CN104761593B - A method of alpha-arbutin is extracted from fermentation liquid based on membrane separation technique - Google Patents
A method of alpha-arbutin is extracted from fermentation liquid based on membrane separation technique Download PDFInfo
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- CN104761593B CN104761593B CN201510186065.4A CN201510186065A CN104761593B CN 104761593 B CN104761593 B CN 104761593B CN 201510186065 A CN201510186065 A CN 201510186065A CN 104761593 B CN104761593 B CN 104761593B
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- arbutin
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- 239000007788 liquid Substances 0.000 title claims abstract description 40
- 238000000855 fermentation Methods 0.000 title claims abstract description 33
- 230000004151 fermentation Effects 0.000 title claims abstract description 33
- 239000012528 membrane Substances 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000000926 separation method Methods 0.000 title claims abstract description 10
- BJRNKVDFDLYUGJ-ZIQFBCGOSA-N alpha-Arbutin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-ZIQFBCGOSA-N 0.000 title claims description 31
- 229940033280 alpha-arbutin Drugs 0.000 title claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000010521 absorption reaction Methods 0.000 claims abstract description 17
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- 238000002425 crystallisation Methods 0.000 claims abstract description 9
- 230000008025 crystallization Effects 0.000 claims abstract description 9
- 238000001471 micro-filtration Methods 0.000 claims abstract description 9
- 239000000919 ceramic Substances 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims description 28
- 229920005989 resin Polymers 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011148 porous material Substances 0.000 claims description 7
- 229930182470 glycoside Natural products 0.000 claims description 6
- 235000012871 Arctostaphylos uva ursi Nutrition 0.000 claims description 5
- 244000003892 Vaccinium erythrocarpum Species 0.000 claims description 5
- 239000003957 anion exchange resin Substances 0.000 claims description 3
- 150000002338 glycosides Chemical class 0.000 claims description 3
- 239000003463 adsorbent Substances 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000003672 processing method Methods 0.000 claims description 2
- 239000008213 purified water Substances 0.000 claims description 2
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N Arbutin Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 abstract description 27
- 235000019441 ethanol Nutrition 0.000 abstract description 17
- 229960000271 arbutin Drugs 0.000 abstract description 13
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000000605 extraction Methods 0.000 abstract description 5
- 241001656831 Arctous alpina Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000005189 flocculation Methods 0.000 description 5
- 230000016615 flocculation Effects 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 208000003351 Melanosis Diseases 0.000 description 2
- 102000003425 Tyrosinase Human genes 0.000 description 2
- 108060008724 Tyrosinase Proteins 0.000 description 2
- -1 glycoside compound Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- 235000016357 Mirtillo rosso Nutrition 0.000 description 1
- 244000077923 Vaccinium vitis idaea Species 0.000 description 1
- 235000017606 Vaccinium vitis idaea Nutrition 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a kind of methods for extracting a- arbutin from fermentation liquid based on membrane separation technique, method includes the following steps: the micro-filtration of (1) fermentation liquid；(2) micro-filtrate absorption and parsing；(3) concentration and decoloration of desorbed solution；(4) concentration and crystallization of destainer.The present invention applies to Ceramic Membranes Separating Technique in the pretreatment of a- arbutin fermentation liquid, and compared with the method for arbutin in the extraction fermentation liquid that flocculated with ethyl alcohol, easy to operate, safety coefficient is high, and production cost is low, high income, and purity Coriolis mass is good.
Description
Technical field
The present invention relates to the extractive technique fields of alpha-arbutin, more particularly to a kind of membrane separation technique that is based on is from fermentation liquid
The method for extracting alpha-arbutin.
Background technique
Arbutin belongs to quinhydrones glycoside compound, the entitled 4-Hydroxyphenyl-D-glucopyranoside of chemistry, and natural black bearberry former times is equal
Be α-black bearberry former times, be present in the plants such as black bearberry, cowberry, be it is a kind of it is non-stimulated, without hypersensitive natural whiting active material.α-
Arbutin, which has, significantly to be inhibited tyrosinase activity, and the deposition of tyrosinase in skin is reduced, and is had bleaching to skin, is prevented
The effect of discoloration and nti-freckle is internationally recognized efficient freckle removing and whitening agent, and domestic and international demand is huge, wide market.
