CN1239977A - 叶黄素类的稳定水分散液及稳定的水分散性干粉,其制备以及用途 - Google Patents
叶黄素类的稳定水分散液及稳定的水分散性干粉,其制备以及用途 Download PDFInfo
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Abstract
叶黄素的稳定的水分散液或稳定的水分散性干粉的制备,其中包括a)在与水混溶的有机溶剂中或在水和与水混溶的有机溶剂的混合物中,在高于30℃,制备至少一种叶黄素的分子分散液,其中加或不加乳化剂和/或食用油;b)将此溶液与保护性胶体的混合物的水溶液混合,b1)其中所述混合物含有至少一种低分子量保护性胶体组分和至少一种高分子量保护性胶体组分,其平均分子量差至少为10000;b2)将溶剂组分转移至水相并以微分散相形成叶黄素的疏水相;c)如果适当,将所得分散液中不含所述溶剂和水以制备水分散性干粉,并在包衣物质存在或不存在下干燥。
Description
胡萝卜素类化合物主要分为两类:胡萝卜素类和叶黄素类。与纯的多烯烃胡萝卜素如β-胡萝卜素或番茄红素相比,叶黄素类还含有氧官能团如羟基、环氧基和/或氧代基团。此类的典型代表特别是虾青素、鸡油菌黄质和玉米黄质。
叶黄素类在自然界非常常见,并特别发现于玉米(玉米黄质)、绿豆(黄体素)、辣椒(辣椒黄素)、蛋黄(黄体素)并还见于甲壳纲动物和鲑(虾青素)中,他们赋予了这些食物的特征色。
这些多烯有些可工业合成,有些可从天然原料中分离,它们是食物和饲料工业及制药业的重要着色剂,是制药领域中合成染料的替代品。
所有叶黄素都不溶于水,而在脂肪和油中的溶解度也很低。此种有限的溶解度和对氧化的高度敏感妨碍了由合成得到的相对粗颗粒产物在食品和饲料着色中的直接应用,因为粗结晶形式的该物质着色效果很差。这些不利于叶黄素实际应用的结果特别是出现在水基质中,因为叶黄素在其中完全不溶解。
在食品的直接着色中改善的着色效果只有通过特殊制备的制剂才能达到,在该制剂中活性化合物以细颗粒的形式存在,并通过保护性胶体对其进行防氧化保护,也可不进行此保护。此外,这些用于饲料中的制剂给叶黄素带来了较高的生物利用度并因此间接改善了着色效果,例如,在着色蛋黄或鱼时。
为了改善着色效率并增加吸收度或生物利用度,描述了很多方法,所有这些方法的目的是降低活性化合物的晶体粒度并使其粒度小于10μm。
特别是描述于Chimia 21(1967)329,WO91/06292和WO94/19411中的一些方法,利用用胶体磨研磨的胡萝卜素类并因此获得了2至10μm的粒度。
此外,有一些结合乳化/喷雾干燥的方法,例如,DE-A-1211911或EP-A-0410236。
按照EP-B-0065193所述,细粉状β-胡萝卜素制剂通过在50至200℃将β-胡萝卜素溶解于挥发性的与水混溶的有机溶剂中来制备,如果适宜可升高压力,制备时间不多于10秒。通过立即快速与保护性胶体的水溶液混合,在0至50℃将β-胡萝卜素由所得分子分散液中沉淀。在此方式中,得到桔黄色β-胡萝卜素水溶胶。随后将此分散液喷雾干燥得到自由流动的干粉,该干粉可溶解于水中,形成清澈的桔黄色分散液。
但是,对于EP-B-0065193制备的叶黄素微小颗粒活性化合物分散液观察到如下现象。
含叶黄素的活性化合物水分散液常是胶体不稳定的,特别是当它们浓缩时。由于活性化合物颗粒的絮凝作用,一些发生沉淀,一些成为霜,再想将此分散液转变为干粉是不可能的。
此外,对于带有羰基官能团的叶黄素,用作唯一保护胶体的明胶可交联,以致形成凝胶,该凝胶不再扩散,这同样不能进一步转变为干粉。
因为上述方法存在的问题,在着色作用和生物利用度方面对含叶黄素的制剂的高要求总是不能满足。
本发明的目的是提供一种制备叶黄素的稳定水分散液的方法。此外,提供稳定的粉状叶黄素制剂,通过该制剂可获得良好的着色作用和高的生物利用度。
我们发现通过制备叶黄素的稳定水分散液或稳定的水分散性干粉的方法,本发明可达到此目的,该方法包括
a)在与水混溶的有机溶剂中或在水和与水混溶有机溶剂的混合物中,在高于30℃,制备至少一种叶黄素的分子分散液,其中加或不加乳化剂和/或食用油;
b)将此溶液与保护性胶体混合物的水溶液混合,
b1)其中所述混合物含有至少一种低分子量保护性胶体组分和至少一种高分子量保护性胶体组分,其平均分子量差至少为10000;
