CN109880858A - A kind of method of free fatty acid content in reduction marine phospholipids - Google Patents
A kind of method of free fatty acid content in reduction marine phospholipids Download PDFInfo
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- CN109880858A CN109880858A CN201910204089.6A CN201910204089A CN109880858A CN 109880858 A CN109880858 A CN 109880858A CN 201910204089 A CN201910204089 A CN 201910204089A CN 109880858 A CN109880858 A CN 109880858A
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- marine phospholipids
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Abstract
The invention discloses a kind of methods of free fatty acid content in reduction marine phospholipids.The method of free fatty acid content in the reduction marine phospholipids includes the steps that converting phosphatide for the free polyunsaturated fatty acid containing there are three and more than three double bonds in thick marine phospholipids.The method of free fatty acid content in the reduction marine phospholipids, content of phospholipid is improved while reducing acid value, and also assure the content of the polyunsaturated fatty acids such as EPA, DHA, reduce the loss of the ingredients such as liposoluble vitamin, separating degree is high, and the structure of phosphatide will not be destroyed, improve the quality of product.
Description
Technical field
The present invention relates to a kind of methods of free fatty acid content in reduction marine phospholipids.
Background technique
Domestic and international numerous studies confirm marine phospholipids in adjuvant therapy of heart cerebrovascular diseases, diabetes, reduction arthritis
Shape alleviates premenstrual syndrome and dysmenorrhea, anti-oxidant etc. with safe and reliable effect, sends out in functional nutrient food industries
There is good development prospect in terms of exhibition.Studies have shown that marine phospholipids eicosapentaenoic acid rich in (EPA) He Ershi bis-
The n-3 polyunsaturated fatty acids and VitAVitE abundant, astaxanthin etc. such as carbon acid (DHA) it is fat-soluble at
Point, wherein the multi-pass such as EPA and DHA cross chemical bond in conjunction with phosphatide.Influence in view of freshness of raw material to product quality, general thick sea
The content of free fatty acid is higher in foreign phosphatide, and acid value needs further mostly at 10mg/g or more (even as high as 60mg/g)
Removing this part free fatty acid just can be used as raw-food material.
At present in oil prodution industry, the removal methods of free fatty acid are mainly include the following types: (1) neutralizes depickling method: should
Method is while free fatty acid is in using sodium hydroxide and in grease to reduce acid value, will cause in marine phospholipids phosphatide and
The sodium soap that the saponification of glyceride, neutralization reaction and saponification generate can be such that reaction system emulsifies as emulsifier,
Cause water-oil separating difficult.(2) molecularly distilled: this method realizes object by different material molecular tools difference
Matter separation, but usually molecular distillation temperature is higher (mostly at 160 DEG C or more), the knot of lasting high temperature destructible functionality phosphatide
Structure is not suitable for the depickling of marine phospholipids.(3) supercritical fluid extraction depickling method: although this method has certain effect, but set
Standby investment is big, process costs are high, and liposoluble vitamin in marine phospholipids, shrimp can be also removed while removing free fatty acid
The ingredients such as green element and triglycerides.(4) Dalian Polytechnic University Zhou great Yong etc. develops the acid stripping method of acetone solvent, though this method
The free fatty acid content in marine phospholipids so can also be effectively reduced, but it is raw equally to remove the fat-soluble dimension in marine phospholipids
Element, astaxanthin and triglycerides ingredient cause the loss of marine phospholipids mobility variation and nutritional ingredient.In addition, due to ocean
Also contain a certain amount of EPA and DHA in the free fatty acid of phosphatide, above-mentioned various acid stripping methods also result in n-3 how unsaturated
The loss of fatty acid.
Summary of the invention
In order to compensate for the shortcomings of the prior art, the present invention provides free fatty acid contents in a kind of reduction marine phospholipids
Method uses urea adduct method tentatively to remove the saturated fatty acid and low unsaturated fat to dissociate in thick marine phospholipids first
Acid, then phosphatide is converted to by phosphatidase or lipase-catalyzed free polyunsaturated fatty acid and generation ester synthesis reaction, it is dropping
Content of phospholipid is improved while low acid value, improves the quality of product, reduces the loss late of product.
The present invention is achieved through the following technical solutions:
A kind of method of free fatty acid content in reduction marine phospholipids, the method includes dissociating in marine phospholipids
Containing there are three and three double bonds more than polyunsaturated fatty acid be converted into phosphatide the step of.
The polyunsaturated fatty acid is converted into phosphatide by reacting with glycerophosphoryl substance, the glycerophosphoryl
Substance is any one in glyceryl phosphoryl choline, glycerophosphoryl inositol, glycerophosphorylethanolamine or glycerophosphoryl serine
Or it is several.
