CN104292094B - A kind of extracting method of high purity Phloretin - Google Patents
A kind of extracting method of high purity Phloretin Download PDFInfo
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- CN104292094B CN104292094B CN201410513412.5A CN201410513412A CN104292094B CN 104292094 B CN104292094 B CN 104292094B CN 201410513412 A CN201410513412 A CN 201410513412A CN 104292094 B CN104292094 B CN 104292094B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Abstract
The present invention relates to a kind of extracting method of high purity Phloretin, present method comprises: the step such as raw material pulverizing, extraction, concentrated, centrifugal, Macroporous Adsorption Resin, crystallization, acid hydrolysis, present method operation is simple to operation, industrially produce high-quality bulk article Phloretin, purity >=98%.
Description
Technical field
The present invention relates to a kind of extracting method of high purity Phloretin, belong to chemical field.
Background technology
Phloretin molecular formula: C15H14O5; English name: Phloretin; Another name: Dihydronaringenin tri-hydroxyl phenol-acetone 2,4,6-trihydroxy--3-(4-hydroxy phenyl) Propiophenone; CAS:60-82-2; Molecular weight: 274.28; Plant origin: the dry root skin of rosaceous plant apple; Physical properties: be soluble in methyl alcohol, ethanol and acetone, be slightly soluble in chloroform, be insoluble in water, sherwood oil and benzene, side's prismatic or plate crystal (ethanol or methyl alcohol), fusing point 230 ~ 231 °, (α) 17D-126.6 ± 2 ° (Glacial acetic acid).
Phloretin is used as the agent of skin natural whiting always, and its energy restraint of tyrosinase is active, melanochrome is active, and skin whitening, has desalination effect to various skin splash.Find that it also has anti-inflammatory according to current research, immunosuppression, the effects such as cardiovascular protection, there is potential very big market demand.The technique of current existing extraction Phloretin adopts semi-synthesizing technology to prepare mostly, or obtains Phloretin with solvent extraction through macroporous resin enrichment enzymolysis; With an organic solvent easily cause residual.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of extracting method of high purity Phloretin, and present method operation is simple to operation, and products obtained therefrom quality is high, Phloretin content >=98%, and raw material is easy to get.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of extracting method of high purity Phloretin, comprising:
1) dried apple fruit root bark is pulverized, cross 10 mesh sieves, extracting screen underflow drops in extractor, ethanol boiling reflux extracts 3 times, merging filtrate, merging filtrate is concentrated into the 3-4 of the screen underflow weight dropping into extractor doubly, concentrated solution is cooled to 30-40 DEG C, use supercentrifuge centrifugation, removing centrifugation, centrifugate enters next step operation;
2) centrifugate enters macroporous adsorptive resins, for charging terminal when dropping to the resin height of bed 3/5 with the muddy light yellow and feeding liquid color of effluent liquid, after having entered feed liquid, first be washed till effluent liquid water white transparency by purified water, then use the desorb of massfraction 50-70% ethanol, start to collect when own weak yellow liquid flows out, collect the stripping liquid of resin column volume 3.5-5 times of volume altogether, stripping liquid concentration and recovery ethanol, obtains concentrated solution;
3) concentrated solution is positioned over 2-5 DEG C of crystallization 24H, crystal Büchner funnel suction filtration, filtrate discards, and precipitates 65-75 DEG C of vacuum-drying 2-3H;
4) dried precipitation being joined concentration is in the Hcl of 1-4% (massfraction), be heated to 90-95 DEG C of insulation 2-4H, with laboratory reaction still reaction 2-3H, the completely rear solution of question response is cooled to 30-40 DEG C of suction filtration, the crystal of gained after suction filtration is washed with pure water, being washed till pH value is 4-7, crystal 65-75 DEG C of vacuum-drying 2-3H and get final product.
On the basis of technique scheme, the present invention can also do following improvement.