b2)将所述溶剂组分转移至水相并以微分散相形成叶黄素的疏水相;
c)如果适当,为了制备水分散性干粉,使所得分散液不含所述溶剂和水,并在包衣物质存在或不存在下干燥。
本发明还涉及稳定的、含叶黄素的、在冷水中可分散的干粉,该干粉可特别好地用于给食品和饲料以及药物给药形式着色。
本发明的制剂一般以如下方式制备:将叶黄素(一种或多种),加或不加乳化剂和/或食用油,溶解于与水混溶的有机溶剂中,温度优选50至240℃,特别是100至200℃,特别优选140至180℃,如果适当可加压。
因为高温作用可降低所需的异构体高全反式比例,故叶黄素(一种或多种)溶解非常快,例如按秒计算,为0.1至10秒,特别优选不超过1秒。为了快速制备此分子分散液,使用高压,例如20巴至80巴,优选30至60巴是有利的。
将所得分子分散液立即与冷却的或不冷却的保护胶体的水溶液混合,优选以保持混合温度为约35℃至80℃方式进行。
在此过程中,该溶剂组分转移至水相并以微分散相形成叶黄素(一种或多种)的疏水相。
考虑到对方法和仪器的更详细的说明,将EP-B-0065193引入作为参考。
令人惊奇的是,现已发现,如果不同于在至今描述的制剂方法中那样而在一种或多种分子分散溶解的叶黄素的上述沉淀时首先使用至少一种低分子量组分的水保护性胶体分散液,然后再使用至少一种高分子量组分的另一种水保护性胶体分散液,低和高分子量聚合物的平均分子量至少差10000,优选至少差30000,则可得到胶体稳定的且无交联的微颗粒活性化合物分散液。
但是,还可以将两步沉淀在至少一种低分子量组分和至少一种高分子量组分的混合物中一步进行,所述两组分平均分子量至少差10000,优选至少差30000。
所用保护性胶体为来自下列物质的低或高分子量组分,例如,明胶、鱼明胶、淀粉、糊精、植物蛋白、果胶、阿拉伯胶、酪蛋白或酪蛋白酸盐或这些的混合物,此含蛋白的保护性胶体,特别是非凝胶低分子量蛋白水解物和高分子量凝胶化明胶,是优选的。但是,也可使用聚(乙烯醇)、聚乙烯基吡咯烷酮、甲基纤维素、羧甲基纤维素、羟丙基纤维素和藻酸盐。低分子量保护性胶体组分的平均分子量(Mw)优选为10000至50000,特别是15000至30000,而高分子量组分的平均分子量优选大于60000。低分子量保护性胶体组分的重量比例为5至95%优选20至80%,特别优选30至60%。为了增加最终产品的机械稳定性,将胶体与软化剂如糖或糖醇如蔗糖、葡萄糖、乳糖、转化糖、山梨醇、甘露醇或甘油混合是有利的。
此保护性胶体和软化剂与叶黄素溶液的比例,一般的选择方式应使最终所得产品含0.5至20%(重量),优选10%(重量)的叶黄素,10至50%(重量)保护性胶体,20至70%(重量)软化剂,所有比例是基于粉末的干重,其中加或不加小量的稳定剂。
进行本发明可使用的叶黄素类是已知的天然可得或合成的此类化合物的代表,它们可用作着色工具,如虾青素、玉米黄质、鸡油菌黄质、辣椒黄素和黄体素。
为了增加此活性化合物对氧化的稳定性,有利的是加入稳定剂如α-生育酚、叔丁基化羟基甲苯、叔丁基化羟基茴香醚、抗坏血酸或乙氧喹。可将它们加入水相或溶剂相,但是优选将它们与着色剂一起在溶剂相中溶解,其中加或不加乳化剂。可使用的乳化剂为,例如,棕榈酸抗坏血酸酯、聚甘油脂肪酸酯、脱水山梨醇脂肪酸酯、丙二醇脂肪酸酯或卵磷脂,其基于叶黄素(一种或多种)的浓度为0至200%(重量),优选10至150%(重量),特别优选20至80%(重量)。
在一些情况中,在溶剂相中溶解其它生理可接受的油如芝麻油、玉米油、棉籽油、豆油或花生油以及中链植物脂肪酸的酯也是有利的,它们基于叶黄素(一种或多种)的浓度为0至500%(重量),优选10至300%(重量),特别优选20至100%(重量),该油然后与水相混合时以极细形式与活性化合物及所述添加剂一起沉淀出。
根据所用保护性胶体的类型和用量,得到深色粘稠液体。可以通过例如用与水不混溶的溶解萃取或根据沸点以本领域技术人员已知的方式,如通过蒸馏,如果适当可在减压条件下进行,而将溶剂除去。在此情况下,已证明将使用异丙醇时得到的共沸物不用除去水而直接用作溶剂是有利并可能的。但是,优选在除去水的同时通过喷雾干燥或喷雾制粒将溶剂分离。
得到用保护性胶体包封的稳定干粉,该胶体含有至少一种低分子量组分和至少一种高分子量组分,其平均分子量差至少为10000。当使用水溶性胶体时,此干粉可再溶解于水中,使活性化合物均匀地极细分布,其中此化合物的粒度小于1μm。在光化学稳定实验中,这样得到的活性化合物的水溶胶,尽管分布极细,但是其稳定性超乎寻常。
