CN105339349B - 用于保持类胡萝卜素化合物的异构体比率的新方法 - Google Patents
用于保持类胡萝卜素化合物的异构体比率的新方法 Download PDFInfo
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- CN105339349B CN105339349B CN201480035118.6A CN201480035118A CN105339349B CN 105339349 B CN105339349 B CN 105339349B CN 201480035118 A CN201480035118 A CN 201480035118A CN 105339349 B CN105339349 B CN 105339349B
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- carotenoid compounds
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- alkali metal
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Classifications
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- C07C45/86—Use of additives, e.g. for stabilisation
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
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- A23K20/105—Aliphatic or alicyclic compounds
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Abstract
本发明涉及一种用于通过使用有机酸的至少一种碱金属盐和/或碱土金属盐来保持类胡萝卜素化合物的立体异构体比率的方法,还涉及具体的制剂以及该具体制剂的用途。
Description
本发明涉及用于保持类胡萝卜素化合物的立体异构体比率的方法,涉及具体制剂,以及该具体制剂的用途。
类胡萝卜素(其在本专利申请的上下文中也被命名为类胡萝卜素化合物)一般由结合的碳氢异戊二烯的单元组成,具有交替的单键和双键。类胡萝卜素会吸收某些频率的光能并将其传递给叶绿素用于光合作用。
类胡萝卜素对动物以及人类的营养很重要,并且还具有抗氧化性能。
类胡萝卜素被分成两组:
·胡萝卜素(只包含H和C原子),和
·胡萝卜醇(还包含O原子)。
在自然界中发现的类胡萝卜素主要以全反式立体异构形式存在。但类胡萝卜素有立体异构化(即转化为其它的立体异构形式)的趋势。在本发明的上下文中,E-形式、Z-形式和E/Z-形式的混合物都表示立体异构形式。立体异构化通常会产生许多不同的立体异构结构的混合物,例如:
“*”(=星号)是端基(R1和R2)的位置。
在例如吸光性、生物利用度等方面,类胡萝卜素化合物的所有立体异构形式通常具有不同的性能。因此,发生异构化时,含有类胡萝卜素化合物的制剂的性能可能发生变化。
因此,本发明的目的是要找到一种方法,其能保持类胡萝卜素化合物的立体异构体比率,以使包含类胡萝卜素的制剂的性能不改变。
从现有技术(WO2013010820)已知,特定的矿物盐能够稳定类胡萝卜素化合物的立体异构体比率。
由于该方法的重要性,需要不断的改进。
出人意料的是,已发现,类胡萝卜素化合物的异构化受至少一种有机酸碱金属盐和/或碱土金属盐的添加的影响。该添加的结果是立体异构形式(或者两种或更多种立体异构形式的混合物)被稳定了。防止或减缓了立体异构化。
因此,本发明涉及一种用于保持式(I)的类胡萝卜素化合物的立体异构体比率的方法
其中R1和R2彼此相互独立地为
其特征在于:至少一种式(I)的化合物与基于式(I)化合物的总重量小于1重量%(wt-%)的至少一种有机酸碱金属盐和/或碱土金属盐混合。
星号标记到主链的键。一般,类胡萝卜素化合物以溶液或乳液的形式存在。该溶液或乳液随后可以在进一步的步骤进行干燥(喷雾干燥、冷冻干燥),与其它制剂或成分混合等。
在这样的制剂中,类胡萝卜素化合物的浓度可以根据该制剂的用途而变化。合适的溶剂是类胡萝卜素化合物可溶于其中的溶剂,如乙酸乙酯、二氯甲烷、氯仿、丙酮等。
