CN105506008A - Preparation method for monoglyceride rich in omega-3 fatty acid - Google Patents
Preparation method for monoglyceride rich in omega-3 fatty acid Download PDFInfo
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- CN105506008A CN105506008A CN201510874165.6A CN201510874165A CN105506008A CN 105506008 A CN105506008 A CN 105506008A CN 201510874165 A CN201510874165 A CN 201510874165A CN 105506008 A CN105506008 A CN 105506008A
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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 relates to a preparation method for monoglyceride rich in omega-3 fatty acid. The preparation method comprises the following steps: taking an organic solvent as an extraction agent to extract algae oil; adding hexane and silica gel into a chromatographic column, and then adding the algae oil into the chromatographic column to obtain triacylglycerol; mixing triacylglycerol and ethanol, and meanwhile adding immobilized lipase A-CALA and a little water for reaction to obtain a monoglyceride crude product rich in omega-3 fatty acid; mixing the monoglyceride crude product with food-grade n-hexane according to proportion, conducting extraction for 3 times, collecting an ethanol phase, and conducting rotary evaporation to remove ethanol and water to obtain purified monoglyceride rich in omega-3 fatty acid. Through the adoption of the process condition, the total content of omega-3 fatty acid in monoglyceride after enzymic catalytic reaction can reach 90% or above.
Description
Technical field
The present invention relates to a kind of preparation method being rich in omega-fatty acid Tegin 55G.
Background technology
Tegin 55G (monoacylglycerols, MAGs) is the apolar substance that a class has hydrophobic grouping and hydrophilic radical, and its output accounts for 50% of state's internal emulsifying agent ultimate production.MAGs, as emulsifying agent, has been widely used in the fields such as food, pharmacy, makeup.The exploitation Tegin 55G that is rich in omega-fatty acid is one of the popular direction in current research and development modified grease field as emulsifying agent or additive application to the research of field of food.As everyone knows, omega-fatty acid (as SDA(18:4n-3), EPA(20:5n-3) and DHA(22:6n-3) be the necessary lipid acid of human body, they have promote infant growth, strengthen body immunity, the biological function of the aspect such as antitumor, preventing apoplectic and gout.Current, production technology mainly chemical catalysis and the enzyme catalysis method of Tegin 55G.Although chemical catalysis is that main production has the method for the Tegin 55G of saturated fatty acid at present, there is low cost and advantage in short-term, under high temperature, easily cause the oxidation of oil, and then produce the phenomenon such as by product, look change.Produce Tegin 55G by chemical method and there is the high shortcoming of fusing point, directly affects the application of Tegin 55G.The Tegin 55G that omega-fatty acid is rich in enzyme catalysis preparation has the advantages such as efficient, single-minded, reaction conditions is gentle, by product is few, recycling enzyme, will be the one preferred technique being applied to suitability for industrialized production.The developed country such as American-European, Japanese to maintain the leading position (CamilaA.Palla in the research of oil modification and industrial applications thereof always
etal, 2014; Aditya
etal, 2014; LalitMohanNegi
etal, 2014).In recent years, pilot scale level has been entered into, as (Alicia.R such as Alicia.R to developing the research of being rich in the Tegin 55G of omega-fatty acid abroad
etal, 2012) people utilize Novi to believe the fish oil preparation of 435 enzyme alcoholysis catfish livers can reach the 2-Tegin 55G of 20-25% (wt%=60-75mol%), its omega-fatty acid content can reach 35.5%, is mainly used in sweet three fat of development functionality and substitutes infant's butter fat.At Feltes(FeltesM.M.C
etal, 2013) review paper in point out, utilize fish oil exploitation to be rich in the Tegin 55G of omega-fatty acid and sweet two fat are applied to field of food, there is broad mass market prospect.Subsequently, ZhengGuo team of Aarhus, Denmark university (Angela
etal, 2016) and research and utilization Novi believes that 435 enzyme catalysis sardines fish oil and glycerine carry out glycerolysis reaction and prepares containing 31.7%(wt%) Tegin 55G of omega-fatty acid, be successfully amplified to pilot scale level.And the domestic research to this aspect is in blank temporarily.Therefore, the functional Tegin 55G that omega-fatty acid is rich in research and development is applied to the field such as food, pharmacy, has great importance.
