CN103525876A - Method for enriching alkoxy glycerol in shark liver oil - Google Patents

Method for enriching alkoxy glycerol in shark liver oil Download PDF

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CN103525876A
CN103525876A CN201310433291.9A CN201310433291A CN103525876A CN 103525876 A CN103525876 A CN 103525876A CN 201310433291 A CN201310433291 A CN 201310433291A CN 103525876 A CN103525876 A CN 103525876A
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liver oil
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shark liver
chain alcohol
akgs
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CN103525876B (en
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孙兆敏
李兆杰
薛长湖
郭正霞
徐杰
薛勇
王玉明
王静凤
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Ocean University of China
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Abstract

本发明提供了一种富集鲨鱼肝油中烷氧基甘油的方法,其通过将鲨鱼肝油与短链醇、脂肪酶混合反应,去除未反应的原料和副产物,获得烷氧基甘油的富集产物。本发明提供的新型的富集鲨鱼肝油中烷氧基甘油的方法,其通过酶促醇解和分子蒸馏技术的联合使用以富集鲨鱼肝油中烷氧基甘油,采用该方法无需消耗烧碱和有毒、易挥发的有机溶剂,不产生对环境有害的废弃物,且能保留鲨鱼肝油中的天然n-3系列多不饱和脂肪酸,防止营养成分的浪费。The present invention provides a method for enriching alkoxyglycerol in shark liver oil, which is obtained by mixing and reacting shark liver oil with short-chain alcohol and lipase to remove unreacted raw materials and by-products to obtain enrichment of alkoxyglycerol product. The novel method for enriching alkoxyglycerols in shark liver oil provided by the present invention is to enrich alkoxyglycerols in shark liver oil through the joint use of enzymatic alcoholysis and molecular distillation technology, and the method does not need to consume caustic soda and toxic , Volatile organic solvents, no wastes harmful to the environment, and can retain the natural n-3 series polyunsaturated fatty acids in shark liver oil to prevent the waste of nutrients.

Description

一种富集鲨鱼肝油中烷氧基甘油的方法A method for enriching alkoxyglycerol in shark liver oil

技术领域technical field

本发明涉及海洋生物技术领域,尤其涉及一种富集鲨鱼肝油中烷氧基甘油的方法。The invention relates to the technical field of marine life, in particular to a method for enriching alkoxyglycerol in shark liver oil.

背景技术Background technique

烷氧基甘油(Alkoxyglycerols)是存在于人体细胞、体液、母乳以及骨髓中的一种含醚键的脂质,其种类取决于烷基链的长度和不饱和度,常见的烷氧基甘油的烷基链主要是C12:0(烷基链中含有12个碳原子并且不含有双键)、C14:0(烷基链中含有14个碳原子并且不含有双键)、C16:0(烷基链中含有16个碳原子并且不含有双键)、C16:1(烷基链中含有16个碳原子并且含有一个双键)、C18:0(烷基链中含有18个碳原子并且不含有双键)和C18:1(烷基链中含有18个碳原子并且含有一个双键)。烷氧基甘油作为一种特殊的抗氧化剂,能够穿透细胞膜到达细胞内起到抗氧化的作用,而常规的抗氧化剂如维生素C和维生素E等只能在细胞外起作用,烷氧基甘油的生理功能还包括抗肿瘤、提高男性生殖能力和提高机体免疫力等。Alkoxyglycerols are lipids containing ether bonds that exist in human cells, body fluids, breast milk and bone marrow. The type depends on the length and degree of unsaturation of the alkyl chain. Common alkoxyglycerols Alkyl chains are mainly C12:0 (the alkyl chain contains 12 carbon atoms and does not contain double bonds), C14:0 (the alkyl chain contains 14 carbon atoms and does not contain double bonds), C16:0 (alkane Contains 16 carbon atoms in the base chain and does not contain a double bond), C16:1 (contains 16 carbon atoms in the alkyl chain and contains a double bond), C18:0 (contains 18 carbon atoms in the alkyl chain and does not contain contains a double bond) and C18:1 (18 carbon atoms in the alkyl chain and contains a double bond). As a special antioxidant, alkoxyglycerol can penetrate the cell membrane and reach the cell to play an antioxidant role, while conventional antioxidants such as vitamin C and vitamin E can only work outside the cell, alkoxyglycerol Physiological functions also include anti-tumor, improving male reproductive ability and improving the body's immunity.

