CN1125145C - 叶黄素的稳定水分散体和稳定的水可分散干燥粉末、及其制备和应用 - Google Patents
叶黄素的稳定水分散体和稳定的水可分散干燥粉末、及其制备和应用 Download PDFInfo
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- CN1125145C CN1125145C CN00806761A CN00806761A CN1125145C CN 1125145 C CN1125145 C CN 1125145C CN 00806761 A CN00806761 A CN 00806761A CN 00806761 A CN00806761 A CN 00806761A CN 1125145 C CN1125145 C CN 1125145C
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- Prior art keywords
- xenthophylls
- water
- astaxanthin
- stable
- dried powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
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- A—HUMAN NECESSITIES
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Abstract
本发明涉及一种选自由虾青素、黄体素和玉米黄质组成的组中的叶黄素稳定水分散体或稳定的水可分散干燥粉末的制备方法,它是通过a)将一种或多种上述叶黄素在大于30℃下溶解在水混溶性有机溶剂或水与水混溶性有机溶剂的混合物中;b)将该溶液与保护胶体的水溶液进行混合,由此溶剂成分可转换为水相,并且叶黄素的疏水相可形成纳分散相的形式;和c)任选地,可通过分离出溶剂和水并干燥而将所得分散体转换为水可分散干燥粉末,该步骤任选地在涂敷材料存在下进行。本发明的特征在于,在方法的步骤b)中所使用的保护胶体是酪蛋白或酪蛋白酸盐。
Description
本发明涉及一种选自由虾青素、黄体素(Lutein)和玉米黄质组成的组中的叶黄素(Xanthophylls)稳定水分散体和稳定的水可分散干燥粉末,及其制备和应用。
人们将类胡罗卜素分为两个主组,即胡罗卜素和黄体素。与叶黄素不同,胡罗卜素是纯的多烯碳氢化合物,例如,β-胡罗卜素或番茄红素,而叶黄素中还有象羟基、环氧和/或氧代基团之类的氧官能团。该组的典型代表尤其是虾青素、黄体素和玉米黄质。
叶黄素广泛遍布于自然界中,并且尤其存在于玉米中(玉米黄质)、绿豆中(黄体素)、辣椒中(辣椒红)、蛋黄中(黄体素)以及虾蟹和鲑中(虾青素),由此它将其特征颜色赋于这些食品上。
这些既可在技术上制成又可分离自自然界的多烯代表重要的用于食品工业和饲料工业以及用于药物领域的着色物质,并且就象在虾青素的情况下一样,其是具有前维生素A活性的活性物质。
所有叶黄素均是不溶于水的,而在油脂和油中人们发现也只有很小的溶解度。该受限溶解度以及高氧化敏感性阻碍了合成所获得的相对粗粒产品在食品和饲料着色中的直接使用,因为用粗结晶形式的物质只会提供较差的着色结果。这种对于叶黄素实际使用的不良效果尤其对含水介质明显。
只有用特别制备的制剂,其中采用以精细分散形式的活性物质以及任选地通过保护胶体进行防氧化保护,从而可以在对食品直接染色时获得改进的颜色效果。此外,在饲料中使用这些制剂导致了较高的叶黄素的生物利用,并因此可间接地获得较好的颜色效果,例如在蛋黄或鱼着色中。
为了改进颜色并为提高可吸收性以及生物利用性,已描述过各种方法,其目的就是使活性物质结晶颗粒尺寸减小,并且处于10μm以下的颗粒大小范围。
在Chimia21,329(1967)、WO91/06292以及WO94/19411中描述了许多方法,其借助于胶体磨磨碎类胡罗卜素,并由此获得了2至10μm的颗粒大小。
此外,还存在一些关于乳化/喷雾干燥组合方法,例如在DE-A-1211911或在EP-A-0410236中所述。
按照欧洲专利EP-B-0065193,如下制备精细粉末状β胡萝卜素制剂,即将β胡萝卜素在50℃和200℃之间的温度下任选在超大气压下在10秒以下的时间内溶解在可与水混合的挥发性有机溶剂中。β胡萝卜素从所得分子分散的溶液通过在0℃和50℃之间的温度下十分迅速地与保护胶体水溶液混合而沉淀。由此而获得带有橘黄色的胶体分散β胡萝卜素水溶胶。紧接着的分散体喷雾干燥提供了一种自由流动干燥粉末,其可溶解在水中形成透明橘黄色分散体。