Further, 1) in, described ethanol is massfraction 40-70% ethanol, described boiling reflux extracts first time in 3 times and extracts, and massfraction 40-70% ethanol consumption is 15 times of the screen underflow weight dropping into extractor, filters after extracting 1.5h, filtrate is for subsequent use, and filter residue enters and extracts next time; Second time is extracted, and massfraction 40-70% ethanol consumption is 13 times of the screen underflow weight dropping into extractor, and filter after extracting 1h, filtrate is for subsequent use, and filter residue enters and extracts next time; Third time extracts, and massfraction 40-70% ethanol consumption is 10 times of the screen underflow weight dropping into extractor, and filter after extracting 1h, filtrate is for subsequent use;
Further, 1) in, described supercentrifuge rotating speed is 4000r/min, centrifugal 10 minutes.
Further, 2) in, described macroporous adsorbent resin type is the one in resin DM130 (the anti-medical stock company in Shandong, Shandong commercially available prod), HPD100 (Cangzhou Bon Adsorption Material Science and Technology Co., Ltd commercially available prod), LXA-8 (Xi'an Lanxiao Sci-Tech Co., Ltd. commercially available prod), LSA-21 (Xi'an Lanxiao Sci-Tech Co., Ltd. commercially available prod);
Further, 2) in, described concentrated solution volume is 1:1 with the volume ratio of the screen underflow dropping into extractor.
Further, 4) in, the add-on of described precipitation and concentration 1-4% (massfraction) Hcl is the hydrochloric acid that 1 gram of precipitation adds 15 milliliters of 1-4%.
The invention has the beneficial effects as follows:
Present method provides a kind of macroporous resin to be separated the method combined with acid hydrolysis purifying Phloretin, and operation is simple to operation, industrially produces high-quality bulk article Phloretin, purity >=98%, and color is incarnadine.
Accompanying drawing explanation
Fig. 1 is the HPLC figure of the embodiment of the present invention 1 products obtained therefrom;
Fig. 2 is the HPLC figure of the embodiment of the present invention 2 products obtained therefrom;
Embodiment
Be described principle of the present invention and feature below, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Embodiment 1
Get apple fruit root bark dried feed and pulverize 10 mesh sieves, extracting screen underflow 80g drops in extractor, massfraction 65% ethanol boiling reflux extracts 3 times, first time extracts, massfraction 65% ethanol consumption is 15 times of the screen underflow weight dropping into extractor, filter after extracting 1.5h, filtrate is for subsequent use, and filter residue enters and extracts next time, second time is extracted, and massfraction 65% ethanol consumption is 13 times of the screen underflow weight dropping into extractor, and filter after extracting 1h, filtrate is for subsequent use, and filter residue enters and extracts next time, third time extracts, massfraction 65% ethanol consumption is 10 times of the screen underflow weight dropping into extractor, filter after extracting 1h, merging filtrate, concentrating under reduced pressure carries out solvent recuperation, solution 300Ml after recycling design, high speed centrifugation is separated, and centrifugal rotational speed is 4000r/min, and the time is 10 minutes, centrifugation removes, and centrifugate enters next step operation, centrifugate enters macroporous adsorptive resins LXA-8 enriching and purifying, for charging terminal when dropping to the resin height of bed 3/5 with the muddy light yellow and feeding liquid color of effluent liquid, after having entered feed liquid, first be washed till effluent liquid water white transparency by purified water, then use the desorb of massfraction 50-70% ethanol, start to collect when own weak yellow liquid flows out, collect the stripping liquid of resin column volume 3.5-5 times of volume altogether, stripping liquid concentration and recovery ethanol, obtains concentrated solution 50ml, concentrated solution is positioned over 2-5 DEG C of crystallization 24H, crystal Büchner funnel suction filtration, filtrate discards, precipitate 65-75 DEG C of vacuum-drying 2-3H, obtain 12.58g, detecting phlorizin content by HPLC is 84.75%, massfraction 60% ethanol adding 5 times of weight in phlorizin dry powder is dissolved in 80 DEG C of water-baths and dissolves, centrifugal while hot, supernatant concentration places crystallization to 3 times amount volumes, suction filtration, crystal joins in concentration 2% (massfraction) HCl and is heated to 95 DEG C of insulation 2h, the add-on of described crystal and concentration 2% (massfraction) Hcl is the hydrochloric acid that 1 gram of crystal adds 15 milliliter 2%, with laboratory reaction still reaction 1-3H.Treat liquid cool to room temperature 200 order filter cloth suction filterings after reacting completely, wash be deposited to pH6-7 with pure water, precipitation vacuum-drying, temperature is not higher than 70 DEG C.Products obtained therefrom content is detected by HPLC and namely arrives 98.82% Phloretin.
