CN104356184B - A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system - Google Patents
A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system Download PDFInfo
- Publication number
- CN104356184B CN104356184B CN201410721860.4A CN201410721860A CN104356184B CN 104356184 B CN104356184 B CN 104356184B CN 201410721860 A CN201410721860 A CN 201410721860A CN 104356184 B CN104356184 B CN 104356184B
- Authority
- CN
- China
- Prior art keywords
- jasminoidin
- phase system
- aqueous phase
- purified
- isopropanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- 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
- C07H1/08—Separation; Purification from natural products
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)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the jasminoidin extracting method of a kind of high yield and purity.The present invention provides the method for the gentleest isolated and purified jasminoidin of Two-phase system, comprise the steps: with fruit of Fructus Gardeniae raw material production Gardenia Yellow waste liquid, it is obtained jasminoidin crystallization first product through isopropoxide double-aqueous phase system extract and separate, concentrate drying, then obtains the jasminoidin crystallization that purity is more than 98.5% after recrystallization.The present invention from medicine-food two-purpose herb resource isolated and purified go out highly purified jasminoidin natural product.The method is easy and simple to handle, green high-efficient, and economy saves time, is prone to amplify.It has not only widened the double-aqueous phase system kind of extraction jasminoidin, improves the efficiency that jasminoidin is isolated and purified, and this technique also apply be applicable to extraction and the production of other pigments.
Description
Technical field
The invention belongs to the technical field that natural product active ingredient extracts, be specifically related to a kind of method that high yield and purity extract jasminoidin from fruit of Fructus Gardeniae.
Background technology
Jasminoidin is a kind of effective ingredient in cape jasmine fruit, has the effect such as antioxidation, antiinflammatory, in aspect extensive application such as medicine, health care, biological detection.Jasminoidin is iridoid glycoside compounds, different name geniposide.Natural edible coloring agent gardenia blue and gardenia red mainly can be made in food industry.In the 56 kinds of pigments listed in China GB2760-2007 " food additive use sanitary standard ", cyanine only has gardenia blue pigment and phycocyanobilin (i.e. phycocyanin pigment) two kinds.At present, on natural blue pigment market at home and abroad, all supply falls short of demand, therefore active development high efficiency extraction jasminoidin technology, will have great realistic meaning and considerable market prospect.It is extracted in the existing patent report of China about jasminoidin, but the method for these patents is used mostly Flavonoids by Macroporous Adsorption Resin prepares jasminoidin.As patent CN1939458A uses macroporous absorption to prepare Fructus Gardeniae extract, owing to macroporous adsorbent resin endoporus remaining atent solvent is high, pretreatment difficulty is big, and desorbing is insufficient, affects separating effect, resin regeneration difficulty, and production cost increases.And the same model resin that same manufacturing enterprise produces, between each batch, specific surface area and functional group content difference are big, in isolated and purified middle poor reproducibility, are unfavorable for continuous prodution.Double-aqueous phase system (ATPE) has easy to operate with it, and separation efficiency is high, and to many characteristics such as separate substance zero destructions, the product being widely used in the fields such as biochemistry, cytobiology and biochemical industry separates and extracts.Though the research that existing document report utilizes ethanol/dipotassium hydrogen phosphate double-aqueous phase system to carry out jasminoidin extraction, the jasminoidin purity obtained only has 62.12%, and yield is 96.32%.The factor affecting double-aqueous phase system extraction efficiency mainly has solvent species, the kind of salt and solvent and the mass ratio of salt.Even if during same double-aqueous phase system extraction different material, due to structure and the character impact on solvent solvability of extract, solvent and the mass ratio of salt in its system are the most variant.Isopropanol has the advantages such as inexpensive, low toxicity, viscosity are less, and there is not been reported with the inorganic salt formation isolated and purified jasminoidin of double-aqueous phase system to make extractant currently with isopropanol.To this end, we are by isopropanol and the stability of the double-aqueous phase system of potassium salt, sodium salt and ammonium salt and studying the alkoxide ratio in system and pH value, set up the isopropanol/salt aqueous two-phase new system of isolated and purified jasminoidin.The method is easy and simple to handle, green high-efficient, and economy saves time, is prone to amplify.It has not only widened the double-aqueous phase system kind of extraction jasminoidin, improves the efficiency that jasminoidin is isolated and purified, and this technique also apply be applicable to extraction and the production of other pigments.
Summary of the invention
It is an object of the invention to provide a kind of method utilizing aqueous two phase extraction technique height yield and purity to extract jasminoidin.Utilize fruit of Fructus Gardeniae raw material production Gardenia Yellow waste liquid, it is obtained jasminoidin crystallization first product through isopropanol-salt double-aqueous phase system extract and separate, concentrate drying, then after recrystallization, obtains high-purity gardenoside crystal.
