CN115260006A - Method for separating and purifying magnolol and honokiol in magnolia officinalis extract by molecular distillation - Google Patents
Method for separating and purifying magnolol and honokiol in magnolia officinalis extract by molecular distillation Download PDFInfo
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- CN115260006A CN115260006A CN202210940859.5A CN202210940859A CN115260006A CN 115260006 A CN115260006 A CN 115260006A CN 202210940859 A CN202210940859 A CN 202210940859A CN 115260006 A CN115260006 A CN 115260006A
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- honokiol
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- 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 202
- 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 69
- 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 69
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000000199 molecular distillation Methods 0.000 title claims abstract description 25
- 241001673966 Magnolia officinalis Species 0.000 title claims abstract description 22
- 239000000284 extract Substances 0.000 title claims abstract description 17
- 238000000926 separation method Methods 0.000 claims description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 16
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 6
- 230000007547 defect Effects 0.000 abstract description 2
- 239000000419 plant extract Substances 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 description 9
- 239000010408 film Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 241000218378 Magnolia Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000218377 Magnoliaceae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960005233 cineole Drugs 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the field of plant extracts, and discloses a method for purifying magnolol and honokiol in a magnolia officinalis extract by molecular distillation. The method utilizes the property difference of magnolol and honokiol in a molecular distillation system, thereby separating and obtaining high-purity magnolol and honokiol. The invention overcomes the defects of the prior art and provides a method for separating magnolol and honokiol, which is rapid, green, low in cost and free of solvent residue.
Description
Technical Field
The invention relates to the field of plant extracts, in particular to a refining method of a high-purity magnolia officinalis extract.
Background
The main effective components of the dry bark, root bark and branch bark of Magnolia officinalis (Magnolia officinalis) or Magnolia officinalis (M. Officinalis Rehd. Et wils. Var. Bioloba) belonging to Magnoliaceae family are magnolol and honokiol. The research shows that magnolol and honokiol have strong inhibitory activity on bacteria such as escherichia coli, dysentery bacillus, staphylococcus aureus and the like, and various plant pathogenic fungi and the like. Magnolol and honokiol are isomers, although the structures of the magnolol and honokiol are similar, the magnolol and honokiol have differences in solubility, smell and antibacterial activity, the application focuses of the magnolol and honokiol are different, and the preparation of high-purity magnolol and honokiol has important significance for researching and applying magnolia officinalis resources.
At present, most of magnolol and honokiol are mainly derived from refining of magnolia officinalis extract. Most processes have the problems of low yield, low purity, complicated process or high cost and the like. At present, the extraction method of magnolol and honokiol mainly comprises the following steps: pH control method, derivatization method, solvent recrystallization method, column chromatography method and the like, and the molecular distillation technology is not used for preparing high-purity magnolol and honokiol.
By utilizing the difference of pKa values of magnolol and honokiol, honokiol and magnolol are separated out or dissolved out in water sequentially by adjusting pH. (Chinese invention patents: 201010189489.3, 200910155908.9, 201410161323.9, 201811432321.3 and 201811432276.1) the method needs a large amount of water, phenolic pollutants in wastewater are difficult to solve, and honokiol produced by a pH method is more easily oxidized and discolored due to salt.
The magnolol derivative is generated by utilizing the structural difference between magnolol and honokiol and then separated (Chinese patent invention: 201810991607.9). The method has complex process, introduces new impurities and is difficult to meet the requirement of industrial production.
The solubility difference of magnolol and honokiol in an organic solvent is utilized, and recrystallization separation is carried out for multiple times (Chinese patent invention: 201110409723.3, 202010501257.0 and 200810027077.2).
The magnolol and honokiol are separated by column chromatography, the filler generally comprises macroporous resin, polyamide resin, silica gel and the like, and the eluent comprises alkali liquor or organic solvent (Chinese patent inventions: 201410386682.4, 201010200809.0, 2015104336.2 and 201710940611.8). The column chromatography has small treatment capacity, high cost, large solvent consumption, and less optimal filler cost and utilization rate.
The research of molecular distillation for processing the magnolia officinalis extract is Chinese invention patent 01130129.5, the content of magnolia officinalis total phenols in the magnolia officinalis oil is enriched by utilizing the molecular distillation technology, and the aim of separating magnolol and honokiol is not achieved. The main reason is that the raw material of the invention is the magnolia oil with very complex components, and the property difference between magnolol and honokiol in molecular distillation is not found. Magnolol and honokiol easily form an azeotrope with alpha-eucalyptol and the like in the magnolia oil, so that the purity is not high; the magnolol and honokiol have boiling point difference of 5-10 ℃, and are easy to be condensed into solid state to lose fluidity; excessive vacuum easily causes the honokiol to sublimate and reduces the purity of the honokiol in the light component.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for separating magnolol and honokiol quickly, green and low in cost without solvent residues.
In order to realize the purpose, the invention adopts the following technical scheme:
a separation method of magnolol and honokiol comprises the following steps:
(1) Melting cortex Magnolia officinalis extract with total phenol content not less than 90% at 90-95 deg.C;
(2) Performing primary separation on the extract, wherein the primary separation process conditions comprise a sample introduction flow rate of 10-12L/h, a pressure of 100-500 Pa, a temperature of a thin film evaporator of 150-160 ℃, a cooling temperature of a cold trap of 4-10 ℃, and mainly removing water and other low-boiling-point impurities contained in the extract to obtain a primary heavy component;
(3) Performing secondary separation on the primary heavy component, wherein the secondary separation process conditions comprise that the pressure is 30-50 Pa, the molecular distillation temperature is 210-215 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and separating to obtain a secondary light component, namely, magnolol with the content of 90-92%, and a secondary heavy component, namely, honokiol with the content of 85-90%;
(4) In order to obtain magnolol with content of not less than 98%, the secondary light component (magnolol with content of 90-92%) is purified again for 1 time by the above method;
(5) In order to obtain honokiol with content of not less than 98%, the heavy component (honokiol with content of 85-90%) is purified again for 1 time by the method.
