CN104829578A - Clean preparation method of naringenin - Google Patents
Clean preparation method of naringenin Download PDFInfo
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- CN104829578A CN104829578A CN201410053353.8A CN201410053353A CN104829578A CN 104829578 A CN104829578 A CN 104829578A CN 201410053353 A CN201410053353 A CN 201410053353A CN 104829578 A CN104829578 A CN 104829578A
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- Prior art keywords
- naringenin
- crude product
- naringin
- preparation technology
- acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
Abstract
A clean preparation method of naringenin includes following main processes: (1) hydrolysis of naringin; (2) preparation of a crude product of the naringenin; (3) preparation of a finish product of the naringenin; and (4) treatment of acidic liquid. In the invention, the naringin which is easily to obtain is used as a raw material to prepare the naringenin being more than 98% in content (HPLC) and rhamnose being more than 99% in content (HPLC) through hydrolysis. Compared with an extraction method, a totally-synthetic method and a micro-biological converting method in the prior art, the method is simple in operation, is high in yield and is low in cost. The acidic liquid generated through hydrolysis is treated well for turning the waste into resources and the rhamnose in the acidic liquid is extracted. The whole process can save resources, is environmental-friendly and is suitable for industrial production.
Description
Technical field
What the present invention relates to a kind of naringenin cleans preparation technology.
Background technology
Naringenin (Naringenin; Naringetol), another name Naringenin, 4 ', 5,7-trihydroxyflavone, naringenin.The nucleocapsid etc. of main raw material Anacardiaceae plant stalk tree (Amacardi-um occidentaleL.) fruit; Rosaceous plant oriental cherry (Prunus yedoensis Mats.) bud, plum (P.mumeSiebet Zucc.) bud.CAS NO:480-41-1, molecular formula C
15h
12o
5, molecular weight 272.25, fusing point 247 ~ 250 DEG C.Structural formula is as follows:
Naringenin is white, needle-shaped crystals, fine powder.Be dissolved in methyl alcohol, ethanol, ether and benzene, water-soluble hardly.The reaction of hydrochloric acid magnesium powder is in cherry red, and tetrahydro boron sodium reaction is red-violet colour, molish reaction negative.Naringenin is the aglycon of naringin, belongs to flavanone kind composition, has multiple pharmacological effect.(1) antibacterial: to have stronger anti-microbial effect to golden yellow glucose coccus, large intestine, dysentery and Corynebacterium diphtheriae, also have effect to fungi; (2) anti-inflammatory: with the increase of dosage, naringenin obviously suppresses to implant the inflammation caused by wool ball, produces effective the suppression to the ear edge edema of IPR, vLPR; (3) oxidation and removing free radicals effect: naringenin is mainly by the Cu of its chelating
2+, or provide proton and free radical to neutralize, or by autoxidation, the lipid peroxidation of LDL is shielded, naringenin is to active oxygen O
2-having obvious scavenging(action), may be realize scavenging free radicals by naringenin self for hydroxide.(4) reducing blood lipid: under certain dosage, naringenin can make serum TC, TG, LDL-C significantly decline, and relatively improve Serum HDL-C, has the effect of reducing blood-fat; (5) antitumor action: naringenin can regulate body T lymphocyte level, repair the secondary immunodeficiency because tumour or radiotherapy, chemotherapy cause, strengthen the effect killing and wounding cancer cells, there is the effect of conditioner body immunity function and Tumor suppression growth; (6) spasmolysis and cholagogic: naringenin also has the effect of stronger increase laboratory animal choleresis, is act on comparatively powerhouse in flavonoid compound; (7) cough-suppressing phlegm-dispelling functions: utilize phenolsulfonphthalein as disease effect indicator of dispelling, description of test naringenin has stronger cough-suppressing phlegm-dispelling functions.In addition, also there is the effects such as prevention and therapy hepatopathy, anti-platelet clotting, atherosclerosis, the field such as medicine, food can be widely used in.Be used for the treatment of bacteriological infection, calm, anticancer class medicine, application forms mainly contains suppository, lotion, injection liquid, tablet, capsule etc.
At present, naringenin mainly extracts from natural phant, and production technique completes primarily of operations such as alcohol extracting, extraction, chromatography, crystallizations.In addition, the preparation of naringenin is by naringin hydrolysis method, and complete synthesizing process, microbe transformation method obtains.The present invention be easy to get in a large number naringin for raw material, by being hydrolyzed obtained naringenin and rhamnosyl, have simple to operate, yield is high, and cost is low, eco-friendly feature, be applicable to suitability for industrialized production.
Summary of the invention
First naringin hydrolysis: Hesperidin, with purified water heating for dissolving, adds acid solution hydrolysis, obtains naringenin reactant.
