CN107105693B - 用于增加包含多不饱和ω-6脂肪酸的组合物的稳定性的方法 - Google Patents
用于增加包含多不饱和ω-6脂肪酸的组合物的稳定性的方法 Download PDFInfo
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- CN107105693B CN107105693B CN201580070558.XA CN201580070558A CN107105693B CN 107105693 B CN107105693 B CN 107105693B CN 201580070558 A CN201580070558 A CN 201580070558A CN 107105693 B CN107105693 B CN 107105693B
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- lysine
- fatty acids
- polyunsaturated omega
- acid
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Abstract
本发明涉及增加包含多不饱和Ω‑6脂肪酸的组合物对抗氧化的稳定性的方法。所述方法包含以下步骤:(i)提供包含至少一种多不饱和Ω‑6脂肪酸组分的起始组合物;(ii)提供赖氨酸组合物;(iii)混合起始组合物和赖氨酸组合物的含水、水‑醇或醇溶液,并随后使所获得的混合物经历喷雾干燥条件,因此形成包含衍生自赖氨酸的阳离子与衍生自多不饱和Ω‑6脂肪酸的阴离子的至少一种盐的固体产物组合物;所述产物组合物表现出溶剂含量SC选自以下:SC<5wt%,SC<3wt%,SC<1wt%,SC<0.5wt%。可获自这种喷雾干燥方法的组合物和这种组合物用于制造食物、营养和医药产品的用途也包括于本发明。
Description
通过在过去数十年中收集的广泛证据,增补性摄入多不饱和脂肪酸(PUFAs)已与众多健康益处相关联。在最突出的例子中有心血管疾病的预防和炎性病症症状的减轻,然而,也已经报道了尤其是,防止某些类型的癌症的促进和发展阶段,降低血压和血胆固醇以及在治疗抑郁和精神分裂症、阿尔兹海默病、读写困难和注意力缺乏或多动症中的积极效果。此外,由于某些PUFAs被认为对于脑、神经系统和眼的生长是必要的,现如今在婴幼儿营养中常规地增补特定的PUFAs。
然而,它们对氧化性变质的高敏性阻碍了包含PUFAs的食物、营养和医药产品的生产。氧化对于营养和器官感受两者都有负面结果;即,营养价值变化如基础脂肪酸的破坏、腐败产生异味和明显的气味;色泽变化诸如脂肪和油色变深,以及失去香味。PUFAs的氧化产生挥发性次级氧化产物的复杂混合物,而且这些引起特别令人反感的异味。
为了针对氧化性变质稳定PUFAs,在本领域中已描述有并应用于工业中的三种不同策略(Arab-Tehrany E.等人,Trends in Food Science&Technology 25(2012)24-33):
-添加抗氧化剂,
-微胶囊化,和
-气调包装。
尽管这些策略确实为许多氧化相关性问题提供了解决方案,为了应对当前状况和反映特定技术和经济的极限条件的未来潜在背景中依旧存在的挑战,仍需要新的研发进展。
现在发现通过包含以下步骤的工艺能够稳定包含多不饱和Ω-6脂肪酸的组合物对抗氧化:
(i)提供包含至少一种多不饱和Ω-6脂肪酸组分的起始组合物;
(ii)提供赖氨酸组合物;
(iii)混合起始组合物与赖氨酸组合物的含水、水-醇或醇溶液,并随后使所得化合物经历喷雾干燥条件,就此形成包含衍生自赖氨酸的阳离子与衍生自多不饱和Ω-6脂肪酸的阴离子的至少一种盐的固体产物组合物;所述产物组合物具有选自以下的溶剂含量SC:SC<5wt%、SC<3wt%、SC<1wt%、SC<0.5wt%。
在本发明的上下文中术语PUFA与术语多不饱和脂肪酸可相互替换地使用并如下定义:脂肪酸的分类基于碳链的长度和饱和特性。短链脂肪酸具有2至约6个碳并且典型地是饱和的。中链脂肪酸具有约6至约14个碳并且也典型地是饱和的。长链脂肪酸具有16至24或更多的碳且可以是饱和的或不饱和的。在较长链脂肪酸中,可有一个或多个不饱和位点,分别出现术语“单饱和的”和“多饱和的”。在本发明的上下文中具有20或更多碳原子的长链多不饱和脂肪酸被指定为多不饱和脂肪酸或PUFAs。