用X射线衍射图谱鉴定,在叶黄素水分散液和由其制备的干粉制剂中,存在的活性化合物有70至100%的无定型含量。此外,叶黄素全反式异构体的含量至少50%。
本发明的制剂极其适于作食品和饲料的着色剂。在饲料行业使用的典型领域是,例如,在水产养殖中给鱼着色,及给蛋黄着色和在家禽背部焙烤皮肤。
实施例举例说明了本发明。
实施例1
在可加热的容器中,在30℃将40g虾青素和15.4g花生油悬浮于12.3g乙氧喹在288g异丙醇/水(88/12,w/w)中。将此悬浮液在混合室中在混合温度为170℃与587g异丙醇/水(88/12,w/w)混合,其保留时间为0.2秒。所述保留时间后,将所得分子分散虾青素溶液立即进入另一个混合室,其中混合角度为90°,通过高压泵加入11340g明胶水溶液,其pH调节到了9,其中除含有84g明胶A(100 Bloom,Mw=94000)外,还含有42g Gelita Sol P(Mw=21000)和92g蔗糖,虾青素在45℃以胶体分散体形式沉淀出,其平均粒度为166nm。
然后,将此分散液浓缩并用本领域技术人员已知的方法转变为自由流动的干粉,其平均粒度为237nm。将此干粉再溶解于水中,形成清澈的红色分散液,此再分散液的颜色强度比原分散液的只降低了约10%。
对比实施例
在可加热的容器中,在30℃将40g虾青素和15.4g花生油悬浮于12.3g乙氧喹在288g异丙醇/水(88/12,w/w)中。将此悬浮液在混合室中在混合温度为170℃与548g异丙醇/水(88/12,w/w)混合,其保留时间为0.2秒。所述保留时间后,将所得分子分散虾青素溶液立即进入另一个混合室,其中混合角度为90°,通过高压泵加入11280g明胶水溶液,其pH调节到了9,其中除含有126g明胶A(100 Bloom,Mw=94000)外,还含有91g蔗糖,虾青素在45℃以胶体分散体形式沉淀出,其平均粒度为232nm。
此分散液浓缩的同时,活性化合物颗粒絮凝出,其颜色强度降低到了起始值的60%。通过动力光分散方法,测量平均粒度为370nm。通过与实施例1类似的方法制备的干粉仅仅可部分再分散。
Claims (9)
1.制备叶黄素类的稳定水分散液或稳定的水分散性干粉的方法,该方法包括
a)在与水混溶的有机溶剂中或在水和与水混溶的有机溶剂的混合物中,在高于30℃,制备至少一种叶黄素的分子分散液,其中加或不加乳化剂和/或食用油;
b)将此溶液与保护性胶体的混合物的水溶液混合,
b1)其中所述混合物含有至少一种低分子量保护性胶体组分和至少一种高分子量保护性胶体组分,其平均分子量差至少为10000;
b2)将溶剂组分转移至水相并以微分散相形成叶黄素的疏水相;
c)如果适当,为了制备水分散性干粉,使所得分散液不含所述溶剂和水,并在包衣物质存在或不存在下干燥。
2.权利要求1所述的方法,其中所用保护性胶体是低分子量非凝胶化蛋白水解物和较高分子量凝胶明胶的混合物。
3.权利要求1和2所述的方法,其中低分子量保护性胶体组份的比例为占保护性胶体总重量的5至95%。
4.权利要求1至3所述的方法,其中叶黄素的分子分散液分两步与含保护性胶体的水相混合,首先叶黄素的分子分散液只与低分子量保护性胶体组份混合,然后与高分子量保护性胶体组份混合。
5.如权利要求1至4所要求保护的那样可得到的稳定的叶黄素水分散液。
6.权利要求5所述的稳定的叶黄素水分散液,其中存在的活性化合物有70至100%的无定型含量。
7.权利要求5和6的稳定的叶黄素水分散液,其中存在的活性化合物中全反式异构体含量至少为50%。
8.一种稳定的水分散性叶黄素干粉,其被保护性胶体包封,该胶体含有至少一种低分子量组份和至少一种高分子量组份,它们的平均分子量差至少10000。
9.权利要求5至8所要求保护的稳定的叶黄素水分散液和/或稳定的水分散性叶黄素干粉作为食物、药物和/或动物饲料的添加剂的用途。
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DE19651681A DE19651681A1 (de) | 1996-12-12 | 1996-12-12 | Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthopyllen, deren Herstellung und Verwendung |