然而,用按照EP-B-0065193所制成的叶黄素的纳颗粒活性物质分散体,还观察到下列现象。
水性的、含叶黄素的活性物质分散体,尤其是浓缩时,是胶体不稳定的。由于活性物质颗粒的絮凝,其一部分沉淀,一部分乳油化,使得将分散体变为干燥粉末是不再可能的。
在带有羰基官能团的叶黄素情况下,也可能存在作为保护胶体使用的明胶的交联,由此形成凝胶,其不会再分散,并且同样不会转变为干燥粉末。
因此,由于上述方法的所述问题,将不总能满足对于含有叶黄素的制剂的有关颜色和生物利用的高要求。
就象在WO98/26008中所述的,通过将低分子和高分子保护胶体混合使用,可以改进含有叶黄素的干燥粉末的再分散性。
本发明的目的在于,提供一种制备选自由虾青素、黄体素和玉米黄质组成的组中的叶黄素的稳定的水分散体的方法。还提供一种所述叶黄素的稳定的粉末制剂,用此制剂可获得良好的颜色和高的生物利用度。
我们发现,该发明目的可通过下述方法而实现,即一种制备叶黄素的稳定水分散体或稳定的水可分散干燥粉末的方法,其中叶黄素选自由虾青素、黄体素和玉米黄质组成的组中,其包括:
a)将一种或多种选自由虾青素、黄体素和玉米黄质组成的组中的叶黄素在高于30℃的温度下溶解在水混溶性有机溶剂或水与水混溶性有机溶剂的混合物中;
b)将该溶液与保护胶体的水溶液进行混合,由此溶剂成分转换为水相,并且叶黄素的疏水相形成纳分散相的形式;和
c)任选地,通过分离出溶剂和水并进行干燥而将所得分散体转换为水可分散干燥粉末,该步骤任选地在涂敷材料存在下进行,
其特征在于,在方法步骤b)中所使用的保护胶体是酪蛋白或酪蛋白酸盐。
按照本发明的制剂通常是如下制备:将至少一种上述叶黄素,任选地与食用油一起,在30℃以上温度下,尤其在50℃和240℃之间,特别是在100℃和200℃之间,特别优选是140℃到180℃,任选地在压力下,溶解在水混溶性的有机溶剂中。
由于暴露于高温可能降低所希望的高全反异构体含量,所以使叶黄素/叶黄素混合物尽可能快地溶解,例如在秒范围内,如0.1到10秒,最好是在1秒以下。为了快速地制备分子分散溶液,有利的是采用升高压力,例如在20巴到80巴范围内,最好是30到60巴。
然后直接地,将任选地冷却的酪蛋白或酪蛋白酸盐水溶液加入到由此获得的分子分散溶液中,优选使混合温度设定为约35℃到80℃。
在此期间,溶剂成分转化成了水相,而叶黄素/叶黄素混合物的疏水相形成了纳分散相。
关于方法和装置描述的细节在此可参考EP-B-0065193有关的表述。
低和/或高分子量的酪蛋白或酪蛋白酸盐或其混合物被用作保护胶体。优选使用具有10000到100000分子量的酪蛋白酸钠,特别优选分子量为20000到60000的,例如,Lacto Bretagne Associes S.A.公司(法国)供应的具有约38000MW的酪蛋白酸钠。
对于所用的酪蛋白或酪蛋白酸盐的细节尤其可参见Ullmann′sEncyclopedia of Industrial Chemistry,第6版,1998Electronic Release,第11.1章,Wiley-VCH,Weinheim,德国和CD Rmpp Chemie Lexikon-Version1.0,Stuttgart/New York:Georg Thieme Verlag1995以及其中所引文献。
为了提高最终产品的机械稳定性,有利的是将增塑剂如糖或糖醇如蔗糖、葡萄糖、乳糖、转化糖、山梨醇、甘露醇或丙三醇添加到胶体中。
保护胶体和增塑剂对于叶黄素溶液的比例通常可这样选择,使最终产品具有0.5和30重量%、优选为5到25重量%、特别优选为10到23重量%之间的叶黄素,10到70重量%的保护胶体,10-70重量%的增塑剂,所有百分比含量均基于粉末的干重计,以及任选地含有少量的稳定剂。
进行本发明可以使用的叶黄素可以是公知天然的或合成的化合物虾青素、黄体素和/或玉米黄质。对于本发明的方法来说,优选的叶黄素是虾青素。
为了提高活性物质对氧化分解的稳定性,有利的是使用稳定剂,如α-生育酚,叔丁基羟基甲苯,叔丁基羟基苯甲醚,抗坏血酸或乙氧喹。它们或是加入到水相中或是加入到溶剂相中,但优选是将其与叶黄素一起溶解在溶剂相中。
在一些情况下还可能有利的是,在溶剂相中还溶解一种生理上许可的油,例如芝麻油,玉米油,棉花籽油,豆油或花生油,以及中链(mittlekettiger)植物脂肪酸酯,其浓度相对于叶黄素/叶黄素混合物为0到500重量%,优选是10到300重量%,尤其优选是20到100重量%,然后,在与水相混合时将其与活性物质以及上述添加剂一起以极细颗粒形式测定。
令人惊奇的是,通过按照本发明将酪蛋白或酪蛋白酸盐用作保护胶体,从而可省去使用额外的乳化剂,如维生素C棕榈酸酯(Ascorbylpalmitat)。