根据完善建立的命名法的脂肪酸中双键的个数和位置将PUFAs归类。取决于离脂肪酸的甲基末段最近的双键位置有两个主系列或家族的LC-PUFAs:Ω-3系列在第三碳含有双键,而Ω-6系列在第六碳之前都没有双键。因此,二十二碳六烯酸(“DHA”)具有22碳链长,起于距甲基末段第三碳的6个双键并标示为“22:6n-3”(全-顺-4,7,10,13,16,19-二十二碳烯酸)。其它重要的Ω-3PUFA是二十碳五烯酸(“EPA”),其被标示为“20:5n-3”(全-顺-5,8,11,14,17-二十碳五烯酸)。重要的Ω-6PUFA是花生四烯酸(“ARA”),其被指示为“20:4n-6”(全-顺-5,8,11,14-二十二碳四烯酸)。
其它Ω-3PUFAs包括:
二十碳三烯酸(ETE)20:3(n-3)(全-顺-11,14,17-二十碳三烯酸),二十碳四烯酸(ETA)20:4(n-3)(全-顺-8,11,14,17-二十碳四烯酸),二十一碳五烯酸(HPA)21:5(n-3)(全-顺-6,9,12,15,18-二十一碳五烯酸),二十二碳五烯酸(鱼泡酸)(DPA)22:5(n-3)(全-顺-7,10,13,16,19-二十二碳五烯酸),二十四碳五烯酸24:5(n-3)(全-顺-9,12,15,18,21-二十四碳五烯酸),二十四碳六烯酸(尼生酸)24:6(n-3)(全-顺-6,9,12,15,18,21-二十四碳六烯酸)。
其它Ω-6PUFAs包括:
二十碳二烯酸20:2(n-6)(全-顺-11,14-二十碳二烯酸),双高-γ-亚麻酸(DGLA)20:3(n-6)(全-顺-8,11,14-二十碳三烯酸),二十二碳二烯酸22:2(n-6)(全-顺-13,16-二十二碳二烯酸),肾上腺酸22:4(n-6)(全-顺-7,10,13,16-二十二碳四烯酸),二十二碳五烯酸(Osbond acid)22:5(n-6)(全-顺-4,7,10,13,16-二十二碳五烯酸),二十四碳四烯酸24:4(n-6)(全-顺-9,12,15,18-二十四碳四烯酸),二十四碳五烯酸24:5(n-6)(全-顺-6,9,12,15,18-二十四碳五烯酸)。
在本发明的实施方式中优选的Ω-6PUFAs是花生四烯酸("ARA")和γ-亚麻酸("GLA")。
不受理论束缚,通过本发明的方法实现的针对氧化提高的稳定性是赖氨酸与PUFA之间盐生成的结果。对于保留自由酸,或形成酯部分或形成无机盐如Na+、K+、Ca2+或Mg2+的PUFAs,没有观察到相应的稳定性增加。
通过本发明的方法针对氧化可被稳定的包含多不饱和Ω-6脂肪酸的组合物可以是以实质量包含游离多不饱和Ω-6脂肪酸的任何组合物。这种组合物可进一步以游离形式包含其它天然存在的脂肪酸。另外,这种组合物可进一步包含在室温下和标准大气压下本身为固体、液体或气体的成分。相应的液体成分包括通过蒸发可易于除去的成分并因此可以被考虑为挥发性成分,以及通过蒸发难以除去的成分并因此可以被考虑为非挥发性成分。在本发明的上下文中,气体成分可看作为挥发性的成分。典型的挥发性成分是水、醇和超临界二氧化碳。
通过本发明的方法针对氧化可被稳定的包含多不饱和Ω-6脂肪酸的组合物可以获自于任何适宜的原材料,其此外可以是通过任何加工这种原材料的适宜方法加工过的。典型的原材料包括动物衍生的产品诸如蛋,但特别是衍生自微生物特别是真菌和/或藻发酵的材料。典型地,这种材料,还包含实质量的其它天然存在的脂肪酸。加工这种原材料的典型方法可包括用于获得粗制油的步骤如萃取和分离原材料,以及用于精加工粗制油的步骤如沉淀和脱胶、脱氧(de-acidification)、漂白,和除臭,和用于由精制油制造Ω-6PUFA-浓缩物的步骤如脱氧、转酯化、浓缩和除臭的进一步的步骤(参见例如EFSA ScientificOpinion on Fish oil for Human Consumption)。原材料的任何加工可进一步包括用于至少部分转化Ω-6PUFA-酯为相应的游离Ω-6PUFAs或其无机盐的步骤。
通过本发明的方法针对氧化可被稳定的包含多不饱和Ω-6脂肪酸的优选组合物可通过裂解酯键和随后去除之前结合成酯的醇获自主要由Ω-6PUFAs和其它天然存在的脂肪酸的酯组成的组合物。优选地,酯裂解在碱性条件下进行。用于酯裂解的方法是本领域中熟知的。
在本发明的上下文中针对氧化来稳定组合物表示这种组合物对抗氧化的稳定性是提高的。一种量化组合物针对氧化的稳定性的测量方式是酸败试验(Rancimat test)中的诱导时间。用于进行酸败试验的方案是本领域中熟知的和/或由用于进行酸败试验的仪器的制造商提供。对于组合物针对氧化的稳定性的可替代的测量方式可如下获得:任何组合物或化合物的二或更多样品针对氧化的稳定性可以通过(1)初始测量样品的氧化程度,然后通过(2)使样品经历可比的(氧化)条件和(3)测量样品此后的氧化程度进行对比。其氧化程度具有最小增加的样品表现出在给定条件下针对氧化的最高稳定性,而其氧化程度具有最大增加的样品表现出在给定条件下针对氧化的最低稳定性。样品氧化程度的增加可以绝对项表示,即作为经历氧化条件之前和之后获取的差值,或,可替代地,所述增加可以以相对项表示,即作为经历氧化条件前和后获取值的比。明显地,由暴露于氧化条件导致的氧化程度的降低说明针对氧化很高水平的稳定性,其应当被解释为甚至比将样品暴露于可比的氧化条件下结果发生不变的氧化程度的样品稳定性水平更高。