Embodiment 2
Get apple fruit root bark dried feed and pulverize 10 mesh sieves, extracting screen underflow 200g, drop in extractor, massfraction 65% ethanol boiling reflux extracts 3 times, first time extracts, and massfraction 65% ethanol consumption is 15 times of the screen underflow weight dropping into extractor, filters after extracting 1.5h, filtrate is for subsequent use, and filter residue enters and extracts next time, second time is extracted, and massfraction 65% ethanol consumption is 13 times of the screen underflow weight dropping into extractor, and filter after extracting 1h, filtrate is for subsequent use, and filter residue enters and extracts next time, third time extracts, massfraction 65% ethanol consumption is 10 times of the screen underflow weight dropping into extractor, filter after extracting 1h, merging filtrate, concentrating under reduced pressure carries out solvent recuperation, solution 600Ml after recycling design, high speed centrifugation is separated, and centrifugal rotational speed is 4000r/min, and the time is 10 minutes, centrifugation removes, and centrifugate enters next step operation, centrifugate enters macroporous adsorptive resins LXA-8 enriching and purifying, for charging terminal when dropping to the resin height of bed 3/5 with the muddy light yellow and feeding liquid color of effluent liquid, after having entered feed liquid, first be washed till effluent liquid water white transparency by purified water, then use the desorb of massfraction 50-70% ethanol, start to collect when own weak yellow liquid flows out, collect the stripping liquid of resin column volume 3.5-5 times of volume altogether, stripping liquid concentration and recovery ethanol, obtains concentrated solution 130ml, concentrated solution is positioned over 2-5 DEG C of crystallization 24H, crystal Büchner funnel suction filtration, filtrate discards, precipitate 65-75 DEG C of vacuum-drying 2-3H, obtain 30.16g, detecting phlorizin content by HPLC is 88.71%, massfraction 60% ethanol adding 5 times of weight in phlorizin dry powder is dissolved in 80 DEG C of water-baths and dissolves, centrifugal while hot, supernatant concentration places crystallization to 3 times amount volumes, suction filtration, crystal joins in concentration 2% (massfraction) HCl and is heated to 95 DEG C of insulation 2h, the add-on of described crystal and concentration 2% (massfraction) Hcl is the hydrochloric acid that 1 gram of crystal adds 15 milliliter 2%, with laboratory reaction still reaction 1-3H.Treat liquid cool to room temperature 30 DEG C 200 order filter cloth suction filterings after reacting completely, wash be deposited to PH6-7 with pure water, precipitation vacuum-drying, temperature is not higher than 70 DEG C.Products obtained therefrom content is detected by HPLC and namely arrives 99.02% Phloretin.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (5)
1. an extracting method for high purity Phloretin, is characterized in that, comprising:
1) dried apple fruit root bark is pulverized, cross 10 mesh sieves, extracting screen underflow drops in extractor, ethanol boiling reflux extracts 3 times, merging filtrate, merging filtrate is concentrated into the 3-4 of the screen underflow weight dropping into extractor doubly, concentrated solution is cooled to 30-40 DEG C, use supercentrifuge centrifugation, removing centrifugation, centrifugate enters next step operation;
2) centrifugate enters macroporous adsorptive resins, for charging terminal when dropping to the resin height of bed 3/5 with the muddy light yellow and feeding liquid color of effluent liquid, after having entered feed liquid, first be washed till effluent liquid water white transparency by purified water, then the desorb of massfraction 50-70% ethanol is used, own weak yellow liquid starts to collect when flowing out, collect the stripping liquid of resin column volume 3.5-5 times of volume altogether, stripping liquid concentration and recovery ethanol, obtain concentrated solution, described macroporous adsorbent resin type is the one in resin DM130, HPD100, LXA-8, LSA-21;
3) concentrated solution is positioned over 2-5 DEG C of crystallization 24 hours, crystal Büchner funnel suction filtration, filtrate discards, and precipitates 65-75 DEG C of vacuum-drying 2-3 hour;
4) dried precipitation being joined concentration is in the hydrochloric acid of 1-4%, be heated to 90-95 DEG C of insulation 2-4 hour, with laboratory reaction still reaction 2-3 hour, the completely rear solution of question response is cooled to 30-40 DEG C of suction filtration, the crystal of gained after suction filtration is washed with pure water, being washed till pH value is 4-7, crystal 65-75 DEG C vacuum-drying 2-3 hour and get final product.
