CN113584093B - Preparation method of structured lipid with high DHA content and product thereof - Google Patents
Preparation method of structured lipid with high DHA content and product thereof Download PDFInfo
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- CN113584093B CN113584093B CN202110874662.1A CN202110874662A CN113584093B CN 113584093 B CN113584093 B CN 113584093B CN 202110874662 A CN202110874662 A CN 202110874662A CN 113584093 B CN113584093 B CN 113584093B
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6463—Glycerides obtained from glyceride producing microorganisms, e.g. single cell oil
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Abstract
The invention discloses a preparation method of structured lipid with high DHA content and a product thereof, which comprises the steps of cooling DHA grease to crystallize saturated triglyceride to form crystal nuclei, increasing the temperature, adding non-selective lipase or alkaline chemical catalyst to carry out ester exchange reaction, and crystallizing and separating saturated fatty acid from a reaction system in the form of saturated triglyceride by utilizing melting point difference to obtain the structured lipid product with high DHA content. Compared with products obtained by other enrichment technologies, the product has higher degree of unsaturation and lower DHA loss.
Description
Technical Field
The invention belongs to the technical field of grease, and particularly relates to a preparation method of structural lipid with high DHA content and a product thereof.
Background
Human milk contains small amounts of functional long chain polyunsaturated fatty acids (LC-PUFAs), such as docosahexaenoic acid (DHA, C22: 6n-3) and arachidonic acid (ARA, C20: 4n-6), which are of great physiological significance for infants. DHA is enriched in phospholipids in the retina and brain gray matter, accounting for 3-5% of the dry weight of the tissue, and is thus essential for the development of vision and brain in infants. In adults, DHA can be converted and synthesized by using alpha-linolenic acid (C18: 3n-3) as a precursor, but because of the low expression level of fatty acid chain elongases and desaturases in infants, the endogenous synthesis of long-chain polyunsaturated fatty acids is not sufficient to meet the growth and development requirements, and therefore infants need to supplement DHA by feeding. The latest literature indicates that the average level of DHA in the global breast milk is 0.37 ± 0.11% of total fatty acids, respectively.
When infants cannot obtain breast feeding, infant formula becomes a good substitute for breast milk. The infant formula milk powder is a breast milk substitute which is based on the existing cognition on breast milk and simulates the components and even the physical structure of the breast milk. However, breast milk is an extremely delicate and complex nutritional system, and its simulation is limited. As far as fat is concerned, the best product to date mimicking breast milk fat is human milk replacement fat, which has been widely reported over the past decades and commercialized by Loders Croklaan and Advanced Lipids companies. With the deepening of the cognition on breast milk and the development of nutritional knowledge, the trace lipids such as LC-PUFAs, DHA and ARA, etc., which have important physiological functions, are also receiving high attention. Currently, most commercial infant formulas have been formulated and supplemented according to the DHA and ARA content of the mother's milk.
The DHA source is mainly deep sea fish oil and single cell microorganism fermentation. With regard to sources of DHA for infant formulas, deep sea fish oil contains significant amounts of eicosapentaenoic acid (EPA, C20:5 n-3). EPA is a competitive inhibitor of ARA and, at high concentrations, preferentially enters the cellular phospholipid synthesis pathway and inhibits ARA phospholipid synthesis, thereby reducing the synthesis of ARA-containing eicosanoids such as prostaglandins, a phenomenon which inhibits neonatal growth. Therefore, the DHA additives used in the current formula are mainly derived from microbial oils and fats, and the strains include Crypthecodinium cohni, Schizochyttrum sp, and Ulkenia sp. These fats and oils are rich in DHA and contain little EPA. The DHA content of the grease produced by microbial fermentation is about 50%, and the content of saturated fatty acid is high. Therefore, the removal of saturated fatty acids in the grease and the improvement of the DHA content through a certain process are of great significance to the application of the grease containing DHA.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made keeping in mind the above and/or other problems occurring in the prior art.
The invention aims to provide a preparation method of structured lipid with high DHA content and a product thereof, wherein pre-crystallization and directional ester exchange are combined, saturated triglyceride in DHA grease forms crystal nuclei by reducing the temperature, then the temperature is properly increased, non-position selective lipase or alkaline catalyst is added for ester exchange reaction, the reaction balance of the ester exchange reaction is broken by utilizing melting point difference, saturated fatty acid in the grease is crystallized and separated out in the form of saturated triglyceride in the reaction process, and finally unsaturated fatty acid is directionally enriched, so that the DHA content in the product is improved.
