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CN1090571A - 用作香化剂的新化合物及其制备方法 - Google Patents

用作香化剂的新化合物及其制备方法 Download PDF

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CN1090571A
CN1090571A CN93114462A CN93114462A CN1090571A CN 1090571 A CN1090571 A CN 1090571A CN 93114462 A CN93114462 A CN 93114462A CN 93114462 A CN93114462 A CN 93114462A CN 1090571 A CN1090571 A CN 1090571A
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克劳德·诺弗里
简·马里·提恩逖
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Abstract

本发明涉及上面通式的化合物和这些化合物的 生理可接受盐。这些化合物用于作香化剂。

Description

本发明涉及从糖精衍生制得的用作香化剂的新化合物及其制备方法。
这些新化合物主要用于香化各种各样的产品，尤其是饮料，食品，糖果，软点心，口香糖，保健产品和化妆用品，还有化妆品，药物和兽用产品。
众所周知，用于工业规模生产的香化剂必须首先具有强的香化效能，使限定使用成本成为可能，其次要具有满意的稳定性，也就是和使用条件相容的稳定性。
二肽衍生物N-L-α-天冬氨基-L-苯丙氨酸-1-甲酯，通称为糖精且具有下式：
在目前市场上的香化剂中应用最广泛（US3，492，131）。此化合物非常有价值的贡献之一是它的化学结构以L-天冬氨酸和L-苯丙氨酸两个天然的氨基酸为基础。以重量为基准，此化合物相对弱的香化效能约是蔗糖的120-180倍。尽管有良好的器官感觉特性，此化合物的主要缺点是由于香化强度相对低使它的产品昂贵，且在一定的香化剂使用条件下，该化合物的稳定性相当低，特别是在中性介质条件下，限制了该化合物的工业应用范围。
因而，食品工业显然需要一种新的香化剂，它具有高香化活性以降低其成本价格，且它至少与糖精一样稳定，如果它不是更稳定，那么尤其在中性介质中应至少与糖精一样稳定。因此，人们已经合成出了香化二肽或二肽类似物（见，例如，J.M.Janusz  in  Progress  in  Sweetenters，Ed.T.H.Grenby，Elsevier，London，1989，pp.1-46），但是至今，除了糖精，似乎没有满足香化剂主要要求的，即优良的器官感觉特性，用以降低使用成本的足够高香化强度和足够的稳定性。
我们非常意外地发现，糖精上附加一定基团，尤其选择适当的烃基，连到糖精的游离胺基上，能极大地提高其香化效能;用这种方法，糖精的香化效能可提高近80倍，香化强度随基团R的具体性质而变化。这个发现是形成本发有的基础。
N-L-α-天冬氨基-L-苯丙氨酸乙基，异丙基，丙基和叔丁基酯（US3，492，131）和N-L-α-天冬氨基-L-酪氨酸1-甲酯（US3，475，403）具有相同的特性。
按照第一个特征，本专利申请的目的是包括下列通式的化合物
Figure 931144620_IMG9
其中R选自CH3（CH2）2CH2，（CH3）2CHCH2，（CH3）CHCH2CH2，CH3CH2CH（CH3）CH2，（CH3CH2）2CHCH2，（CH3）3CCH2CH2，环己基，环庚基，环辛基，环戊苯甲基，环己苯甲基，3-苯丙基，3-甲基-3-苯基丙基，3，3-二甲基环戊基，3-甲基环己基，3，3，5，5-四甲基环己基，2-羟基环己基，3-（4-羟基-3-甲氧基苯基）丙基，3-（4-羟基-3-甲氧基苯基）-2-丙烯基，3-（4-羟基-3-甲氧基苯基）-1-甲基丙基和3-（4-羟基-3-甲氧基苯基）-1-甲基-2-丙烯基，X是选自CH3，CH2CH3，CH（CH3）2，CH2CH2CH3和C（CH3）3基，Z是氢原子或羟基和这些化合物的生理可受盐。
具有高香化效能的N-取代糖精衍生物在先有技术中已有描述。因而，文献EP-0107597（US  4，645，678）描述的糖精的N-苯氨基甲酰或N-硫基氨基甲酰基化合物，它们的香化效能是蔗糖的55，000倍。然而，这些N-苯氨基甲酰或N-苯硫基氨基甲酰基官能团和本发明的化合物的N-烃基官能没有相似结构。
其它的N-取代糖精衍生物也有描述（见，例如，J.M.Janusz，op.cit.），但是这些化合物与本发明的N-烃基衍生物也没有结构关系。
事实上，此技术陈述中的偏见一直阻止了本技术领域的熟练人员把注意力放在寻找具有高香化效能的糖精的N-烃基衍生物上。因此，仅把文献中描述的糖精N-烃基衍生物，即下式的N-〔N，N-二甲基-L-α-天冬酰基〕-L-苯丙氨酸1-甲酯：
Figure 931144620_IMG10
描述成有苦味（R.H.Mazur等，J.Amer.Chem.Soc.，1969，91，2684-2691）。
此外，本发明人进行的研究已经领先观察糖精N-烃基衍生物的器官感觉性是完全不可预见的，并且具有非常相似结构的烃基官能团导致糖精衍生物具有甜味，苦甜（bittersweet），苦味或没有味道，这是事实上存在的。更进一步讲，文献EP-0338946（US4，935，517），这些申请人描述了L-天冬氨酸（n＝1）或L-谷氨酸（n＝2）的N-烃基衍生物，其具有下面通式：
Figure 931144620_IMG11
其中R基是饱和或不饱和具有5-13个碳原子的无环的、环状或无环与环状混和的烃基官能团，R1基是4-氰苯基，2-氰基吡啶-5-基或2-氰基嘧啶-5-基并且n等于1或2。
本发明的化合物不同于现有技术中这些化合物，因为它们是具体的L-天冬氨酸化合物，本发明化合物包含有与文献EP-0338946所定义的不相类似结构的官能团R1，其活性取决于选择的很具体的N-烃基官能团。
本申请的发明人已经完成了结构/活性关系的研究。事实上，发明人已经领先观察在现有技术文献EP-0338946中与糖精化合的化合物中导致苦味或苦甜（bittersweet）味的最有效的N-烃基官能团。这时n-庚基尤其是适用的，它导致先有技术文件中的一种最甜的化合物，但是，该官能团与糖精化合时产生的化合物尝后具有很强苦味。
实验已经表明，在一般的用于食品加工条件下本发明典型化合物的稳定性比糖精的高。这是最为重要的，因为糖精用于食品加工的限制因素之一是源于在接近中性（即PH值为7左右）介质中其极低的稳定性，这对如下产品经常遇到：乳制品，软点心，其它需要高温烹调的制品，口香糖和牙膏。
促进老化的研究，通过对具有发明特征的化合物，即N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯在pH值为7的水溶液中在70℃进行延期加热，该化合物的香化效能比蔗糖的高10，000倍，表明半衰期大约6个小时，而在相同条件下糖精的半衰期只有10分钟;本发明化合物的稳定性比糖精的高36倍。发明特性的其它化合物也获得对比结果。
与代表香化剂主要应用之一的软饮料PH相当的PH值接近3的酸性介质中也证明，本发明化合物的稳定性如果不是较高至少也够高。
由于其高香化效能，本发明化合物和糖精相比较的另一个优点是其用在食品生产上时可以使用非常少量的活性剂。因而，由于使用本发明的香化剂，使得在食品生产中经常考虑存在的糖精的某种组分，即L-苯丙氨酸和甲醇，极大地减少。因此，例如，在1升软饮料中用大约7mg本发明描述的N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯代替550mg天冬氨酸是可能的，尽管同时保持相同的器官感觉的特性，但易于消耗的L-苯丙氨酸和甲醇的量减少近似80倍。
本发明因此可以第一次提供具有优良器官感觉特性的糖精或其类似物的新N-烃基衍生物，以重量为基准，它的高香化效能是蔗糖香化效能的近10，000倍，和糖精相比，其稳定性至少相近或更高些，其在食品加工上效果增加了可能多种用途。
发明的一个特殊优点的具体表现是有下列通式：
Figure 931144620_IMG12
其中R和前面定义的相同。
代表本发明特殊优点的具体实施化合物是N-〔N-3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯（表1的化合物6），通式如下：
Figure 931144620_IMG13
或N-〔N-〔3-（4-羟基-3-甲氧基苯基）丙基〕-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯（表1的化合物18），通式如下：
或另外N-〔N-（3-苯基丙基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯（表1的化合物12），通式如下：
Figure 931144620_IMG15
本发明化合物也可用生理可接受的无机或有机酸或碱盐化，达到提高它们溶解度的效果。这些化合物以盐酸盐或钠盐，钾盐，铵盐，钙盐或镁盐形式盐化时较有利。
按照第二个特点，本专利申请的目的是盖括本发明化合物作为香化剂，香化组合物，其中至少一种上述定义的化合物作为香化剂被包容，和本发明化合物用于香化有关介绍的各种各样的产品的用途。
本发明的香化剂可加到任何希望有甜味的食品中，假设以有效比例加入以达到希望的甜味水平。甜味剂最佳使用浓度依赖于各种因素，例如：香化剂的香化效能，储存条件和产品用途，产品的特定组成和希望达到的甜味水平。任何有资格的人通过常规灵敏分析可容易地测定为得到食品所必须使用的香化剂的最佳比例。根据化合物的香化效能，本发明香化剂通常以下面比例加到食品中，在每千克或每升的食品中加入0.5mg-50mg香化剂。浓缩产品显然含有大量的香化剂，然后根据计划的最后用途来稀释。
本发明的香化剂可以纯的形式加到产品中使其变甜，但是，因为香化剂的香化效能高，一般要与适当的载体或增量剂混合。
适当的载体或增量剂选自下列一组物质是有利的，聚葡萄糖，淀粉，麦芽糖糊精，纤维素，甲基纤维素，羧甲基纤维素和其它纤维素衍生物，藻酸钠盐，果胶，树胶，乳糖，麦芽糖，葡萄糖，亮氨酸，甘油，甘露糖醇，山梨醇，碳酸氢钠，磷酸，柠檬酸，酒石酸，富马酸，苯甲酸，山梨酸，丙酸和它们的钠盐，钾盐和钙盐及其等同物。
按照本发明，香化剂本身可用于食品，作为仅一种香化剂或和其它的香化剂组合，例如蔗糖，玉米糖浆，果糖，甜的二肽衍生物或其类似物（糖精，alitame），新橙皮苷，二氢查耳酮，氢化异麦芽糖，卡哈苡苷，L糖，甘草甜，木糖醇，山梨醇，甘露糖醇，acesulfame，糖精和它们的钠盐，钾盐，铵盐和钙盐，环己烷氨基磺酸和它的钠盐，钾盐和钙盐，sucralose，monellin，thaumatin，及其等同物。
