CN103450299A - Method for simultaneously preparing esculoside and esculetin - Google Patents
Method for simultaneously preparing esculoside and esculetin Download PDFInfo
- Publication number
- CN103450299A CN103450299A CN 201310425575 CN201310425575A CN103450299A CN 103450299 A CN103450299 A CN 103450299A CN 201310425575 CN201310425575 CN 201310425575 CN 201310425575 A CN201310425575 A CN 201310425575A CN 103450299 A CN103450299 A CN 103450299A
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- China
- Prior art keywords
- ethyl acetate
- extraction
- cichorigenin
- bark
- vitamin
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- ILEDWLMCKZNDJK-UHFFFAOYSA-N esculetin Chemical compound C1=CC(=O)OC2=C1C=C(O)C(O)=C2 ILEDWLMCKZNDJK-UHFFFAOYSA-N 0.000 title claims abstract description 21
- XHCADAYNFIFUHF-TVKJYDDYSA-N esculin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC2=C1OC(=O)C=C2 XHCADAYNFIFUHF-TVKJYDDYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 16
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 title abstract 3
- QNHQEUFMIKRNTB-UHFFFAOYSA-N aesculetin Natural products C1CC(=O)OC2=C1C=C(O)C(O)=C2 QNHQEUFMIKRNTB-UHFFFAOYSA-N 0.000 title abstract 3
- GUAFOGOEJLSQBT-UHFFFAOYSA-N aesculetin dimethyl ether Natural products C1=CC(=O)OC2=C1C=C(OC)C(OC)=C2 GUAFOGOEJLSQBT-UHFFFAOYSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000605 extraction Methods 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000013078 crystal Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- 239000000843 powder Substances 0.000 claims abstract description 6
- 238000001953 recrystallisation Methods 0.000 claims abstract 5
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000000737 periodic effect Effects 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000006228 supernatant Substances 0.000 claims description 7
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 102000011759 adducin Human genes 0.000 claims description 2
- 108010076723 adducin Proteins 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000002137 ultrasound extraction Methods 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- GMRNMZUSKYJXGJ-UHFFFAOYSA-N Fraxetin Natural products C1=CC(=O)C(=O)C2=C1C=C(OC)C(O)=C2O GMRNMZUSKYJXGJ-UHFFFAOYSA-N 0.000 description 1
- CRSFLLTWRCYNNX-UHFFFAOYSA-N Fraxin Natural products OC=1C(OC)=CC=2C=CC(=O)OC=2C=1OC1OC(CO)C(O)C(O)C1O CRSFLLTWRCYNNX-UHFFFAOYSA-N 0.000 description 1
- 241000565359 Fraxinus chinensis Species 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HAVWRBANWNTOJX-UHFFFAOYSA-N fraxetin Chemical compound C1=CC(=O)OC2=C1C=C(OC)C(O)=C2O HAVWRBANWNTOJX-UHFFFAOYSA-N 0.000 description 1
- CRSFLLTWRCYNNX-QBNNUVSCSA-N fraxin Chemical compound OC=1C(OC)=CC=2C=CC(=O)OC=2C=1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CRSFLLTWRCYNNX-QBNNUVSCSA-N 0.000 description 1
- 208000006750 hematuria Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a method for simultaneously preparing esculoside and esculetin, and in particular relates to a continuous countercurrent ultrasonic extraction method. The method comprises the following steps: adding ethanol liquor to ash bark crude powder; after carrying out continuous countercurrent ultrasonic extraction, carrying out solid-liquid separation to obtain leach liquor; carrying out solid-liquid separation to obtain supernate; concentrating under reduced pressure; adding distilled water to dissolve; firstly, extracting for 2 times by chloroform; extracting the water layer extracted by chloroform through ethyl acetate for times; combining the ethyl acetate extracting liquor; drying by anhydrous sodium sulfate; recovering the solvent under reduced pressure till dryness; adding methanol to separate out yellow acicular crystals; repeatedly crystallizing for many times by a recrystallization solvent to obtain the esculetin; partially concentrating water extracted by ethyl acetate to separate out yellowish crystals; repeatedly crystallizing for many times by the recrystallization solvent to obtain the esculoside. The method provided by the invention has the advantages of simplicity in process, short extraction time, high extraction rate and reasonable utilization of raw materials, and is environment-friendly and easy for industrial production.
