费品:可可、咖啡、咖啡因、可可碱、哌嗪二酮类、维生素类、氨基酸类、酪蛋白、大豆蛋白质、布洛芬、水杨酸、葡糖醛酸内酯、对乙酰氨基酚、右美沙芬、柑桔苷、牛磺酸、大环内酯、对乙酰氨基酚、乙酰水杨酸、西咪替丁、雷尼替丁、阿莫西林、对乙酰氨基酚、头孢菌素类、苦木、丙二醇、三醋汀、钾、锌、洛哌丁胺、柠檬碱、类黄酮、异黄酮、多酚、薄荷油、D-薄荷脑、水解的植物蛋白、苦肽类、防腐剂类、枸橼酸、奎宁、尿素、精油类、美拉德反应产物、啤酒、蛇麻草、葎草酮、反式-异构葎草酮、蛇麻酮、希鲁酮和它们的混合物。
11.如权利要求1或2所述的方法,其中所述一种或多种产生不适感的成分选自下组:甜料、饮料、口香糖、营养制品和药物。
12.如权利要求1或2所述的方法,其中所述一种或多种产生不适感的成分包含选自下组的人造甜料:阿司帕坦、乙酰舒泛K、糖精、三氯蔗糖、环拉酸钠和它们的混合物。
13.如权利要求1或2所述的方法,其中所述一种或多种产生不适感的成分包含选自下组的甜料:甜菊糖、罗汉果提取物、甘草甜素、紫苏糖、柑桔苷双氢查耳酮、新橙皮苷双氢查耳酮、罗汉果苷V、悬钩子苷、悬钩子提取物、甜叶菊苷A和它们的混合物。
14.如权利要求1或2所述的方法,其中所述一种或多种产生不适感的成分包含选自下组的消费品:可可、咖啡、咖啡因、可可碱、哌嗪二酮类、维生素类、氨基酸类、酪蛋白、大豆蛋白质、布洛芬、水杨酸、葡糖醛酸内酯、对乙酰氨基酚、右美沙芬、柑桔苷、牛磺酸、大环内酯、对乙酰氨基酚、乙酰水杨酸、西咪替丁、雷尼替丁、阿莫西林、对乙酰氨基酚、头孢菌素类、苦木、丙二醇、三醋汀、钾、锌、洛哌丁胺、柠檬碱、类黄酮、异黄酮、多酚、薄荷油、D-薄荷脑、水解的植物蛋白、苦肽类、防腐剂类、枸橼酸、奎宁、尿素、精油类、美拉德反应产物、啤酒、蛇麻草、葎草酮、反式-异构葎草酮、蛇麻酮、希鲁酮和它们的混合物。
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-
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Non-Patent Citations (7)
Title |
---|
70928-91-5;STN;《REGISTRY》;19841116;1 * |
85120-34-9;STN;《REGISTRY》;19841116;1 * |
92037-41-7;STN;《REGISTRY》;19841116;1 * |
JP昭60-109537A 1985.06.15 |
STN.70928-91-5.《REGISTRY》.1984, |
STN.85120-34-9.《REGISTRY》.1984, |
STN.92037-41-7.《REGISTRY》.1984, |
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