The preparation of the second naringenin crude product: naringenin reactant cools, precipitation, throw out is with plate-and-frame filter press press filtration, and purified water is washed, and vacuum-drying, obtains naringenin crude product.
The preparation of the 3rd naringenin fine work: naringenin crude product, with a certain amount of dissolution with solvents, adds activated carbon decolorizing, filters, and filtrate concentrates, and crystallization is centrifugal, dry, obtains naringenin fine work.
Tetracid water treatment: press filtration acid liquid neutralizes, filters, and fermentation is filtered, and concentrated, crystallization, obtains crude product rhamnosyl.Crude product rhamnosyl, with dissolve with methanol, adds activated carbon decolorizing, filtered while hot, and filtrate concentrates, and concentrated solution crystallization is centrifugal, dry, obtains fine work rhamnosyl.
Embodiment
By the 1500kg purified water suction reactor of accurate measurement, under stirring, regulate water liquid pH1 ~ 2 with the vitriol oil, add the antioxidant of 1.0 ~ 1.5%, slowly add naringin 200.0kg, sealed reactor mouth, heating, closes heat-carrying steam valve when question response still upward pressure table indicator pressure reaches 0.10MPa, treats that pressure rises to 0.15MPa and starts timing, keep still internal pressure at 0.12 ~ 0.15Mpa, reaction 1 ~ 4h.Clarify bright solution in reaction process and become muddy gradually, detect after sampling process, start step-down after reacting completely, obtain naringenin reactant.Under abundant stirring, reactor interlayer passes into tap water cooling, leaves standstill, uses plate-and-frame filter press press filtration, pressing filtering liquid merging treatment.Filter cake purified water is washed, until filtrate pH value is in neutral.Transfer in drying machine by naringenin wet product good for press filtration, under-(0.01 ~ 0.03) Mpa, dry 6 ~ 8h, obtains naringenin crude product.
By the 450k ethanol of accurate-metering negative pressure sucting reaction still, under stirring, naringenin crude product 50kg is added reactor, add gac 2.5kg, reflux, closing volume after temperature 65 ± 5 DEG C of stirring and refluxing dissolve 30min, start boosting, start when pressure rises to 0.10 ~ 0.12MPa to filter.The feed liquid of filtering squeezes into crystallizer be concentrated into 1/3 of original volume under-(0.03 ~ 0.05) Mpa after, opens and stirs, open water coolant, stirred crystallization.Pour advantages of good crystallization material into centrifuge, when whizzer liquid outlet mother liquor becomes to drip, the naringenin wet product after centrifugal is transferred in drying machine, dry under-(0.02 ~ 0.04) MPa.After checking that dry mass is qualified, hand over and pulverize post.After pulverizing completes, the sampling of friendship through-station detects, and determine that mixed batch batch joins total mixed machine, mixing completes.Material is divided in polyethylene packaging bag, first internal packing, pricks sealing, then outer packaging, pricks sealing, and labeling is put in storage.
In being produced by naringenin crude product, the acid liquid of press filtration squeezes into settling tank, add pasty state hydrated barta furnishing under abundant stirring neutral, press filtration, filtrate adds the yeast fermentation 72h of 5%, press filtration, concentrated under filtrate decompression, concentrated solution proportion 1.08 ~ 1.20, adds proper amount of acetone and rhamnosyl crystal seed, at 5 ~ 10 DEG C of crystallization 96h, centrifugal, vacuum-drying at 50 DEG C, obtains rhamnosyl crude product.Crude product rhamnosyl with 99% dissolve with methanol, then adds 5 ~ 8% gacs, 65 ± 2 DEG C of stirring heating, starts to filter after reflux decolour 30min.Filtrate reduced in volume is to proportion 1.08 ~ 1.20, and squeeze into crystallizer and stir, crystallizer passes into water coolant, stirred crystallization 24h.Pour advantages of good crystallization material into centrifuge, centrifugal good rhamnosyl wet product transfers to dry 3.5h in drying machine.After checking that dry mass is qualified, blowing is weighed, and hands over and pulverizes post.Pulverized by dried rhamnosyl pulverizer, the material sampling after pulverizing detects.Determine that mixed batch batch is joined total mixed machine, mixing completes.Material is divided in polyethylene packaging bag, first internal packing, pricks sealing, and in outer packaging, prick sealing, labeling is put in storage.
Claims (8)
1. naringenin clean a preparation technology, it is characterized in that, take naringin as raw material, this technique is successively through following steps:
(1) naringin hydrolysis: Hesperidin is with dissolution with solvents, and acid adjustment post-heating is hydrolyzed, and obtains naringenin reactant.
(2) preparation of naringenin crude product: naringenin reactant cools, precipitation, throw out is with plate-and-frame filter press press filtration, and purified water is washed, and vacuum-drying, obtains naringenin crude product.