The method of described a kind of isolated and purified jasminoidin, it is characterised in that: prepare isopropanol and salt double-aqueous phase system drawing diagram under room temperature, determine that suitable double-aqueous phase system is isopropanol/salt double-aqueous phase system according to becoming phase stability.
The method of described a kind of isolated and purified jasminoidin, it is characterised in that: drawing the salt used by double-aqueous phase system phasor is potassium salt, sodium salt or ammonium salt.Described potassium salt is K2HPO4、K2CO3、KCl；Sodium salt is Na2CO3、NaCl、Na2SO4；Ammonia salt is NH4Cl、(NH4)2SO4、NH4HCO3Deng.
The method of described a kind of isolated and purified jasminoidin, it is characterized in that: under room temperature, prepare isopropanol and sodium salt double-aqueous phase system, Gardenia Yellow waste liquid is joined this double-aqueous phase system, at 10～50 DEG C, temperature constant magnetic stirring 30～60min under the conditions of 300r/min, regulate pH simultaneously, jasminoidin is made to be enriched with, stand 60～100min, it is centrifuged 20～40min through 1000～2000rpm, isolate jasminoidin enrichment phase ,-0.04～-0.09MPa, under the conditions of 20～90 DEG C, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out recrystallization with organic solvent, obtain highly purified jasminoidin crystal.
The method of described a kind of isolated and purified jasminoidin, it is characterised in that described isopropanol and sodium salt double-aqueous phase system concretely isopropanol and sodium carbonate, described sodium carbonate and isopropanol mass percent can be 5%～30%, and system pH can be 9～12.
The method of described a kind of isolated and purified jasminoidin, it is characterised in that any one in the solvent of described recrystallization concretely acetone, ethyl acetate or petroleum ether, the volume of described recrystallization solvent is 4～10 times of jasminoidin just quality.
The present invention utilizes isopropanol-salt Two-phase system isolated and purified Gardenia Yellow waste liquid, obtains high-purity gardenoside crystal through recrystallization with high yield.The method is easy and simple to handle, green high-efficient, and economy saves time, is prone to amplify.It has not only widened the double-aqueous phase system kind of extraction jasminoidin, improves the efficiency that jasminoidin is isolated and purified, and this technique also apply be applicable to extraction and the production of other pigments.The present invention, relative to Two-phase system of the prior art isolated and purified Gardenia Yellow waste liquid, achieves following effect:
1. the present invention have developed a kind of isopropanol-salt Two-phase system isolated and purified Gardenia Yellow waste liquid, specially isopropanol-sodium carbonate double-aqueous phase system, not relevant report in prior art；
2. under the conditions of the present invention, it is possible to purity reach 98.5% crystal, yield be up to 98.2% acquisition target product jasminoidin, create unforeseeable technique effect compared to prior art.
Detailed description of the invention
Below by specific embodiment, the method for the present invention is illustrated, but the invention is not limited in this.
Experimental technique described in following embodiment, if no special instructions, is conventional method；Described reagent and material, if no special instructions, the most commercially obtain.
Embodiment
1
Double-aqueous phase system 20mL is prepared by sodium carbonate and isopropanol mass percent 10% under room temperature, the Gardenia Yellow waste liquid 5mL of concentration is joined this double-aqueous phase system, temperature constant magnetic stirring (10 DEG C, 300r/min) 40min, regulates pH=9 simultaneously, jasminoidin is made to be enriched with, stand 80min, be centrifuged 30min through 1500rpm, isolate jasminoidin enrichment phase, at-0.06MPa, under the conditions of 20 DEG C, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out being recrystallized to give jasminoidin crystal by the ethyl acetate of 8 times of volumes.The purity measuring jasminoidin is 98.5%, and product yield reaches 98.2%.
Embodiment
2
Double-aqueous phase system 20mL is prepared by sodium carbonate and isopropanol mass percent 30% under room temperature, the Gardenia Yellow waste liquid 5mL of concentration is joined this double-aqueous phase system, temperature constant magnetic stirring (35 DEG C, 300r/min) 30min, regulates pH=9 simultaneously, jasminoidin is made to be enriched with, stand 60min, be centrifuged 20min through 1000rpm, isolate jasminoidin enrichment phase, at-0.04MPa, under the conditions of 50 DEG C, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out being recrystallized to give jasminoidin crystal with the petroleum ether of 4 times of volumes.The purity measuring jasminoidin is 96.7%, and product yield reaches 96.6%.
