CN103667379A - Method for preparing breast milk fat substitute through lipase-catalyzed acidolysis of algae oil - Google Patents
Method for preparing breast milk fat substitute through lipase-catalyzed acidolysis of algae oil Download PDFInfo
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Abstract
The invention discloses a method for preparing a breast milk fat substitute through lipase-catalyzed acidolysis of algae oil. According to the method, the triglyceride-rich algae oil and oleic acid are mixed and catalyzed by lipase to be subjected to acidolysis so as to synthesize the breast milk fat substitute suitable for direct usage by infants; the mixing mass ratio of the algae oil to the oleic acid is in a range of 1:1-1:9; the mass ratio of the lipase in a reaction system is in a range of 3%-12%; the reaction temperature is in a range of 25-90 DEG C; and the reaction time is in a range of 0.5 h-10 h. Most breast milk fat substitutes used in China at the present stage depend on imports, and the method is beneficial to domestic large-scale production and development, so that the import pressure is reduced. Compared with breast milk fat substitutes prepared from traditional raw materials, the method has the advantages that the algae oil which is safe in source and easy to obtain is used for preparing the breast milk fat substitute, the substitute is rich in polyunsaturated fatty acid such as DPA (docosapentaenoic acid) and DHA (docosahexaenoic acid), and the substitute is more beneficial to growth and development of the infants.
Description
Technical field
The invention belongs to technical field of biochemical industry, be specifically related to a kind of method that lipase-catalyzed algae oil source triglyceride level transesterification is prepared into the human milk fat substituted product of high nutritive value.
Background technology
Function should be extremely similar with natural human milk fat for the human milk fat substituted product of high-quality (Human milk fat substitute, HMFS).As everyone knows, infant's enteron aisle is the nutrition transhipment station growing, and required nutrient digestion, the absorption of its growth and development all relies on healthy intestinal function.The formula milk that adds HMFS, fat mols structure changes, and can effectively reduce the possibility that calcium soap occurs, thus softening stool reduces the obstructed probability that constipation even occurs of infant's enteron aisle; Reduce nutrient loss, effectively improve infant for absorption and the utilization of the mineral substance such as energy and calcium; Promote skeleton development, can effectively reduce calcium soap and form, do not affect the absorption of calcium, calcium is fully precipitated in bone, thereby better support infant physique and bone naturally to grow up.Therefore, the chemical structure of HMFS and lipid acid composition are the important factors that affects baby formula milk powder trophic function.
At present, the raw material of the HMFS of synthetic mainly contains the mixing of following one or more greases and prepares: the one, derive from the grease in animal, as lard, fish oil and butter fat; The 2nd, derive from plant, as plam oil, high oleic sunflower oil, Canola Oil, soybean oil, palm kernel oil, Oleum Cocois, the multiple oil plant of safflower wet goods.It is synthetic that synthetic method mainly contains physical mixed method, chemical catalysis and enzyme process.Wherein, under lipase-catalyzed, these two kinds of techniques of the transesterification reaction of compound lard, grease and mixed fatty acid transesterification reaction are due to selectivity and high efficiency and the recommended utilization of its height.
By above-mentioned sorting technique, the Study on Preparation present situation of HMFS is as follows: (1) patent CN102229866A discloses a kind ofly take lard as raw material, through except after cholesterol with oleic acid at Sn-1, under 3 specific lipase effects, prepare OPO; (2) patent CN101940241A discloses a kind of with Mekong Delta catfish grease and application and prepare the method for HMFS; (3) patent US5,601,860 disclose and a kind of plam oil and soybean oil are in harmonious proportion and prepare the method for HMFS; (4) patent EP0376628 be take vegetables oil as raw material, with the random transesterify preparation of chemical catalyst; (5) patent CN102776077A, US4876107, US5658768, EP0496456 and WO1994/268551 disclose and take the method for common vegetables oil (as plam oil, soybean wet goods) as the synthetic HMFS of raw material and fatty acid ester exchange.To sum up, these starting material sources are often subject to all many-sided restrictions, and nutritive value is also very different; Preparation process is loaded down with trivial details, and unsaturated fatty acids is oxidizable, and production cost is high; The Humanistic Factors such as country variant, area, nationality and culture background affect outwardness.