The operating procedure of the reaction are as follows: thick marine phospholipids are first dissolved in the first solvent, qs glycerin phosphinylidyne is then added
Choline and enzyme preparation catalyst are uniformly mixed, and are reacted, remove the first solvent and enzyme preparation catalyst after reaction, obtain
Marine phospholipids product.
Preferably, first solvent be n-hexane, chloroform, methylene chloride, the tert-butyl alcohol, ether, ethyl acetate or
Any one or a few in petroleum ether.
Preferably, the enzyme preparation catalyst is phosphatidase or lipase, including but not limited to phospholipase A1, phosphatidase
A2, and from antarctic candida, rhizomucor miehei, Rhizopus arrhizus lipase.
Preferably, the additive amount of glycerophosphoryl substance is the 10%-50% of marine phospholipids quality, and enzyme preparation catalyst adds
Dosage is the 5%-20% of marine phospholipids quality, and the first amount of solvent is 1-10 times of marine phospholipids quality, and the reaction time is
2-12h, reaction temperature are 30-70 DEG C.
After being reacted in order to avoid saturated fatty acid, low unsaturated fatty acid and the glyceryl phosphoryl choline etc. in thick marine phospholipids
Leading to the content of EPA, DHA reduces, it is preferable that the method for reducing free fatty acid content in marine phospholipids further includes in ester
The step of carrying out depickling to marine phospholipids before synthetic reaction, depickling removing is mainly the saturated fat to dissociate in marine phospholipids
Acid, the low unsaturated fatty acid containing one or two double bond.
The method of depickling is urea adduct method, specific steps are as follows:
Urea, marine phospholipids are dissolved in the second solvent at the first temperature by a certain percentage, obtain the first mixed solution,
First mixed solution is cooled to second temperature, precipitated urea crystallization is then demultiplex out urea crystals, obtains the second mixed solution,
The second solvent in the second mixed solution is removed, the marine phospholipids of preliminary depickling are obtained；
For the marine phospholipids purified as far as possible, after removing the second solvent in the second mixed solution, by what is obtained
Marine phospholipids are then demultiplex out urea crystals, the second solvent of removing, obtain depickling again by further precipitated urea crystallization is concentrated
The second marine phospholipids.
Preferably, the mass ratio of the second solvent and urea, marine phospholipids is 10:(0.1-2): (0.1-4), the second solvent are
Volumetric concentration is the methanol or ethyl alcohol of 70%-100%, and the first temperature is 70 DEG C -80 DEG C, and second temperature is 20 DEG C or less.
Advantageous effects of the invention:
The method of free fatty acid content in reduction marine phospholipids provided by the invention, by phosphatidase or lipase-catalyzed
Free polyunsaturated fatty acid and glyceryl phosphoryl choline, oily phosphinylidyne inositol, glycerophosphorylethanolamine or glycerophosphoryl serine
Ester synthesis reaction occurs and is converted into phosphatide, also improves content of phospholipid while reducing product acid value.
After being reacted in order to avoid saturated fatty acid, low unsaturated fatty acid and the glyceryl phosphoryl choline etc. in thick marine phospholipids
Leading to the content of EPA, DHA reduces, before ester synthesis reaction using urea adduct method tentatively remove in thick marine phospholipids dissociate
Saturated fatty acid and low unsaturated fatty acid, during urea clathrate, straight chain or close to straight chain saturated fatty acid and it is low not
Saturated fatty acid, which is easily accessible in urea crystal pipeline, to be formed urea inclusion and crystallizes out from solution, and more more of double bond
Monounsaturated fatty acid molecule volume is larger, it is difficult to enters in crystal pipeline, it can be by saturated fatty acid and low unsaturated fatty acid
Removing.
The method of the present invention such as improves content of phospholipid, and also assures EPA, DHA at more insatiable hungers while reducing acid value
With the content of fatty acid, reduce the loss of the ingredients such as liposoluble vitamin, separating degree is high, and will not destroy the knot of phosphatide
Structure improves the quality of product.
Specific embodiment:
Below with reference to embodiment, the invention will be further described, but the present invention is not limited thereto, the system in embodiment
Preparation Method is customary preparation methods, is no longer described in detail.