本领域中已知数种用于量化样品的氧化程度的测量方式。在本发明最宽泛的意义中,任何这些测量方式都是可以使用的。在本发明优选的实施方式中一个或多个以下测量方式被用于量化氧化程度:过氧化值(PV)、茴香胺值(AV)、Totox值。PV是初级氧化产物的测量方式(在双键处形成过氧化氢物),且AV是次级降解产物的测量方式(羰基化合物)。Totox值以Totox=2*PV+AV计算(其中PV被指定为每kg样品毫当量的O2)。用于确定过氧化值(PV)和茴香胺值(AV)的方法已描述于文献中(参见例如Official Methods and RecommendedPractices of the AOCS,6th Edition 2013,Edited by David Firestone,ISBN 978-1-893997-74-5;或,例如PV可根据Ph.Eur.2.5.5(01/2008:20505)确定,AV可根据Ph.Eur.2.5.36(01/2008:20536)确定)。
用于确定样品的过氧化值(PV)的示例性方法如下进行:
试剂和溶液:
1.乙酸-氯仿溶液(7.2ml乙酸和4.8ml氯仿)。
2.饱和的碘化钾溶液。黑暗中存储。
3.硫代硫酸钠溶液,0.1N。商购可得的。
4.1%淀粉溶液。商购可得的。
5.蒸馏或去离子水。
方法:
实施试剂的空白确定。
1.称量2.00(±0.02)g样品进入100ml的玻璃塞锥形烧瓶。记录重量精确到0.01g。
2.通过量筒,添加12ml的乙酸-氯仿溶液。
3.旋转烧瓶直至样品完全溶解(小心地在平板炉上加热可能是必要的)。
4.使用1ml的莫尔吸量管,添加0.2ml的饱和碘化钾溶液。
5.塞住烧瓶并旋转烧瓶内容物1分钟整。
6.立即通过量筒添加12ml的蒸馏水或去离子水,塞住并剧烈摇晃从而将碘从氯仿层释放。
7.用0.1N硫代硫酸钠填充量管。
8.如果溶液的起始颜色是深橘红色,缓慢地滴定,混合直至颜色变浅。如果溶液起始为浅琥珀色,进行第9步。
9.使用分散装置,添加1ml的淀粉溶液作为指示剂。
10.滴定直至蓝灰色在含水(上层)中消失。
11.精确记录所使用的滴定剂的毫升数至十进制小数点后2位。
计算:
S=样品滴定
B=空白滴定
过氧化值=(S-B)*N硫代硫酸盐*1000/样品重量
用于确定样品的茴香胺值(AV)的示例性方法如下进行:
茴香胺值被定义为根据以下方法在100ml溶剂和试剂的混合物中含1g待测物质的溶液在1cm杯中测量的光密度的100倍。尽可能快地进行操作,避免暴露于光化光。
测试溶液(a):溶解0.500g待测物质于三甲基戊烷并用相同的溶剂稀释至25.0ml。
测试溶液(b):向5.0ml的测试溶液(a)中加入p-茴香胺在冰醋酸中的2.5g/l溶液1.0ml,摇晃并避免光亮地存储。
参照溶液:向5.0ml的三甲基戊烷中加入p-茴香胺在冰醋酸中的2.5g/l溶液1.0ml,摇晃并避免光亮地存储。使用三甲基戊烷作为校正液在最大于350nm测量测试溶液(a)的吸光度。使用参照溶液作为校正液于350nm测量测试溶液(b)的吸光度10分钟整。由下述表达式计算茴香胺值(AV):
AV=(25*(1.2*A1-A2))/m
A1=测试溶液(b)于350nm的吸光度,
A2=测试溶液(a)于350nm的吸光度,
m=测试溶液(a)中待测物质的量,以克计。
当通过(1)测量氧化度、(2)经历氧化条件和(3)再次测量氧化度来对比样品针对氧化的稳定性时,在本发明的上下文中,优选地,在步骤(1)和(3)中的氧化度通过确定过氧化值(PV)和/或茴香胺值(AV)来评测;此外,优选地,在步骤(2)中的氧化条件选自以下之一:在开放容器中暴露于空气室温储存至少十天的经定义时段;在开放容器中暴露于空气50℃储存至少3天的经定义时段。
在本发明的上下文中通过一种方法增加组合物针对氧化的稳定性表示在所述组合物经历了该方法后描述组合物针对氧化的稳定性的至少一种测量,例如至少一种如上所述的测量被提高。
在本发明的上下文中包含至少一种多不饱和Ω-6脂肪酸组分的起始组合物可以是包含实质量的至少一种多不饱和Ω-6脂肪酸组分的任何组合物,其中游离Ω-6PUFA(用“游离”意指游离羧酸官能团的存在)的每种类型(即分子种类)构成不同多不饱和Ω-6脂肪酸组分。这种组合物可进一步以游离形式包含其它天然存在的脂肪酸。另外,这种组合物可进一步包含在室温下和标准大气压下本身为固体、液体或气体的成分。相应的液体成分包括通过蒸发可易于除去的成分并因此可以被考虑为挥发性成分,以及通过蒸发难以除去的成分并因此可以被考虑为非挥发性成分。在本发明的上下文中,气体成分可看作为挥发性的成分。典型的挥发性成分是水、醇和超临界二氧化碳。