天然的烷氧基甘油主要以二酰基烷氧基甘油的形式存在于鲨鱼肝脏脂质中,也少量存在于其他海产动物如海星组织中,且不同种类的鲨鱼肝脏脂质所含烷氧基甘油相差很大。天然鲨鱼肝油中烷氧基甘油最高的含量多在20%左右,最少的则在5%以下。目前商品化的烷氧基甘油产品主要是烷氧基甘油含量约20%的天然鲨鱼肝油产品,而烷氧基甘油含量低的鲨鱼肝油则没有得到有效利用。Natural alkoxyglycerols mainly exist in shark liver lipids in the form of diacyl alkoxyglycerols, and also exist in small amounts in other marine animals such as starfish tissues, and different types of shark liver lipids contain alkoxyglycerols A big difference. The highest content of alkoxyglycerol in natural shark liver oil is about 20%, and the lowest is below 5%. Currently commercialized alkoxyglycerin products are mainly natural shark liver oil products with alkoxyglycerol content of about 20%, while shark liver oil with low alkoxyglycerin content has not been effectively utilized.

为了获得高含量的烷氧基甘油,通常的做法是先将鲨鱼肝油完全皂化,提取其中的不皂化物后再经进一步纯化,所得产物为游离烷氧基甘油、胆固醇和维生素E等的混合物,该方法通常需要耗费大量烧碱以及有毒、易挥发的有机溶剂,产生的废水还会污染环境,除此之外,鲨鱼肝油中所含的对人体有益的其他成分如n-3系列多不饱和脂肪酸(如二十碳五烯酸EPA和二十二碳六烯酸DHA)也会以皂化物的形式被脱除,造成营养成分的浪费。In order to obtain a high content of alkoxyglycerol, the usual practice is to completely saponify the shark liver oil first, extract the unsaponifiable matter therein and then further purify, and the resulting product is a mixture of free alkoxyglycerin, cholesterol and vitamin E, etc. This method usually needs to consume a large amount of caustic soda and toxic and volatile organic solvents, and the waste water produced will also pollute the environment. In addition, other components beneficial to the human body contained in shark liver oil such as n-3 series polyunsaturated fatty acids (such as eicosapentaenoic acid EPA and docosahexaenoic acid DHA) will also be removed in the form of saponification, resulting in waste of nutrients.

发明内容Contents of the invention

本发明所要解决的技术问题是提供一种新型的富集鲨鱼肝油中烷氧基甘油的方法,其通过酶促醇解和分子蒸馏技术的联合使用以富集鲨鱼肝油中烷氧基甘油,采用该方法无需消耗烧碱和有毒、易挥发的有机溶剂,不产生对环境有害的废弃物,且能保留鲨鱼肝油中的天然n-3系列多不饱和脂肪酸,防止营养成分的浪费。The technical problem to be solved by the present invention is to provide a novel method for enriching alkoxyglycerols in shark liver oil, which uses enzymatic alcoholysis and molecular distillation techniques to enrich alkoxyglycerols in shark liver oil. The method does not need to consume caustic soda and toxic and volatile organic solvents, does not generate environmentally harmful waste, and can retain the natural n-3 series polyunsaturated fatty acids in the shark liver oil to prevent waste of nutrients.

为了解决上述技术问题,本发明提供了一种富集鲨鱼肝油中烷氧基甘油的方法,其通过将鲨鱼肝油与短链醇、脂肪酶混合反应,去除未反应的原料和副产物,获得烷氧基甘油的富集产物。In order to solve the above-mentioned technical problems, the present invention provides a method for enriching alkoxyglycerol in shark liver oil, by mixing and reacting shark liver oil with short-chain alcohol and lipase to remove unreacted raw materials and by-products to obtain alkoxyglycerol Oxyglycerol enrichment product.