The algae oil in pure natural source is loved by the people, and is rich in nutritious polyunsaturated fatty acid (European Journal of Lipid Science and Technology, 2013,115 (9): 965-976).Wherein, in fragmentation kettle algae (Schizochytrium sp.) and dino flagellate (Crypthecodinium cohnii) oil, contain abundant docosahexenoic acid (Docosahexaenoic acid, DHA), clupanodonic acid (Docosapentenoic acid, the omega-3 unsaturated fatty acid such as DPA), content is up to more than 50%.DHA, is commonly called as " DHA (docosahexaenoic acid) ", is the fundamental element that nervous system cell is grown and maintained, and is brain and amphiblestroid important composition composition.DHA can only be transformed by alpha-linolenic acid in human body, or directly obtains from food.At present oil-rich microalgae can be cultivated at large scale fermentation under manual control condition, and the algae oil of separated preparation is safe and reliable, pollution-free, be of high nutritive value, without features such as the extra DHA of interpolation, is the desirable glyceride stock of preparation HMFS.But, the own characteristic that algae oil forms and distributes due to lipid acid in its triglyceride level, its sn-1,3 contain a certain amount of palmitinic acid, unfavorable to growing of infant, can not directly be used as HFMS, need to build efficiently, low consumption, timesaving preparation technology.So far, have no report using easily obtaining, the algae oil of edible safety is as the directed synthetic HMFS of material, enzyme method acidolysis.
In recent years, low-temperature microwave technology (Bioresource Technology, 2010,101 (13): 4851-4861) with micro-fluidic reactor technology (Nature, 2006,442 (7101): 368-373), because microwave and microreactor have larger impact to enzymic activity, be better than the reinforcing effect of traditional batch formula reactor to enzyme, research and application in biocatalysis and biosynthesizing field are subject to extensive concern day by day.Compare with traditional reactor, microwave field reinforced and efficient heat transfer and mass transfer microreactor impel enzymatic reaction efficiently to carry out, and have greatly improved the space-time yield of target product, (the Bioresource Technology that shortened the reaction times, 2013,149 (0): 367-374).In addition, microreactor can pass through to increase quantity or the length of reactor microchannel, thereby realizes the technique amplification of mass-producing and serialization.Yet low-temperature microwave technology and microreactor technology are in the directional transformation of enzyme law catalysis natural fats and oils, there is not relevant report preparation HMFS aspect.Therefore, the present invention in enzymatic algae oil preparation HMFS, is applied to by microwave and microreactor technology the HMFS that DHA is rich in preparation in batch reactor.
The object of the invention is to, the problems referred to above that exist for existing HMFS for infant formula and preparation method thereof, provide a kind of method of being prepared by algae oil enzyme process to HMFS.Adopt based on the synthetic HMFS of enzymatic algae oleic acid solution have be of high nutritive value, safe and reliable and without features such as the extra DHA of interpolation, and technological operation is easy, can obviously improve algae oil triglyceride level Sn-1, the content distribution of 3 unsaturated fatty acidss.The more important thing is; low-temperature microwave technology and microreactor technology are applied to enzymatic transesterification is combined in HMFS; the HMFS for preparing algae oil source for mass-producing from now on provides fundamental basis and technical support, for the production domesticization of external monopolization product, improve the resource utilization of oil-rich microalgae, the industrial chain of extending China's dairy industry has positive practical guided significance.
Summary of the invention
The technical problem solving: the associated problem that the present invention is directed to existing HMFS for infant formula and preparation method thereof, take oil-rich microalgae as raw material, provide a kind of lipase-catalyzed algae oil source triglyceride level transesterification to be prepared into form with human milk fat approach, the method for the DHA type HMFS of high nutritive value, Sn-1 in selective enrichment triglyceride level, the content of the unsaturated fatty acidss such as 3 upper DHA, the HMFS preparing need not additionally add DHA again.
Technical scheme: the method for the human milk fat substituted product of a kind of fatty enzymatic acidolysis algae oil preparation, step is:
1) in algae powder, extract the algae oil that is rich in triglyceride level: microalgae powder raw material is cleaned, after oven dry, algae powder is carried out to solvent extraction method, and adopt ultrasonic wave auxiliary, power is 200W, then pass through underpressure distillation, then centrifugal, the crude fat obtaining dewaters, then refining, the algae that must be rich in triglyceride level is oily;
2) the synthetic human milk fat substituted product of lipase-catalyzed algae oleic acid solution: the algae oil that is rich in triglyceride level that step 1) is obtained is that substrate carries out enzyme process transesterification reaction at lipase-catalyzed lower and lipid acid, described algae oil with lipid acid mixing quality than being 1:1～1:9; The mass ratio that lipase accounts for reaction system is 3%～12%; Temperature of reaction is 25～90 ℃; Reaction times is 0.5h～10h.After transesterification reaction, through underpressure distillation, isolate the resulting grease of reaction refining, obtain human milk fat substituted thing.