Description
technical field:
The present invention relates to a kind of method that simultaneously prepares Vitamin C2 and Cichorigenin, relate in particular to a kind of method of utilizing the continuous countercurrent supersound extraction.
background technology:
Dry bark or trunk bark that the bark of ash is five kind of plant such as Oleaceae plants Chinese ash, it is China's conventional Chinese medicine simply, the successive dynasties book on Chinese herbal medicine is all on the books, containing Vitamin C2, Cichorigenin, fraxin, Fraxetin and resin, tannin and a small amount of starch etc., its cold nature, bitter, the function heat-clearing and damp-drying drug, be apt to control diarrhea due to damp-heat and dysentery, damp and hot rheumatism also had to the effect of clearing away damp-heat, suitable numbness pain relieving, modern study proves, the bark of ash has relieving inflammation and relaxing pain and reduces the effect of hematuria acid, is used for the treatment of gout excellent.Wherein Vitamin C2 and Cichorigenin have stronger oxidation-resistance.Find in recent years the great attention that the efficient natural antioxidant has been subject to people from herbal medicine, there is vast potential for future development.
Less about the research report of Vitamin C2 in the bark of ash and Cichorigenin at present, by the exploration to extracting method, for the industrialization of extracting Vitamin C2 and Cichorigenin from the bark of ash lays the foundation, meet the need of market.
summary of the invention:
The objective of the invention is fully to develop the value of the bark of ash, a kind of method of simultaneously extracting Vitamin C2 and Cichorigenin be provided, the method has advantages of that technique is simple, extraction efficiency is high, power consumption less, extraction time is short, is easy to realize suitability for industrialized production.
The present invention includes following steps:
A. get the bark of ash and pulverize, cross 100 mesh sieves;
B. add 95% ethanol of 5 ~ 10 times of bark of ash grain weight amounts in bark of ash powder, under 60 ~ 80 ℃, under 50 ~ 70KHz, solid-liquid separation after continuous countercurrent supersound extraction 2 ~ 3h, obtain supernatant liquor;
C. by the above-mentioned supernatant liquor concentrating under reduced pressure obtained, add distilled water to dissolve, first use chloroform extraction 2 times, the water layer that chloroform extraction is crossed is extracted with ethyl acetate 2 ~ 4 times, combined ethyl acetate extraction liquid, anhydrous sodium sulfate drying, decompression and solvent recovery is to dry, add methyl alcohol and separate out yellow needle-like crystal, 60 ~ 90% methanol aqueous solution periodic crystallisation 2 times, obtain Cichorigenin;
D. the stripped water section of ethyl acetate is concentrated, separate out micro-yellow crystals, the methanol aqueous solution periodic crystallisation with 60 ~ 90% 2 times, obtain Vitamin C2.
The present invention selects continuous countercurrent supersound extraction Vitamin C2 and Cichorigenin, uses minimum solvent to obtain maximum solubleness, has improved extraction effect, significantly reduced solvent load, reduced energy consumption, can realize continuous operation, be easy to realize suitability for industrialized production simultaneously.In addition, at present less to the extraction research of Vitamin C2 and Cichorigenin, the present invention has utilized raw material fully, has obtained two kinds of products of Vitamin C2 and Cichorigenin simultaneously, for the development and utilization of the bark of ash opens up a new way.
Further illustrate the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
embodiment:
Embodiment 1:
Get 100g through pulverizing, cross the bark of ash powder of 100 mesh sieves, 95% ethanol that adds 5 times of bark of ash grain weight amounts, solid-liquid separation after continuous countercurrent supersound extraction 2h under 70 ℃, under 60KHz, obtain supernatant liquor, concentrating under reduced pressure, add distilled water to dissolve, first use chloroform extraction 2 times, the water layer that chloroform extraction is crossed is extracted with ethyl acetate 4 times, the combined ethyl acetate extraction liquid, anhydrous sodium sulfate drying, decompression and solvent recovery, to dry, adds methyl alcohol and separates out yellow needle-like crystal, 60% methanol aqueous solution periodic crystallisation 2 times, obtain Cichorigenin, productive rate is 3.58%; The stripped water section of ethyl acetate is concentrated, separate out micro-yellow crystals, the methanol aqueous solution periodic crystallisation with 60% 2 times, obtain Vitamin C2, and productive rate is 2.01%.
Embodiment 2:
Get 100g through pulverizing, cross the bark of ash powder of 100 mesh sieves, 95% ethanol that adds 10 times of bark of ash grain weight amounts, solid-liquid separation after continuous countercurrent supersound extraction 3h under 80 ℃, under 50KHz, obtain supernatant liquor, concentrating under reduced pressure, add distilled water to dissolve, first use chloroform extraction 2 times, the water layer that chloroform extraction is crossed is extracted with ethyl acetate 3 times, the combined ethyl acetate extraction liquid, anhydrous sodium sulfate drying, decompression and solvent recovery, to dry, adds methyl alcohol and separates out yellow needle-like crystal, 80% methanol aqueous solution periodic crystallisation 2 times, obtain Cichorigenin, productive rate is 4.01%; The stripped water section of ethyl acetate is concentrated, separate out micro-yellow crystals, the methanol aqueous solution periodic crystallisation with 80% 2 times, obtain Vitamin C2, and productive rate is 2.24%.