进一步,所述方法包括:Further, the method includes:

第一步,在反应器中加入鲨鱼肝油、短链醇和脂肪酶,搅拌均匀,加热至一定的温度下继续搅拌反应;In the first step, add shark liver oil, short-chain alcohol and lipase into the reactor, stir evenly, heat to a certain temperature and continue stirring reaction;

第二步,将第一步反应后产物过滤,回收脂肪酶固体;In the second step, the product after the first step is filtered to reclaim the lipase solid;

第三步,将第二步过滤后的产物减压蒸馏脱除未反应的短链醇;In the third step, the product after the second step is filtered under reduced pressure to remove unreacted short-chain alcohols;

第四步,将第三步获得的产物采用分子蒸馏的方法脱除反应过程中生成的脂肪酸-短链醇酯副产物,获得烷氧基甘油的富集产物。The fourth step is to remove the fatty acid-short-chain alcohol ester by-product generated during the reaction by molecular distillation from the product obtained in the third step, and obtain an enriched product of alkoxyglycerol.

所述第一步中,反应温度为30~60℃,反应时间为4~72h,所述短链醇的添加量为鲨鱼肝油质量的5%~100%,所述脂肪酶的添加量为鲨鱼肝油质量的1%~15%。In the first step, the reaction temperature is 30-60°C, the reaction time is 4-72h, the added amount of the short-chain alcohol is 5%-100% of the mass of shark liver oil, and the added amount of the lipase is shark liver oil. 1% to 15% of the mass of cod liver oil.

所述短链醇为碳原子为1~4个的一元醇,优选甲醇、乙醇、丙醇、正丁醇,进一步优选乙醇。The short-chain alcohol is a monohydric alcohol with 1 to 4 carbon atoms, preferably methanol, ethanol, propanol, n-butanol, more preferably ethanol.

在第一步中,所述短链醇的加入方式可以为一次性加入,也可以在搅拌过程中分批加入。In the first step, the short-chain alcohol can be added in one time or in batches during stirring.

所述脂肪酶的来源很广,可以通过微生物发酵生产,也可以从动物胰脏中提取,优选的脂肪酶为来源于酵母菌、霉菌或者动物胰脏的固定化或非固定化脂肪酶。The lipase has a wide range of sources and can be produced by microbial fermentation or extracted from animal pancreas. The preferred lipase is immobilized or non-immobilized lipase derived from yeast, mold or animal pancreas.

本发明还提供了一种富集鲨鱼肝油中烷氧基甘油的方法,其包括:The present invention also provides a method for enriching alkoxyglycerol in shark liver oil, which includes:

第一步,在反应器中加入鲨鱼肝油、短链醇和脂肪酶,搅拌均匀,加热至30~60℃的温度下搅拌反应4~72h,所述短链醇的添加量为鲨鱼肝油质量的5%~100%,所述脂肪酶的添加量为鲨鱼肝油质量的1%~15%,所述短链醇的加入方式可以为一次性加入,也可以在搅拌过程中分批加入;In the first step, add shark liver oil, short-chain alcohol and lipase into the reactor, stir evenly, heat to 30-60° C. and stir for 4-72 hours. The amount of added short-chain alcohol is 5% of the quality of shark liver oil. % to 100%, the added amount of the lipase is 1% to 15% of the quality of the shark liver oil, and the short-chain alcohol can be added in one time or in batches during the stirring process;

第二步,将第一步反应后产物过滤,回收脂肪酶固体;In the second step, the product after the first step is filtered to reclaim the lipase solid;

第三步,将第二步过滤后的产物减压蒸馏脱除未反应的短链醇;In the third step, the product after the second step is filtered under reduced pressure to remove unreacted short-chain alcohols;

第四步,将第三步获得的产物采用分子蒸馏的方法脱除反应过程中生成的脂肪酸-短链醇酯副产物,获得烷氧基甘油的富集产物。The fourth step is to remove the fatty acid-short-chain alcohol ester by-product generated during the reaction by molecular distillation from the product obtained in the third step, and obtain an enriched product of alkoxyglycerol.