Be rich in edible oil mainly fish oil and the marine microalgae algae oil of omega-fatty acid.In recent years, culture fishery consumes the fish oil in the whole world 83%, and the direct edible fish oil of the mankind only accounts for 6% of total amount.In June, 2015, the price that FAOGlobefish has disclosed fish oil is 2400/ton, fish oil price is high compared with last year 300/ton; In addition, in the first half of the year in this year, China is import 25.3 ten thousand tons of fish oil, to meet domestic market demand.The fish oil of high price and the factor of dependence on import directly constrain the functional Tegin 55G that omega-fatty acid is rich in exploitation.Based on marine food chain angle analysis, ocean fish enrichment omega-fatty acid is mainly from the marine microalgae being rich in omega-fatty acid.To a certain extent, the alternative fish oil development functionality Tegin 55G of algae oil being rich in omega-fatty acid is feasible; And 2009, EU Committee's (file: Decisions2009/777) approved schizochytrium algae oil can be used as foodstuff additive.Therefore, utilize the functional Tegin 55G of the algae oil exploitation high nutritive value being rich in ω-3, this technology can be solved and face oil sources problem.
Developed country's development functionality Tegin 55G also faces how to screen and has that specificity is strong, catalytic efficiency is high and the lipase of environmental protection.Commercial lipase conventional at present has nonselective immobilized lipase (e.g., Novozyme435, CALA etc.) and 1,3 optionally enzyme (as TLIM, RMIM, AK-20 etc.).As stated above, utilize Tegin 55G prepared by the enzyme catalysiss such as Novozyme435, total omega-fatty acid content of the equal or a little higher than raw material fish oil of its omega-fatty acid total content.Finding and have the hydrolysis saturated fatty acid of edible oil and the lipase of monounsaturated fatty acids, is the difficult problem that the Tegin 55G technology of ω-3 lipase is rich in current exploitation.2011, professor XuebingXu of Aarhus, Denmark university studied the biological marking discovery of CALA lipase: in ethanol condition, 8 carbochains of this enzyme energy hydrolysate oil and oleic acid; But they do not utilize this enzyme alcoholysis fish oil development functionality Tegin 55G further.
Summary of the invention
Object of the present invention is exactly the algae oil being rich in omega-fatty acid is raw material, utilizes environmental protection, Tegin 55G that omega-fatty acid is rich in enzyme catalysis method preparation efficiently.
For realizing technical scheme that object of the present invention adopts and step is:
1, algae oil extracts.Take a certain amount of micro-algae powder, using organic solvent as extraction agent, utilize accelerated solvent extraction to extract algae oil, extraction temperature is 40 ~ 125 DEG C, extraction time 25 ~ 120min, and extraction times is 2 ~ 5 times.After extraction terminates, extraction liquid is placed in vacuum rotary evaporator organic dissolution to be evaporated, after evaporation, gained residuum is algae oil.
Organic solvent of the present invention refers to chloroform, normal hexane, ethanol or methyl alcohol.
Add organic solvent in micro-algae powder of the present invention, its ratio is micro-algae powder (g): organic solvent (mL)=1:15 ~ 35.
2, triacylglycerol is separated.Chromatographic column adds hexane, adds 80g silica gel simultaneously, and the algae oil then step 1 obtained joins in chromatographic column;
Be separated and remove the grease of non-polar component with 500mL normal hexane-ether elution chromatography post, wherein normal hexane: the volume ratio of ether is 90:5;
The triacylglycerol obtaining and be rich in omega-fatty acid is separated, wherein normal hexane: the volume ratio of ether is 90:10 with 1000mL normal hexane-ether elution chromatography post;
3, the synthesis of the Tegin 55G of omega-fatty acid is rich in.
The triacylglycerol of said extracted is mixed with ethanol, adds immobilized lipase A-CALA and little water carries out the Tegin 55G crude product that alcoholysis reaction obtains being rich in omega-fatty acid simultaneously.Alcoholysis reaction condition is: the consumption of mass ratio 1:1 ~ 4 of triacylglycerol and ethanol, temperature of reaction 25 ~ 55 DEG C, immobilized lipase A-CALA account for Tegin 55G quality 5 ~ 12.5%, amount of water account for the total mass of Tegin 55G and ethanol 2 ~ 9%, the reaction times is 10h ~ 48h, stirring velocity 500r/min.
Described immobilized lipase A-CALA is purchased from Novozymes Company of Denmark.
4, the purifying of the Tegin 55G of omega-fatty acid is rich in.
The reaction product Tegin 55G crude product being rich in omega-fatty acid step 3 obtained mixes with the parts by volume ratio of food grade normal hexane according to 1:9, through 3 extractions, collect ethanol phase, the Tegin 55G being rich in omega-fatty acid after rotary evaporation obtains purifying after removing second alcohol and water.