据此,不考虑挥发性成分的典型起始组合物具有PUFA-含量PC(即一种或多种游离多不饱和Ω-6脂肪酸的总含量)至少15wt%,直至85wt%以游离形式的其它天然存在的脂肪酸,和直至5wt%在室温下和标准大气压下本身为固体或液体的其它成分。然而,较高级别的多不饱和Ω-6脂肪酸可通过纯化各起始物料获得。在本发明的优选实施方式中,不考虑挥发性成分的起始组合物,具有PUFA-含量PC(即一种或多种游离多不饱和Ω-6脂肪酸的总含量)至少30wt%,直至70wt%以游离形式的其它天然存在的脂肪酸,和直至5wt%在室温下和标准大气压下本身为固体或液体的其它成分。在本发明的其它优选实施方式中,不考虑挥发性成分的起始组合物,具有PUFA-含量PC(即一种或多种游离多不饱和Ω-6脂肪酸的总含量)至少50wt%,直至50wt%以游离形式的其它天然存在的脂肪酸,和直至5wt%在室温下和标准大气压下本身为固体或液体的其它成分。在本发明的其它优选实施方式中,不考虑挥发性成分的起始组合物,具有PUFA-含量PC(即一种或多种游离多不饱和Ω-6脂肪酸的总含量)至少75wt%,直至25wt%以游离形式的其它天然存在的脂肪酸,和直至5wt%在室温下和标准大气压下本身为固体或液体的其它成分。在本发明的其它优选实施方式中,不考虑挥发性成分的起始组合物,具有PUFA-含量PC(即一种或多种游离多不饱和Ω-6脂肪酸的总含量)至少75wt%,直至25wt%以游离形式的其它天然存在的脂肪酸,和直至1wt%在室温下和标准大气压下本身为固体或液体的其它成分。
在本发明方法的步骤(ii)中,所提供的赖氨酸组合物是包含实质量游离赖氨酸(Lys)的组合物。所述赖氨酸组合物可进一步包含在室温下和标准大气压下本身为固体、液体或气体的成分。相应的液体成分包括通过蒸发可易于除去的成分并因此可以被考虑为挥发性成分,以及通过蒸发难以除去的成分并因此可以被考虑为非挥发性成分。在上下文中气体成分被考虑为挥发性的成分。典型的挥发性的成分是水、醇和超临界二氧化碳。不考虑挥发性成分的典型赖氨酸组合物包含至少95wt%、97wt%、98wt%、或99wt%的游离赖氨酸。不考虑挥发性成分的优选赖氨酸组合物包含至少98wt%的游离赖氨酸。
在本发明不考虑挥发性成分的优选实施方式中,起始组合物主要包含游离PUFAs和其它天然存在的游离形式的脂肪酸,且赖氨酸组合物主要包含游离赖氨酸,因此所得产物组合物主要由赖氨酸与PUFAs和其它天然存在的脂肪酸的盐组成。
据此,在本发明的优选实施方式中,步骤(i)中的起始组合物和步骤(ii)中的赖氨酸组合物以这种方式提供,即至少sp wt%的所述产物组合物由衍生自赖氨酸的阳离子与衍生自一种或多种多不饱和Ω-6脂肪酸和其它天然存在的脂肪酸的阴离子的一种或多种盐组成,其中sp选自90、95、97、98、99、100。
在本发明方法的步骤(iii)中,起始组合物与赖氨酸组合物合并。可通过允许形成包含衍生自赖氨酸的阳离子与衍生自多不饱和Ω-6脂肪酸的阴离子的至少一种盐的产物组合物的任何方式实现合并。据此,典型的合并起始组合物和赖氨酸组合物的途径是混合每一含水、水-醇或醇溶液并随后去除溶剂。备选地,取决于起始组合物和赖氨酸组合物的剩余成分,可不必添加溶剂而能足够地直接合并起始组合物和赖氨酸组合物。在本发明的上下文中,合并起始组合物和赖氨酸组合物的优选方式是混合每一含水、水-醇或醇溶液并随后去除溶剂。
在本发明的上下文中,衍生自赖氨酸的阳离子是获自赖氨酸质子化的阳离子。
在本发明的上下文中,衍生自多不饱和Ω-6脂肪酸的阴离子是获自多不饱和Ω-6脂肪酸去质子化的阴离子。
应当注意的是赖氨酸与多不饱和脂肪酸的盐本身是本领域中已知的(参见EP0734373 B1),然而,不为所知的是这种盐相比游离PUFAs或PUFA-酯类针对氧化降解表现出较高的稳定性。
鉴于赖氨酸与Ω-6PUFAs的所述盐所固有的稳定性,不必向这些盐添加实质量的抗氧化剂。据此,在本发明的优选实施方式中,在步骤(iii)中获得的所述产物组合物包含无实质量的抗氧化剂,其中无实质量表示该组合物包含少于5wt%、3wt%、1wt%或0.1wt%的抗氧化剂。在进一步优选的实施方式中,所述产物组合物根本不包含抗氧化剂。在本发明的优选实施方式中,所述产物组合物包含无实质量的抗氧化剂,其中无实质量表示所述产物组合物包含少于5wt%、3wt%、1wt%或0.1wt%的抗氧化剂且其中所述抗氧化剂选自维生素C及其酯类、异抗坏血酸及其酯类、维生素E及其酯类、多酚类及其酯类、类胡萝卜素、没食子酸及其酯类、丁羟茴醚及其酯类、丁羟甲苯及其酯类、迷迭香油、己基间苯二酚及其酯类。在进一步优选的实施方式中,所述产物组合物根本不包含抗氧化剂,其中所述抗氧化剂选自维生素C及其酯类、异抗坏血酸及其酯类、维生素E及其酯类、多酚类及其酯类、类胡萝卜素、没食子酸及其酯类、丁羟茴醚及其酯类、丁羟甲苯及其酯类、迷迭香油、己基间苯二酚及其酯类。
