CN103819521A - Method for preparing flavonoid compound from flavanone compound - Google Patents
Method for preparing flavonoid compound from flavanone compound Download PDFInfo
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- CN103819521A CN103819521A CN201410060765.4A CN201410060765A CN103819521A CN 103819521 A CN103819521 A CN 103819521A CN 201410060765 A CN201410060765 A CN 201410060765A CN 103819521 A CN103819521 A CN 103819521A
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Abstract
The invention provides a general method for preparing a flavonoid compound from a flavanone compound, and belongs to the medicinal and chemical field. The method comprises a dehydrogenation or dehydrogenation and hydrolysis desugaring process, and concretely comprises the following steps: dissolving ferric iron salt comprising iron trichloride and the like, pyridine derivatives comprising pyridine and the like, iodine and flavanone in alcohol, reacting in a water bath to flavones dehydrogenation, adding an acid to neutralize pyridine or hydrolyze, and adding a deferrization agent comprising phosphoric acid and the like for deferrization to obtain flavones or flavonoid aglycone. The method has the advantages of simplicity, easy implementation, high yield and purity, great reduction of the consumption of iodine and pyridine, and low cost, and is suitable for the industrialized large-scale production of flavonoid compounds by dehydrogenating flavanone or the preparation of the flavonoid compounds from flavanone compounds.
Description
Technical field
The present invention relates to be prepared by flavanone kind composition the method for flavonoid compound, its field is chemistry and medical.
Background technology
Extensively there is occurring in nature in flavanone kind composition, rich content, and extraction process is simple, cheap, as Hesperidin, naringin etc.So, a little less than the pharmacological action of flavanone compound, need to prepare corresponding flavonoid compound, prepare diosmin, naringin as Hesperidin and prepare Rhoifoloside, naringenin is prepared apigenin.Common method for making be with pyridine be solvent, iodine is dehydrogenating agent, after completion of the reaction, needs to reclaim pyridine and iodine.This method has following shortcoming at least: one, pyridine consumption is large, as 1kg Hesperidin, needs with about 5.8L pyridine.Two, pyridine reclaims difficulty, and reason is that pyridine boiling point is 115 ℃, the hydrogen iodide that the normal phenolic hydroxy group of flavonoid compound and dehydrogenation generate, and energy and pyridine salify, cause it and be difficult to be recovered.Through reclaim under reduced pressure operation, the pyridine rate of recovery only can reach 70%.Three, in decompression process, there is a small amount of pyridine to be drawn out of, pyridine breath malodor, contaminate environment, and damage employee's health.Four, flavanone dehydrogenation, needs equimolar iodine, and iodine is expensive, reclaims iodine, needs special equipment, comprises the equipment such as precipitation, suction filtration, the distillation of centrifugal, iodine of iodine.Five, iodine easily distils, and removal process has certain loss, and in environment, has pungent iodine gas.
Because flavanone kind composition kind is more, its Oxidative Dehydrogenation is also more for flavonoid compound, can not enumerate, and existing prepare diosmin and naringin take Hesperidin and prepares Rhoifoloside or apigenin and be illustrated as representative.