In order to solve the technical problems, the invention provides the following technical scheme: a method for preparing structural lipid with high DHA content comprises,
and (2) cooling the DHA grease to crystallize saturated triglyceride to form crystal nuclei, raising the temperature, adding non-selective lipase or an alkaline chemical catalyst to perform an ester exchange reaction, and crystallizing and separating saturated fatty acid from a reaction system in the form of saturated triglyceride by utilizing the melting point difference to obtain a structured lipid product with high DHA content.
As a preferred embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: the DHA-containing microbial oil is one or more of microbial oils produced by fermenting microalgae such as Crypthecodinium cohni, Schizochytrium sp.
As a preferred embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: the method comprises the steps of cooling DHA grease to crystallize saturated triglyceride to form crystal nuclei, heating the microbial grease rich in DHA to 50-70 ℃, keeping the temperature for 15-45 min, then cooling the microbial grease to 10-18 ℃ at a speed of 5-15 ℃/h, and keeping the temperature for 2-4 h to crystallize the saturated triglyceride to form the crystal nuclei.
As a preferable embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: and raising the temperature by 20-25 ℃ at a speed of 2-5 ℃/h.
As a preferred embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: adding non-selective lipase to carry out ester exchange reaction, adding 8-12% of the non-selective lipase, reacting for 24-48 h, and stirring at a speed of 500-800 r/min.
As a preferable embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: the non-selective Lipase comprises Novozym 435 or Lipase AY-30 SD.
As a preferred embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: adding an alkaline chemical catalyst to perform an ester exchange reaction, adding 0.5-1.5% of the alkaline chemical catalyst, reacting for 24-48 h, stirring at a speed of 500-800 r/min, adding deionized water to stop the reaction after the reaction is finished, and washing with water to remove the alkaline chemical catalyst.
As a preferred embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: the basic chemical catalyst comprises sodium methoxide or sodium ethoxide.
As a preferable embodiment of the method for preparing the structured lipid with high DHA content of the present invention, wherein: crystallizing and separating out saturated fatty acid from a reaction system in a saturated triglyceride form by utilizing melting point difference, separating solid fat by adopting a low-temperature crystallization process after finishing an ester exchange reaction, reducing the temperature of the grease to 10-15 ℃ at the speed of 3-6 ℃/h, keeping the temperature for 5-10 h, and filtering or centrifugally separating the solid fat to obtain the liquid oil.
It is another object of the present invention to provide a product obtained by the method for preparing a structured lipid with high DHA content as described in any of the above.
Compared with the prior art, the invention has the following beneficial effects:
the palmitic acid is crystallized and separated out from a reaction system in the form of tripalmitin triglyceride by utilizing the melting point difference and the directional ester exchange technology, so that the unsaturated triglyceride is directionally enriched while the saturated triglyceride is enriched; saturated triglyceride crystallization needs the existence of crystal nucleus, through at first reducing the temperature of grease to lower degree, makes the saturated triglyceride in the grease form the crystal nucleus, is favorable to the crystallization enrichment of the saturated triglyceride that generates, suitably improves the temperature again to be favorable to promoting reaction efficiency, the product DHA content of obtaining is higher.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, embodiments accompanying the present invention are described in detail below with reference to examples.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1
DHA-rich algal oil from schizochytrim sp was selected as the starting material, the fatty acid composition of which is shown in table 1.
TABLE 1 fatty acid composition of DHA oils
| Fatty acid (mol%) | Content (c) of |
| C14:0 | 2.4 |
| C16:0 | 33.5 |
| C18:0 | 1.3 |
| C18:1 | 0.6 |
| C20:4 | 1.4 |
| C20:5 | 1.2 |
| C22:5 | 10.9 |
| C22:6 | 48.7 |
Adding microbial oil rich in DHA into a container, charging nitrogen, heating the oil to 60 ℃, keeping for 30min, reducing the temperature to 18 ℃ at 5 ℃/h, keeping for 2h, crystallizing saturated triglyceride therein to form crystal nuclei, heating the temperature to 25 ℃ at the speed of 2 ℃/h, adding 10% of non-position-selective lipase Novozym 435 into the mixture to perform oriented transesterification, wherein the reaction time is 24h, the stirring speed is 600 r/min, after the reaction is finished, centrifuging or filtering to separate the lipase, reducing the temperature to 13 ℃ at the speed of 3 ℃/h, keeping for 5h to crystallize, and finally separating solid fat by centrifuging or filtering to obtain liquid oil. The fatty acid composition of the resulting liquid oil is shown in table 2:
TABLE 2 fatty acid composition of the product after directional transesterification
Example 2
DHA-rich algal oil from Crypthecodinium cohnii was selected as the starting material, and the fatty acid composition is shown in table 3.