本发明还提供一种烷氧基甘油,其是通过如下方法制备而成的:The present invention also provides a kind of alkoxyglycerol, which is prepared by the following method:

第一步,在反应器中加入鲨鱼肝油、短链醇和脂肪酶,搅拌均匀,加热至一定的温度下继续搅拌反应;In the first step, add shark liver oil, short-chain alcohol and lipase into the reactor, stir evenly, heat to a certain temperature and continue stirring reaction;

第二步,将第一步反应后产物过滤,回收脂肪酶固体;In the second step, the product after the first step is filtered to reclaim the lipase solid;

第三步,将第二步过滤后的产物减压蒸馏脱除未反应的短链醇;In the third step, the product after the second step is filtered under reduced pressure to remove unreacted short-chain alcohols;

第四步,将第三步获得的产物采用分子蒸馏的方法脱除反应过程中生成的脂肪酸-短链醇酯副产物,获得烷氧基甘油的富集产物。The fourth step is to remove the fatty acid-short-chain alcohol ester by-product generated during the reaction by molecular distillation from the product obtained in the third step, and obtain an enriched product of alkoxyglycerol.

本发明还提供了上述的富集鲨鱼肝油中烷氧基甘油的方法在制备保健产品中的应用。The present invention also provides the application of the above method for enriching alkoxyglycerol in shark liver oil in the preparation of health care products.

本发明还提供了一种保健产品,其包括上述方法制备而成的烷氧基甘油的富集产物。The present invention also provides a health care product, which includes the enriched product of alkoxyglycerin prepared by the above method.

有益效果Beneficial effect

本发明提供的新型的富集鲨鱼肝油中烷氧基甘油的方法,其通过酶促醇解和分子蒸馏技术的联合使用以富集鲨鱼肝油中烷氧基甘油,采用该方法无需消耗烧碱和有毒、易挥发的有机溶剂,不产生对环境有害的废弃物,且能保留鲨鱼肝油中的天然n-3系列多不饱和脂肪酸,防止营养成分的浪费。The novel method for enriching alkoxyglycerols in shark liver oil provided by the present invention is to enrich alkoxyglycerols in shark liver oil through the joint use of enzymatic alcoholysis and molecular distillation technology, and the method does not need to consume caustic soda and toxic , Volatile organic solvents, no wastes harmful to the environment, and can retain the natural n-3 series polyunsaturated fatty acids in shark liver oil to prevent the waste of nutrients.

具体实施方式Detailed ways

本发明提供了一种富集鲨鱼肝油中烷氧基甘油的方法,其通过将鲨鱼肝油与短链醇、脂肪酶混合反应,去除未反应的原料和副产物,获得烷氧基甘油的富集产物。The present invention provides a method for enriching alkoxyglycerol in shark liver oil, which is obtained by mixing and reacting shark liver oil with short-chain alcohol and lipase to remove unreacted raw materials and by-products to obtain enrichment of alkoxyglycerol product.

进一步,所述方法包括:Further, the method includes:

第一步,在反应器中加入鲨鱼肝油、短链醇和脂肪酶,搅拌均匀,加热至一定的温度下继续搅拌反应;In the first step, add shark liver oil, short-chain alcohol and lipase into the reactor, stir evenly, heat to a certain temperature and continue stirring reaction;

第二步,将第一步反应后产物过滤,回收脂肪酶固体;In the second step, the product after the first step is filtered to reclaim the lipase solid;

第三步,将第二步过滤后的产物减压蒸馏脱除未反应的短链醇;In the third step, the product after the second step is filtered under reduced pressure to remove unreacted short-chain alcohols;

第四步,将第三步获得的产物采用分子蒸馏的方法脱除反应过程中生成的脂肪酸-短链醇酯副产物,获得烷氧基甘油的富集产物。The fourth step is to remove the fatty acid-short-chain alcohol ester by-product generated during the reaction by molecular distillation from the product obtained in the third step, and obtain an enriched product of alkoxyglycerol.