There are two types of the molecular configurations of arbutin: alpha-arbutin and β-arbutin.Wherein the inhibition melanin of alpha-arbutin is raw
Effect ratio β-high ten times of arbutin of production.The arbutin extracted from natural fruit and plant is at high cost, and quantity is few, is unable to satisfy
Market needs.It is β-arbutin that chemical synthesis, which produces black bearberry, and whitening effect is poor, and has certain side effect.And α-black bearberry
The production of glycosides is to carry out sugared transfer reaction by fermented and cultured specified microorganisms using the enzymatic of specified microorganisms and obtain, adopt
The bear glycosides glycosides produced with microorganism conversion, is alpha-arbutin, identical with the alpha-arbutin effect naturally extracted.α-at present
Arbutin is completely instead of β-arbutin in cosmetics.
The production technology for extracting black bearberry former times from fermentation liquid at present, is all made of in fermentation liquid and high concentration ethanol is added, and leads to
The ethyl alcohol of excessive concentrations makes the substance in fermentation liquid generate flocculation denaturation, while the characteristic of ethyl alcohol can be dissolved in using arbutin,
Arbutin in fermentation liquid is transferred in ethanol solution, then is filtered with plate, ethanol solution and flocculation in fermentation liquid are become
Property substance separation.By way of vacuum concentration, the ethanol distillation in ethanol solution is come out, the water phase for obtaining arbutin is molten
Liquid.This method will use the ethyl alcohol of 85% concentrations above, and there are great security risk, high production cost, works in middle production
Skill route is long, and yield is low, unstable quality.
Summary of the invention
The present invention is proposed and a kind of is mentioned from fermentation liquid based on membrane separation technique to solve the above-mentioned deficiency of the prior art
The method for taking alpha-arbutin.
In order to solve the above-mentioned technical problem, the invention adopts the following technical scheme: a kind of membrane separation technique that is based on is from fermentation
The method of alpha-arbutin is extracted in liquid, comprising the following steps:
(1) micro-filtration of fermentation liquid: the filter membrane for being 50nm~1000nm by membrane aperture by alpha-arbutin fermentation liquid removes α-
Most thallus and biggish albumen and impurity particle in arbutin fermentation liquid, and then obtain micro-filtrate；Liquid stream pressure when micro-filtration
Power is 0.1~0.4MPa, and fluid temperature is 10~50 DEG C, and cycles of concentration is 6~12 times, and dialysis water is accounted for volume percentage
The 10~50% of feed volume；
(2) absorption and parsing of micro-filtrate: the micro-filtrate that above-mentioned steps are obtained passes through polar macroporous adsorbent resin column, to
After α-black bearberry former times in micro-filtrate is adsorbed on resin column, alpha-arbutin desorbed solution is obtained by parsing；
(3) concentration and decoloration of desorbed solution: concentration is carried out to desorbed solution, is taken off again by adsorbing resin after concentration
Color processing, and then obtained destainer；
(4) it the concentration and crystallization of destainer: after destainer is carried out concentration, then carries out crystallization treatment and then obtains institute
The alpha-arbutin product needed.
Further, filter membrane is pellumina, ceramic membrane or PVC film in the step (1).
Further, absorption and analyzing and processing method are first by micro-filtrate with 1~5BV/H flow velocity warp in the step (2)
Large pore resin absorption column is crossed, then resin column is cleaned with 1~5BV/H flow velocity with the purified water of 2~5 times of resin column volumes, is finally used
Desorbed solution crosses column with 1~5BV/H flow velocity, collects desorbed solution；The large pore resin absorption column be AB-8 resin, DA201 resin,
DM301 resin or XAD-16 resin, the ethanol solution that the desorbed solution is 10%~50%.
