CN106588542A - Plant squalene concentrated solution and preparation method thereof - Google Patents
Plant squalene concentrated solution and preparation method thereof Download PDFInfo
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- CN106588542A CN106588542A CN201611224934.9A CN201611224934A CN106588542A CN 106588542 A CN106588542 A CN 106588542A CN 201611224934 A CN201611224934 A CN 201611224934A CN 106588542 A CN106588542 A CN 106588542A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
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Abstract
The invention discloses a plant squalene concentrated solution and a preparation method thereof. The preparation method comprises the following steps: (1) liquid-liquid extraction: preparing a settled solution in a ratio of a raw material (acid value-free oil, wherein vitamin E and phytosterol are separated and extracted from a deodorizing distillate of plant oil): an extraction agent a (m/v)=1: (1-3), then adding an extraction agent b for extraction, severely shaking the solution at room temperature and leaving the solution to stand to layer; washing the extraction agent a layer till an aqueous phase is free of obvious turbidity, and dehydrating an organic phase for later use to obtain an extraction agent a-squalene solution; and (2) activated carbon adsorption: adding activated carbon into the extraction agent a-squalene solution in the step (1), stirring the solution at room temperature, filtering the solution and distilling the solution at a reduced pressure to remove the solvent to obtain the plant squalene concentrated solution. The preparation method disclosed by the invention is mild in process condition and environmental-friendly, and obtains a squalene concentrated solution product with relatively low cost and energy consumption on the premise of ensuring the treatment capacity and the yield, wherein the content of squalene reaches 75-90%.
Description
Technical field
The present invention relates to biomedicine technical field, more particularly to a kind of plant squalene concentrated solution and preparation method thereof.
Background technology
Squalene (Squalene) is a kind of lipid non-saponifiable matter, and molecular formula is C30H50, chemical name 2,6,10,15,
19,23- hexamethyl -2, the alkene of 6,10,14,18,22- tetracosa carbon six is a kind of highly undersaturated straight chain triterpenoid compound.
Squalene is a kind of colourless or slightly yellow transparent oily liquid, is soluble in normal hexane, ether, petroleum ether, acetone and carbon tetrachloride,
Slightly soluble ethanol, it is water insoluble.Due to the activity of Squalene it is higher, it is oxidizable, need to add appropriate antioxidant when stored.
Squalene is the precursor of sterol in all cells, is a kind of very important functional grease, is resisted with extremely strong
Oxidation, effect of scavenging radical.Squalene has the function of carrying oxygen of similar erythrocyte, is combined with oxygen in body and generates activation
Oxygen closes Squalene, and the transport in blood circulation discharges oxygen to after body cell of termination, promotes the biology in body metabolism
Oxidation-reduction reaction, so as to increase Utilization ability of the histiocyte to oxygen, improves tolerance of the body to anoxia, prevent because
Anoxia and the generation of various diseases that causes.Meanwhile, Squalene has infiltration, diffusion and bactericidal action, human body skin secretions
In Squalene and sterol can safeguard that skin emolliency is lubricious.Additionally, research shows Squalene to hypertension, diabetes, coronary heart disease
And cancer has therapeutical effect, general hepatic is better than to hepatitis B negative conversion rate.Especially Squalene have resist purple
The function of outside line injury, thus be often largely used in skin care item.
Squalene is mainly the extraction from the liver oil of deepwater shark.As deepwater shark quantity is gradually reduced, part
Species are endangered, and this source is increasingly deficient, in short supply, so the new Squalene of searching is originated and developed obtaining accordingly
Method just seems extremely important.It has now been found that, Squalene is widely present in animals and plants, microorganism or marine microalgae body.
Due to plant squalene wide material sources and cheap, therefore research emphasis are gradually turned to plant by researcher.
There are various Squalene extraction processes with plant origin as raw material at present, respectively there is feature, but in some defects, it is main
There is the following aspects：
(patent publication No. CN102089263A) " deodorization distillate and/or physics of vegetable oil of French Sophim
The extracting method of contained Squalene, sterol and Vitamin E in refine condensate ", University Of Tianjin's (patent publication No.