Embodiment 1:
Weigh 40g catfish lecithin (acid value 42.1mg/g, content of phospholipid 70.1%), 70% ethyl alcohol of 100g and 20g
Nitrogen charging hermetic seal after urea mixing, is completely dissolved in 70 DEG C of heating water bath magnetic agitations, obtains homogeneous and transparent mixed liquor；It should
Mixed liquor, which is placed in 5 DEG C of cold baths, makes mixeding liquid temperature be reduced to 20 DEG C or less and precipitated urea crystallization, filters or is centrifuged later
Obtain clear marine phospholipids ethanol solution；Marine phospholipids ethanol solution is concentrated into the 30% of original volume under vacuum conditions,
And filter or be centrifuged again and obtain clear marine phospholipids ethyl alcohol concentrate, ethyl alcohol is removed later obtains the sea for tentatively reducing acid value
Foreign phosphatide is 12.4mg/g through detection acid value.
It takes the preliminary marine phospholipids 10g for reducing acid value to be dissolved in the 50g tert-butyl alcohol and is preheated to 60 DEG C, antarctic candida is added
4h is reacted in nitrogen-filled seal after lipase B 1.0g and glyceryl phosphoryl choline 1.0g, is centrifuged off lipase, t-butanol solution later
The tert-butyl alcohol is removed through vacuum distillation, finally obtains the marine phospholipids product that acid value is 1.2mg/g, through detecting, content of phospholipid is
98.42%.
Embodiment 2:
Weigh 1g catfish lecithin (acid value 42.1mg/g, content of phospholipid 70.1%), 100% ethyl alcohol of 100g and 1g
Nitrogen charging hermetic seal after urea mixing, is completely dissolved in 80 DEG C of heating water bath magnetic agitations, obtains homogeneous and transparent mixed liquor；It should
Mixed liquor, which is placed in 5 DEG C of cold baths, makes mixeding liquid temperature be reduced to 20 DEG C or less and precipitated urea crystallization, filters or is centrifuged later
Obtain clear marine phospholipids ethanol solution；Marine phospholipids ethanol solution is concentrated into the 30% of original volume under vacuum conditions,
And filter or be centrifuged again and obtain clear marine phospholipids ethyl alcohol concentrate, ethyl alcohol is removed later obtains the sea for tentatively reducing acid value
Foreign phosphatide is 16.5mg/g through detection acid value.
It takes the preliminary marine phospholipids 10g for reducing acid value to be dissolved in the 100g tert-butyl alcohol and is preheated to 70 DEG C, phospholipase A1 is added
12h is reacted in nitrogen-filled seal after 2.0g and glycerophosphoryl inositol 2.0g, is centrifuged off lipase later, and t-butanol solution is steamed through decompression
The removing tert-butyl alcohol is evaporated, the marine phospholipids product that acid value is 4.9mg/g, through detecting, content of phospholipid 95.33% are finally obtained.
Embodiment 3:
Weigh 20g catfish lecithin (acid value 42.1mg/g, content of phospholipid 70.1%), 95% ethyl alcohol of 100g and 5g
Nitrogen charging hermetic seal after urea mixing, is completely dissolved in 80 DEG C of heating water bath magnetic agitations, obtains homogeneous and transparent mixed liquor；It should
Mixed liquor, which is placed in 5 DEG C of cold baths, makes mixeding liquid temperature be reduced to 20 DEG C or less and precipitated urea crystallization, filters or is centrifuged later
Obtain clear marine phospholipids ethanol solution；Marine phospholipids ethanol solution is concentrated into the 30% of original volume under vacuum conditions,
And filter or be centrifuged again and obtain clear marine phospholipids ethyl alcohol concentrate, ethyl alcohol is removed later obtains the sea for tentatively reducing acid value
Foreign phosphatide is 7.4mg/g through detection acid value.
It takes the preliminary marine phospholipids 10g for reducing acid value to be dissolved in 100g n-hexane and is preheated to 50 DEG C, phospholipase A2 is added
12h is reacted in nitrogen-filled seal after 0.5g and glycerophosphorylethanolamine 2.0g, is centrifuged off lipase later, t-butanol solution is through depressurizing
The distillation removing tert-butyl alcohol, finally obtains the marine phospholipids product that acid value is 2.2mg/g, through detecting, content of phospholipid 97.81%.
Embodiment 4:
Weigh 30g catfish lecithin (acid value 42.1mg/g, content of phospholipid 70.1%), 95% ethyl alcohol of 100g and 10g
Nitrogen charging hermetic seal after urea mixing, is completely dissolved in 80 DEG C of heating water bath magnetic agitations, obtains homogeneous and transparent mixed liquor；It should
Mixed liquor, which is placed in 5 DEG C of cold baths, makes mixeding liquid temperature be reduced to 20 DEG C or less and precipitated urea crystallization, filters or is centrifuged later
Obtain clear marine phospholipids ethanol solution；Marine phospholipids ethanol solution is concentrated into the 30% of original volume under vacuum conditions,
And filter or be centrifuged again and obtain clear marine phospholipids ethyl alcohol concentrate, ethyl alcohol is removed later obtains the sea for tentatively reducing acid value
Foreign phospholipid prod is 9.2mg/g through detection acid value.