2. extracting method according to claim 1, it is characterized in that, 1) in, described ethanol is the ethanol of massfraction 40-70%, described boiling reflux extracts first time in 3 times and extracts, and massfraction 40-70% ethanol consumption is 15 times of the screen underflow weight dropping into extractor, extracts after 1.5 hours and filters, filtrate is for subsequent use, and filter residue enters and extracts next time; Second time is extracted, and massfraction 40-70% ethanol consumption is 13 times of the screen underflow weight dropping into extractor, and extract after 1 hour and filter, filtrate is for subsequent use, and filter residue enters and extracts next time; Third time extracts, and massfraction 40-70% ethanol consumption is 10 times of the screen underflow weight dropping into extractor, and extract after 1 hour and filter, filtrate is for subsequent use.
3. extracting method according to claim 1, is characterized in that, 1) in, described supercentrifuge rotating speed is 4000r/min, centrifugal 10 minutes.
4. extracting method according to claim 1, is characterized in that, 2) in, described concentrated solution volume is 1:1 with the volume ratio of the screen underflow dropping into extractor.
5. extracting method according to claim 1, is characterized in that, 4) in, the add-on of described precipitation and concentration 1-4% hydrochloric acid is the hydrochloric acid that 1 gram of precipitation adds 15 milliliters of 1-4%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20190289886A1 (en) | 2015-12-01 | 2019-09-26 | Symrise Ag | Substance mixtures |
| CN105924420B (en) * | 2016-04-29 | 2018-10-19 | 中南林业科技大学 | The method that Quercetin and phloretin are extracted from Camellia Leaves |
| CN106344447A (en) * | 2016-08-31 | 2017-01-25 | 陈雄 | Preparing raw material of composite face cream using apple skin |
| CN109180457B (en) * | 2018-08-08 | 2021-10-26 | 嘉兴欣贝莱生物科技有限公司 | Separation and purification process for biologically synthesizing phloretin |
| CN110156582A (en) * | 2019-06-01 | 2019-08-23 | 苏州禾研生物技术有限公司 | A kind of preparation method of high-purity phloretin |
| CN112811997B (en) * | 2021-03-02 | 2024-03-29 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for extracting and purifying phlorizin from apple flowers |
Citations (2)
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| CN101811949A (en) * | 2010-05-14 | 2010-08-25 | 上海利盛生化有限公司 | Purification method of phloretin powder |
| CN102701938A (en) * | 2012-06-11 | 2012-10-03 | 成都中医药大学 | Method for extracting and purifying phloretin from Malus toringoides(Rehd.) Hughes. and Malus tiansitoria(Batal.)Schneid. |
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Patent Citations (2)
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| CN101811949A (en) * | 2010-05-14 | 2010-08-25 | 上海利盛生化有限公司 | Purification method of phloretin powder |
| CN102701938A (en) * | 2012-06-11 | 2012-10-03 | 成都中医药大学 | Method for extracting and purifying phloretin from Malus toringoides(Rehd.) Hughes. and Malus tiansitoria(Batal.)Schneid. |
Non-Patent Citations (2)
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| 正交试验法优选苹果树皮中根皮素的提取方法;吕海涛等;《食品研究与开发》;20110331;第32卷(第3期);60-63 * |
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