CN101830770A " method that Squalene is extracted from plant oil deodorizing distillate ") and Xi'an Guo Bang Industrial Co., Ltd.s
(patent publication No. CN204022706U) " a kind of natural low content Vitamin E concentrated solution is the system that raw material extracts Squalene " is main
Will be by boiling point difference, using rectification or the Methods For Purification Squalene of molecular distillation, its shortcoming is mainly under hot conditionss easily
Cause the oxidation of Squalene；
A kind of " side for preparing Squalene as raw material with Nicotiana tabacum L. of Agricultural University Of South China's (patent publication No. CN102161611A)
" a kind of level chromatography method extracts plant oil deodorizing distillate for method ", HeFei University of Technology's (patent publication No. CN103708992A)
The method of middle Squalene ", Analysis and Measurements Center, Chinese Academy of Tropical Agriculture Sciences's (patent publication No. CN101417916A) " Semnostachya menglaensis H. P. Tsui
Tea Squalene and preparation method thereof " and Guangxi Normal University (patent publication No. CN1670005A) " plant squalene and its system
Squalene separation means involved in Preparation Method " mainly according to the polarity difference of heterogeneity in raw material, using silica gel (or oxygen
Change aluminum) the Methods For Purification Squalene of column chromatography, its shortcoming is mainly that quantity of sample handling is little, solvent usage amount is big, single batch is time-consuming
Long, energy consumption is larger；
Nanjing University of Technology's (patent publication No. CN104086348A) " a kind of technique of complex extractions Squalene " is according to angle
Multiple double bonds in zamene molecule self character can with silver ion formed complex so as to by it from raw material separating-purifying, its lack
Point is silver nitrate as precious metal chemical complex, and expensive cost limits its commercial application；
Tianjin profit hundred million gives birth to medical and health Science and Technology Co., Ltd.'s (patent publication No. CN103804337A) " multi-stage countercurrent
Liquid-liquid extraction method extracts the new technology of Vitamin E and Squalene " can be by the larger VE of different polarities and Squalene by continuous
The method of extraction is separated, but cannot separate the other impurities similar to Squalene polarity.
The content of the invention
The technical problem to be solved is to overcome the shortcomings of background technology, there is provided one kind is by simple liquid-liquid
The technique that mode of the extraction in combination with activated carbon static adsorption prepares plant squalene concentrated solution.Present invention process is at guarantee
On the premise of reason amount and yield, using relatively low cost and energy consumption the higher Squalene concentrated solution of content is obtained.
The technical problem to be solved is also resided in and overcomes the shortcomings of background technology, there is provided said method is obtained to plant
Object angle zamene concentrated solution.Squalene content is up to 75～90% in Squalene that the present invention is prepared concentration liquid product.
The technical scheme that present invention solution above-mentioned technical problem is adopted is as follows：
A kind of preparation method of plant squalene concentrated solution, comprises the steps：
(1) liquid-liquid extraction：By raw material (plant oil deodorizing distillate separation and Extraction go out Vitamin E and plant sterol after nothing
Acid value oil)：Extractant a (m/v)=1:1～3 is made into settled solution, adds extractant b and is extracted, and room temperature is acutely after concussion
Stratification, extractant a layers are washed to water mutually without substantially muddy, standby after organic phase dehydration；
(2) activated carbon adsorption：Activated carbon is added in the extractant a- Squalene solution of step (1), is stirred at room temperature, mistake
Vacuum distillation desolvation after filter, obtains Squalene concentrated solution.
In above-mentioned technical proposal, " raw material：Extractant a (m/v)=1 " refers to the ratio of 1mg raw materials and 1ml extractant a.
Preferably, in the step (1), the raw material is olive oil, soybean oil, Semen Maydis oil, Oleum Helianthi, Oleum Brassicae campestriss take off
Smelly distillation separation and Extraction go out after Vitamin E and plant sterol without any one or more in acid value oil, wherein Squalene
Content 15～30%.
It is highly preferred that in the step (1), the raw material for soybean oil deodorizer distillate separation and Extraction go out Vitamin E and
After plant sterol without acid value oil, wherein Squalene content 15～30%.
