CN85103128A - The extracting method of magnolol and Honokiol - Google Patents
The extracting method of magnolol and Honokiol Download PDFInfo
- Publication number
- CN85103128A CN85103128A CN 85103128 CN85103128A CN85103128A CN 85103128 A CN85103128 A CN 85103128A CN 85103128 CN85103128 CN 85103128 CN 85103128 A CN85103128 A CN 85103128A CN 85103128 A CN85103128 A CN 85103128A
- Authority
- CN
- China
- Prior art keywords
- honokiol
- magnolol
- acid
- magnolia
- extracting
- 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.)
- Pending
Links
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 13
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 title claims abstract description 12
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 241000218378 Magnolia Species 0.000 claims abstract description 8
- 241000196324 Embryophyta Species 0.000 claims abstract description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000000284 extract Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000003916 acid precipitation Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 241001673966 Magnolia officinalis Species 0.000 description 1
- 241000194019 Streptococcus mutans Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000001013 cariogenic effect Effects 0.000 description 1
- 239000004075 cariostatic agent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is a technology of extracting magnolol and Honokiol from plants such as the bark of official magnolia and Magnolia bilola.Process using alkali lye extracts, the acid solution acid precipitation, handles with the hexanaphthene equal solvent again, obtains magnolol and Honokiol crystalline novel process.
Description
The invention belongs to plant amedica and use the extracts active ingredients field.
One is used for from plant, is particularly useful for from the bark of official magnolia (Magnolia offic-inalis) or Magnolia bilola, extracts the method for magnolol and Honokiol in (Magnolia biloba).
Magnolol C
18H
18O
2Mp105 ° of Honokiol G
18H
18O
2Mp87.5 °
Magnolol and Honokiol are isomerss, often are present in the same plant, and especially for seeing, available different extracting method obtains more in Magnoliacea plant.
Pharmacology and clinical trial certificate, these two kinds of materials have very strong bacteriostatic action, to main cariogenic bacteria---the MIC (minimum inhibitory concentration) of streptococcus mutans is 7ug/ml, is extremely effective clinically therefore, and a kind of strong anti-caries agent of being badly in need of.
Prior art is to be soluble in organic solvent according to magnolol and Honokiol, and is insoluble in the characteristics of water, adopts the ether alcohol kind solvent directly to extract from raw material, uses the method for different solvent crystallizations again, obtains the two mixed crystallization.Because this method range of choice is big, is mixed with a large amount of impurity in the extracting solution, separate relatively difficulty.In addition, because of repeatedly with an organic solvent, technical process is long, has problems such as three-waste pollution and cost height, is unsuitable for industrial production.
Task of the present invention is to overcome the deficiencies in the prior art, and the extracting method of a suitable suitability for industrialized production is provided.
The present invention finishes as follows:
Can generate the characteristic of water-soluble salt with some mineral alkali such as sodium hydroxide, potassium hydroxide according to phenolic compound, the present invention directly extracts magnolol and Honokiol with the solution of above-mentioned mineral alkali earlier from raw material, adding a kind of mineral acid example hydrochloric acid, nitric acid or sulfuric acid then in extracting solution makes them emanate out in the acidic solution middle reaches, refining with a kind of organic solvent again, obtain magnolol and Honokiol mixed crystallization.The most handy hexanaphthene of organic solvent, also available benzene, chloroform or ethyl acetate.
The present invention greatly simplifies technical process owing to adopted the very strong extracting method of specific aim, and with water as extracting solvent, significantly reduced three-waste pollution, reduced cost, yield improves 5 to 10 times than present technology, has bigger practical value.
Example of the present invention:
Take by weighing 15.5 kilograms of bark of official magnolia root skins, be cut into the wide strip of 0.1～0.5cm, the diacolation bucket of packing into, the sodium hydroxide solution diacolation with 0.3～0.5% is to colourless, percolate is transferred PH to 1～2 with 6N hydrochloric acid, separates out flocks, centrifuging one throw out, dry back porphyrize is used the hexanaphthene refluxing extraction, and extracting solution was placed 12 hours, separate out crystallization, filter crystallization, mother liquor is concentrated into small volume, have crystallization to separate out again, the leaching crystallization merges secondary and gives brilliant, altogether 1542 grams, yield is 9.95%, content is 98.86%
Claims (4)
1. one is used for from plant, is particularly useful for extracting from the bark of official magnolia or Magnolia bilola the method for magnolol and Honokiol mixed crystallization, it is characterized in that elder generation directly extracts above material with a kind of aqueous solution of mineral alkali from raw material; Use a kind of mineral acid acidizing extracting liquid then, separate out crude product; With the refining crude product of a kind of organic solvent, obtain the mixed crystallization of magnolol and Honokiol again.