本发明的化合物可以按文献已描述的多种方法制备。因此，按照第三个特点，本专利申请的目的是包括一种优选的方法，其在于用作为R基前体的醛或酮缩合下式化合物：
Figure 931144620_IMG16
由于缩合形成的中间体亚胺随着选择的还原剂例如，氰基氢硼化钠而原位地还原，直接产生本发明化合物（ohfune等，Chemistry  letters，1984，441-444，描述了还原的N-单烷基化方法）。
例如R是（CH3）3CCH2CH2本发明化合物从式（CH3）3CCH2CHO的商业用醛母体3，3-二甲基丁醛获得。
应该注意到本发明的化合物从糖精或其类似物直接制备。就糖精衍生物来说，由于糖精是商品，人们已经熟练地掌握了合成，这是特别有价值的优点。
发明化合物以其酸或盐的形式纯化，用标准技术，例如，重结晶或色谱来完成。它们的结构和纯度用普通的技术检测（薄层色谱，高效液相色谱，红外光谱，核磁共振，元素分析）。
完成发明的方法和由此得出的优点，从后面的实施例中可以清楚明显地看到。
在这些实施例中，八个有经验的人评价所描述的化合物的香化效能。评价工作是在2%，5%或10%的不同浓度蔗糖对照溶液下在水溶液中比较化合物的味道。与蔗糖相比较，试验化合物的香化效能对相同香化强度来说相当于化合物与蔗糖间的重量比，即大多数人认为和参比的蔗糖溶液的甜味具有相同的香化强度时。
发明化合物和糖精的稳定性，通过用高效液相色谱（HPLC）测定在70℃的酸性介质（磷酸缓冲PH为3）或中性介质（磷酸缓冲PH为7）老化后产品的残留量来获得。以这种方式测得的化合物稳定性用它的半衰期来评定（相当于50%降解的时间）。
做为制备实施例，下式的N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯（表1中第6个实施例）合成如下：
Figure 931144620_IMG17
把4g（39.8mmol）商售的3，3-二甲基丁醛加到混有10.6g（36.2mmol）的糖精和1.6g（25.3mmol）氰基氢硼化钠的50毫升溶液中。在室温搅拌该溶液24小时，然后真空浓缩干燥，用1N的盐酸水溶液处理残留物至接近中性，滤掉形成的胶状沉淀，真空下干燥，用乙醇/水（1/1）混合液重结晶或以乙腈重结晶产生9g（产率62%）的N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯。
以重量为基准，通过与2%，5%和10%的蔗溶液比较，此化合物的香化效能大约相当于蔗糖的10，000倍。
和糖精比较，本发明化合物的7mg/l水溶液的香化强度相当于550mg/l糖精溶液的香化强度，相当于其香化效能比糖精的高大约80倍。
通过实施例，按照本发明表1给出了从糖精获得的其它化合物的香化效能，这是通过用与上所述相似的低级醇，这对本技术领域熟练人员很容易获得。香化效能用相当于2%蔗糖溶液地行评价。
表1
Figure 931144620_IMG18
No.  R  香化效能
1 CH3CH2CH2CH2400
2 (CH3)2CHCH2500
3 (CH3)2CHCH2CH21300
4 (R,S)-CH3CH2CH(CH3)CH2900
5 (CH3CH2)2CHCH22000
6 (CH3)3CCH2CH210000
7  环已基  800
8  环庚基  900
9  环辛基  1000
10  环戊甲基  1500
11  环已甲基  800
12 C6H5CH2CH2CH21500
13 (R,S)-C6H5CH(CH3)CH2CH21200
14  3,3-二甲基环戊基  150
15  (R,S)-3-甲基环已基  1000
16  3,3,5,5-四甲基环已基  1000
17  (R,S)-2-羟基环已基  800
18 (3-OCH3,4-OH)C6H3CH2CH2CH22500
19 (3-OCH3,4-OH)C6H3CH=CHCH22000
20 (R,S)-(3-OCH3,4-OH)C6H3CH2CH2CH(CH3) 500
21 (R,S)-(3-OCH3,4-OH)C6H3CH=CHCH(CH3) 500
通过通式化合物的附加实施例，N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-乙酯的香化效能是蔗糖的2000倍，N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-酪氨酸1-甲酯的香化效能是蔗糖的4000倍（通过与2%的蔗糖溶液比较）。
附图1表示，与糖精（曲线a）相比本发明的几个特性化合物的稳定性曲线比较图。实施例为表1中的化合物2，5和6（分别为曲线b，c和d），这些曲线是在70℃加热浓度为1g/l的PH为3的酸性介质溶液的促进老化过程中得到的。在这些实验条件下，糖精的半衰期为24小时，而本发明化合物2的半衰期约为35小时，化合物5的半衰期约为96小时，化合物6的半衰期约为55小时，对应的稳定性比糖精高4倍。
与糖精（曲线a）相比附图2给出了表1中化合物2，5和6的稳定性曲线（分别为曲线b，c和d）比较图，这些曲线在70℃加热浓度为1g/l的PH值为7的中性介质溶液的促进老化过程中得到的。在这些条件下，糖精的稳定性非常低（半衰期10分钟），而本发明化合物中化合物2的半衰期为4小时15分钟，化合物5的半衰期为10小时，化合物6的半衰期为6小时，对应的稳定性比糖精高60倍。