The selection of extractant of the present invention is based on following principle：First, extractant a and extractant b must immiscible or slightly soluble；
Secondly, extractant a and extractant b certain for Squalene has dissolubility, and solvability a ＞ b；Finally, in raw material
Dissolubility of the highly polar compound (such as the impurity such as Vitamin E, plant sterol, pigment for containing in raw material) in extractant b
More than extractant a.
Preferably, in the step (1), the extractant a is aprotic apolar organic solvent.
It is highly preferred that in the step (1), the extractant a is any in petroleum ether, normal hexane, isobutyltrimethylmethane., pentane
It is a kind of.
Most preferably, in the step (1), the extractant a is petroleum ether or normal hexane.
Preferably, in the step (1), the extractant b is polar organic solvent.
It is highly preferred that in the step (1), the extractant b is any one in DMF, DMSO, acetonitrile, methanol.
Most preferably, in the step (1), the extractant b is DMF.
Preferably, in the step (1), extractant a:Extractant b (v/v)=1:1～3.
It is highly preferred that in the step (1), extractant a:Extractant b (v/v)=1:2.
Preferably, in the step (1), the washing times of the extractant a layers are 3～4 times.
Preferably, in the step (1), organic phase dehydration is carried out using anhydrous sodium sulfate.
Preferably, in the step (2), the activated carbon is selected from coal system, shell system, wooden source powder shape or graininess
Activated carbon.
It is highly preferred that in the step (2), the activated carbon is wooden source powder shaped activated carbon.
It is further preferred that in the step (2), the activated carbon is sugar class activated carbon.
Most preferably, in the step (2), the activated carbon is the JH-311 of activated carbon company limited of Shanghai Jinhu County production
Type sugar uses class activated carbon.
Preferably, in the step (2), with raw material：Activated carbon (m/m)=1:1～5 adds activated carbon.
It is highly preferred that in the step (2), with raw material：Activated carbon (m/m)=1:3 add activated carbon.
Preferably, in the step (2), the time being stirred at room temperature is 10～30min.
Plant oil deodorizing distillate is oils and fatss when during deodorising process or physical refining from vegetable oil vapor distillation
The mixture of the various fractions collected, this material has the outward appearance and denseness of similar acid sludge.Initially, deodorization distillate is taken as
The leftover bits and pieces of vegetable oil are used in feed industry, but with the continuous progress of technology and technique, it has been found that this thing in fact
In matter contain various very valuable, nutrient substance with multiple biological activities, key component be free fatty, glyceride,
Tocopherol, sterol, Squalene etc., wherein Squalene content is generally 0.5～2.5%.
The present invention Vitamin E and plant sterol are gone out with soybean oil deodorizer distillate separation and Extraction after without acid value oil as original
Material, wherein Squalene content 15～30%, main component be a small amount of Vitamin E and plant sterol and high boiling point glyceride, steroid alkene,
Waxiness and pigment.The a small amount of VE remained in raw material and other polar compounds are separated initially with the method for liquid-liquid extraction, together
When can remove a part pigment；Secondly non-polar compound therein is removed using activated carbon adsorption, after being enriched with
Squalene concentrates liquid product, wherein Squalene content 75～90%.
Squalene content is too low in raw material of the present invention and the too high enforcement that can all affect technical solution of the present invention and technology effect
The realization of fruit, specifically：When Squalene content is less than 15% in raw material of the present invention, the Squalene content of final products is unable to reach
More than 75%；Conversely, it is higher than that 30%, then liquid-liquid extraction step and activated carbon adsorption are walked to work as Squalene content in raw material of the present invention
It is one of rapid to lose meaning.
In the present invention, raw material is obtained after soybean oil deodorizer distillate separation and Extraction is gone out into Vitamin E and plant sterol
Without acid value oil, wherein the method for extracting Vitamin E and plant sterol can be any method well known in the prior art, for example, tie up
Raw element E can be extracted using ion exchange resin or molecular distillation, and plant sterol can be extracted using cold analysis, and these methods will not
Affect the enforcement of technical solution of the present invention.