所述第一步中,反应温度为30~60℃,反应时间为4~72h,所述短链醇的添加量为鲨鱼肝油质量的5%~100%,所述脂肪酶的添加量为鲨鱼肝油质量的1%~15%。In the first step, the reaction temperature is 30-60°C, the reaction time is 4-72h, the added amount of the short-chain alcohol is 5%-100% of the mass of shark liver oil, and the added amount of the lipase is shark liver oil. 1% to 15% of the mass of cod liver oil.

所述短链醇为碳原子为1~4个的一元醇,优选甲醇、乙醇、丙醇、正丁醇,进一步优选乙醇。The short-chain alcohol is a monohydric alcohol with 1 to 4 carbon atoms, preferably methanol, ethanol, propanol, n-butanol, more preferably ethanol.

在第一步中,所述短链醇的加入方式可以为一次性加入,也可以在搅拌过程中分批加入。In the first step, the short-chain alcohol can be added in one time or in batches during stirring.

所述脂肪酶优选来源于酵母菌、霉菌或者动物胰脏的固定化或非固定化脂肪酶。The lipase is preferably immobilized or non-immobilized lipase derived from yeast, mold or animal pancreas.

所述第三步中的减压蒸馏条件为常规技术,其采用常规条件即可,优选为减压蒸馏温度为40~80℃,真空度为-0.070Mpa~-0.095Mpa。The vacuum distillation conditions in the third step are conventional techniques, and conventional conditions can be used. Preferably, the vacuum distillation temperature is 40-80° C., and the vacuum degree is -0.070Mpa~-0.095Mpa.

所述第四步中的分子蒸馏脱除技术为常规技术,采用其常规条件即可,优选为分子蒸馏的条件为:蒸馏温度130~180℃,蒸馏压力为0.1Pa~100Pa。The molecular distillation removal technology in the fourth step is a conventional technology, and the conventional conditions can be used. The preferred molecular distillation conditions are: distillation temperature 130-180°C, distillation pressure 0.1Pa-100Pa.

本发明还提供了一种富集鲨鱼肝油中烷氧基甘油的方法,其包括:The present invention also provides a method for enriching alkoxyglycerol in shark liver oil, which includes:

第一步,在反应器中加入鲨鱼肝油、短链醇和脂肪酶,搅拌均匀,加热至30~60℃的温度下搅拌反应4~72h,所述短链醇的添加量为鲨鱼肝油质量的5%~100%,所述脂肪酶的添加量为鲨鱼肝油质量的1%~15%,所述短链醇的加入方式可以为一次性加入,也可以在搅拌过程中分批加入;In the first step, add shark liver oil, short-chain alcohol and lipase into the reactor, stir evenly, heat to 30-60° C. and stir for 4-72 hours. The amount of added short-chain alcohol is 5% of the quality of shark liver oil. % to 100%, the added amount of the lipase is 1% to 15% of the quality of the shark liver oil, and the short-chain alcohol can be added in one time or in batches during the stirring process;

第二步,将第一步反应后产物过滤,回收脂肪酶固体;In the second step, the product after the first step is filtered to reclaim the lipase solid;

第三步,将第二步过滤后的产物减压蒸馏脱除未反应的短链醇;In the third step, the product after the second step is filtered under reduced pressure to remove unreacted short-chain alcohols;

第四步,将第三步获得的产物采用分子蒸馏的方法脱除反应过程中生成的脂肪酸-短链醇酯副产物,获得烷氧基甘油的富集产物。The fourth step is to remove the fatty acid-short-chain alcohol ester by-product generated during the reaction by molecular distillation from the product obtained in the third step, and obtain an enriched product of alkoxyglycerol.

本发明还提供一种烷氧基甘油,其是通过如下方法制备而成的:The present invention also provides a kind of alkoxyglycerol, which is prepared by the following method:

第一步,在反应器中加入鲨鱼肝油、短链醇和脂肪酶,搅拌均匀,加热至一定的温度下继续搅拌反应;In the first step, add shark liver oil, short-chain alcohol and lipase into the reactor, stir evenly, heat to a certain temperature and continue stirring reaction;

第二步,将第一步反应后产物过滤,回收脂肪酶固体;In the second step, the product after the first step is filtered to reclaim the lipase solid;

第三步,将第二步过滤后的产物减压蒸馏脱除未反应的短链醇;In the third step, the product after the second step is filtered under reduced pressure to remove unreacted short-chain alcohols;

第四步,将第三步获得的产物采用分子蒸馏的方法脱除反应过程中生成的脂肪酸-短链醇酯副产物,获得烷氧基甘油的富集产物。The fourth step is to remove the fatty acid-short-chain alcohol ester by-product generated during the reaction by molecular distillation from the product obtained in the third step, and obtain an enriched product of alkoxyglycerol.