2. be hydrochlorinate sodium or hydrochlorinate potassium by the mineral alkali described in the claim 1.
3. be hydrochloric acid, nitric acid or sulfuric acid by the mineral acid described in the claim 1.
4. be hexanaphthene, benzene, chloroform or ethyl acetate by the organic solvent described in the claim 1, wherein with hexanaphthene for well.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 85103128 CN85103128A (en) | 1985-04-30 | 1985-04-30 | The extracting method of magnolol and Honokiol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 85103128 CN85103128A (en) | 1985-04-30 | 1985-04-30 | The extracting method of magnolol and Honokiol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN85103128A true CN85103128A (en) | 1987-02-04 |
Family
ID=4792983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 85103128 Pending CN85103128A (en) | 1985-04-30 | 1985-04-30 | The extracting method of magnolol and Honokiol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN85103128A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006129898A1 (en) * | 2005-05-30 | 2006-12-07 | Korea Institute Of Oriental Medicine | A mass separation method of magnolol from magnoliae cortex ormagnoliae radix |
| CN102070411A (en) * | 2011-01-22 | 2011-05-25 | 李文东 | Method for refining honokiol |
| CN101445430B (en) * | 2008-12-30 | 2011-08-31 | 浙江工业大学 | Magnolol and separation method thereof |
| CN101759532B (en) * | 2009-12-31 | 2013-01-23 | 浙江工业大学 | Method for extracting magnolol and honokiol from magnolia officinalis |
| CN102952002A (en) * | 2011-08-22 | 2013-03-06 | 冉志龙 | Method for refining magnolol through supersonic extraction separating technology |
| CN106588580A (en) * | 2016-11-23 | 2017-04-26 | 成都金瑞基业生物科技有限公司 | Method for preparing high-purity magnolol from Mangnolia officinalis |
| CN108794306A (en) * | 2018-05-08 | 2018-11-13 | 广西大学 | A method of preparing high-purity magnolia bark phenol monomer and honokiol monomer |
| CN108947778A (en) * | 2018-08-28 | 2018-12-07 | 北京国康本草物种生物科学技术研究院有限公司 | A method of it introducing intermediate and separates Magnolia cortex P.E |
| CN109646992A (en) * | 2019-01-28 | 2019-04-19 | 周继铭 | The method of cannabidiol enriched substance is extracted from industrial hemp |
-
1985
- 1985-04-30 CN CN 85103128 patent/CN85103128A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006129898A1 (en) * | 2005-05-30 | 2006-12-07 | Korea Institute Of Oriental Medicine | A mass separation method of magnolol from magnoliae cortex ormagnoliae radix |
| CN101445430B (en) * | 2008-12-30 | 2011-08-31 | 浙江工业大学 | Magnolol and separation method thereof |
| CN101759532B (en) * | 2009-12-31 | 2013-01-23 | 浙江工业大学 | Method for extracting magnolol and honokiol from magnolia officinalis |
| CN102070411A (en) * | 2011-01-22 | 2011-05-25 | 李文东 | Method for refining honokiol |
| CN102070411B (en) * | 2011-01-22 | 2013-04-24 | 李文东 | Method for refining honokiol |
| CN102952002A (en) * | 2011-08-22 | 2013-03-06 | 冉志龙 | Method for refining magnolol through supersonic extraction separating technology |
| CN106588580A (en) * | 2016-11-23 | 2017-04-26 | 成都金瑞基业生物科技有限公司 | Method for preparing high-purity magnolol from Mangnolia officinalis |
| CN108794306A (en) * | 2018-05-08 | 2018-11-13 | 广西大学 | A method of preparing high-purity magnolia bark phenol monomer and honokiol monomer |
| CN108947778A (en) * | 2018-08-28 | 2018-12-07 | 北京国康本草物种生物科学技术研究院有限公司 | A method of it introducing intermediate and separates Magnolia cortex P.E |
| CN108947778B (en) * | 2018-08-28 | 2021-11-05 | 北京国康本草物种生物科学技术研究院有限公司 | Method for separating magnolia bark extract by introducing intermediate |
| CN109646992A (en) * | 2019-01-28 | 2019-04-19 | 周继铭 | The method of cannabidiol enriched substance is extracted from industrial hemp |
| CN109646992B (en) * | 2019-01-28 | 2021-03-23 | 周继铭 | Method for extracting cannabidiol concentrate from industrial cannabis sativa |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |