CN1278826A - N－[N－(3,3－二甲基丁基)－L－α－天冬氨酰]－L－苯丙氨酸1－甲基酯的金属配合物 - Google Patents
N－[N－(3,3－二甲基丁基)－L－α－天冬氨酰]－L－苯丙氨酸1－甲基酯的金属配合物 Download PDFInfo
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Abstract
本发明公开了二肽类甜味剂,它们是式(Ⅰ)所代表的N－[N－(3,3－二甲基丁基)－L－α－天冬氨酰]－L－苯丙氨酸1－甲基酯的金属配合物,其中Xp+选自Al3+、Fe2+、Fe3+、Ca2+、Mg2+和Zn2+,Yq－选自Cl－、SO4 2－、PO4 3－和CH3COO－;x为1至4的数目和pn=qm。本发明还涉及一种含本发明金属配合物的液体低卡甜味剂。
Description
发明领域
本发明涉及新的甜味剂。本发明尤其涉及N-烷基化的天冬甜素衍生物N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯(即neotame)的金属配合物。本发明还涉及一种含所述金属配合物的液体低卡(low calorie)甜味剂。
相关背景技术
已知各种N-取代的天冬甜素衍生物，例如公开于美国专利5，480，668的那些，可用作甜味剂。尤其是，N-烷基化的天冬甜素衍生物N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯已知是非常有效的甜味剂，因为据报道按重量计其甜度是天冬甜素的50倍，是蔗糖的10，000倍。
由于甜味剂常被用于水溶液和饮料中，因此，甜味剂具有可接受的溶解速率和商业可利用之有效水平的溶解度是重要的。美国专利4，031，258公开了一些二肽类甜味剂的无机盐，其具有提高的溶解度和溶解性。美国专利4，448，716公开了一些具有提高的溶解速度和溶解性的二肽类甜味剂金属配合物。但是，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯没有被公开或提示。
已经知道，通过转化成盐，可以改善天冬甜素和其他肽类的物理性质和稳定性。这在例如美国专利4，031，258和4，153，737中已经公开。美国专利4，153，737还讲述了低卡甜味剂浓缩液。
但是，从结构上讲，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯与天冬甜素的区别在于，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯在氨基氮上存在庞大的新己基取代基。
天冬甜素 Neotame
这种结构区别导致这些化合物理化性质上的巨大差异。例如，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的熔点为80℃，而天冬甜素的熔点为248℃。另外，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯在有机溶剂中的溶解度比天冬甜素高，而在水中比天冬甜素低得多。还知道N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯在某些pH条件下的稳定性比天冬甜素高，这在美国专利5，480，688中已有描述。这两种化合物在甜度上的显著差异是它们化学不相似性的进一步表现。
而且，还已知伯氨基例如天冬甜素上的伯氨基(pKa 7．7)的pKa值通常不同于仲氨基例如N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯上的仲氨基(pKa 8．1)的pKa值。此外，已知氨基酸的pKa值对食物应用具有较大影响(Labuza，T．P．和Basisier，M．W．1992，“Physical Chemistry of Foods”，H．G．Schwartzber和R．W．Hartel(Eds．)，Marcel Dekker，Inc．，NewYork)。还已知仲氨基不能与羰基化合物形成席夫碱型化合物，而伯胺能。而且，正如甜度上的巨大差异所例证，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯具有不同于天冬甜素的生理性能。这些差异清楚地表明，其中一种化合物的特征和性能，不能说成是对另一种化合物特征和性能的提示。
虽然N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯是高效甜味剂，但它不易溶于水，并会产生喷粉问题。因此，需要这样的N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯衍生物，它们在水性体系中有良好的溶解度和溶解性能，并且避免了精细粉末所常遇到喷粉问题。如果N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯的稳定性能被提高，那将也是有利的。
发明概述
本发明涉及二肽类甜味剂，它们是N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯的金属配合物，在水性体系中具有良好的溶解度和溶解性能。尤其是，本发明的N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的金属配合物由下式代表，
其中Xp+选自Al3+、Fe2+、Fe3+、Ca2+、Mg2+和Zn2+，而Yq-选自Cl-、
HCOO-和CH3COO-；x为1至4的数目和pn=qm。本发明还涉及一种含本发明金属配合物的液体低卡甜味剂。附图简述
附图是在0．05％重量靶浓度下N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯与相当的neotame浓度(即在每种情况下所给出的neotame浓度相同)的N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的氯化钙和硫酸锌配合物在水中的溶解度比较曲线图。发明详述