One, diosmin: a kind of flavonoid medicine of diosmin (Diosmin); there is enhancing intravenous tension; reduce capillary permeability and build up resistance; protection microcirculation; increase lymphatic contractility effect and lymphatic drainage velocity function, clinical in acute or chronic hemorrhoid and limbs venous return obstacle.The most separated from figwort Scrophularia nodosa as far back as 1925, within 1962 years, use as a medicine first.In Europe, diosmin has exceeded 30 years as the use of vascular protection medicament and chronic venous Remedies for diseases, and its global Year's consumption is about 3000 tons.In natural phant, content is lower, and extraction cost is higher, and existing preparation technology all obtains through iodine and pyridine Oxidative Dehydrogenation with Hesperidin.China is Hesperidin output big country, produces several kilotons of Hesperidin per year.Therefore, prepare diosmin with Hesperidin and there is stronger advantage.Right Hesperidin is water insoluble, alcohol equal solvent, dissolves in pyridine, DMSO.Because DMSO boiling point is higher, be difficult to reclaim, therefore multiplex pyridine is as the solvent that dissolves Hesperidin, double as acid scavenger.But Hesperidin, through iodine dehydrogenation, generates diosmin, and its solubleness in pyridine and DMSO is very little, causes pyridine or DMSO large usage quantity.Take pyridine as example, its consumption conventionally reach Hesperidin 5 times of amounts ([1] Gao Yongjin. strengthen intravenous tension medicine diosmin synthesis progress research [J]. China Chemical Industry trade, 2013, (7): 226; [2] Chen Zhiyu. diosmin synthesis technique analyze [J]. Chinese science and technology in length and breadth, 2011, (7): 315; [3] Li Yushan, Wang Jingan. the synthesis technique [J] of diosmin. laboratory study and exploration, 2010,29(8): 39-41; [4] Zhang Guangyue, opens strong. the production method [P] of diosmin. and China, CN101089009A, 2007.12.19).Yang edemas etc. adopt Microwave-assisted firing method, with I
2make catalyzer with NaI, with K
2cO
3, NaOH ethanolic soln and pyridine mixed solvent set up reaction system as action solvent, de-Hesperidin hydroformylation step is prepared to diosmin.Though certain embodiments has avoided high temperature and reaction solvent system to use in a large number the high boiling solvent such as pyridine, dimethyl sulfoxide (DMSO), but use the organic solvents such as more methyl alcohol, ethanol, and subsequent disposal is loaded down with trivial details, the synthetic total recovery of diosmin is below 90%, and industrialization cost is higher ([5] yang edema, Liu Maodong still, Lei Guoping, Zhu Zhenyu. a kind of diosmin bulk drug synthetic method [P] that meets EP7 version quality standard. China, CN102653549A, 2012.09.05).The production system of a kind of diosmin such as Jin Haixia, is characterized in that, comprise reaction recovery system, in and in filtering system, dissolving crude product filtering system, work in-process and filtering system, be pulverized and mixed system, iodine recovery system, methanol/ethanol recovery system.In reaction process, use a large amount of organic solvents, and the organic solvent rate of recovery closely can reach 90%, environmental pollution is larger, and step is more, and its industrialization cost is still higher.([6] Jin Haixia, Yang Xiangnong, Zhao Jingsong, Wang Ping. a kind of production system [P] of diosmin. China, CN202011848U, 2011.10.19)
Two, apigenin: apigenin (apigenin) is a kind of flavonoid compound, has the effects such as antitumor, anti-oxidant, anti-inflammatory, calmness, wherein outstanding with its antitumor action.Compared with other Flavonoid substances (Quercetin, kaempferia galamga flavones), apigenin has low toxicity, without features such as mutagenicities.Though apigenin is extensively present in various fruits and vegetables, its content in natural product is on the low side, extracts raw materials cost higher using natural phant as apigenin, cannot meet the need of market.Its preparation method is by synthetic or semi-synthetic.It is that raw material and aubepine carry out condensation acquisition compound ii under the catalysis of alkali that Yang Jian etc. pass through with 2,4-dimethoxy-6-hydroxy acetophenone; Under the condition existing at catalyzer, carry out ring-closure reaction, obtain compound III; Under oxygen barrier