所述第一步中,反应温度为30~60℃,反应时间为4~72h,所述短链醇的添加量为鲨鱼肝油质量的5%~100%,所述脂肪酶的添加量为鲨鱼肝油质量的1%~15%。In the first step, the reaction temperature is 30-60°C, the reaction time is 4-72h, the added amount of the short-chain alcohol is 5%-100% of the mass of shark liver oil, and the added amount of the lipase is shark liver oil. 1% to 15% of the mass of cod liver oil.

所述短链醇为碳原子为1~4个的一元醇,优选甲醇、乙醇、丙醇、正丁醇,进一步优选乙醇。The short-chain alcohol is a monohydric alcohol with 1 to 4 carbon atoms, preferably methanol, ethanol, propanol, n-butanol, more preferably ethanol.

在第一步中,所述短链醇的加入方式可以为一次性加入,也可以在搅拌过程中分批加入。In the first step, the short-chain alcohol can be added in one time or in batches during stirring.

所述脂肪酶的来源很广,可以通过微生物发酵生产,也可以从动物胰脏中提取,优选的脂肪酶为来源于酵母菌、霉菌或者动物胰脏的固定化或非固定化脂肪酶。The lipase has a wide range of sources and can be produced by microbial fermentation or extracted from animal pancreas. The preferred lipase is immobilized or non-immobilized lipase derived from yeast, mold or animal pancreas.

本发明以生物酶为催化剂,反应条件温和;由于脂肪酶对脂肪酸的选择性,使得短链的饱和脂肪酸及低不饱和度的脂肪酸优先与短链醇发生反应,在富集烷氧基甘油的同时起到富集n-3多不饱和脂肪酸的作用,反应过程避免使用大量的有毒、易挥发溶剂,而未反应的短链可通过减压蒸馏实现回收,整个工艺过程无固体和液体废弃物的排放。In the present invention, biological enzymes are used as catalysts, and the reaction conditions are mild; due to the selectivity of lipase to fatty acids, short-chain saturated fatty acids and fatty acids with low unsaturation are preferentially reacted with short-chain alcohols. At the same time, it plays the role of enriching n-3 polyunsaturated fatty acids. The reaction process avoids the use of a large amount of toxic and volatile solvents, and the unreacted short chains can be recovered by vacuum distillation. There is no solid or liquid waste in the whole process. emissions.

以下采用实施例来详细说明本发明的实施方式,借此对本发明如何应用技术手段来解决技术问题,并达成技术效果的实现过程能充分理解并据以实施。The following examples are used to describe the implementation of the present invention in detail, so as to fully understand and implement the process of how to apply technical means to solve technical problems and achieve technical effects in the present invention.

实施例1Example 1

称取含8%烷氧基甘油的天然鲨鱼肝油100g(EPA和DHA含量分别为4.13%和7.59%)于250mL反应器中,加入40g无水乙醇和固定化南极假丝酵母脂肪酶Lipozyme435(Novozymes公司提供)3.0g,加热至50℃并搅拌反应24h。反应结束后将反应混合物过滤,所得油状混合物经减压蒸馏(70℃、-0.088MPa的条件下)脱除未反应的乙醇,再经分子蒸馏(蒸馏温度150℃、蒸馏压强0.1Pa的条件下)脱除反应混合物中的脂肪酸乙酯,即得含20.59%烷氧基甘油的产物40g,产物中的EPA和DHA含量分别为7.72%和22.35%。Weigh 100 g of natural shark liver oil containing 8% alkoxyglycerol (EPA and DHA contents are 4.13% and 7.59%, respectively) in a 250 mL reactor, add 40 g of absolute ethanol and immobilized Candida antarctica lipase Lipozyme435 (Novozymes Provided by the company) 3.0g, heated to 50°C and stirred for 24h. After the reaction, the reaction mixture was filtered, and the resulting oily mixture was distilled under reduced pressure (70°C, -0.088MPa) to remove unreacted ethanol, and then molecularly distilled (distillation temperature 150°C, distillation pressure 0.1Pa) ) to remove the fatty acid ethyl ester in the reaction mixture to obtain 40 g of a product containing 20.59% alkoxyglycerol, and the contents of EPA and DHA in the product were 7.72% and 22.35%, respectively.