根据本发明,所述产物组合物表现出针对氧化比起始组合物更高的稳定性。这意味着至少一种表述组合物针对氧化的稳定性的测量,例如至少一种如上所述的测量,指明针对氧化所述产物组合物比起始组合物更高的稳定性。
在本发明的优选实施方式中,为促使形成定量的盐,游离羧酸官能团和赖氨酸以大约等摩尔量提供。据此,在本发明方法的优选实施方式中,在步骤(ii)中的赖氨酸组合物以如下方式提供,即在步骤(i)中提供的起始组合物中羧酸官能团的量n(ca)和在步骤(ii)中提供的赖氨酸组合物中游离赖氨酸的总量n(lys)的比率R=n(ca)/n(lys)在选自0.9<R<1.1、0.95<R<1.05、0.98<R<1.02的范围内。在特别优选的实施方式中,R在0.98<R<1.02的范围内。在步骤(i)中提供的起始组合物中羧酸官能团的量n(ca)可以通过本领域中熟知的标准分析方法例如酸碱滴定法来确定。
在本发明的优选实施方式中,在步骤(i)中提供的所述起始组合物不包含实质量的脂肪酸酯类,因此产生同样避免实质量脂肪酸酯类的产物组合物。据此,在本发明的优选实施方式中,在步骤(i)中提供的所述起始组合物不包含多于x(fe)wt%的脂肪酸酯类,因此产生的产物组合物包含最大为x(fe)wt%的脂肪酸酯类,其中x(fe)选自5、3、1、0.3、0。在特别优选的实施方式中x(fe)为1。
如上所注意到的,赖氨酸与多不饱和脂肪酸的盐本身是本领域中已知的(参见EP0734373 B1),不为所知的是这种盐相比游离PUFAs或PUFA-酯类针对氧化降解表现出较高的稳定性。重要的是,此外,赖氨酸-PUFA盐被描述为“很厚的透明油,其在低温下转化为蜡样表观和稠度的固体”(参见EP 0734373 B1,第1页,47至48行)。作为结果,本领域技术人员不能预见赖氨酸与Ω-6PUFAs的盐能够通过喷雾干燥方法获得。相反,技术人员会预期这种盐(a)在喷雾干燥条件下归因于没有实质量的溶剂、抗氧化剂和保护包衣在温度升高下的氧化损坏而变坏,和(b)鉴于这种盐呈蜡样固体的假定表观,结块成团而机械性阻碍了喷雾干燥法。因此引人关注的是,现在,发现赖氨酸与Ω-6PUFAs的盐能够真的通过喷雾干燥以温和的方式获得。喷雾干燥的条件,总是必须匹配于所使用的特定喷雾干燥设备。然而,在所述情况中的这种匹配完全在本领域技术人员的常规实验室工作范围内。
为了实施根据本发明的方法的喷雾干燥步骤,使用含水、水-醇或醇溶液。发现PUFAs的Lys-盐在无水醇溶剂中溶解性差。还发现这种盐在纯净水中以高浓度溶解时呈凝胶样表观。可因此采用水-醇溶剂体系来避免这种问题。据此,在本发明的优选实施方式中,经历喷雾干燥条件的混合溶剂是包含20wt%至90wt%水和80wt%至10wt%醇溶剂的水-醇溶剂体系。
所述固体产物组合物的实施将取决于喷雾干燥条件和所使用的底物而变化,然而,现在发现在固体产物组合物中即使非常低的溶剂含量也不发生氧化性损害。如上指出,这是预想不到的。优选地,因此根据本发明获得具有低溶剂含量的固体产物组合物。因此,根据本发明在步骤(iii)中起始组合物和赖氨酸组合物的含水、水-醇或醇溶液首先混合,并随后经历喷雾干燥条件,因此产生包含衍生自赖氨酸的阳离子和衍生自多不饱和Ω-6脂肪酸的阴离子的至少一种盐的固体产物组合物,具有选自以下的溶剂含量SC:SC<5wt%、SC<3wt%、SC<1wt%、SC<0.5wt%。在本发明特别优选的实施方式中SC选自SC<1wt%。
本发明进一步包括可获自本发明的任何方法的组合物。
本发明进一步包括可获自本发明任何方法的组合物的用途,其用于包含多不饱和Ω-6脂肪酸的食品的制造。
在本发明的上下文中食品包括但不限于烤制食品、维生素增补剂、规定饮食的增补剂、饮料粉、生面团、面糊,烤制食品类包括例如糕点、芝士蛋糕、派、杯状蛋糕、饼干(cookies)、条块(bars)、面包、卷(rolls)、饼干(biscuits)、松饼、油酥糕点、司康饼,和油煎面包块;液体食品例如饮料、能量饮料、婴儿配方奶粉、液体食物、果汁、复合维生素糖浆、膳食替代品、药用食品,和糖浆;半固体食品如婴幼儿食品、酸奶、奶酪、谷物食品、烙饼粉(pancake mixes);压成块的精制食品(food bars)包括能量条;经加工的肉食;冰激凌;冰冻的甜品;冰冻酸奶;华夫饼粉(waffle mixes);色拉调料;和替代蛋粉(replacement eggmixes);和其它饼干(cookies)、薄脆饼干、甜食、小吃、派、即食麦片/小吃条块(snackbars),和烤面饼(toaster pastries);咸点心如马铃薯片、玉米脆片、墨西哥玉米片、挤压膨化食品、爆米花、椒盐卷饼(pretzels)、炸薯条(potato crisps),和坚果(nuts);特色小吃如蘸酱、干果小吃、肉类小吃、熏炸猪皮、健康食品条块和稻米/玉米糕;糖果零食如糖果;速熟食品,如方便面、速溶汤块或速溶汤颗粒。