TABLE 3 fatty acid composition of DHA oils
| Fatty acid (mol%) | Content (wt.) |
| C14:0 | 15.5 |
| C16:0 | 17.1 |
| C18:0 | 12.1 |
| C18:1 | 0.97 |
| C22:5 | 0.2 |
| C22:6 | 52.3 |
Adding microbial oil rich in DHA into a container, charging nitrogen, heating the oil to 70 ℃, keeping for 15min, reducing the temperature to 15 ℃ at 15 ℃/h, keeping for 3h, crystallizing saturated triglyceride therein to form crystal nuclei, heating the temperature to 20 ℃ at the speed of 3 ℃/h, adding 12% of non-position-selective Lipase AY-30SD into the mixture to perform directional transesterification reaction for 36h, stirring at the speed of 500 r/min, centrifuging or filtering to separate Lipase after the reaction is finished, reducing the temperature to 15 ℃ at the speed of 5 ℃/h, keeping for 8h to crystallize, and finally centrifuging or filtering to separate solid fat to obtain liquid oil. The fatty acid composition of the resulting liquid oil is shown in table 4:
TABLE 4 fatty acid composition of the product after directional transesterification
| Fatty acid (mol%) | Content (wt.) |
| C14:0 | 7.22 |
| C16:0 | 8.50 |
| C18:0 | 4.33 |
| C18:1 | 1.22 |
| C22:5 | 1.01 |
| C22:6 | 77.73 |
Example 3
DHA-rich algal oil from Ulkenia sp. was selected as the starting material, the fatty acid composition of which is shown in table 5.
TABLE 5 fatty acid composition of DHA oils
| Fatty acid (mol%) | Content (wt.) |
| C14:0 | 2.4 |
| C16:0 | 37.2 |
| C18:0 | 0.8 |
| C20:4 | 0.4 |
| C20:5 | 0.6 |
| C22:5 | 10.6 |
| C22:6 | 46.2 |
Adding microbial oil rich in DHA into a container, charging nitrogen, heating the oil to 50 ℃, keeping for 45min, reducing the temperature to 12 ℃ at 10 ℃/h, keeping for 5h, crystallizing saturated triglyceride therein to form crystal nuclei, heating the temperature to 23 ℃ at the speed of 3 ℃/h, adding 8% of non-position-selective lipase Novozym 435 into the oil to perform directional ester exchange reaction for 48h at the stirring speed of 800 r/min, centrifuging or filtering to separate lipase after the reaction is finished, reducing the temperature to 10 ℃ at the speed of 6 ℃/h, keeping for 10h to crystallize, and finally centrifuging or filtering to separate solid fat to obtain liquid oil. The fatty acid composition of the resulting liquid oil is shown in table 6:
TABLE 6 fatty acid composition of the product after directional transesterification
| Fatty acid (mol%) | Content (wt.) |
| C14:0 | 1.00 |
| C16:0 | 5.80 |
| C18:0 | 0.50 |
| C20:4 | 2.16 |
| C20:5 | 1.82 |
| C22:5 | 15.75 |
| C22:6 | 72.14 |
Example 4
Firstly, adding DHA-rich algae oil from Schizochytrum sp into a container, filling nitrogen, heating the oil to 60 ℃, keeping the temperature for 30min, reducing the temperature to 18 ℃ at 5 ℃/h, keeping the temperature for 2h to crystallize saturated triglyceride therein to form crystal nuclei, heating the temperature to 25 ℃ at the speed of 2 ℃/h, adding 1% sodium ethoxide into the mixture to perform oriented transesterification reaction for 36h, stirring the mixture at the speed of 600 r/min, adding deionized water to stop the reaction after the reaction is finished, washing the mixture for three times to remove a catalyst, reducing the temperature to 13 ℃ at the speed of 3 ℃/h, keeping the reaction for 5h to crystallize, and finally separating solid fat by centrifugation or filtration to obtain liquid oil. The fatty acid composition of the resulting liquid oil is shown in table 7:
TABLE 7 fatty acid composition of the product after directional transesterification
| Fatty acid (mol%) | Content (c) of |
| C14:0 | 1.72 |
| C16:0 | 9.87 |
| C18:0 | 1.10 |
| C18:1 | 0.94 |
| C20:4 | 1.88 |
| C20:5 | 1.72 |
| C22:5 | 14.58 |
| C22:6 | 68.18 |
Example 5
Adding DHA-rich algal oil derived from Ulkenia sp into a container, charging nitrogen, heating the oil to 70 ℃, keeping for 15min, reducing the temperature to 15 ℃ at 15 ℃/h, keeping for 3h, crystallizing saturated triglyceride therein to form crystal nuclei, heating the temperature to 20 ℃ at the speed of 3 ℃/h, adding 0.5% sodium methoxide into the oil to perform directional transesterification reaction for 48h, stirring at the speed of 800 r/min, adding deionized water to stop the reaction after the reaction is finished, washing with water for three times to remove a catalyst, reducing the temperature to 15 ℃ at the speed of 5 ℃/h, keeping for 8h to crystallize, and finally separating solid fat by centrifugation or filtration to obtain liquid oil. The fatty acid composition of the resulting liquid oil is shown in table 8:
TABLE 8 fatty acid composition of the product after directional transesterification