condition and under acidic conditions, heat and slough after methoxyl group, obtain apigenin.Its step is many, and productive rate is low, and consumption of organic solvent is many, environmental pollution is serious, with the semi-synthetic apigenin of naringin, its cost higher ([1] Yang Jian, Wu Ting, Yang Bo, Wu Yuanshuan. a kind of method [P] of preparing apigenin, China, CN100371335 ℃, 2008.2.27).The semi-synthetic apigenin of naringin, existing technique is prepared the semisynthesis of apigenin as research naringins such as Wen Yongju, doubles as acid scavenger using the pyridine of 2 times of amounts of naringin as solvent, and iodine is as dehydrogenating agent, prepare Rhoifoloside, its Rhoifoloside is hydrolyzed and obtains apigenin again in ethylene glycol.Because Rhoifoloside is in organic solvent, solubleness is little, needs a large amount of organic solvents, and the boiling point of ethylene glycol is high, is difficult to reclaim.Therefore, this processing step is many, and organic solvent consumption is large, contaminate environment ([2] Wen Yongju, Shen is beautiful. the research of the semi-synthetic apigenin of naringin. and Jiangsu agricultural sciences, 2012,40(5): 252-253).The semisynthetic preparation technology of apigenin of the invention such as Chen Xin, comprises two kinds of approach, and one is to obtain rhoifolin by naringin through dehydrogenation, then obtains apigenin by rhoifolin hydrolysis; Another kind of approach is first naringin hydrolysis to be obtained to naringenin, then obtains apigenin by naringenin dehydrogenation.But in these two kinds of techniques, all use bromine dehydrogenation, therefore phenolic hydroxyl group needs first acetylize protection, method is loaded down with trivial details, productive rate not high ([3] Chen Xin, the semi-synthetic versulin preparing process [A] of Li Pingxin. China, CN1640872A, 2005.7.20).Yan Weidong etc., take naringenin as raw material, take Isosorbide-5-Nitrae-dioxy hexanaphthene as reaction solvent, generate thick product apigenin with iodine generation oxidative dehydrogenation under alkali existence condition.Through multistep recrystallization, obtain refining apigenin.Its invention step is more, and productive rate is not high, and uses and may have the Isosorbide-5-Nitrae-dioxy of carcinogenesis hexanaphthene, environmental pollution large ([4] Yan Weidong, Cao Dan, Shao Yundong. the semisynthesis [A] of apigenin. China, CN100371335C, 2008.2.27).
Summary of the invention
The present invention designs a kind of method of being prepared corresponding flavonoid compound by flavanone kind composition, economizes the method for iodine, province's pyridine in certain embodiments, can significantly reduce iodine, pyridine consumption, thereby reaches the object that reduces environmental pollution and reduce product cost.
Method by flavanone kind composition Oxidative Dehydrogenation for flavonoid compound: comprise A, two kinds of approach of B, wherein A approach (flavanone only Oxidative Dehydrogenation for flavonoid): dissolve iodine and trivalent iron salt with alcohol, flavanone kind composition (7-(I)-Shi), pyridine and its derivatives, heating, airtight stirring reaction for some time, generate ferrous salt and flavonoid, dilute with alcohol, acid neutralization pyridine and its derivatives, water bath heat preservation, add deferrization agent to be stirred to iron-free complexing color, stir evenly, water bath heat preservation, suction filtration, washing, filter cake is placed in to the alcoholic solution of phosphoric acid, rinse 2-3 time, obtain flavonoid compound (7-(II)-Shi),
(the first dehydrogenation of hesperidin of B approach, be hydrolyzed again desugar and prepare Flavone aglycone): dissolve iodine, trivalent iron salt, flavanone kind composition, pyridine and its derivatives with alcohol, heating, airtight stirring reaction for some time, generate ferrous salt and flavonoid, with alcohol dilution, it is more than 1 times that acid adding is organic bases, and powder takes a policy, in water-bath more than 40 ℃, hydrolysis for some time, TLC/HPLC tracks to without glucosides, filters.Filter cake, adds the alcoholic solution of deferrization agent, is stirred to iron-free complexing color, water bath heat preservation, and suction filtration, washing, is placed in filter cake the alcoholic solution of phosphoric acid, and rinse 2-3 time, to obtain final product.