本发明进一步包括可获自本发明任何方法的组合物的用途,其用于包含多不饱和Ω-6脂肪酸的营养品的制造。
在本发明的上下文中营养品包括任何类型的营养食品、营养或规定饮食的增补剂,例如用于增补维生素、矿物质、纤维、脂肪酸或氨基酸。
本发明进一步包含可获自本发明任何方法的组合物的用途,其用于包含多不饱和Ω-6脂肪酸的医药产品的制造。
优选的本发明方法由以下选择之一表征:
●0.90<R<1.10,x(fe)=5;PC=15;SC<1wt%
●0.90<R<1.10,x(fe)=3;PC=15;SC<1wt%
●0.90<R<1.10,x(fe)=2;PC=15:SC<1wt%
●0.90<R<1.10,x(fe)=1;PC=15;SC<1wt%
●0.95<R<1.05,x(fe)=5;PC=15;SC<1wt%
●0.95<R<1.05,x(fe)=3;PC=15;SC<1wt%
●0.95<R<1.05,x(fe)=2;PC=15;SC<1wt%
●0.95<R<1.05,x(fe)=1;PC=15;SC<1wt%
●0.98<R<1.02,x(fe)=5;PC=15;SC<1wt%
●0.98<R<1.02,x(fe)=3;PC=15;SC<1wt%
●0.98<R<1.02,x(fe)=2;PC=15;SC<1wt%
●0.98<R<1.02,x(fe)=1;PC=15;SC<1wt%
●0.90<R<1.10,x(fe)=5;PC=30;SC<1wt%
●0.90<R<1.10,x(fe)=3;PC=30;SC<1wt%
●0.90<R<1.10,x(fe)=2;PC=30:SC<1wt%
●0.90<R<1.10,x(fe)=1;PC=30;SC<1wt%
●0.95<R<1.05,x(fe)=5;PC=30;SC<1wt%
●0.95<R<1.05,x(fe)=3;PC=30;SC<1wt%
●0.95<R<1.05,x(fe)=2;PC=30;SC<1wt%
●0.95<R<1.05,x(fe)=1;PC=30;SC<1wt%
●0.98<R<1.02,x(fe)=5;PC=30;SC<1wt%
●0.98<R<1.02,x(fe)=3;PC=30;SC<1wt%
●0.98<R<1.02,x(fe)=2;PC=30;SC<1wt%
●0.98<R<1.02,x(fe)=1;PC=30;SC<1wt%
●0.90<R<1.10,x(fe)=5;PC=50;SC<1wt%
●0.90<R<1.10,x(fe)=3;PC=50;SC<1wt%
●0.90<R<1.10,x(fe)=2;PC=50:SC<1wt%
●0.90<R<1.10,x(fe)=1;PC=50;SC<1wt%
●0.95<R<1.05,x(fe)=5;PC=50;SC<1wt%
●0.95<R<1.05,x(fe)=3;PC=50;SC<1wt%
●0.95<R<1.05,x(fe)=2;PC=50;SC<1wt%
●0.95<R<1.05,x(fe)=1;PC=50;SC<1wt%
●0.98<R<1.02,x(fe)=5;PC=50;SC<1wt%
●0.98<R<1.02,x(fe)=3;PC=50;SC<1wt%
●0.98<R<1.02,x(fe)=2;PC=50;SC<1wt%
●0.98<R<1.02,x(fe)=1;PC=50;SC<1wt%
●0.90<R<1.10,x(fe)=5;PC=75;SC<1wt%
●0.90<R<1.10,x(fe)=3;PC=75;SC<1wt%
●0.90<R<1.10,x(fe)=2;PC=75:SC<1wt%
●0.90<R<1.10,x(fe)=1;PC=75;SC<1wt%
●0.95<R<1.05,x(fe)=5;PC=75;SC<1wt%
●0.95<R<1.05,x(fe)=3;PC=75;SC<1wt%
●0.95<R<1.05,x(fe)=2;PC=75;SC<1wt%
●0.95<R<1.05,x(fe)=1;PC=75;SC<1wt%
●0.98<R<1.02,x(fe)=5;PC=75;SC<1wt%