本发明涉及N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的金属配合物，即neotame的金属配合物。美国专利5，480，688、5，510，508、和5，728，862叙述了N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯的制备，这些专利全文并入本文作为参考。因此，熟悉本领域的普通技术人员无须过多的实验就能容易地制得起始原料。
将N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯和一种金属盐加入到一定量的溶剂中，以有效溶解N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯和金属盐，然后搅拌一段时间以形成金属配合物，这样可制得本发明金属配合物。合适的溶剂包括水、甲醇、乙醇、丙醇、丁醇、丙酮、乙腈、四氢呋喃、二甲基甲酰胺、和二甲亚矾。通过真空蒸发溶剂，可收集金属配合物产品。金属配合物产品还可通过冷冻干燥或喷雾干燥所形成的溶液进行收集。
在本发明金属配合物的制备中，合适使用的金属盐包括金属阳离子Xp+与阴离子Yq-所形成的任何盐，其中Xp+选自Al3+、Fe2+、Fe3+、Ca2+、Mg2+和Zn2+，而Yq-选自Cl-、
和CH3COO-。这些盐的分子式为(Xp+)n(Yq-)m，其中pn=qm，以使得该盐为电中性。本发明配合物不需要使得N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯与盐的比例为1∶1，而是还包括其变化形式。
本发明尤其优选的金属配合物包括氯化钙、氯化镁、氯化铁、氯化铝或硫酸锌和N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯之间所形成的那些金属配合物。
相对于N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯而言，相信本发明的金属配合物具有多种改善的性能。尤其是增加了水溶解性和极大提高了该成分的溶解速度。这样Neotame金属配合物是甜味的，相信这些甜味剂金属配合物将具有改善的稳定性。因此，N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的这些金属配合物将尤其可用于饮料体系中，特别是因为在提供例如桌面甜味剂(table top sweeteners)所需快速溶解的情况下，减少了或者不必要另外的方法或机械调制。可以使用本领域技术人员熟知的方法将本发明金属配合物与公知的增量剂一起混合，制备片状、粉末和粒状的甜味剂。本发明金属配合物的另一优点是不具有与N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯相关的喷粉问题。
将本发明高浓度的金属配合物溶解在水或醇体系例如水、丙二醇、水／丙二醇混合液、乙醇或水／乙醇混合液中，可将该金属配合物制备成液体低卡甜味剂。这种液体低卡甜味剂可用于例如胶冻甜食、果味饮料、谷类食品、制蛋糕用混合配料、果汁、糖浆、色拉调料、宠物食品、碳酸软饮料、桌面甜味剂等各种食品中。这些用途并非限定性的，因为还有其他用途，包括咳嗽药、滋补品等等。特别感兴趣的本发明的一个实施方案是液体桌面甜味剂，用作蔗糖和其他已知甜味剂的替代品。这种液体低卡甜味剂一般含至多40％重量的N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的金属配合物，当然，其浓度取决于所需的最终应用。
下文实施例意在说明本发明某些优选的实施方案，并不是试图对本发明进行限定。
实施例1
N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的氯化钙配合物
室温下，将二水合氯化钙(3．23g，0．0220mol)和N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯(8．72g，0．0220mol)溶解在80ml甲醇中。33℃和室真空(house vacuum)下旋转蒸发除去大量甲醇。残余溶剂用机械真空泵除去，得到标题配合物(11．2g)。该配合物(0．2g)在不到120秒内(经目测)和在不到140秒内(经分光光度法测定)溶解在水(100ml)中。
实施例2
N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的氯化镁配合物
室温下，将六水合氯化镁(6．80g，0．0334mol)和N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯(13．26g，0．0334mol)溶解在100ml甲醇中。33℃和室真空下旋转蒸发除去大量甲醇。残余溶剂用机械真空泵除去，得到标题配合物(17．7g)。该配合物(0．2g)在不到120秒内(经目测)溶解在水(100ml)中。
实施例3
N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯的硫酸锌配合物
室温下，将七水合氯化锌(8．86g，0．0308mol)和N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯(12．21g，0．0308mol)溶解在120ml甲醇中。33℃和室真空下旋转蒸发除去大量甲醇。残余溶剂用机械真空泵除去，得到标题配合物(17．2g)。该配合物(0．2g)在不到140秒内(经目测)和在不到180秒内(经分光光度法测定)溶解在水(100ml)中。
比较实施例1
N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯在水中的溶解