In this reaction process, using alcohol as solvent, pyridine and its derivatives is as acid scavenger, iodine is as dehydrogenating agent, and ferric iron, as oxygenant, can generate iodine by iodine oxide ion, generation divalence ferrous iron, divalence ferrous iron and flavones complex compound, can enlarge markedly flavones solubleness in alcoholic solvent.
The said alcohol of the present invention, can be monohydroxy-alcohol, dibasic alcohol, trivalent alcohol: monohydroxy-alcohol is as methyl alcohol, ethanol, propyl alcohol etc., dibasic alcohol is as ethylene glycol, 1,2-propylene glycol, 1, ammediol etc., trivalent alcohol, as glycerol etc., can be also the mixture of above-mentioned alcohol, wherein preferentially selects ethylene glycol or glycerol.
The said ferric iron of the present invention, mainly refer to trivalent iron salt, can be iron trichloride, ferric bromide, iron acetate etc., preferably FERRIC CHLORIDE ANHYDROUS, the molar weight of its trivalent iron salt mole dosage+iodine approximates the molar weight of flavanone, and by this method, the amount of iodine can reduce arbitrarily, but can not reduce to zero, as can be 1/5,1/10,1/100 etc. of original iodine consumption.
The said pyridine and its derivatives of the present invention, mainly refers to pyridine, 2-picoline, 3-picoline, 4-picoline, 5-picoline, 6-picoline, 2,6-lutidine etc., wherein preferred pyridine.
The said acid of the present invention, mainly refers to phosphoric acid, sulfuric acid, hydrochloric acid, Hydrogen bromide, acetic acid, oxalic acid, Citric Acid, tartrate, or any two kinds and above mixing use, and concentration is not limit, preferably hydrochloric acid, sulfuric acid, phosphoric acid.
The said deferrization agent of the present invention, mainly refers to phosphoric acid, SODIUM PHOSPHATE, MONOBASIC, Sodium phosphate dibasic, vat powder, preferably phosphoric acid.
The said flavanone kind composition of the present invention, meets (I) general formula, wherein R in flavanone and flavones parent nucleus
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9may be-H ,-OH ,-OCH
3,-glc(-Glucose) ,-rutinose(rue glycosyl,-O-β-Dglucopyranosyl (6 → 1) rhamcopyranosy) ,-O-β-Dglucopyranosyl (2 → 1) rhamcopyranosy(neohesperidose base) in arbitrary group, the representational compound of its flavanone is as Hesperidin (CAS:520-26-3), naringin (CAS:10236-47-2), naringenin (CAS:480-41-1), Hesperitin (CAS:520-33-2), eriodictyol (CAS:552-58-9) etc.
The said flavanone kind composition of the present invention, meets (II) general formula, wherein R in flavanone and flavones parent nucleus
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9may be-H ,-OH ,-OCH
3,-glc(-Glucose),-rutinose(rue glycosyl,-O-β-Dglucopyranosyl (6 → 1) rhamcopyranosy),-O-β-Dglucopyranosyl (2 → 1) rhamcopyranosy(neohesperidose base) in arbitrary group, its flavones representative compound is as Rhoifoloside (CAS:17306-46-6), apigenin-7-O-glucoside (CAS:578-74-5), apigenin (CAS:520-36-5), diosmin (CAS:520-27-4), diosmetin-7-O-glucoside (CAS:20126-59-4), diosmetin (CAS:520-34-3) etc.