此外,已经发现,可以获得叶黄素的胶体稳定的并且不交联的纳米颗粒的活性物质分散体,其粘度特性近似于牛顿流体。该类型流体的区别特征在于其流动阻力,其通过牛顿方程τ=h·D所定义,它是在给定温度下的一种物质常数(τ=屈服应力,D=剪切陡度,h=动态粘度)。牛顿流体的流动特性曲线图可得出在给定温度下的近似的一条直线。尤其是,活性物质分散体的粘度可以在40℃和60℃温度下在10-2sec-1和10+2sec-1的剪切范围内具有小于±50%的变化。
该近似牛顿粘度特性的优点尤其在于,活性物质分散体,尤其是在浓缩以后,要比结构粘度分散体情况更容易地加以泵送。此外,在喷雾干燥情况下,近似牛顿的活性物质分散体具有的优点在于,喷射头的参数可以很容易地加以优化,并且在喷射头中对该分散体行为要求是不严格的。
此外,已观察到,该方法避免了叶黄素高凝聚体(H-Aggregaten)的形成。
类胡萝卜素的聚集是在公知文献中和许多公开出版物中所描述的一种现象[P.Song,T.A.Moore,Photochemistry and Photobiology(光化学和光生物学),19,435-441(1974);A.V.Ruban,P.Horton,A.J.Young,J.Photochem.Photobiol.B:Biol.,21,229-234(1993);V.R.Salares,N.M.Young,P.R.Carey,H.J.Bemstein,Journal of Raman Spectroscopy(喇曼光谱学杂志),6(6),282-288(1977)]。
例如,类胡萝卜素的凝聚体可以通过类胡萝卜素在水混溶性的有机溶剂如异丙醇,乙醇,丙酮或四氢呋喃中的溶液与水混合而形成。
因此,正如上面的文献中所述,通过水与有机溶剂的正确比例选择就可以产生所谓的高凝聚体或环凝聚体(J-Aggregaten)。
对于高凝聚体,可以理解为一种“类似纸牌游戏”的多烯链的堆积(纸牌叠式聚积),其表现出在紫外线光谱/可见光谱下显现的与单体现有形式的吸收相比新的在320和400nm之间范围内的向短波长移(向蓝移)谱带特性。相反,环凝聚体显示出线性多烯头尾连接(头尾聚积体)或其排列为鱼骨形(鱼骨形聚积体)。两种排列均会引起多烯紫外线吸收中的红移。
对于鳟鱼的饲料试验已经表明,叶黄素的高凝聚体,尤其是虾青素的高凝聚体,比相对应的环凝聚体显示出较差的生物利用率,而生物利用率代表按照本发明方法制成的分散体以及干燥粉末的进一步的优点。
取决于酪蛋白或酪蛋白酸盐的使用量,可以获得深色粘稠液体。溶剂的去除例如可通过用水不混溶性的溶剂提取,或是根据沸点,以本身已知的方式,如通过蒸馏,任选地在减压下进行。在这种情况下,已经表明有利和可能的是,使用用没有除去水的异丙醇直接作为溶剂而获得的共沸物。然而,溶剂的除去优选是通过喷雾干燥或喷雾粒化而与水的除去一起进行。
这样,本发明还涉及一种叶黄素的稳定水分散体以及稳定的水可分散干燥粉末,其中叶黄素选自由虾青素、黄体素和玉米黄质组成的组中,其是可按照上述方法获得的。
获得稳定干燥粉末并用酪蛋白、酪蛋白酸盐或其混合物作为保护胶体而包覆。该干燥粉末可以重新溶解在水中以得到低于1μm的粒度范围的活性物质均匀精细分布。在光化学稳定试验中,证明了如此获得的活性物质水溶胶不管是否精细分布但确是特别稳定的。
无论是在叶黄素水分散体中,还是在由其所制成的干燥粉末中,依照X射线衍射图确定,所存在的活性物质显示出无定形含量在70-100%之间,优选是在90-100%之间。此外,叶黄素的全反异构体含量为至少50%,优选70%。
按照本发明的制剂特别适于作为食品和饲料的着色物质以及药品的添加剂。在饲料领域中典型的应用范围是,例如在水培养中的鱼着色以及在家禽饲料中的蛋黄和鸡皮着色。
在下面的实施例中,将详细解释按照本发明方法的实施。
实施例1
在一可加热装置中,在30℃温度下将40g虾黄素悬浮在294g异丙醇/水(88/12,w/w)中。将该悬浮液在170℃混合温度下在混合室中与536g的异丙醇/水(88/12,w/w)进行0.2秒滞留时间的混合。在所述滞留时间以后,立即将产生的分子分散虾黄素溶液送入下一个混合室中,在该室中在混合角90°下通过高压泵混合10.4kg酪蛋白酸钠水溶液,该溶液中除含108g酪蛋白酸盐以外还包含36g的蔗糖,并且已被调节到pH9。由此在45℃温度下沉淀出具有144nm平均颗粒大小的胶体分散形式的虾青素。
然后,将分散体浓缩,并且采用本身已知的方式,将其转变为具有129nm平均颗粒大小的自由流动的22%含量的虾青素干燥粉末。该干燥粉末可再溶解到水中形成一种透明红色分散体,该再分散体的颜色强度比原来的分散体仅低约10%。
Claims (12)