Adopt the processing condition described in patent of the present invention, after enzymic catalytic reaction, in Tegin 55G, the total content of omega-fatty acid can reach more than 90%.
Embodiment
Embodiment 1
1, algae oil is extracted.Take 10g Nannochloropsis oceanica algae powder, add 350mL normal hexane: the mixed solution of ethanol (1:2, v/v), utilize accelerated solvent extraction to extract algae oil, extraction conditions is: temperature 75 DEG C, extraction time 50min, re-extract 3 times.After extraction terminates, extracting solution is placed in vacuum rotary evaporator by normal hexane, ethanol evaporation, after evaporation, gained residuum is algae oil.
2, heterogeneity algae oil separating.Chromatographic column adds hexane, adds 80g silica gel simultaneously, and the algae oil then step 1 obtained joins in chromatographic column;
The grease removing non-polar component is separated, wherein normal hexane: the volume ratio of ether is 90:5 with 500mL normal hexane-ether elution chromatography post;
Be separated with 1000mL normal hexane-ether elution chromatography post and obtain triacylglycerol, wherein normal hexane: the volume ratio of ether is 90:10.
3, the synthesis of the Tegin 55G of omega-fatty acid is rich in.The triacylglycerol of the algae oil of said extracted is utilized to mix with ethanol, add immobilized lipase A-CALA and little water simultaneously and carry out the Tegin 55G that omega-fatty acid is rich in alcoholysis reaction preparation, reaction conditions is: the consumption of the mass ratio 1:3 of triacylglycerol and ethanol, temperature of reaction 35 DEG C, immobilized lipase A-CALA account for triacylglycerol quality 12.5%, amount of water account for the total mass of Tegin 55G and ethanol 6%, under reaction times 46h, stirring velocity 500r/min condition reaction preparation be rich in the Tegin 55G crude product of omega-fatty acid.
Described lipase (immobilized lipase A-CALA) is purchased from Novozymes Company of Denmark.
4, the purifying of the Tegin 55G of omega-fatty acid is rich in.
Above-mentioned reaction product and food grade normal hexane (1:9, v/v) are mixed, through 3 extractions, each extraction time 50min, collects ethanol phase, obtains the Tegin 55G being rich in omega-fatty acid after rotary evaporation removes second alcohol and water.
Adopt the processing condition described in patent of the present invention, after enzymic catalytic reaction, in Tegin 55G, the total content of omega-fatty acid can reach 92%.
Embodiment 2
1, algae oil is extracted.Take 10g Isochrysis galbana algae powder, add 200mL normal hexane: the mixed solution of methyl alcohol (1:2, v/v), utilize accelerated solvent extraction to extract algae oil, extraction conditions is: temperature is 75 DEG C, and extraction time is 45min, repeats extraction 5 times.After extraction terminates, extracting solution is placed in vacuum rotary evaporator organic dissolution to be evaporated, after evaporation, gained residuum is algae oil.
2, heterogeneity algae oil separating.Chromatographic column adds hexane, adds 80g silica gel simultaneously, and the algae oil then step 1 obtained joins in chromatographic column;
The grease of non-polar component is removed, wherein normal hexane: the volume ratio of ether is 90:5 with 500mL normal hexane-ether elution chromatography post;
Be separated with 1000mL normal hexane-ether elution chromatography post and obtain triacylglycerol crude product, wherein normal hexane: the volume ratio of ether is 90:10.
3, the synthesis of the triacylglycerol crude product of omega-fatty acid is rich in.Utilize the triacylglycerol of the algae oil of above-mentioned extraction and ethanol to carry out alcoholysis reaction and prepare the Tegin 55G crude product being rich in omega-fatty acid; Reaction conditions is: the mass ratio of triacylglycerol and ethanol is 1:4, temperature of reaction is 30 DEG C, the consumption of immobilized lipase A-CALA accounts for triacylglycerol quality 12.5%, amount of water account for the total mass of Tegin 55G and ethanol 5%, the reaction times be under 40h, stirring velocity 500r/min condition reaction prepare the Tegin 55G being rich in omega-fatty acid.
Described lipase (immobilized lipase A-CALA) is purchased from Novozymes Company of Denmark.
4, the purifying of the Tegin 55G of omega-fatty acid is rich in.
Above-mentioned reaction product and food grade normal hexane (1:9, v/v) are extracted 3 times, collects ethanol phase, each extraction time 50min, collect ethanol phase, after rotary evaporation removes second alcohol and water, obtain the Tegin 55G being rich in omega-fatty acid.