(3) preparation of naringenin fine work: naringenin crude product, with a certain amount of dissolution with solvents, adds activated carbon decolorizing, filters, and filtrate concentrates, and crystallization is centrifugal, dry, obtains naringenin fine work.
(4) sour water process: press filtration acid liquid neutralizes, filters, and fermentation is filtered, and concentrated, crystallization, obtains crude product rhamnosyl.Crude product rhamnosyl, with dissolve with methanol, adds activated carbon decolorizing, filtered while hot, and filtrate concentrates, and concentrated solution crystallization is centrifugal, dry, obtains fine work rhamnosyl.
2. a kind of naringenin according to claim 1 clean preparation technology, it is characterized in that, the solvent dissolving naringin in step (1) is water, methyl alcohol, ethanol, in acetone any one, any two kinds or any three kinds mix with arbitrary proportion; Acid reagent is hydrochloric acid, sulfuric acid, in phosphoric acid any one, any two kinds or any three kinds mix with arbitrary proportion; Antioxidant is vitamins C, in S-WAT any one, any two kinds mix with arbitrary proportion.
3. a kind of naringenin according to claim 1 clean preparation technology, it is characterized in that, the solvent load dissolving naringin in step (1) is 5 ~ 10 times of naringin; Reaction solution adjust pH 1 ~ 2; Antioxidant consumption is 1.0 ~ 1.5%; Reaction 1 ~ 4h.
4. a kind of naringenin according to claim 1 clean preparation technology, it is characterized in that, the feature of reaction process is that solution first clarifies rear muddiness in step (1), the feature of react be filtrate after reacting liquid filtering again acid hydrolysis without precipitation generation.
5. a kind of naringenin according to claim 1 clean preparation technology, it is characterized in that, with plate-and-frame filter press press filtration in step (2), purified water is washed till effluent liquid pH value in neutral, vacuum-drying under one (0.01 ~ 0.03) Mpa, obtains naringenin crude product.
6. a kind of naringenin according to claim 1 clean preparation technology, it is characterized in that, the solvent dissolving naringin crude product in step (3) is methyl alcohol, ethanol, acetone, in purified water any one, any two kinds or any three kinds mix with arbitrary proportion; Activated carbon dosage is 3 ~ 6% of crude product amount.
7. a kind of naringenin according to claim 1 clean preparation technology, it is characterized in that, in step (4), press filtration acid liquid is neutral with pasty state hydrated barta adjust pH, filtrate adds the yeast fermentation 96h of 4 ~ 5%, press filtration, filtrate reduced in volume, to proportion 1.08 ~ 1.20, adds proper amount of acetone and seeded crystallization; The crude product methyl alcohol heating for dissolving of 99%, adds 5 ~ 8% gacs, filtrate reduced in volume, crystallization, vacuum-drying.
8. according to claim 1,2,3,4,5,6, a kind of naringenin described in 7 clean preparation technology, it is characterized in that, take naringin as raw material, one one-step hydrolysis can obtain the naringenin of purity more than 98%, is extracted rhamnosyl in acid liquid, and whole process has accomplished resources conservation, environmental friendliness.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410053353.8A CN104829578A (en) | 2014-02-12 | 2014-02-12 | Clean preparation method of naringenin |
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| CN201410053353.8A CN104829578A (en) | 2014-02-12 | 2014-02-12 | Clean preparation method of naringenin |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279088A (en) * | 2016-08-23 | 2017-01-04 | 湖南华诚生物资源股份有限公司 | A kind of method extracting high-purity naringenin for raw material with pomelo peel |
| CN112645920A (en) * | 2020-12-07 | 2021-04-13 | 桂林莱茵生物科技股份有限公司 | Method for co-producing naringenin and rhamnose from young pomelo fruits |
| CN112851616A (en) * | 2021-01-25 | 2021-05-28 | 三原润禾生物科技有限公司 | Semi-synthesis method of eriodictyol |
-
2014
- 2014-02-12 CN CN201410053353.8A patent/CN104829578A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279088A (en) * | 2016-08-23 | 2017-01-04 | 湖南华诚生物资源股份有限公司 | A kind of method extracting high-purity naringenin for raw material with pomelo peel |
| CN106279088B (en) * | 2016-08-23 | 2018-07-06 | 湖南华诚生物资源股份有限公司 | A kind of method that high-purity naringenin is extracted using pomelo peel as raw material |
| CN112645920A (en) * | 2020-12-07 | 2021-04-13 | 桂林莱茵生物科技股份有限公司 | Method for co-producing naringenin and rhamnose from young pomelo fruits |
| CN112851616A (en) * | 2021-01-25 | 2021-05-28 | 三原润禾生物科技有限公司 | Semi-synthesis method of eriodictyol |
| CN112851616B (en) * | 2021-01-25 | 2023-09-26 | 三原润禾生物科技有限公司 | Semisynthesis method of eriodictyol |
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