实施例2Example 2

称取含20%烷氧基甘油的鲨鱼肝油50g(EPA和DHA含量分别为0.93%和2.59%)与30g无水异丙醇混合搅拌预热至45℃,加入2.5g固定化脂肪酶Lipozyme TL IM(Novozymes公司提供),搅拌反应12h。反应结束后将反应混合物过滤,所得油状混合物经减压蒸馏(70℃、-0.088MPa的条件下)脱除未反应的异丙醇,再经分子蒸馏(蒸馏温度160℃、蒸馏压强0.1Pa的条件下)脱除反应混合物中的脂肪酸异丙醇酯,即可得到含36.62%烷氧基甘油的产物,其EPA和DHA的含量分别为1.34%和8.21%。Weigh 50g of shark liver oil containing 20% alkoxyglycerol (EPA and DHA contents are 0.93% and 2.59% respectively) and mix with 30g of anhydrous isopropanol, stir and preheat to 45°C, add 2.5g of immobilized lipase Lipozyme TL IM (provided by Novozymes), stirred for 12 hours. After the reaction, the reaction mixture was filtered, and the resulting oily mixture was distilled under reduced pressure (70°C, -0.088MPa) to remove unreacted isopropanol, and then molecularly distilled (distillation temperature 160°C, distillation pressure 0.1Pa) conditions) to remove the fatty acid isopropanol ester in the reaction mixture, the product containing 36.62% alkoxyglycerol can be obtained, and the contents of EPA and DHA are 1.34% and 8.21% respectively.

所有上述的首要实施这一知识产权,并没有设定限制其它形式的实施这种新产品和/或新方法。本领域技术人员将利用这一重要信息,上述内容修改,以实现类似的执行情况。但是,所有修改或改造基于本发明新产品属于保留的权利。All of the foregoing are primary implementations of this intellectual property and are not intended to limit other forms of implementation of this new product and/or new method. Those skilled in the art will, with this important information, modify the above to achieve a similar implementation. However, all modifications or alterations to the new product based on the present invention belong to reserved rights.

以上所述,仅是本发明的较佳实施例而已,并非是对本发明作其它形式的限制,任何熟悉本专业的技术人员可能利用上述揭示的技术内容加以变更或改型为等同变化的等效实施例。但是凡是未脱离本发明技术方案内容,依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与改型,仍属于本发明技术方案的保护范围。The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention to other forms. Any skilled person who is familiar with this profession may use the technical content disclosed above to change or modify the equivalent of equivalent changes. Example. However, any simple modifications, equivalent changes and modifications made to the above embodiments according to the technical essence of the present invention without departing from the content of the technical solution of the present invention still belong to the protection scope of the technical solution of the present invention.

Claims (10)