Described solvent is ether, ethanol, propyl carbinol, acetone, normal hexane, hexanaphthene, sherwood oil, chloroform, ethyl acetate or butylacetate.
Described micro-algae kind is schizochytrium limacinum (Schizochytrium sp.), dino flagellate (Crypthecodinium cohnii), chlorella (Chorella spp.).
Described lipase is Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, Lipase SP435, Lipase SP382, Candida rugosa lipase, Lipase MC7, Lipozyme TL IM, Novozym435, Candida antarctica lipase B, R275A lipase or porcine pancreatic lipase.
Described lipid acid is oleic acid.
Beneficial effect: the present invention adopts sn-1,3 specific fat enzyme catalysis algae oil & fat acid cuts are to synthetic HMFS.Because the palmitic acid content on algae oil triglyceride level sn-2 position is relatively high, the palmitic acid content on the sn-2 position in reacting final product is also relatively high, can guarantee with natural human milk fat on sn-2 position palmitic acid content suitable, reach more than 40%.Meanwhile, algae oil triglyceride level sn-1, is rich in DPA and DHA on 3, and this human milk fat substituted produce product add in formula milk, do not need extra add free DPA and DHA again.The more important thing is; low-temperature microwave technology and microreactor technology are applied to enzymatic transesterification is combined in HMFS; the HMFS for preparing algae oil source for mass-producing from now on provides fundamental basis and technical support, for the production domesticization of external monopolization product, improve the resource utilization of oil-rich microalgae, the industrial chain of extending China's dairy industry has positive practical guided significance.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
The qualitative and quantitative analysis of lipid acid adopts high resolution gas chromatography.Condition is: Agilent6820 gas chromatograph, chromatographic column model HP-INNOWAX length is 30m, internal diameter is 0.25 μ m, adopt gradient increased temperature mode, 80 ℃ of initial temperatures, 250 ℃ of post case top temperatures, 250 ℃ of rear injection port top temperatures, 280 ℃ of rear detector top temperatures, amount to 43min, and sample size is 1 μ L.
Wherein, in product, yield method of calculation are:
Embodiment 1:
The process of triglyceride level in micro-algae is extracted in the present embodiment explanation.
Dried algae powder is mixed with solvent ether, under ultrasonic (200W) subsidiary conditions, heat lixiviate 0.5h, suction filtration slagging-off, underpressure distillation obtains crude fat at 45 ℃, dewaters after centrifugal, and final purification, obtains the triglyceride level of algae oil.
After esterification, through gas chromatographic detection.In algae oil, contain lauric acid (Lauric acid, C
14:0) and palmitinic acid (Palmitic acid, C
16:0) saturated fatty acid (Saturated fatty acid, SFA), be respectively 5.5% and 19.1%; In addition unsaturated fatty acids (Unsaturated fatty acids, USFA) oleic acid (Oleic acid, C,
18:1), linolic acid (Linoleic acid, C
18:2), DPA(Docosapentenoic acid, C
22:5) and DHA(Docosahexaenoic Acid, C
22:6) content be respectively 19.9%, 1.6%, 16.1% and 36.4%.
Solvent can also be ethanol, propyl carbinol, acetone, normal hexane, hexanaphthene, sherwood oil, chloroform, ethyl acetate or butylacetate
Refining described in the embodiment of the present invention adopts mature technology, and concrete steps comprise: come unstuck, depickling, decolouring and deodorization.The algae oil (being rich in triglyceride level) that this embodiment prepares will be for following examples.
Embodiment 2:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 2.82g oleic acid (1:1 mol ratio), add 0.37g(3% substrate weight) Sn-1,3 specific lipase Lipozyme RM IM, temperature of reaction is 90 ℃, the reaction times is 10h.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively the band of scraping Sn-2 position Tegin 55G and sweet three esters.Add 2mL normal hexane and 2mL0.5MKOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content (Sn-2 position FA content is that on sn-2 position, this FA accounts for the total content of this FA of triglyceride level) is in Table 1.