将N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯(0．1-0．2g)溶解在水(100ml)中。该化合物在5-8分钟内(经目测)完全溶解。1．0g N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸 1-甲基酯溶解在100ml水中需要大约45分钟。
本发明其他变化和改进对熟悉本领域的技术人员将是显而易见的。除了权利要求所述之外，本发明不作其他限定。
Claims (5)
1．一种下式所代表的N-[N-(3，3-二甲基丁基)-L-α-天冬氨酰]-L-苯丙氨酸1-甲基酯的金属配合物，
其中Xp+选自Al3+、Fe2+、Fe3+、Ca2+、Mg2+和Zn2+，Yq-选自Cl-、SO4 2-、PO4 3-和CH3COO-；x为1至4的数目和pn=qm。
2．权利要求1的金属配合物，其中(Xp+)n(Yq-)m是氯化钙、氯化镁、氯化铁、氯化铝或硫酸锌。
3．一种液体低卡甜味剂组合物，该组合物含有下式所代表的二肽类甜味剂金属配合物，该盐溶解在一种或多种可消费的溶剂中，其浓度占组合物重量至多约40％，以提供高浓度的液体低卡甜味剂，
其中Xp+选自Al3+、Fe2+、Fe3+、Ca2+、Mg2+和Zn2+，Yq-选自Cl-、SO4 2-、 和CH3COO-；x为1至4的数目和pn=qm。
4．权利要求3的液体低卡甜味剂，其中溶剂是乙醇、丙二醇、水、乙醇／水或丙二醇／水。
5．权利要求4的液体低卡甜味剂，其中(Xp+)n(Yq-)m是氯化钙、氯化铁、氯化铝、氯化镁或硫酸锌。
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| US5850897P | 1997-09-11 | 1997-09-11 | |
| US60/058,508 | 1997-09-11 |
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| CN1278826A true CN1278826A (zh) | 2001-01-03 |
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| US (1) | US6146680A (zh) |
| EP (1) | EP1012170A1 (zh) |
| CN (1) | CN1278826A (zh) |
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| SK (1) | SK3252000A3 (zh) |
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| AU3904800A (en) * | 1999-03-22 | 2000-10-09 | Nutrasweet Company, The | Cereals and cereal-based food sweetened with n-(9n-(3,3- dimethylbutyl) -l-alpha- aspartyl) -l-phenylalanine 1-methyl ester |
| WO2000057725A1 (en) * | 1999-03-26 | 2000-10-05 | The Nutrasweet Company | PARTICLES OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER |
| WO2000069282A1 (en) * | 1999-05-13 | 2000-11-23 | The Nutrasweet Company | Modification of the taste and physicochemical properties of neotame using hydrophobic acid additives |
| US20030008047A1 (en) * | 2000-03-17 | 2003-01-09 | Schroeder Steve A. | Stability enhancement of sweeteners using salts containing divalent or trivalent cations |
| US7326430B2 (en) * | 2000-07-18 | 2008-02-05 | The Nutrasweet Company | Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems |
| US6225493B1 (en) * | 2000-08-21 | 2001-05-01 | The Nutrasweet Company | Metal ion assisted N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester isomer resolution |
| US20080008790A1 (en) * | 2006-06-30 | 2008-01-10 | Michael Jensen | Seasoned food, seasoning, and method for seasoning a food product |
| US7923047B2 (en) * | 2006-06-30 | 2011-04-12 | Conagra Foods Rdm, Inc. | Seasoning and method for seasoning a food product while reducing dietary sodium intake |
| US20110097449A1 (en) * | 2006-06-30 | 2011-04-28 | Conagra Foods Rdm, Inc. | Seasoning and method for seasoning a food product while reducing dietary sodium intake |