Embodiment
3
Double-aqueous phase system 20mL is prepared by sodium carbonate and isopropanol mass percent 30% under room temperature, the Gardenia Yellow waste liquid 5mL of concentration is joined this double-aqueous phase system, temperature constant magnetic stirring (50 DEG C, 300r/min) 60min, regulates pH=12 simultaneously, jasminoidin is made to be enriched with, stand 100min, be centrifuged 40min through 2000rpm, isolate jasminoidin enrichment phase, at-0.09MPa, under the conditions of 90 DEG C, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out being recrystallized to give jasminoidin crystal with the acetone of 10 times of volumes.The purity measuring jasminoidin is 96.9%, and product yield reaches 95.4%.
Embodiment
4
Double-aqueous phase system 20mL is prepared by dipotassium hydrogen phosphate and isopropanol mass percent 10% under room temperature, the Gardenia Yellow waste liquid 5mL of concentration is joined this double-aqueous phase system, temperature constant magnetic stirring (50 DEG C, 300r/min) 60min, regulates pH=9 simultaneously, jasminoidin is made to be enriched with, stand 100min, be centrifuged 40min through 2000rpm, isolate jasminoidin enrichment phase, at-0.09MPa, under the conditions of 90 DEG C, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out being recrystallized to give jasminoidin crystal with the acetone of 10 times of volumes.The purity measuring jasminoidin is 93.6%, and product yield reaches 95.5%.
Claims (4)
1. the method for isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system, it is characterised in that utilize fruit of Fructus Gardeniae raw material production Gardenia Yellow waste liquid, obtains jasminoidin by it through isopropanol-salt double-aqueous phase system extract and separate, concentrate drying
Crude product, then after organic solvent recrystallization, obtain high-purity gardenoside crystallization；Wherein said isopropanol-salt double-aqueous phase system is isopropanol-sodium carbonate system, and sodium carbonate is 5%～30% with the mass percent of isopropanol.
The method of the most isolated and purified jasminoidin, it is characterized in that including step in detail below: under room temperature, prepare isopropanol-salt double-aqueous phase system, Gardenia Yellow waste liquid is joined this double-aqueous phase system, at 10～50 DEG C, temperature constant magnetic stirring 30～60min under the conditions of 300r/min, regulation pH=9～12 simultaneously, jasminoidin is made to be enriched with, stand 60～100min, it is centrifuged 20～40min through 1000～2000rpm, isolate jasminoidin enrichment phase,-0.04～-0.09MPa, jasminoidin crystal crude product is obtained through vacuum rotating concentrate drying under the conditions of 20～90 DEG C, recrystallization is carried out with organic solvent, obtain highly purified jasminoidin crystal.
The method of isolated and purified jasminoidin the most according to claim 1 and 2, it is characterised in that: described organic solvent is the mixture of one or more of ethyl acetate, acetone or petroleum ether.
The method of the most isolated and purified jasminoidin, it is characterised in that: described organic solvent is ethyl acetate, and addition is 4～10 times of jasminoidin crude product quality.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410721860.4A CN104356184B (en) | 2014-12-03 | 2014-12-03 | A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410721860.4A CN104356184B (en) | 2014-12-03 | 2014-12-03 | A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104356184A CN104356184A (en) | 2015-02-18 |
| CN104356184B true CN104356184B (en) | 2016-07-27 |
Family
ID=52523514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410721860.4A Expired - Fee Related CN104356184B (en) | 2014-12-03 | 2014-12-03 | A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104356184B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037461B (en) * | 2015-07-08 | 2018-06-05 | 邵阳学院 | Multistage aqueous two-phase separated in synchronization Gardenoside and Gardenia Yellow |
| CN107325859A (en) * | 2017-08-16 | 2017-11-07 | 杨杰东 | Antifriction antiwear type lubricating oil additive and preparation method thereof |
| CN107722078B (en) * | 2017-10-18 | 2020-07-10 | 青岛大学 | Method for extracting, separating and purifying phlorizin by n-propanol-potassium sodium tartrate aqueous two-phase system |
| CN108047288B (en) * | 2017-12-12 | 2021-10-15 | 四川旭阳药业有限责任公司 | Preparation method of geniposide |
| CN112480194B (en) * | 2020-11-26 | 2022-05-31 | 浙江工业大学 | Method for simultaneously preparing high-purity geniposide and gardenia yellow by one-step two-aqueous-phase extraction |