Table 1.Sn-1, each fatty acid content of prosposition
Embodiment 3:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 14.1g oleic acid (1:5 mole), add 2.1g(9% substrate weight) Sn-1,3 specific lipase LipozymeRMIM, temperature of reaction is 65 ℃, the reaction times is 3h.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 2.
Table 2.Sn-1, each fatty acid content of prosposition
Embodiment 4:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), add 1.26g(7% substrate weight) Sn-1,3 specific lipase Lipozyme RM IM, temperature of reaction is 65 ℃, the reaction times is 3h.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 3.
Table 3.Sn-1, each fatty acid content of prosposition
Embodiment 5:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), add 1.26g(7% substrate weight) Sn-1,3 specific lipase Lipozyme RM IM, temperature of reaction is 65 ℃, microwave reinforced power is 10W, time 10min.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 4.
Table 4.Sn-1, each fatty acid content of prosposition
Embodiment 6:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), add 1.26g(7% substrate weight) Sn-1,3 specific lipase Lipozyme RM IM, temperature of reaction is 65 ℃, microwave reinforced power is 800W, time 5min.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 5.
Table 5.Sn-1, each fatty acid content of prosposition
Embodiment 7:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), add 1.26g(7% substrate weight) Sn-1,3 specific lipase Lipozyme RM IM, temperature of reaction is 65 ℃, microwave reinforced power is 80W, time 20min.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 6.
Table 6.Sn-1, each fatty acid content of prosposition
Embodiment 8:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), by 60mg Sn-1,3 specific lipase Lipozyme RM IM are immobilized in long 5cm filling bed type microreactor, and temperature of reaction is 65 ℃, time 2.5h.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 7.
Table 7.Sn-1, each fatty acid content of prosposition
Embodiment 9:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), by 240mg Sn-1,3 specific lipase Lipozyme RM IM are immobilized in long 20cm filling bed type microreactor, temperature of reaction is 65 ℃, and reaction 2.5h can reach the effect of 5h in popular response device.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 8.
Table 8.Sn-1, each fatty acid content of prosposition
Embodiment 10:
The present embodiment explanation is with the process of lipase-catalyzed algae oil (being rich in triglyceride level) and oleic acid ester permutoid reaction.
Refining algae oil (content of triglyceride 98%) 9.5g and 8.47g oleic acid (1:3 mol ratio), by 60mg Sn-1,3 specific lipase Lipozyme RM IM are immobilized in long 5cm filling bed type microreactor, and temperature of reaction is 65 ℃, time 2.5h.
Reaction finishes rear taking-up 300 μ L, adds 50mg porcine pancreatic lipase hydrolysis 5min, by extracted with diethyl ether, gets organic layer and carries out thin-layer chromatography, respectively scraping Sn-2 position Tegin 55G and sweet three ester bands.Add 2mL normal hexane and 2mL0.5M KOH-methanol solution to react 30min in 65 ℃ of shaking baths, carry out esterification, then carry out gas chromatographic detection, Sn-1, prosposition fatty acid content is in Table 9.
Table 9.Sn-1, each fatty acid content of prosposition
Before and after table 10. reaction, algae oil total fatty acids and Sn-2 position lipid acid form and human milk fat contrast
A: China Dairy Industry, 2009,37 (8): 41-44
Note: the corresponding embodiment 1 of algae oil before reaction in table 10, the corresponding embodiment 5 of algae oil after reaction.Wherein sn-2 position lipid acid is the ratio that each lipid acid of sn-2 position accounts for sn-2 position total fatty acids.
HMFS prepared by table 11. present method and GB require contrast
| Content of triglyceride (%) | GB requirement | DHA type HMFS |
| Sn-2 position palmitinic acid accounts for the ratio of all palmitinic acids | ≥52 | ≥54 |
| UPU(U unsaturated fatty acids, P saturated fatty acid) | ≥40 | ≥41 |
| Palmitinic acid triglyceride level | ﹤10 | ﹤5 |
Note: described in table 11 specifically data from embodiment 5.