1. a method for AKGs in enrichment shark liver oil, is characterized in that: by by shark liver oil and short chain alcohol, lipase hybrid reaction, remove unreacted raw material and by product, obtain the product that contains the AKGs after enrichment.
2. the method for AKGs in enrichment shark liver oil as claimed in claim 1, is characterized in that, comprising:
The first step adds shark liver oil, short chain alcohol and lipase in reactor, stirs, and is heated to continue stirring reaction at certain temperature;
Second step, reacts the first step to after product and filters, and reclaims lipase solid;
The 3rd step, the product underpressure distillation after second step is filtered removes unreacted short chain alcohol;
The 4th step, the method that the product that the 3rd step is obtained adopts molecular distillation to remove removes the lipid acid-short chain alcohol ester by product generating in reaction process, obtains the enriched product of AKGs.
3. the method for AKGs in enrichment shark liver oil as claimed in claim 1 or 2, it is characterized in that: in the described the first step, temperature of reaction is 30~60 ℃, reaction times is 4~72h, the addition of described short chain alcohol is 5%~100% of shark liver oil quality, and the addition of described lipase is 1%~15% of shark liver oil quality.
4. the method for AKGs in the enrichment shark liver oil as described in claims 1 to 3, is characterized in that: described short chain alcohol is that carbon atom is the monohydroxy-alcohol of 1-4, particular methanol, ethanol, propyl alcohol, propyl carbinol, further preferred alcohol.
5. the method for AKGs in the enrichment shark liver oil as described in claim 1 to 4, is characterized in that: in the first step, the mode that adds of described short chain alcohol can add for disposable, also can in whipping process, add in batches.
6. the method for AKGs in the enrichment shark liver oil as described in claim 1 to 5, is characterized in that: described lipase is immobilization or the non-immobilized lipase that derives from yeast, mould or animal pancreas.
7. a method for AKGs in enrichment shark liver oil, is characterized in that, comprising:
The first step, in reactor, add shark liver oil, short chain alcohol and lipase, stir, be heated to stirring reaction 4~72h at the temperature of 30~60 ℃, the addition of described short chain alcohol is 5%~100% of shark liver oil quality, the addition of described lipase is 1%~15% of shark liver oil quality, and the mode that adds of described short chain alcohol can add for disposable, also can in whipping process, add in batches;
Second step, second step, reacts the first step to after product and filters, and removes unreacted lipase;
The 3rd step, the product underpressure distillation after second step is filtered removes unreacted short chain alcohol;
The 4th step, the method that the product that the 3rd step is obtained adopts molecular distillation to remove removes the lipid acid-short chain alcohol ester by product generating in reaction process, obtains the product that contains the AKGs after enrichment.
8. an AKGs, is characterized in that: described AKGs is prepared from by the following method,
The first step adds shark liver oil, short chain alcohol and lipase in reactor, stirs, and is heated to continue stirring reaction at certain temperature;
Second step, reacts the first step to after product and filters, and reclaims lipase solid;
The 3rd step, the product underpressure distillation after second step is filtered removes unreacted short chain alcohol;
The 4th step, the product that the 3rd step is obtained adopts the method for molecular distillation to remove the lipid acid-short chain alcohol ester by product generating in reaction process, obtains the enriched product of AKGs.
9. the application of the method for AKGs in preparing healthcare product in the enrichment shark liver oil described in claim 1 to 7.
10. a healthcare product, it comprises the product that contains the AKGs after enrichment that method is prepared from described in claim 1 to 7.
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CN110029133A (en) * 2019-03-12 2019-07-19 自然资源部第三海洋研究所 A kind of method of saturated fatty acid and unsaturated fatty acid in separation DHA algal oil
CN111662152A (en) * 2020-07-06 2020-09-15 浙江工商大学 Method for extracting squalene from crude shark liver oil
CN111848368A (en) * 2020-07-06 2020-10-30 浙江工商大学 Method for improving the purity of shark liver alcohol in shark liver oil

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CN102669661A (en) * 2012-05-07 2012-09-19 海南加华海产生物制药集团有限公司 Shark liver oil soft capsule and production method thereof

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CN1378846A (en) * 2002-03-22 2002-11-13 海南加华海产生物制药有限公司 Shark-liver oil softgel
CN102133231A (en) * 2011-03-23 2011-07-27 济南康麦国际贸易有限公司 Product prepared by shark cartilage for supplementing calcium and promoting metabolism and development of cartilage and preparation method thereof
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CN105132153B (en) * 2015-08-19 2019-06-14 威海博宇食品有限公司 A method of preparing squid liver oil
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CN111848368A (en) * 2020-07-06 2020-10-30 浙江工商大学 Method for improving the purity of shark liver alcohol in shark liver oil
CN111662152B (en) * 2020-07-06 2023-04-11 浙江工商大学 Method for extracting squalene from crude shark liver oil

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