| CN114702836A (en) * | 2022-04-23 | 2022-07-05 | 南京林业大学 | Method for extracting and purifying pigment from jujube residues |
| CN116495753B (en) * | 2023-04-26 | 2024-06-18 | 中国科学院生态环境研究中心 | Method for recycling industrial waste salt through recrystallization and purification |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102212092A (en) * | 2011-05-31 | 2011-10-12 | 广西大学 | Preparation method for high-purity jasminoidin |
| CN102399251A (en) * | 2011-12-20 | 2012-04-04 | 广西大学 | Method for preparing high-purity geniposide |
| CN103087129A (en) * | 2013-03-12 | 2013-05-08 | 广西山云生化科技有限公司 | Method for extracting geniposide from gardenia yellow pigment waste liquor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59164717A (en) * | 1983-03-09 | 1984-09-17 | Takeda Chem Ind Ltd | Ameliorant of disorder due to stress |
| US6635758B2 (en) * | 2000-09-25 | 2003-10-21 | Industrial Technology Research Institute | Process for extracting glycoside using an aqueous two-phase system |
-
2014
- 2014-12-03 CN CN201410721860.4A patent/CN104356184B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102212092A (en) * | 2011-05-31 | 2011-10-12 | 广西大学 | Preparation method for high-purity jasminoidin |
| CN102399251A (en) * | 2011-12-20 | 2012-04-04 | 广西大学 | Method for preparing high-purity geniposide |
| CN103087129A (en) * | 2013-03-12 | 2013-05-08 | 广西山云生化科技有限公司 | Method for extracting geniposide from gardenia yellow pigment waste liquor |
Non-Patent Citations (5)
| Title |
|---|
| 亲水有机溶剂/无机盐双水相萃取技术在分离提纯生物物质中的应用;李丽敏等;《光谱实验室》;20111130;第28卷(第6期);第3073-3078页 * |
| 利用双水相萃取栀子黄废液中的栀子苷酶法生产栀子蓝色素的研究;梁华正等;《食品科学》;20090201;第30卷(第3期);第156页1.3以及表1 * |
| 双水相萃取体系的研究;王志华等;《应用化学》;20010331;第18卷(第3期);第173-175页 * |
| 无机盐/低分子有机物双水相体系的研究及其应用;辜鹏;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20090515;第B015-4页 * |
| 栀子苷在乙腈水体系中诱导相分离分配行为;盛碧等;《应用化学》;20140228;第31卷(第2期);第231-236页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104356184A (en) | 2015-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104356184B (en) | A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system | |
| CN105037461B (en) | Multistage aqueous two-phase separated in synchronization Gardenoside and Gardenia Yellow | |
| CN104447470A (en) | Method for preparing lycium barbarum lutein by HSCCC (high-speed countercurrent chromatography) separation | |
| CN108236678B (en) | Method for extracting and preparing bamboo leaf flavone by using ionic liquid | |
| CN103087075A (en) | Simple and new technology for extracting and purifying arteannuin and artemisinic acid from southernwood through single process | |
| CN101411466A (en) | Method for preparing cape jasmine yellow pigment using cape jasmine as raw material | |
| CN101037467B (en) | Method for separating purifying ursolic acid from loquat leaf | |
| CN110003071A (en) | A kind of industrial method quickly and efficiently extracting lutein and quercetagetin | |
| CN101531825B (en) | Technology of extracting mulberry red pigment | |
| CN102321135B (en) | Method for separating and purifying cordycepin by utilizing high-speed counter-current chromatography | |
| CN104193595A (en) | Method for extracting piceatannol from passionflower seeds | |
| CN102093374A (en) | Method for efficiently extracting camptothecin derivative | |
| CN101885925A (en) | Method for extracting brown pigment from oil-tea camellia husks | |
| CN104311616B (en) | A kind of extraction high purity cortex fraxini and method of fraxin from Cortex Fraxini | |
| CN103420969A (en) | Method for extracting anthocyanidin in grape juice | |
| CN105131841A (en) | Extraction method of pepper oleoresin | |
| CN101948628B (en) | Method for preparing high-purity norbixin | |
| CN102558248A (en) | Method for extracting polyphenol from chestnut shells | |
| CN104710294A (en) | Perillaldehyde extraction method | |
| CN108341751A (en) | A kind of extraction process of capsaicine | |
| CN104231663A (en) | Extraction method for pigment of Rhodomyrtus tomentosa (Ait.) Hassk fruit | |
| CN107353296B (en) | A method of extracting activated protein and eurycomanone from Tongkat Ali | |
| CN102618067A (en) | Method for extracting anthocynins from purple sweet potatoes in continuous countercurrent ultrasonic manner | |
| CN101792612A (en) | Method for purifying yellow pigment in yellow ginger | |
| CN102993143B (en) | Method for rapidly separating alkannic acid monomer from salviae miltiorrhizae |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160727 Termination date: 20171203 |