Example 6
Adding DHA-rich microbial oil derived from Schizochytrium sp into a container, introducing nitrogen, heating the oil to 50 ℃, keeping for 45min, reducing the temperature to 12 ℃ at 10 ℃/h, keeping for 5h to crystallize saturated triglyceride therein to form crystal nuclei, heating the temperature to 23 ℃ at the speed of 3 ℃/h, adding 1.5% sodium ethoxide into the oil to perform oriented transesterification reaction for 24h, stirring at the speed of 400 r/min, adding deionized water to stop the reaction after the reaction is finished, washing with water for three times to remove a catalyst, reducing the temperature to 10 ℃ at the speed of 6 ℃/h, keeping for 10h to crystallize, and finally separating solid fat by centrifugation or filtration to obtain liquid oil. The fatty acid composition of the resulting liquid oil is shown in table 9:
TABLE 9 fatty acid composition of the product after directional transesterification
| Fatty acid (mol%) | Content (wt.) |
| C14:0 | 1.19 |
| C16:0 | 7.50 |
| C18:0 | 0.68 |
| C18:1 | 0.51 |
| C20:4 | 1.19 |
| C20:5 | 1.36 |
| C22:5 | 14.99 |
| C22:6 | 72.57 |
The transesterification reaction is a reversible reaction, and fatty acids on triglyceride are randomly arranged under the action of a catalyst to form the triglyceride. In the reaction process, the saturated triglyceride generated in the reaction process is crystallized and separated from the reaction system by utilizing the difference of melting points, so that the reaction balance is broken, the reaction is continuously carried out towards the direction of generating the saturated triglyceride, and finally the unsaturated triglyceride is enriched. However, the crystallization of saturated triglyceride requires the existence of crystal nuclei, the formation temperature of triglyceride crystal nuclei is far lower than the melting point temperature, but the lower the temperature is, the slower the reaction speed is, and therefore, the improvement of the reaction efficiency is facilitated by lowering the temperature in advance to nucleate the saturated triglyceride and raising the temperature appropriately.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.
Claims (3)
1. A preparation method of structural lipid with high DHA content is characterized by comprising the following steps: comprises the steps of (a) preparing a mixture of a plurality of raw materials,
heating the microbial oil rich in DHA to 50-70 ℃, keeping the temperature for 15-45 min, reducing the temperature to 10-18 ℃ at a speed of 5-15 ℃/h, and keeping the temperature for 2-4 h to crystallize saturated triglyceride therein to form crystal nuclei; the microbial oil containing DHA is obtained by microalgaeCrypthecodinium cohnii、Schizochytruim sp.AndUlkenia sp.one or more of microbial oils produced by fermentation;
then raising the temperature, and raising the temperature by 20-25 ℃ at the speed of 2-5 ℃/h;
adding non-position selective lipase or alkaline chemical catalyst, performing ester exchange reaction, and crystallizing and separating out saturated fatty acid from the reaction system in the form of saturated triglyceride by using melting point difference to obtain a structural lipid product with high DHA content;
adding non-position-selective lipase for ester exchange reaction, adding 8-12% of non-position-selective lipase, reacting for 24-48 h, and stirring at 500-800 r/min;
adding an alkaline chemical catalyst to perform an ester exchange reaction, adding 0.5-1.5% of the alkaline chemical catalyst, reacting for 24-48 h, stirring at a speed of 500-800 r/min, adding deionized water to terminate the reaction after the reaction is finished, and washing with water to remove the alkaline chemical catalyst;
crystallizing and separating out saturated fatty acid from a reaction system in a saturated triglyceride form by utilizing melting point difference, separating solid fat by adopting a low-temperature crystallization process after finishing an ester exchange reaction, reducing the temperature of the grease to 10-15 ℃ at the speed of 3-6 ℃/h, keeping the temperature for 5-10 h, and filtering or centrifugally separating the solid fat to obtain the liquid oil.
2. A method for preparing structural lipids with high DHA content according to claim 1, wherein: the non-position selective Lipase comprises Novozym 435 or Lipase AY-30 SD.
3. The method for preparing structured lipids with high DHA content according to claim 1, wherein: the basic chemical catalyst comprises sodium methoxide or sodium ethoxide.
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