Claims (8)

1、具有如下通式的化合物
Figure 931144620_IMG2
其中R选自CH3(CH2)2CH，(CH3)2CHCH2，(CH3)2CHCH2CH2，CH3CH2CH(CH3)CH2，(CH3CH2)2CHCH2，(CH3)3CCH2CH2，环己基，环庚基，环辛基，环戊甲基，环己甲基，3-苯基丙基，3-甲基-3-苯基丙基，3，3-二甲基环戊基，3-甲基环己基，3，3，5，5-四甲基环己基，2-羟基环己基，3-(4-羟基-3-甲氧基苯基)丙基，3-(4-羟基-3-甲氧基苯基)-2-丙烯基，3-(4-羟基-3-甲氧基苯基)-1-甲基丙基和3-(4-羟基-3-甲氧基苯基)-1-甲基-2-丙烯基，X选自CH3，CH2CH3，CH(CH3)2，CH2CH2CH3和C(CH3)3基，Z是氢原子或OH和此化合物的生理可受盐。
2、按照权利要求1的化合物，该化合物具有如下通式：
其中R如权利要求1中定义所述。
3、按照权利要求2的化合物，该化合物是下式的N-〔N-（3，3-二甲基丁基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯。
Figure 931144620_IMG4
4、按照权利要求2的化合物，该化合物是下式的N-〔N-〔3-（4-羟基-3-甲氧基苯基）丙基〕-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯。
5、按照权利要求2的化合物，该化合物是下式的N-〔N-（3-苯基丙基）-L-α-天冬氨基〕-L-苯丙氨酸1-甲酯。
6、香化剂组合物，其包含至少一种按照权利要求1所述的作为香化剂的化合物。
7、按照权利要求1所述化合物作为香化剂的应用。
8、按照权利要求1所述的化合物的制备方法，其在于用相当于要制备化合物R基的醛或酮母体缩合下式化合物，
Figure 931144620_IMG7
其中X和Z如权利要求1所定义的，然后，用氰基硼氢化钠同位还原得到的亚胺，R如权利要求1所定义的。
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AU664663B2 (en) 1995-11-23
IL107551A0 (en) 1994-02-27
US5480668A (en) 1996-01-02
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WO1994011391A1 (fr) 1994-05-26
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PL306841A1 (en) 1995-04-18
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SK280180B6 (sk) 1999-09-10
CN1038747C (zh) 1998-06-17
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FR2697844B1 (fr) 1995-01-27
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HUT72192A (en) 1996-03-28
NZ257870A (en) 1996-03-26
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RO112621B1 (ro) 1997-11-28
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MD960256A (en) 1998-03-31
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