如果使用乳液体系,那么它通常是水包油乳液。对于这样的乳液来说,可以使用任何通常已知且使用过的油和乳化剂。油的选择以及乳化剂的选择取决于制剂的用途。如果要生产食品或饲料产品,则这些化合物需要是食品级或饲料级的。
合适的油可来自任何来源。它们可以是天然的、改性的或合成的。如果油是天然的,它们可以是植物油或动物油。合适的油是例如椰子油、玉米油、棉花籽油、橄榄油、棕榈油、花生油、油菜籽油(canola oil)、红花油、芝麻油、大豆油、葵花籽油、榛子油、杏仁油、腰果油、澳洲胡桃油(macadamia oil)、芥子油(mongongo nut oil)、巴卡斯果油(PracaxiOil)、山核桃油(pecan oil)、松子油、开心果油(pistachio oil)、美藤果(印加果Plukenetia)油、核桃油、多不饱和脂肪酸如甘油三酸酯和/或乙基酯(例如花生四烯酸、二十碳五烯酸、二十二碳六烯酸和γ-亚麻酸和/或乙基酯)。
任何通常已知和使用过的乳化剂都可以使用。乳化剂可以根据制剂以后的最终用途来选择。合适的乳化剂即为改性(食物)淀粉、果胶、藻酸盐、卡拉胶(carrageenan)、红藻胶、壳聚糖、麦芽糊精、糊精衍生物、纤维素和纤维素衍生物(例如醋酸纤维素、甲基纤维素、羟丙基甲基纤维素)、木素磺酸盐、多糖树胶(如阿拉伯树胶(gum acacia)、阿拉伯胶(gumarabic)、亚麻籽胶、茄替胶(ghatti gum)、罗望子胶(tamarind gum)和阿拉伯半乳聚糖)、明胶(牛、鱼、猪、家禽)、植物蛋白(如浓缩物、分离物、水解物等,来自豌豆、大豆、蓖麻子、棉花籽、马铃薯、甘薯、树薯、油菜籽、葵花籽、芝麻、亚麻子、红花、小扁豆(lentils)、坚果、小麦、大米、玉米、大麦、黑麦、燕麦、羽扇豆和高粱)、动物蛋白包括乳蛋白或乳清蛋白、卵磷酯、脂肪酸的甘油多酯、脂肪酸的甘油单酯、脂肪酸的甘油二酯、山梨糖醇酯、PG酯和糖酯(及其衍生物)。
淀粉可以是物理改性的和化学改性的。预胶化淀粉是物理改性的淀粉的实例。
酸改性的、氧化的、OSA改性的、交联的淀粉酯,淀粉醚和阳离子淀粉是化学改性的淀粉的实例。
制剂可进一步包含其它辅助剂。根据所用制剂的用途,所述辅助剂可有所不同。这些辅助剂对制剂有用,可进一步改善其性能如物理稳定性、储存稳定性、视觉感知等。助剂还可用在食品、饲料或个人护理产品的应用中,改善这些组合物的性能、物理稳定性、储存稳定性、视觉感知、在胃肠道(GI-tract)中的控制释放、pH控制、耐氧化性等。这些助剂的浓度可以变化,取决于这些助剂的用途。
优选的类胡萝卜素化合物是下面这些:
式(Ia)的化合物:
式(Ib)的化合物:
式(Ic)的化合物:
式(Id)的化合物:
式(Ie)的化合物:
式(If)的化合物:
式(Ig)的化合物:
式(Ih)的化合物:
式(Ii)的化合物:
式(Ij)的化合物:
为了稳定类胡萝卜素化合物的比率,基于类胡萝卜素化合物或其混合物的总重量,以小于1wt-%的量添加至少一种有机酸碱金属盐和/或碱土金属盐。优选地小于0.9wt-%,更优选地小于0.8wt-%。通常,基于类胡萝卜素化合物或其混合物的总重量,使用0.0001wt-%到1wt-%量的至少一种有机酸碱金属盐和/或碱土金属盐。
该方法通常在15℃到160℃、优选20℃到130℃、更优选20℃到110℃的温度下进行。
该方法通常在1bar到10bar、优选1bar到8bar、更优选1bar到5bar的压力下进行。
之后,包含小于1wt-%的量的至少一种有机酸碱金属盐和/或碱土金属盐的类胡萝卜素可以原样使用或者用于进一步配制。
异构体比率在组合物本身(仅有类胡萝卜素化合物和有机酸碱金属盐和/或碱土金属盐)中以及在包含该组合物的制剂中均得到稳定。
有机酸优选为R-COOH,其中R为C1-C4-烷基基团。
有机酸碱金属盐和/或碱土金属盐的优选的碱金属和碱土金属是K、Ca和Mg。
优选的有机酸碱金属盐和/或碱土金属盐具有下式:R-COOMe1or(R-COO)2Me2,
其中R为C1-C4-烷基基团,并且
Me1为K+,并且
Me2为Ca2+或Mg2+。
最优选的有机酸盐是乙酸钾(=CH3COOK)。
在β-胡萝卜素(化合物(Ia))的情况下,立体异构化导致颜色深浅的变化。全Z-形式更显微红色,而Z形式是略显微黄色。
因此,本发明的一个优选实施方式涉及用于保持式(Ia)化合物的立体异构体比率的方法
其特征在于,基于所述式(Ia)化合物的总重量,添加小于1wt-%的CH3COOK。
在虾青素(化合物(Ie))的情况下,立体异构化导致化合物不同的生物利用度。全(E)形式的虾青素具有最佳的生物利用度。因此,该形式(或者具有大量的全(E)、至少85%的全(E)的形式)应该被稳定。
因此,本发明的一个优选实施方式涉及用于保持式(Ie)化合物的立体异构体比率的方法