Claims (5)
1. fatty enzymatic acidolysis algae oil is prepared a method for human milk fat substituted product, it is characterized in that step is:
1) in algae powder, extract the algae oil that is rich in triglyceride level: microalgae powder raw material is cleaned, after oven dry, algae powder is carried out to solvent extraction method, and adopt ultrasonic wave auxiliary, power is 200W, then pass through underpressure distillation, then centrifugal, the crude fat obtaining dewaters, then refining, the algae that must be rich in triglyceride level is oily;
2) the synthetic human milk fat substituted product of lipase-catalyzed algae oleic acid solution: the algae oil that is rich in triglyceride level that step 1) is obtained is that substrate carries out enzyme process transesterification reaction at lipase-catalyzed lower and lipid acid, described algae oil with lipid acid mixing quality than being 1:1～1:9; The mass ratio that lipase accounts for reaction system is 3%～12%; Temperature of reaction is 25～90 ℃; Reaction times is 0.5h～10h.After transesterification reaction, through underpressure distillation, isolate the resulting grease of reaction refining, obtain human milk fat substituted thing.
2. the method for the human milk fat substituted product of a kind of fatty enzymatic acidolysis algae oil preparation according to claim 1, is characterized in that described solvent is ether, ethanol, propyl carbinol, acetone, normal hexane, hexanaphthene, sherwood oil, chloroform, ethyl acetate or butylacetate.
3. the method for the human milk fat substituted product of a kind of fatty enzymatic acidolysis algae oil preparation according to claim 1, is characterized in that described micro-algae kind is schizochytrium limacinum (Schizochytrium sp.), dino flagellate (Crypthecodinium cohnii) or chlorella (Chorella spp.).
4. the method for the human milk fat substituted product of a kind of fatty enzymatic acidolysis algae oil preparation according to claim 1, is characterized in that described lipase is Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, Lipase SP435, Lipase SP382, Candida rugosa lipase, Lipase MC7, Lipozyme TL IM, Novozym435, Candida antarctica lipase B, R275A lipase or porcine pancreatic lipase.
5. the method for the human milk fat substituted product of a kind of fatty enzymatic acidolysis algae oil preparation according to claim 1, is characterized in that described lipid acid is oleic acid.
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| CN104186701A (en) * | 2014-07-31 | 2014-12-10 | 江南大学 | Preparation method of human milk substitute fat based on triglyceride composition and evaluating method of human milk substitute fat |
| CN104855542A (en) * | 2015-05-06 | 2015-08-26 | 江南大学 | Preparation method of human milk alternative fat combining enzymatic acidolysis and physical mixing |
| CN105219811A (en) * | 2015-08-25 | 2016-01-06 | 江苏科技大学 | In a kind of microwave, enzymatic mixed fatty acid synthesizes human milk fat substituted product and preparation method thereof |
| CN108018320A (en) * | 2017-12-11 | 2018-05-11 | 中国科学院水生生物研究所 | A kind of method for the GLA being enriched with using immobilized lipase in algae oil |
| CN114774485A (en) * | 2022-03-23 | 2022-07-22 | 青岛海智源生命科技有限公司 | Production method of DHA algae oil rich in Sn-2-position palmitic acid |
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| CN104186701A (en) * | 2014-07-31 | 2014-12-10 | 江南大学 | Preparation method of human milk substitute fat based on triglyceride composition and evaluating method of human milk substitute fat |
| CN104855542A (en) * | 2015-05-06 | 2015-08-26 | 江南大学 | Preparation method of human milk alternative fat combining enzymatic acidolysis and physical mixing |
| CN104855542B (en) * | 2015-05-06 | 2018-10-30 | 江南大学 | The human milk of a kind of combination enzyme process acidolysis and physical mixed substitutes the preparation method of fat |
| CN105219811A (en) * | 2015-08-25 | 2016-01-06 | 江苏科技大学 | In a kind of microwave, enzymatic mixed fatty acid synthesizes human milk fat substituted product and preparation method thereof |
| CN105219811B (en) * | 2015-08-25 | 2019-01-18 | 江苏科技大学 | Enzymatic fatty acid mixed synthesizes human milk fat substituted product and preparation method thereof in a kind of microwave |
| CN108018320A (en) * | 2017-12-11 | 2018-05-11 | 中国科学院水生生物研究所 | A kind of method for the GLA being enriched with using immobilized lipase in algae oil |
| CN108018320B (en) * | 2017-12-11 | 2020-12-15 | 中国科学院水生生物研究所 | Method for enriching GLA in algae oil by using immobilized lipase |
| CN114774485A (en) * | 2022-03-23 | 2022-07-22 | 青岛海智源生命科技有限公司 | Production method of DHA algae oil rich in Sn-2-position palmitic acid |
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