Inventive principle:
Flavanone under the effect of pyridine dehydrogenation, generates flavones and hydrogen iodide, hydrogen iodide and pyridine salify through iodine; Ferric ion and flavanone, pyridine complexing, generate ferric ion-flavanone-pyridine complex.The ferric ion of complexing is in the alkaline system containing pyridine or pyridine derivate, and oxidation capacity declines, and can not be oxidized flavanone, and can increase the solubleness of flavanone kind composition, and this complex compound does not affect the dehydrogenation of iodine and pyridine.Ferric iron-flavanone-pyridine can the stronger I-ion of hydrogen reduction be iodine, and ferric iron-flavanone-pyridine complex generates ferrous iron-flavones-pyridine complex, and this compound also can dissolve in alcohol.Vat powder can reduce iron trichloride, reduce its oxidisability, and iodine is reduced into iodide ion, prevent on the one hand flavones absorption iodine (the oxidable iodide ion of airborne oxygen being precipitated out, generation is insoluble in the iodine of water, can be attached on water-fast flavones surface), (the oxidable ferrous ion of airborne oxygen is to ferric ion to prevent on the other hand the destruction of ferric ion to flavones parent nucleus, the iron ion of trivalent is under acidic conditions, there is stronger oxidisability, can be oxidized flavones parent nucleus, vat powder can be changed ferrous ion, lose oxidation capacity).Add the compound that contains phosphate anion, phosphate anion and ferric iron and ferrous iron complexing action are greater than flavones and ferric iron and ferrous complexing, therefore iron ion is cemented out from flavones complex compound.
embodiment:the invention discloses the general preparation method of various flavanone kind composition Oxidative Dehydrogenations for flavones.Those skilled in the art can use for reference content herein, and different flavanone kind composition Oxidative Dehydrogenations are suitably improved to processing parameter for flavonoid compound, as the kind of adjustment solvent, consumption, temperature etc.Special needs to be pointed out is, various flavanone kind composition Oxidative Dehydrogenations are in flavones, and trivalent iron salt plays the effect of complexing, iodine oxide ion generation iodine, and it is included that they all will be regarded as the present invention.Related personnel obviously can not suitably change or change and combine method as herein described, principle in disengaging content of the present invention, spirit and scope, realizes and apply the technology of the present invention.Embodiment is as follows:
Embodiment 1 naringin is prepared Rhoifoloside
Take rapidly 11.2g FERRIC CHLORIDE ANHYDROUS, add rapidly 30ml pyridine, mix, add 40ml ethylene glycol, 0.5g iodine, after iodine dissolves, add 98% naringin 20g, stir evenly, in 80 ℃ of-90 ℃ of confined reactions of water-bath 3 days, add dehydrated alcohol 60ml, powder 1g takes a policy, stir evenly, add hydrochloric acid 30ml, be stirred to without iron complex color (about 5h), add phosphatase 11 5ml, stir evenly, pour in 2000ml water, stir evenly, 50 ℃ of insulation 1h of water-bath, separate out precipitation, let cool, suction filtration, filter cake is placed in phosphoric acid-ethanol-water solution (5:50:45) 50ml rinse, suction filtration, filter cake is again in 50% ethanol 50ml rinse 2 times, be Rhoifoloside 18.3g, purity 98.5%.
Embodiment 2 Hesperidins are prepared diosmin
Take rapidly 26g FERRIC CHLORIDE ANHYDROUS, add rapidly 80ml pyridine, mix, add 100ml glycerol, 1.5g iodine, after iodine dissolves, add 90% Hesperidin 50g, stir evenly, in 80 ℃ of-90 ℃ of confined reactions of water-bath 4 days, add dehydrated alcohol 100ml, the powder 2g that takes a policy mixes after 30min, add hydrochloric acid 80ml, phosphoric acid 30ml, in 40 ℃ of water-baths, insulation 3h, after stirring, separate out precipitation, let cool, suction filtration, filter cake is placed in phosphoric acid-ethanol-water solution (5:50:45) 100ml rinse, suction filtration, filter cake is again in 80% ethanol 100ml rinse 2 times, obtain diosmin 46.5g, purity 92.6%.