Adopt the processing condition described in patent of the present invention, after enzymic catalytic reaction, in Tegin 55G, the total content of omega-fatty acid can reach 90%.
Claims (7)
1. be rich in a preparation method for omega-fatty acid Tegin 55G, it is characterized in that:
Take a certain amount of micro-algae powder, using organic solvent as extraction agent, utilize accelerated solvent extraction to extract algae oil, after extraction terminates, extraction liquid is placed in vacuum rotary evaporator and organic dissolution is evaporated, residuum is algae oil;
Chromatographic column adds hexane, adds 80g silica gel simultaneously, and the algae oil then step 1 obtained joins in chromatographic column;
Be separated with 500mL normal hexane-ether elution chromatography post and remove the grease of non-polar component; The triacylglycerol obtaining and be rich in omega-fatty acid is separated, wherein normal hexane: the volume ratio of ether is 90:10 with 1000mL normal hexane-ether elution chromatography post;
The triacylglycerol of said extracted is mixed with ethanol, adds immobilized lipase A-CALA and little water carries out the Tegin 55G crude product that alcoholysis reaction obtains being rich in omega-fatty acid simultaneously;
The reaction product Tegin 55G crude product being rich in omega-fatty acid obtained is mixed with food grade normal hexane, through 3 extractions, collects ethanol phase, the Tegin 55G being rich in omega-fatty acid after rotary evaporation obtains purifying after removing second alcohol and water.
2. according to claim 1ly a kind ofly adopt lipase-catalyzed legal system for the method for structure glyceryl ester, it is characterized in that described extraction conditions, extraction temperature is 40 ~ 125 DEG C, extraction time 25 ~ 120min, and extraction times is 2 ~ 5 times.
3. a kind of preparation method being rich in omega-fatty acid Tegin 55G according to claim 1, is characterized in that described organic solvent refers to chloroform, normal hexane, ethanol or methyl alcohol.
4. a kind of preparation method being rich in omega-fatty acid Tegin 55G according to claim 1, it is characterized in that adding organic solvent in described micro-algae powder, its ratio is micro-algae powder (g): organic solvent (ml)=1:15 ~ 35.
5. a kind of preparation method being rich in omega-fatty acid Tegin 55G according to claim 1, is characterized in that the dose volume of normal hexane-ether in described step 2 than being 90:5.
6. a kind of preparation method being rich in omega-fatty acid Tegin 55G according to claim 1, it is characterized in that the alcoholysis described in step 3), reaction conditions is: the consumption of mass ratio 1:1 ~ 4 of triacylglycerol and ethanol, temperature of reaction 25 ~ 55 DEG C, immobilized lipase A-CALA account for Tegin 55G quality 5 ~ 12.5%, amount of water account for the total mass of Tegin 55G and ethanol 2 ~ 9%, the reaction times is 10h ~ 48h, stirring velocity 500r/min.
7. a kind of preparation method being rich in omega-fatty acid Tegin 55G according to claim 1, it is characterized in that the Tegin 55G crude product described in step 4) mixes with food grade normal hexane, is the carrying out according to Tegin 55G crude product and food grade normal hexane parts by volume ratio 1:9.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108486177A (en) * | 2018-02-12 | 2018-09-04 | 广州富诺健康科技股份有限公司 | A method of it is prepared using algae oil and is rich in omega-fatty acid phosphatide |
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| US20130084272A1 (en) * | 2011-09-29 | 2013-04-04 | Philippe Perrin | Compositions, kits and methods for nutritional supplementation with twelve carbon chain fatty acids and twelve carbon chain acylglycerols |
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2015
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Patent Citations (4)
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| WO2006046943A2 (en) * | 2004-10-22 | 2006-05-04 | Martek Biosciences Corporation | Methods for producing lipids by liberation from biomass |
| CN102046801A (en) * | 2008-04-07 | 2011-05-04 | 诺维信公司 | Method for producing monounsaturated glycerides |
| US20130084272A1 (en) * | 2011-09-29 | 2013-04-04 | Philippe Perrin | Compositions, kits and methods for nutritional supplementation with twelve carbon chain fatty acids and twelve carbon chain acylglycerols |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108486177A (en) * | 2018-02-12 | 2018-09-04 | 广州富诺健康科技股份有限公司 | A method of it is prepared using algae oil and is rich in omega-fatty acid phosphatide |
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Application publication date: 20160420 |