Further, the absorption resin in the step (3) is 331 anion exchange resin, the friendship of D315 anion
Change resin or 717 anion exchange resin.
Compared with prior art, the present invention is that the effective extraction separation from fermentation liquid of one kind obtains high-purity α-black bearberry
The method of glycosides, on the basis of existing fermentation method produces and extracts alpha-arbutin, innovative uses Ceramic Membranes Separating Technique
The extraction for carrying out alpha-arbutin in fermentation liquid, effectively separates the arbutin in fermentation liquid with other materials, avoids with highly concentrated
Ethyl alcohol flocculation extraction bring security risk is spent, a large amount of ethyl alcohol has been saved, has greatly reduced production cost.
By process optimization repeatedly, perfect UF membrane extracts the production technology of black bearberry former times in fermentation liquid, instead of highly concentrated
Spend ethyl alcohol flocculation microwave leaching technology.The membrane separation process that the present invention uses optimizes existing fermentation liquor pretreatment technology, gets rid of
The high costs, the technique of high labor intensity such as alcohol flocculation extraction, plate compression, and then improve product yield；The method of the present invention
Have many advantages, such as simple process rationally, extract separating degree height, be high income, easy to operate.After extracting crystallization using the method for the present invention
The alpha-arbutin product of acquisition is through efficient liquid phase chromatographic analysis purity up to 99.5% or more.
Specific embodiment
Invention is described in detail below with reference to embodiment.
Embodiment 1:
The microfiltration membranes for being 1000nm by membrane aperture by alpha-arbutin fermentation liquid 100L, enter film pressure 0.2MPa, out membrane pressure
25 DEG C of operation temperature, after fermentation liquid is concentrated 8 times, dialysis water 25L is added in power 0.1MPa.Cleaner liquid is passed through with 2BV/H flow velocity
DA201 type large pore resin absorption column equally passes through DA201 type macroporous absorption tree with 25% ethyl alcohol desorbed solution with 2BV/H flow velocity
Rouge column is parsed.Desorbed solution is decolourized by D315 type macroporous absorbent resin with 2BV/H flow velocity, is taken off by being concentrated under reduced pressure
Color liquid obtains alpha-arbutin product 408.3g by secondary concentration, crystallization altogether.Alpha-arbutin product is detected through high pressure liquid chromatography
Purity be 99.57%.
Embodiment 2:
The microfiltration membranes for being 500nm by membrane aperture by alpha-arbutin fermentation liquid 100L, enter film pressure 0.2MPa, out film pressure
25 DEG C of operation temperature, after fermentation liquid is concentrated 10 times, dialysis water 30L is added in 0.1MPa.Cleaner liquid is passed through with 2BV/H flow velocity
DA201 type large pore resin absorption column equally passes through DA201 type macroporous absorption tree with 25% ethyl alcohol desorbed solution with 2BV/H flow velocity
Rouge column is parsed.Desorbed solution is decolourized by D315 type macroporous absorbent resin with 2BV/H flow velocity, is taken off by being concentrated under reduced pressure
Color liquid obtains alpha-arbutin product 438.7g by secondary concentration, crystallization altogether.Alpha-arbutin product is detected through high pressure liquid chromatography
Purity be 99.76%.
Embodiment 3:
The microfiltration membranes for being 200nm by membrane aperture by alpha-arbutin fermentation liquid 100L, enter film pressure 0.2MPa, out film pressure
25 DEG C of operation temperature, after fermentation liquid is concentrated 10 times, dialysis water 25L is added in 0.1MPa.Cleaner liquid is passed through with 2BV/H flow velocity
DA201 type large pore resin absorption column equally passes through DA201 type macroporous absorption tree with 25% ethyl alcohol desorbed solution with 2BV/H flow velocity
Rouge column is parsed.Desorbed solution is decolourized by D315 type macroporous absorbent resin with 2BV/H flow velocity, is taken off by being concentrated under reduced pressure
Color liquid obtains alpha-arbutin product 416.4g by secondary concentration, crystallization altogether.Alpha-arbutin product is detected through high pressure liquid chromatography
Purity be 99.62%.