Compared with prior art, technical scheme has the advantage that：
(1) mild condition.Because Squalene belongs to polyunsaturated long-chain alkene, easily aoxidize under the high temperature conditions, therefore
Extracting Squalene using methods such as rectification or molecular distillations will necessarily lose the yield of a part and produce other by-products, and
This method is operated at ambient temperature, and the temperature of vacuum distillation desolvation falls within low temperature range (40～60 DEG C), therefore
Product will not be had an impact；
(2) treating capacity is big.Although silica gel or alumina column chromatography method can obtain the higher Squalene of purity, in order to
Reach higher separating degree to ensure the purity of product, its upper column quantity is necessarily restricted, at the same chromatography time-consuming, and this
The adopted liquid-liquid extraction of invention and activated carbon static adsorption are short due to every batch processing time, therefore have very in treating capacity
Big advantage；
(3) energy consumption is little.Rectification or molecular distillation need larger energy consumption, and column chromatography is and molten due to needing substantial amounts of solvent
Agent is reclaimed and needs also exist for more energy consumption, and the present invention is few due to quantity of solvent, and therefore energy consumption is relatively small to reclaim concentration without the need for high temperature；
(4) environmental friendliness.Solvent involved in the present invention can be recycled and reused, and the activated carbon of absorption also can be more than enough
Secondary repetition is applied mechanically.
Specific embodiment
With reference to embodiment, the specific embodiment of the present invention is described in further detail.Following examples are used for
The present invention is illustrated, but is not limited to the scope of the present invention.
Activated carbon used in following examples is that the JH-311 types sugar of activated carbon company limited of Shanghai Jinhu County production is used
Class activated carbon.
Raw material used in following examples is that soybean oil deodorizer distillate separation and Extraction is gone out into Vitamin E and plant steroid
The rich mixture obtained after alcohol, and the acid value of the rich mixture is 0, Squalene content 15～30%；Wherein Vitamin E
Extracted using ion exchange resin, plant sterol is extracted using cold analysis.
Embodiment 1
Take that soybean oil deodorizer distillate separation and Extraction goes out after Vitamin E and plant sterol without acid value oil (wherein Squalene
The 50g of content 15～30%), adds 150ml petroleum ether, stirs to complete molten, adds 300ml DMF, stands after acutely rocking point
Layer, point sub-cloud DMF phases, upper strata is washed 3 times, point sub-cloud water phase, and upper strata to add and be filtrated to get angle after a small amount of anhydrous sodium sulfate
Zamene-petroleum ether solution, adds 150g activated carbons, and 30min is stirred at room temperature, and filters, and petroleum ether is reclaimed under the conditions of filtrate decompression, obtains
To Squalene concentrated solution, wherein Squalene content 87.37%, yield 81.6%.
Embodiment 2
Take that soybean oil deodorizer distillate separation and Extraction goes out after Vitamin E and plant sterol without acid value oil (wherein Squalene
The 50g of content 15～30%), adds 150ml petroleum ether, stirs to complete molten, adds 300ml DMF, stands after acutely rocking point
Layer, point sub-cloud DMF phases, upper strata is washed 3 times, point sub-cloud water phase, and upper strata to add and be filtrated to get angle after a small amount of anhydrous sodium sulfate
Zamene-petroleum ether solution, adds 200g activated carbons, and 30min is stirred at room temperature, and filters, and petroleum ether is reclaimed under the conditions of filtrate decompression, obtains
To Squalene concentrated solution, wherein Squalene content 88.05%, yield 72.17%.
Embodiment 3
Take that soybean oil deodorizer distillate separation and Extraction goes out after Vitamin E and plant sterol without acid value oil (wherein Squalene
The 50g of content 15～30%), adds 100ml petroleum ether, stirs to complete molten, adds 300ml DMF, stands after acutely rocking point
Layer, point sub-cloud DMF phases, upper strata is washed 3 times, point sub-cloud water phase, and upper strata to add and be filtrated to get angle after a small amount of anhydrous sodium sulfate
Zamene-petroleum ether solution, adds 100g activated carbons, and 30min is stirred at room temperature, and filters, and petroleum ether is reclaimed under the conditions of filtrate decompression, obtains
To Squalene concentrated solution, wherein Squalene content 78.59%, yield 85.51%.