其特征在于,基于所述式(Ie)化合物的总重量,添加小于1wt-%的CH3COOK。
有机酸碱金属盐和/或碱土金属盐可以固体形式以及溶液的形式(或者二者的组合)加入。
此外,本发明还涉及包含至少一种式(I)类胡萝卜素化合物和基于一种或多种式(I)化合物的总重量0.0001到1wt-%的至少一种有机酸碱金属盐和/或碱土金属盐的制剂,
其中R1和R2彼此相互独立地为
用于方法的所有优选项也适用于制剂。
作为上面所述的制剂,包含小于1wt-%的量的至少一种有机酸碱金属盐和/或碱土金属盐的类胡萝卜素化合物可以原样使用或者用于进一步配制。
上面所描述的制剂可用于食品、饲料或个人护理产品。
如上所述的用于食品、饲料或个人护理产品的制剂的量取决于食品、饲料或个人护理产品。
附图1.:9-顺式和13-顺式AXT的形成的浓度-时间图。
附图2.:通过光度计测得的全反式AXT的浓度-时间图。
下面的实施例用于说明本发明。所有的百分比都与重量相关,温度是以摄氏度给出的。
实施例1
将14.1mg的虾青素溶于70ml氯仿。将13.7μgCH3COOK加入该溶液中(通过加入包含在70ml氯仿中的13.7mg CH3COOK的稀释溶液的等分试样)。将溶液均质化,制剂在40℃下调和。保存该溶液,并且定期取出样品,用分光光度计在478nm处对虾青素的浓度进行测定。
实施例2(对比例)
将16.1mg的虾青素溶于80ml氯仿。将16.2μg KCO3加入该溶液中(通过加入包含在70ml氯仿中的16.2mg KCO3的稀释溶液的等分试样)。将溶液均质化,制剂在40℃下调和。保存该溶液,并且定期取出样品,用分光光度计在478nm处对虾青素的浓度进行测定。
实施例3(对比例)
将16.1mg的虾青素溶于80ml氯仿。将溶液均质化,制剂在40℃下调和。保存该溶液,并且定期取出样品,用分光光度计在478nm处对虾青素的浓度进行测定。
图1和图2表明,CH3COOK的加入,能比K2CO3更好地稳定全-E-形式。未经处理的虾青素(不添加任何盐)示出了比率通常如何恶化。
Claims (14)
1.一种用于保持式(I)的类胡萝卜素化合物的立体异构体比率的方法
其中R1和R2彼此相互独立地为
其特征在于:所述式(I)的化合物与基于所述式(I)化合物的总重量小于1wt-%的至少一种有机酸碱金属盐和/或碱土金属盐混合,其中所述有机酸金属盐和/或碱土金属盐是式R-COOMe1或(R-COO)2Me2的化合物,
其中R为C1-C4-烷基基团,并且
Me1为碱金属阳离子,并且
Me2为碱土金属阳离子,并且
其中所述碱金属阳离子和/或碱土金属阳离子是K+、Ca2+和/或Mg2+盐。
2.根据权利要求1的方法,其中,所述类胡萝卜素化合物选自:
3.根据权利要求1的方法,其中,所述类胡萝卜素化合物是
4.根据权利要1的方法,其中,所述类胡萝卜素化合物是
5.根据权利要求1至4中任意一项所述的方法,其中使用CH3COOK。
6.根据权利要求1至4中任意一项所述的方法,其中,基于所述式(I)化合物的总重量,使用0.0001wt-%到1wt.%的所述有机酸碱金属盐和/或碱土金属盐。
7.根据权利要求5所述的方法,其中,基于所述式(I)化合物的总重量,使用0.0001wt-%到1wt.%的所述有机酸碱金属盐和/或碱土金属盐。
8.一种制剂,其包含至少一种式(I)的类胡萝卜素化合物和基于所述式(I)化合物的总重量0.0001wt-%到1wt.%的至少一种有机酸碱金属盐和/或碱土金属盐,
其中R1和R2彼此相互独立地为
其中所述碱金属盐和/或碱土金属盐是来自式R-COOMe1或(R-COO)2Me2的有机酸盐,
其中R为C1-C4-烷基基团,并且
Me1为碱金属阳离子,并且
Me2为碱土金属阳离子,并且
所述有机酸碱金属盐和/或碱土金属盐的碱金属阳离子和/或碱土金属阳离子是K+、Ca2 +和/或Mg2+。
9.根据权利要求8的制剂,其中,所述类胡萝卜素化合物选自:
10.根据权利要求8的制剂,其中,所述类胡萝卜素化合物是
11.根据权利要求8的制剂,其中,所述类胡萝卜素化合物是
12.根据权利要求8至11中任意一项所述的制剂,其中CH3COOK作为盐。
13.根据权利要求8至12中任意一项所述的至少一种制剂在食品、饲料或个人护理产品中的用途。
14.包含权利要求8至12中任意一项所述的至少一种制剂的食品、饲料或个人护理产品。
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PCT/EP2014/062842 WO2014202677A1 (en) | 2013-06-21 | 2014-06-18 | New process for the maintaining of a ratio of isomers of ca-rotenoid compounds |