The above is only this preferred embodiment of the invention, it is noted that for the ordinary skill people of the art
For member, under the premise of not departing from this technology principle, several improvements and modifications can also be made, these improvements and modifications are also answered
It is considered as this protection scope.
Claims (1)
1. a kind of method for extracting alpha-arbutin from fermentation liquid based on membrane separation technique, which comprises the following steps:
(1) micro-filtration of fermentation liquid: the filter membrane for being 50nm~1000nm by membrane aperture by alpha-arbutin fermentation liquid removes α-black bearberry
Most thallus and biggish albumen and impurity particle in glycosides fermentation liquid, and then obtain micro-filtrate；Flow stream pressure is when micro-filtration
0.1~0.4MPa, fluid temperature are 10~50 DEG C, and cycles of concentration is 6~12 times, and water of dialysing accounts for charging with volume percentage
The 10~50% of volume；The filter membrane is pellumina, ceramic membrane or PVC film；
(2) absorption and parsing of micro-filtrate: the micro-filtrate that above-mentioned steps are obtained passes through polar macroporous adsorbent resin column, to micro-filtration
After alpha-arbutin in liquid is adsorbed on resin column, alpha-arbutin desorbed solution is obtained by parsing；In the step (2) absorption with
Analyzing and processing method is that micro-filtrate is first passed through large pore resin absorption column with 1~5BV/H flow velocity, then with 2~5 times of resin column volumes
Purified water resin column is cleaned with 1~5BV/H flow velocity, column is finally crossed with 1~5BV/H flow velocity with desorbed solution, collects desorbed solution；Institute
The large pore resin absorption column stated is DA201 resin, the ethanol solution that the desorbed solution is 10%~50%；
(3) concentration and decoloration of desorbed solution: concentration is carried out to desorbed solution, is carried out at decoloration by adsorbing resin again after concentration
Reason, and then obtained destainer；The absorption resin in the step (3) is D315 anion exchange resin；
(4) it the concentration and crystallization of destainer: after destainer is carried out concentration, then carries out needed for crystallization treatment and then acquisition
Alpha-arbutin product.
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| CN201510186065.4A CN104761593B (en) | 2015-04-15 | 2015-04-15 | A method of alpha-arbutin is extracted from fermentation liquid based on membrane separation technique |
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| CN108329363B (en) * | 2018-01-30 | 2020-10-27 | 安徽华恒生物科技股份有限公司 | Method for removing hydroquinone in alpha-arbutin conversion solution |
| CN114044797A (en) * | 2021-09-30 | 2022-02-15 | 安徽华恒生物科技股份有限公司 | Extraction method and application of alpha-arbutin |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1635139A (en) * | 2004-11-15 | 2005-07-06 | 刘春巧 | Process for preparing alpha-arbutin through fermentation |
| CN101759758A (en) * | 2009-10-22 | 2010-06-30 | 南京泽朗医药科技有限公司 | Preparation method of ursolic acid |
| CN102093442A (en) * | 2011-01-13 | 2011-06-15 | 赵玉红 | Method for separating and purifying arbutin from blueberry |
-
2015
- 2015-04-15 CN CN201510186065.4A patent/CN104761593B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1635139A (en) * | 2004-11-15 | 2005-07-06 | 刘春巧 | Process for preparing alpha-arbutin through fermentation |
| CN101759758A (en) * | 2009-10-22 | 2010-06-30 | 南京泽朗医药科技有限公司 | Preparation method of ursolic acid |
| CN102093442A (en) * | 2011-01-13 | 2011-06-15 | 赵玉红 | Method for separating and purifying arbutin from blueberry |
Non-Patent Citations (1)
| Title |
|---|
| 发酵法生产α-熊果苷及其分离纯化;刘春巧;《中国优秀硕士学位论文全文数据库（电子期刊）》;20100115(第1期);B018-56页；正文第28-35页第四章 * |
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