●0.98<R<1.02,x(fe)=3;PC=75;SC<1wt%
●0.98<R<1.02,x(fe)=2;PC=75;SC<1wt%
●0.98<R<1.02,x(fe)=1;PC=75;SC<1wt%
优选的可获自如说明书中所揭示在步骤(iii)中使用喷雾干燥的本发明方法的组合物由以下选择之一表征:
●0.90<R<1.10,x(fe)=1,SC<3wt%,sp=90
●0.90<R<1.10,x(fe)=1,SC<3wt%,sp=95
●0.90<R<1.10,x(fe)=3,SC<3wt%,sp=90
●0.90<R<1.10,x(fe)=3,SC<3wt%,sp=95
●0.95<R<1.05,x(fe)=1,SC<3wt%,sp=90
●0.95<R<1.05,x(fe)=1,SC<3wt%,sp=95
●0.95<R<1.05,x(fe)=3,SC<3wt%,sp=90
●0.95<R<1.05,x(fe)=3,SC<3wt%,sp=95
●0.98<R<1.02,x(fe)=1,SC<3wt%,sp=95
●0.98<R<1.02,x(fe)=1,SC<3wt%,sp=97
●0.98<R<1.02,x(fe)=3,SC<3wt%,sp=95
●0.98<R<1.02,x(fe)=3,SC<3wt%,sp=97
●0.90<R<1.10,x(fe)=1,SC<1wt%,sp=90
●0.90<R<1.10,x(fe)=1,SC<1wt%,sp=95
●0.90<R<1.10,x(fe)=3,SC<1wt%,sp=90
●0.90<R<1.10,x(fe)=3,SC<1wt%,sp=95
●0.95<R<1.05,x(fe)=1,SC<1wt%,sp=90
●0.95<R<1.05,x(fe)=1,SC<1wt%,sp=95
●0.95<R<1.05,x(fe)=3,SC<1wt%,sp=90
●0.95<R<1.05,x(fe)=3,SC<1wt%,sp=95
●0.98<R<1.02,x(fe)=1,SC<1wt%,sp=95
●0.98<R<1.02,x(fe)=1,SC<1wt%,sp=97
●0.98<R<1.02,x(fe)=3,SC<1wt%,sp=95
●0.98<R<1.02,x(fe)=3,SC<1wt%,sp=97
●0.90<R<1.10,x(fe)=1,SC<0.5wt%,sp=90
●0.90<R<1.10,x(fe)=1,SC<0.5wt%,sp=95
●0.90<R<1.10,x(fe)=3,SC<0.5wt%,sp=90
●0.90<R<1.10,x(fe)=3,SC<0.5wt%,sp=95
●0.95<R<1.05,x(fe)=1,SC<0.5wt%,sp=90
●0.95<R<1.05,x(fe)=1,SC<0.5wt%,sp=95
●0.95<R<1.05,x(fe)=3,SC<0.5wt%,sp=90
●0.95<R<1.05,x(fe)=3,SC<0.5wt%,sp=95
●0.98<R<1.02,x(fe)=1,SC<0.5wt%,sp=95
●0.98<R<1.02,x(fe)=1,SC<0.5wt%,sp=97
●0.98<R<1.02,x(fe)=3,SC<0.5wt%,sp=95
●0.98<R<1.02,x(fe)=3,SC<0.5wt%,sp=97
实验
分析方法:
通过依据Ph.Eur.2.5.5(01/2008:20505)确定过氧化值(PV)量化初级氧化产物(在双键处的过氧化氢物)。通过依据Ph.Eur.2.5.36(01/2008:20536)确定茴香胺值(AV)量化次级氧化产物(羰基化合物)。
通过凝胶-色谱法(GPC,苯乙烯二乙烯苯-相用包含四氢呋喃的三氟乙酸作为洗脱液)量化寡聚的PUFA成分以及它们的衍生物(一同涉及寡聚体含量)。折射率(RI)检测仪用于检测。由于样品成分的特异性应答因素是未知的,基于色谱总面积的级份比例计算比例。
通过Karl-Fischer滴定确定水含量。
通过1-H-NMR光谱确定乙醇含量。
通过用氢氧化钾滴定确定酸值。
实验1:源自花生四烯酸甘油酯的花生四烯酸(ARA)
具有ARA-含量为44.8%、茴香胺值为8.1A/g且过氧化值为4.0mmol/的500g(商购可得的,标准质量)花生四烯酸甘油酯,被置于3L的烧瓶中(用氮气使之惰性)并用500ml乙醇稀释。添加175g的NaOH(50%)溶液和250ml水,且所获得的溶液于30℃-50℃搅拌30分钟。随后,用1250ml水稀释所述反应混合物并之后添加175ml硫磺酸50wt%。随即搅拌10分钟后进行相分离,用每次125ml水3次和之后125ml含水硫酸钠溶液10wt%洗涤产物相。获取具有茴香胺值为4.2A/g和过氧化值为7.2mmol/kg的呈油状的475g花生四烯酸。寡聚体含量未确定。