The above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, on the premise of without departing from the technology of the present invention principle, some improvements and modifications can also be made, these improvements and modifications
Also should be regarded as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of plant squalene concentrated solution, it is characterised in that comprise the steps：
(1) liquid-liquid extraction：By raw material：Extractant a (m/v)=1:1～3 is made into settled solution, adds extractant b and is extracted
Take, stratification after the violent concussion of room temperature；Extractant a layers are washed to water mutually without substantially muddy, standby after organic phase dehydration, obtain
Extractant a- Squalene solution；
(2) activated carbon adsorption：Activated carbon is added in the extractant a- Squalene solution of the step (1), is stirred at room temperature, mistake
Vacuum distillation desolvation after filter, obtains Squalene concentrated solution；
In the step (1), the raw material is the nothing after plant oil deodorizing distillate separation and Extraction goes out Vitamin E and plant sterol
Acid value oil, wherein Squalene content 15～30%；
In the step (1), the extractant a is aprotic apolar organic solvent；
In the step (1), the extractant b is polar organic solvent.
2. a kind of preparation method of plant squalene concentrated solution as claimed in claim 1, it is characterised in that the step (1)
In, the plant oil deodorizing distillate is in olive oil, soybean oil, Semen Maydis oil, Oleum Helianthi, rapeseed oil deodorized distillate
Plant or various.
3. a kind of preparation method of plant squalene concentrated solution as claimed in claim 1, it is characterised in that the step (1)
In, the extractant a is any one in petroleum ether, normal hexane, isobutyltrimethylmethane., pentane；The extractant b be DMF, DMSO,
Any one in acetonitrile, methanol.
4. a kind of preparation method of plant squalene concentrated solution as claimed in claim 1, it is characterised in that the step (1)
In, extractant a:Extractant b (v/v)=1:1～3.
5. a kind of preparation method of plant squalene concentrated solution as claimed in claim 4, it is characterised in that the extractant a:
Extractant b (v/v)=1:2.
6. a kind of preparation method of plant squalene concentrated solution as claimed in claim 1, it is characterised in that the step (1)
In, organic phase dehydration is carried out using anhydrous sodium sulfate.
7. a kind of preparation method of plant squalene concentrated solution as claimed in claim 1, it is characterised in that the step (2)
In, the activated carbon is selected from coal system, shell system, wooden source powder shaped activated carbon.
8. a kind of preparation method of plant squalene concentrated solution as claimed in claim 1, it is characterised in that the step (1)
In, with raw material：Activated carbon (m/m)=1:1～5 adds activated carbon.
9. a kind of preparation method of plant squalene concentrated solution as claimed in claim 8, it is characterised in that with raw material：Activity
Charcoal (m/m)=1:3 add activated carbon.
10. a kind of plant squalene concentrated solution, it is characterised in that prepared using claim 1～9 any one method.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1394144A1 (en) * | 2002-08-20 | 2004-03-03 | Malaysian Palm Oil Board | Extraction of vitamin E, phytosterols and squalene from palm oil |
| CN102089263A (en) * | 2008-07-07 | 2011-06-08 | 索菲姆公司 | Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils |
| CN103804337A (en) * | 2012-11-12 | 2014-05-21 | 天津润亿生医药健康科技股份有限公司 | Novel technology for extracting vitamin E and squalene by employing multi-stage counter-current liquid-liquid extraction method |
| CN104245076A (en) * | 2012-04-16 | 2014-12-24 | 罗盖特兄弟公司 | Method for refining squalene produced by microalgae |
-
2016
- 2016-12-27 CN CN201611224934.9A patent/CN106588542A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1394144A1 (en) * | 2002-08-20 | 2004-03-03 | Malaysian Palm Oil Board | Extraction of vitamin E, phytosterols and squalene from palm oil |
| CN102089263A (en) * | 2008-07-07 | 2011-06-08 | 索菲姆公司 | Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils |
| CN104245076A (en) * | 2012-04-16 | 2014-12-24 | 罗盖特兄弟公司 | Method for refining squalene produced by microalgae |
| CN103804337A (en) * | 2012-11-12 | 2014-05-21 | 天津润亿生医药健康科技股份有限公司 | Novel technology for extracting vitamin E and squalene by employing multi-stage counter-current liquid-liquid extraction method |
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Application publication date: 20170426 |