Embodiment 3 Hesperidins are prepared diosmin
Get 26g FERRIC CHLORIDE ANHYDROUS, add 80ml pyridine, add 0.5g iodine, 120ml ethylene glycol, add 90% Hesperidin 50g, in 80 ℃ of-90 ℃ of confined reactions of water-bath 4 days, add dehydrated alcohol 100ml, the powder 2g that takes a policy mixes after 30min, add hydrochloric acid 80ml, in 45 ℃ of water-baths, be stirred to without iron complex color (about 5h), add phosphatase 24 0ml, stir evenly, import 3000ml, 60 ℃ of insulation 0.5h of water-bath, suction filtration, washing, filter cake is placed in phosphoric acid-ethanol-water solution (5:50:45) 100ml rinse, suction filtration, filter cake is again in 80% ethanol 100ml rinse 1 time, obtain diosmin 45.8g, purity 92.7%.
Embodiment 4 naringins are prepared apigenin
Get 30ml ethylene glycol, add 30ml pyridine, add 11.2g FERRIC CHLORIDE ANHYDROUS, stir evenly, add 0.5g iodine, after iodine dissolves, add 98% naringin 20g, stir evenly, in 80 ℃ of-90 ℃ of confined reactions of water-bath 3 days, add dehydrated alcohol 60ml, the powder 2g that takes a policy mixes after 30min, add hydrochloric acid 40ml, in 80 ℃ of airtight hydrolysis of water-bath 1 day, separate out precipitation, let cool, suction filtration, filter cake is placed in phosphoric acid-ethanol-water solution (5:50:45) 50ml rinse, suction filtration, and filter cake is again in 50% ethanol 50ml rinse 2 times, obtain apigenin 8.5g, purity 98.2%.
Because flavanone kind composition kind is many especially, the explanation of above embodiment is just for helping to understand method of the present invention and core concept thereof.Should be understood that; for the ordinary person of the art; under the premise without departing from the principles of the invention; can also be to various flavanone kind compositions; comprise the flavanone kind composition that the present invention mentions; carry out some improvement, within these improve and also fall into the claims in the present invention protection domain.
Claims (9)
1. prepared the method for flavonoid compound by flavanone kind composition: comprise A, two kinds of approach of B, wherein A approach (flavanone only Oxidative Dehydrogenation for flavonoid): dissolve iodine and trivalent iron salt with alcohol, flavanone kind composition (7-(I)-Shi), pyridine and its derivatives, heating, airtight stirring reaction for some time, generate ferrous salt and flavonoid, dilute with alcohol, acid neutralization pyridine and its derivatives, water bath heat preservation, add deferrization agent to be stirred to iron-free complexing color, stir evenly, water bath heat preservation, suction filtration, washing, filter cake is placed in to the alcoholic solution of phosphoric acid, rinse 2-3 time, obtain flavonoid compound (7-(II)-Shi),
(the first dehydrogenation of hesperidin of B approach, be hydrolyzed again desugar and prepare Flavone aglycone): dissolve iodine, trivalent iron salt, flavanone kind composition, pyridine and its derivatives with alcohol, heating, airtight stirring reaction for some time, generate ferrous salt and flavonoid, with alcohol dilution, it is more than 1 times that acid adding is organic bases, and powder takes a policy, in water-bath more than 40 ℃, hydrolysis for some time, TLC/HPLC tracks to without glucosides, filters.
2. filter cake, adds the alcoholic solution of deferrization agent, is stirred to iron-free complexing color, water bath heat preservation, and suction filtration, washing, is placed in filter cake the alcoholic solution of phosphoric acid, and rinse 2-3 time, to obtain final product.
3. the method for claim 1, it is characterized in that alcohol, can be monohydroxy-alcohol, dibasic alcohol, trivalent alcohol: monohydroxy-alcohol is as methyl alcohol, ethanol, propyl alcohol etc., dibasic alcohol is as ethylene glycol, 1,2-propylene glycol, 1,3-PD etc., trivalent alcohol is as glycerol etc., also can be the mixture of above-mentioned alcohol, wherein preferentially select ethylene glycol or glycerol.