| US20080038411A1 (en) * | 2006-06-30 | 2008-02-14 | Michael Jensen | Seasoning and method for enhancing and potentiating food flavor |
| NZ575995A (en) * | 2006-09-27 | 2011-03-31 | Conagra Foods Rdm Inc | Seasoning and method for enhancing and potentiating food flavor utilizing microencapsulation |
| WO2012026499A1 (ja) * | 2010-08-25 | 2012-03-01 | 味の素株式会社 | アスパルチルジペプチドエステル誘導体の保存方法及び安定化剤 |
| FR3102041A1 (fr) | 2019-10-22 | 2021-04-23 | Aroma Sens | Edulcorant pour liquides de cigarette électronique |
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| US4031258A (en) * | 1972-03-30 | 1977-06-21 | General Foods Corporation | Inorganic salts of dipeptide sweeteners |
| CA1028197A (en) * | 1973-04-02 | 1978-03-21 | Jeffrey H. Berg | Concentrated liquid low calorie sweetener |
| US4448716A (en) * | 1982-03-04 | 1984-05-15 | G. D. Searle & Co. | Dipeptide sweetener-metal complexes |
| FR2697844B1 (fr) * | 1992-11-12 | 1995-01-27 | Claude Nofre | Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation. |
| FR2719590B1 (fr) * | 1994-05-09 | 1996-07-26 | Claude Nofre | Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant. |
| US5728862A (en) * | 1997-01-29 | 1998-03-17 | The Nutrasweet Company | Method for preparing and purifying an N-alkylated aspartame derivative |
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- 1998-09-11 ID IDW20000469A patent/ID27125A/id unknown
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- 1998-09-11 AU AU95679/98A patent/AU9567998A/en not_active Abandoned
- 1998-09-11 BR BR9812767-5A patent/BR9812767A/pt not_active Application Discontinuation
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- 1998-09-11 EP EP98949335A patent/EP1012170A1/en not_active Withdrawn
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| Publication number | Publication date |
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| WO1999012955A1 (en) | 1999-03-18 |
| HUP0003574A2 (hu) | 2001-05-28 |
| US6146680A (en) | 2000-11-14 |
| CA2303433A1 (en) | 1999-03-18 |
| BG104320A (en) | 2001-02-28 |
| SI20329A (sl) | 2001-02-28 |
| EE200000115A (et) | 2000-12-15 |
| SK3252000A3 (en) | 2000-10-09 |
| IL134915A0 (en) | 2001-05-20 |
| NO20001272D0 (no) | 2000-03-10 |
| ID27125A (id) | 2001-03-01 |
| HUP0003574A3 (en) | 2001-08-28 |
| LT2000029A (lt) | 2000-12-27 |
| BR9812767A (pt) | 2000-12-12 |
| AU9567998A (en) | 1999-03-29 |
| TR200000732T2 (tr) | 2001-06-21 |
| PL339190A1 (en) | 2000-12-04 |
| NO20001272L (no) | 2000-05-10 |
| EP1012170A1 (en) | 2000-06-28 |
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