Embodiment 3:
Get 100g through pulverizing, cross the bark of ash powder of 100 mesh sieves, 95% ethanol that adds 8 times of bark of ash grain weight amounts, solid-liquid separation after continuous countercurrent supersound extraction 2.5h under 60 ℃, under 70KHz, obtain supernatant liquor, concentrating under reduced pressure, add distilled water to dissolve, first use chloroform extraction 2 times, the water layer that chloroform extraction is crossed is extracted with ethyl acetate 2 times, the combined ethyl acetate extraction liquid, anhydrous sodium sulfate drying, decompression and solvent recovery, to dry, adds methyl alcohol and separates out yellow needle-like crystal, 90% methanol aqueous solution periodic crystallisation 2 times, obtain Cichorigenin, productive rate is 3.79%; The stripped water section of ethyl acetate is concentrated, separate out micro-yellow crystals, the methanol aqueous solution periodic crystallisation with 90% 2 times, obtain Vitamin C2, and productive rate is 2.15%.
Claims (3)
1. a method that simultaneously prepares Vitamin C2 and Cichorigenin, is characterized in that, comprises the following steps:
A. get the bark of ash and pulverize, cross 100 mesh sieves;
B. add 95% ethanol of 5 ~ 10 times of bark of ash grain weight amounts in bark of ash powder, under 60 ~ 80 ℃, under 50 ~ 70KHz, solid-liquid separation after continuous countercurrent supersound extraction 2 ~ 3h, obtain supernatant liquor;
C. by the above-mentioned supernatant liquor concentrating under reduced pressure obtained, add distilled water to dissolve, first use chloroform extraction 2 times, the water layer that chloroform extraction is crossed is extracted with ethyl acetate for several times, combined ethyl acetate extraction liquid, anhydrous sodium sulfate drying, decompression and solvent recovery is to dry, add methyl alcohol and separate out yellow needle-like crystal, recrystallization solvent periodic crystallisation 2 times, obtain Cichorigenin;
D. the stripped water section of ethyl acetate is concentrated, separate out micro-yellow crystals, with recrystallization solvent periodic crystallisation 2 times, obtain Vitamin C2.
2. a kind of method that simultaneously prepares Vitamin C2 and Cichorigenin according to claim 1 is characterized in that: the number of times of the ethyl acetate extraction described in step c is 2 ~ 4 times.
3. a kind of method that simultaneously prepares Vitamin C2 and Cichorigenin according to claim 1, is characterized in that: the methanol aqueous solution that the recrystallization solvent described in step c and steps d is 60 ~ 90%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201310425575 CN103450299A (en) | 2013-09-18 | 2013-09-18 | Method for simultaneously preparing esculoside and esculetin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201310425575 CN103450299A (en) | 2013-09-18 | 2013-09-18 | Method for simultaneously preparing esculoside and esculetin |
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| Publication Number | Publication Date |
|---|---|
| CN103450299A true CN103450299A (en) | 2013-12-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201310425575 Pending CN103450299A (en) | 2013-09-18 | 2013-09-18 | Method for simultaneously preparing esculoside and esculetin |
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| Country | Link |
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| CN (1) | CN103450299A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106905279A (en) * | 2017-01-19 | 2017-06-30 | 中国农业大学 | A kind of extracting method of Chinese herbaceous peony antioxidation composition |
| CN107501220A (en) * | 2017-08-23 | 2017-12-22 | 佛山市三水区嘉华化学研究院（普通合伙） | A kind of aesculetin and preparation method and application with antioxidant and anti-aging activity |
| CN109134562A (en) * | 2018-10-26 | 2019-01-04 | 宁县恒瑞康生物科技有限公司 | A kind of aesculin purification process |
-
2013
- 2013-09-18 CN CN 201310425575 patent/CN103450299A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106905279A (en) * | 2017-01-19 | 2017-06-30 | 中国农业大学 | A kind of extracting method of Chinese herbaceous peony antioxidation composition |
| CN106905279B (en) * | 2017-01-19 | 2019-03-22 | 中国农业大学 | A kind of extracting method of Chinese herbaceous peony antioxidation ingredient |
| CN107501220A (en) * | 2017-08-23 | 2017-12-22 | 佛山市三水区嘉华化学研究院（普通合伙） | A kind of aesculetin and preparation method and application with antioxidant and anti-aging activity |
| CN109134562A (en) * | 2018-10-26 | 2019-01-04 | 宁县恒瑞康生物科技有限公司 | A kind of aesculin purification process |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20131218 |
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| WD01 | Invention patent application deemed withdrawn after publication |