It takes the preliminary marine phospholipids 10g for reducing acid value to be dissolved in 100g and is preheated to 50 DEG C, phospholipase A2 2.0g and sweet is added
12h is reacted in nitrogen-filled seal after oily phosphinylidyne serine 2.0g, is centrifuged off lipase later, and t-butanol solution is removed through vacuum distillation
The tert-butyl alcohol finally obtains the marine phospholipids product that acid value is 2.2mg/g, through detecting, content of phospholipid 98.01%.
Finally it should be noted that embodiment is the optimal specific embodiment of the present invention, it is not limited to this
Invention, although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, according to
It is so possible to modify the technical solutions described in the foregoing embodiments, or part of technical characteristic is equally replaced
It changes.All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in the present invention
Protection scope within.
Claims (10)
1. a kind of method for reducing free fatty acid content in marine phospholipids, characterized in that the method includes by marine phospholipids
In dissociate containing there are three and three double bonds more than polyunsaturated fatty acid be converted into phosphatide the step of.
2. the method according to claim 1 for reducing free fatty acid content in marine phospholipids, characterized in that more than described not
Saturated fatty acid is converted into phosphatide by reacting with glycerophosphoryl substance, and the glycerophosphoryl substance is glycerophosphoryl
Any one or a few in choline, glycerophosphoryl inositol, glycerophosphorylethanolamine or glycerophosphoryl serine.
3. the method according to claim 2 for reducing free fatty acid content in marine phospholipids, characterized in that the reaction
Operating procedure are as follows: thick marine phospholipids are first dissolved in the first solvent, qs glycerin phosphinylidyne substance and enzyme preparation is then added and urges
Agent is uniformly mixed, and is reacted, removes the first solvent and enzyme preparation catalyst after reaction, obtains marine phospholipids product.
4. the method according to claim 3 for reducing free fatty acid content in marine phospholipids, characterized in that described first
Solvent be n-hexane, chloroform, methylene chloride, the tert-butyl alcohol, ether, ethyl acetate or petroleum ether in any one or it is several
Kind.
5. the method according to claim 3 for reducing free fatty acid content in marine phospholipids, characterized in that the enzyme system
Agent catalyst is phosphatidase or lipase, including but not limited to phospholipase A1, phospholipase A2, and derives from South Pole vacation silk ferment
Mother, rhizomucor miehei, Rhizopus arrhizus lipase.
6. the method according to claim 3 for reducing free fatty acid content in marine phospholipids, characterized in that glycerophosphoryl
The additive amount of substance is the 10%-50% of marine phospholipids quality, and enzyme preparation catalyst loading is marine phospholipids quality
5%-20%, the first amount of solvent are 1-10 times, reaction time 2-12h, reaction temperature 30-70 of marine phospholipids quality
℃。
7. it is according to claim 2 reduce marine phospholipids in free fatty acid content method, characterized in that further include
The step of depickling is carried out to marine phospholipids before ester synthesis reaction.
8. the method according to claim 7 for reducing free fatty acid content in marine phospholipids, characterized in that the side of depickling
Method is urea adduct method, step are as follows:
Urea, marine phospholipids are dissolved in the second solvent at the first temperature by a certain percentage, obtain the first mixed solution, by
One mixed solution is cooled to second temperature, and precipitated urea crystallization is then demultiplex out urea crystals, obtains the second mixed solution, removes
The second solvent in second mixed solution, obtains the marine phospholipids of depickling.
9. the method according to claim 8 for reducing free fatty acid content in marine phospholipids, characterized in that removing second
The marine phospholipids that are obtained after the second solvent in mixed solution by concentration precipitated urea crystallization, be then demultiplex out urea crystals,
The second solvent is removed, the second marine phospholipids of depickling again are obtained.
10. the method according to claim 8 for reducing free fatty acid content in marine phospholipids, characterized in that second is molten
The mass ratio of agent and urea, marine phospholipids is 10:(0.1-2): (0.1-4), the second solvent are that volumetric concentration is 70%-100%
Methanol or ethyl alcohol, the first temperature be 70 DEG C -80 DEG C, second temperature be 20 DEG C or less.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111334369A (en) * | 2020-03-11 | 2020-06-26 | 陕西科技大学 | Method for preparing lecithin type PUFA by enzyme method |
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