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CN115057805A (zh) * | 2022-05-16 | 2022-09-16 | 万华化学集团股份有限公司 | 一种高全反式异构体稳定性角黄素晶体的方法 |
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WO1994010861A1 (en) * | 1992-11-19 | 1994-05-26 | The Procter & Gamble Company | Method for enhancing bioavailability of beta-carotene |
CN101883498A (zh) * | 2007-11-23 | 2010-11-10 | 巴斯夫欧洲公司 | 生产类胡萝卜素溶液的方法 |
WO2013010820A1 (en) * | 2011-07-15 | 2013-01-24 | Dsm Ip Assets B.V. | Process for the maintaining of a ratio of isomers of carotenoid compounds |
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US6051236A (en) * | 1998-11-12 | 2000-04-18 | Pacifichealth Laboratories, Inc. | Composition for optimizing muscle performance during exercise |
JP2002218940A (ja) * | 2001-01-24 | 2002-08-06 | Seiwa Technics:Kk | アスタキサンチン色素含有食品の変色防止剤及び変色防止方法 |
JP2008074717A (ja) * | 2006-09-19 | 2008-04-03 | Fujifilm Corp | カロテノイド含有エマルジョン組成物、その製造方法、該組成物を含む食品、外用剤およびその製造方法 |
US20120064136A1 (en) * | 2010-09-10 | 2012-03-15 | Nanobio Corporation | Anti-aging and wrinkle treatment methods using nanoemulsion compositions |
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WO1994010861A1 (en) * | 1992-11-19 | 1994-05-26 | The Procter & Gamble Company | Method for enhancing bioavailability of beta-carotene |
CN101883498A (zh) * | 2007-11-23 | 2010-11-10 | 巴斯夫欧洲公司 | 生产类胡萝卜素溶液的方法 |
WO2013010820A1 (en) * | 2011-07-15 | 2013-01-24 | Dsm Ip Assets B.V. | Process for the maintaining of a ratio of isomers of carotenoid compounds |
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JP6519087B2 (ja) | 2019-05-29 |
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JP2016528182A (ja) | 2016-09-15 |
KR20160021455A (ko) | 2016-02-25 |
BR112015031572A2 (pt) | 2017-07-25 |
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US20160152540A1 (en) | 2016-06-02 |
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