4. the method for claim 1, it is characterized in that ferric iron, mainly refer to trivalent iron salt, can be iron trichloride, ferric bromide, iron acetate etc., preferably FERRIC CHLORIDE ANHYDROUS, the molar weight of its trivalent iron salt mole dosage+iodine approximates the molar weight of flavanone, by this method, the amount of iodine can reduce arbitrarily, but can not reduce to zero, as can be 1/5,1/10,1/100 etc. of original iodine consumption.
5. the method for claim 1, is characterized in that pyridine and its derivatives, mainly refers to pyridine, 2-picoline, 3-picoline, 4-picoline, 5-picoline, 6-picoline, 2,6-lutidine etc., wherein preferred pyridine.
6. the method for claim 1, is characterized in that acid, phosphoric acid, sulfuric acid, hydrochloric acid, Hydrogen bromide, acetic acid, oxalic acid, Citric Acid, tartrate, or any two kinds and above mixing use, and concentration is not limit, preferably hydrochloric acid, sulfuric acid, phosphoric acid.
7. the method for claim 1, is characterized in that deferrization agent, can be phosphoric acid, SODIUM PHOSPHATE, MONOBASIC, Sodium phosphate dibasic, vat powder, preferably phosphoric acid.
8. the method for claim 1, is characterized in that flavanone kind composition, meets (I) general formula,
Wherein R in flavanone and flavones parent nucleus
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9may be-H ,-OH ,-OCH
3,-glc(-Glucose) ,-rutinose(rue glycosyl,-O-β-Dglucopyranosyl (6 → 1) rhamcopyranosy) ,-O-β-Dglucopyranosyl (2 → 1) rhamcopyranosy(neohesperidose base) in arbitrary group, the representational compound of its flavanone is as Hesperidin (CAS:520-26-3), naringin (CAS:10236-47-2), naringenin (CAS:480-41-1), Hesperitin (CAS:520-33-2), eriodictyol (CAS:552-58-9) etc.
9. the method for claim 1, is characterized in that flavonoid compound, meets (II) general formula,
Wherein R in flavanone and flavones parent nucleus
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
9may be-H ,-OH ,-OCH
3,-glc(-Glucose),-rutinose(rue glycosyl,-O-β-Dglucopyranosyl (6 → 1) rhamcopyranosy),-O-β-Dglucopyranosyl (2 → 1) rhamcopyranosy(neohesperidose base) in arbitrary group, its flavones representative compound is as Rhoifoloside (CAS:17306-46-6), apigenin-7-O-glucoside (CAS:578-74-5), apigenin (CAS:520-36-5), diosmin (CAS:520-27-4), diosmetin-7-O-glucoside (CAS:20126-59-4), diosmetin (CAS:520-34-3) etc.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610244A (en) * | 2014-12-16 | 2015-05-13 | 李玉山 | Halogen cyclic regeneration technology applied to dehydrogenation and hydrolysis reaction |
| CN105949161A (en) * | 2016-06-28 | 2016-09-21 | 温州大学 | Preparation method of 3-arylmercapto flavonoid compound |
| CN115710592A (en) * | 2023-01-09 | 2023-02-24 | 成都欧康医药股份有限公司 | Preparation process of 4',5, 7-trihydroxy flavanone |
-
2014
- 2014-02-24 CN CN201410060765.4A patent/CN103819521A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610244A (en) * | 2014-12-16 | 2015-05-13 | 李玉山 | Halogen cyclic regeneration technology applied to dehydrogenation and hydrolysis reaction |
| CN105949161A (en) * | 2016-06-28 | 2016-09-21 | 温州大学 | Preparation method of 3-arylmercapto flavonoid compound |
| CN105949161B (en) * | 2016-06-28 | 2018-05-15 | 温州大学 | A kind of preparation method of 3- aromatic thiohydroxies chromocor compound |
| CN115710592A (en) * | 2023-01-09 | 2023-02-24 | 成都欧康医药股份有限公司 | Preparation process of 4',5, 7-trihydroxy flavanone |
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Application publication date: 20140528 |