DE19651681.1 | 1996-12-12 |
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US (1) | US6296877B1 (zh) |
EP (1) | EP0944675B1 (zh) |
JP (1) | JP4124821B2 (zh) |
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AT (1) | ATE222278T1 (zh) |
AU (1) | AU743203B2 (zh) |
CA (1) | CA2274467C (zh) |
CO (1) | CO5031308A1 (zh) |
DE (2) | DE19651681A1 (zh) |
DK (1) | DK0944675T3 (zh) |
ES (1) | ES2182139T3 (zh) |
ID (1) | ID21899A (zh) |
IS (1) | IS5072A (zh) |
NO (1) | NO312074B1 (zh) |
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CN102361561A (zh) * | 2009-03-30 | 2012-02-22 | 巴斯夫欧洲公司 | 部分无定形类胡萝卜素颗粒的即用稳定悬浮液 |
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Cited By (3)
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CN101177540B (zh) * | 2006-11-10 | 2010-04-14 | 浙江医药股份有限公司新昌制药厂 | 叶黄素水溶性干粉的制备方法 |
CN102361561A (zh) * | 2009-03-30 | 2012-02-22 | 巴斯夫欧洲公司 | 部分无定形类胡萝卜素颗粒的即用稳定悬浮液 |
CN105876555A (zh) * | 2016-05-27 | 2016-08-24 | 山东农业大学 | 一种紫薯花青素饮料 |
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US6296877B1 (en) | 2001-10-02 |
WO1998026008A1 (de) | 1998-06-18 |
NO312074B1 (no) | 2002-03-11 |
NO992874L (no) | 1999-06-11 |
CO5031308A1 (es) | 2001-04-27 |
TW493976B (en) | 2002-07-11 |
ID21899A (id) | 1999-08-12 |
CA2274467A1 (en) | 1998-06-18 |
EP0944675B1 (de) | 2002-08-14 |
JP4124821B2 (ja) | 2008-07-23 |
CN1101425C (zh) | 2003-02-12 |
ES2182139T3 (es) | 2003-03-01 |
AU5559698A (en) | 1998-07-03 |
DE59707985D1 (de) | 2002-09-19 |
DE19651681A1 (de) | 1998-06-18 |
CA2274467C (en) | 2006-08-01 |
IS5072A (is) | 1999-06-08 |
NO992874D0 (no) | 1999-06-11 |
JP2001506685A (ja) | 2001-05-22 |
NZ336133A (en) | 2001-04-27 |
EP0944675A1 (de) | 1999-09-29 |
DK0944675T3 (da) | 2002-10-07 |
ATE222278T1 (de) | 2002-08-15 |
AU743203B2 (en) | 2002-01-24 |
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