1、一种制备叶黄素的稳定水分散体或稳定的水可分散干燥粉末的方法,其中叶黄素选自由虾青素、黄体素和玉米黄质组成的组中,其包括:
a)将一种或多种选自由虾青素、黄体素和玉米黄质组成的组中的叶黄素在50℃~240℃的温度下溶解在水混溶性有机溶剂或水与水混溶性有机溶剂的混合物中;
b)将该溶液与保护胶体的水溶液进行混合,由此溶剂成分转换为水相,并且叶黄素的疏水相形成纳米分散相的形式;和
c)并且,任选地,通过分离出溶剂和水并进行干燥而将所得分散体转换为水可分散干燥粉末,该步骤任选地在涂敷材料存在下进行,
其特征在于,在方法步骤b)中所使用的保护胶体是酪蛋白或酪蛋白酸盐。
2、按照权利要求1的方法,其特征在于,在所述方法步骤a)中除了叶黄素外还使用可食用油。
3、按照权利要求1或2的方法,其特征在于,不使用附加乳化剂。
4、按照权利要求1至3中任意一项的方法,其特征在于,将虾青素用作叶黄素。
5、按照权利要求1至3中任意一项所述方法所获得的叶黄素稳定水分散体,其中叶黄素选自由虾青素、黄体素和玉米黄质组成的组中。
6、按照权利要求5的叶黄素稳定水分散体,其特征在于,所含叶黄素的无定形含量在70和100%之间。
7、按照权利要求5或6的叶黄素稳定水分散体,其特征在于,所含叶黄素的全反异构体含量为至少50%。
8、按照权利要求5至7任意一项的叶黄素稳定水分散体,其特征在于,其显示出牛顿流体的粘度行为。
9、按照权利要求5至8任意一项的叶黄素稳定水分散体,其特征在于,其是虾青素分散体。
10、按照权利要求1至3中任意一项所述方法所获得的叶黄素稳定水可分散干燥粉末,其中叶黄素选自由虾青素、黄体素和玉米黄质组成的组中。
11、按照权利要求10的叶黄素稳定水可分散干燥粉末,其特征在于,其是虾青素的干燥粉末。
12、将按照权利要求5至11中任意一项所述叶黄素稳定水分散体和/或稳定水可分散干燥粉末用作人类食品、药品和/或动物饲料的添加剂的用途。
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DE19919751A DE19919751A1 (de) | 1999-04-29 | 1999-04-29 | Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthophyllen, deren Herstellung und Verwendung |
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EP (1) | EP1173521B1 (zh) |
JP (1) | JP3694240B2 (zh) |
CN (1) | CN1125145C (zh) |
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DE (2) | DE19919751A1 (zh) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102038644A (zh) * | 2010-12-23 | 2011-05-04 | 沈阳药科大学 | 叶黄素水溶性粉末及其制备工艺 |
CN105142600A (zh) * | 2013-03-15 | 2015-12-09 | 前沿创新有限公司 | 包含高水平水混溶性溶剂之疏水剂的基本上不含表面活性剂的亚微米分散体 |
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CN1348483A (zh) | 2002-05-08 |
JP3694240B2 (ja) | 2005-09-14 |
US6863914B1 (en) | 2005-03-08 |
MXPA01010881A (es) | 2002-05-06 |
NO320106B1 (no) | 2005-10-24 |
EP1173521A1 (de) | 2002-01-23 |
EP1173521B1 (de) | 2002-10-16 |
NO20015238L (no) | 2001-12-28 |
TWI227261B (en) | 2005-02-01 |
AU4551400A (en) | 2000-11-17 |
AR023600A1 (es) | 2002-09-04 |
WO2000066665A1 (de) | 2000-11-09 |
NO20015238D0 (no) | 2001-10-26 |
DE19919751A1 (de) | 2000-11-09 |
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