实验2:源自γ-亚麻酸乙酯的γ-亚麻酸(GLA)
具有GC纯度为99.2%、茴香胺值为19.1A/g且过氧化值为52.1mmol/的500g(商购可得的,标准质量)γ-亚麻酸乙酯,被置于3L的烧瓶中(用氮气使之惰性)并用500ml乙醇稀释。添加170g的NaOH(50%)溶液和250ml水,且所获得的溶液于30℃-50℃搅拌30分钟。随后,用1250ml水稀释所述反应混合物并之后添加175ml硫磺酸50wt%。随即搅拌10分钟后进行相分离,用每次125ml水3次和之后125ml含水硫酸钠溶液10wt%洗涤产物相。获取具有茴香胺值为7.6A/g和过氧化值为5.6mmol/kg的呈油状的500gγ-亚麻酸。寡聚体含量被确定为0.3面积%(凝胶-色谱法,RI-检测仪)。
实验3:源自花生四烯酸(ARA)和L-赖氨酸(L-Lys)的花生四烯酸-L-赖氨酸盐
(ARA-Lys)
源自实验1的70.0g花生四烯酸,基于滴定表现出187mg KOH/g的酸值,被溶于70.0g的乙醇并与34.2g含水L-赖氨酸溶液(51.3%)合并。所获得的均质溶液在加热至40-50℃后用具有进口温度140℃和出口温度约80℃的Büchi B190实验室喷雾干燥器喷雾干燥。获得水含量为0.62%且乙醇含量为<0.1%的81.2g米黄色粉末。该盐表现出茴香胺值为1A/g和过氧化值<1mmol/kg。寡聚体含量被确定为1.1面积%(凝胶-色谱法,RI-检测仪)。
实验4:源自γ-亚麻酸(GLA)和L-赖氨酸(L-Lys)的γ-亚麻酸-L-赖氨酸盐(GLA-
Lys)
源自实验2的70.0g的γ-亚麻酸,基于滴定表现出137.6mg KOH/g的酸值,被溶于70.0g的乙醇并与25.1g含水L-赖氨酸溶液(51.3%)合并。所获得的均质溶液在加热至40-50℃后用具有进口温度140℃和出口温度约80℃的Büchi B190实验室喷雾干燥器喷雾干燥。获得水含量为1.13%且乙醇含量为<0.1%的47.9g米黄色粉末。该盐表现出茴香胺值为5.4A/g和过氧化值为1.0mmol/kg。寡聚体含量被确定为0.6面积%(凝胶-色谱法,RI-检测仪)。
实验5:按在升高的温度(50℃)并暴露于空气下的储存检测花生四烯酸和γ-亚麻
酸及其衍生物的稳定性
各约30g在实验1和2中使用的液体花生四烯酸甘油酯和γ-亚麻酸乙酯以及获自实验1和2的花生四烯酸和γ-亚麻酸被装入500ml的Schott Duran玻璃瓶中。
各约30g获自实验3和4的固体赖氨酸-盐ARA-Lys和GLA-Lys被装入Schott Duran玻璃瓶中。
所有的瓶开盖地被一起置于打开通风阀于50℃的干燥炉中并在这些条件下黑暗储存81天。随后进行的分析结果总结于下表(表1)。
Claims (7)
1.用于增加包含多不饱和Ω-6脂肪酸的组合物针对氧化的稳定性的方法,其包含以下步骤:
(i)提供包含至少一种多不饱和Ω-6脂肪酸组分的起始组合物;
(ii)提供赖氨酸组合物;
(iii)混合起始组合物和赖氨酸组合物的含水、水-醇或醇溶液,且使所得混合物随后经历喷雾干燥条件,就此形成包含至少一种衍生自赖氨酸的阳离子与衍生自多不饱和Ω-6脂肪酸的阴离子的盐的固体产物组合物;所述产物组合物表现出的溶剂含量SC选自以下:SC<5wt%、SC<3wt%、SC<1wt%、SC<0.5wt%;
其中在步骤(i)中的起始组合物和在步骤(ii)中的赖氨酸组合物以这种方式提供,即至少90wt%的所述产物组合物由衍生自赖氨酸的阳离子与衍生自一种或多种多不饱和Ω-6脂肪酸和其它天然存在的脂肪酸的阴离子的一种或多种盐组成。
2.根据权利要求1的方法,其中在步骤(i)中提供的所述起始组合物不包含多于x(fe)wt%的脂肪酸酯类,其中x(fe)选自5、3、2、1、0.3、0。
3.根据权利要求1或2的方法,其中在步骤(i)中的起始组合物和在步骤(ii)中的赖氨酸组合物以这种方式提供,即至少sp wt%的所述产物组合物由衍生自赖氨酸的阳离子与衍生自一种或多种多不饱和Ω-6脂肪酸和其它天然存在的脂肪酸的阴离子的一种或多种盐组成,其中sp选自95、97、98、99、100。
4.获自根据权利要求1至3任一项的方法的组合物。
5.根据权利要求4的组合物的用途,其用于包含多不饱和Ω-6脂肪酸的食品的制造。
6.根据权利要求4的组合物的用途,其用于包含多不饱和Ω-6脂肪酸的营养品的制造。
7.根据权利要求4的组合物的用途,其用于包含多不饱和Ω-6脂肪酸的医药产品的制造。
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