The invention has the beneficial effects that:
1. the method for treating the magnolia bark extract does not need to use solvents comprising water and organic solvents;
2. the process is safe and efficient, simple, pollution-free and suitable for industrial production, and the product quality is high.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the invention and together with the description serve to explain the principles of the invention:
FIG. 1 is a process flow diagram of the present invention;
FIG. 2 is a high performance liquid chromatogram of high purity honokiol obtained in the second embodiment;
FIG. 3 is a high performance liquid chromatogram of high purity magnolol obtained in the second example.
Detailed Description
The first embodiment is as follows:
50 kilograms of magnolia bark extract with the total phenol content of 90.5 percent (wherein the honokiol accounts for 46.7 percent and the magnolol accounts for 43.8 percent) is put into a melting tank, and is melted into liquid at 95 ℃, and then enters first-stage separation at the flow rate of 10L/h under the action of a gear pump; the primary separation pressure is 500 Pa, the temperature of a film evaporator is 150 ℃, the cooling temperature of a cold trap is 4 ℃, and primary light components and primary heavy components are obtained, wherein the primary light components are 0.4 kg of 69.5 percent magnolia officinalis total phenols (37.6 percent of honokiol and 31.9 percent of magnolol); the first-stage heavy component enters secondary separation under the action of another gear pump, the pressure of the second-stage separation is 30 Pa, the temperature of molecular distillation is 210 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and the secondary separation is carried out to obtain 20.5 kg of magnolol (the total phenol content is 98.6 percent, and the honokiol content is 6.5 percent) with the content of the second-stage light component of 92.1 percent, and 22.3 kg of honokiol (the total phenol content is 96.4 percent, and the magnolol content is 8.8 percent) with the content of 87.6 percent.
20.5 kg of magnolol (the total phenol content is 98.6 percent, and the honokiol content is 6.5 percent) with the content of 92.1 percent is put into a melting tank, and after the magnolol is melted into liquid at 95 ℃, the liquid enters first-stage separation at the flow rate of 10L/h under the action of a gear pump; the primary separation pressure is 500 Pa, the temperature of the film evaporator is 150 ℃, and the cooling temperature of the cold trap is 4 ℃ to obtain a primary light component and a primary heavy component, wherein the primary light component is few; the first-stage heavy component enters secondary separation under the action of another gear pump, the pressure of the second-stage separation is 30 Pa, the temperature of molecular distillation is 210 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and the secondary heavy component is separated to obtain 17.8 kg of magnolol (the total phenol content is 99.3 percent, and the honokiol content is 1.1 percent) with the content of 98.2 percent as the second-stage light component, and 2.1 kg of honokiol (the total phenol content is 99.5 percent, and the magnolol content is 49.10 percent) with the content of 50.40 percent as the second-stage heavy component; the yield of high-purity magnolol is 81.3%, the rest 18.7% of high-purity magnolol is mainly in other different components, a small part of high-purity magnolol is condensed in a first-stage cold trap and a tail-end cold trap, and a small part of high-purity magnolol is carried away by a vacuum system.
22.3 kg of 87.6% honokiol (total phenol content is 97.4%, magnolol content is 8.8%) is put into a melting tank, melted into liquid at 95 ℃, and then enters first-stage separation at a flow rate of 10L/h under the action of a gear pump; the primary separation pressure is 500 Pa, the temperature of the film evaporator is 150 ℃, and the cooling temperature of the cold trap is 4 ℃ to obtain a primary light component and a primary heavy component, wherein the primary light component is few; the first-stage heavy component enters secondary separation under the action of another gear pump, the secondary separation pressure is 30 Pa, the molecular distillation temperature is 210 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and secondary light components of 2.1 kg of magnolol (the total phenol content is 99.2 percent, and the honokiol content is 12.5 percent) with the content of 86.7 percent and 19.2 kg of honokiol (the total phenol content is 98.3 percent, and the magnolol content is 0.2 percent) with the content of 98.1 percent are obtained through separation; the yield of high-purity honokiol is 82.2%, the rest 17.8% of honokiol is mainly in other different components, a small part of honokiol is condensed in a first-stage cold trap and a tail-end cold trap, and a small part of honokiol is taken away by a vacuum system.
Example two:
50 kg of magnolia bark extract with the total phenol content of 95.7% (wherein honokiol is 48.4%, and magnolol is 47.3%) is put into a melting tank, melted into liquid at 90 ℃, and enters first-stage separation at the flow rate of 12L/h under the action of a gear pump; the primary separation pressure is 100 Pa, the temperature of a film evaporator is 160 ℃, the cooling temperature of a cold trap is 10 ℃, and primary light components and primary heavy components are obtained, wherein the primary light components are 0.2 kg of magnolia officinalis total phenols with the content of 69.5% (41.1% of honokiol and 28.9% of magnolol); the first-stage heavy component enters secondary separation under the action of another gear pump, the pressure of the second-stage separation is 50 Pa, the temperature of molecular distillation is 215 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and the secondary separation is carried out to obtain 23.5 kg of magnolol with the content of 90.3 percent (the total phenol content is 98.7 percent, and the honokiol is 8.4 percent) and 23.2 kg of honokiol with the content of 89.7 percent (the total phenol content is 96.9 percent, and the magnolol is 7.2 percent).
22.3 kg of 90.3% magnolol (the total phenol content is 97.4%, and the honokiol content is 8.8%) is put into a melting tank, melted into liquid at 90 ℃, and then enters first-stage separation at the flow rate of 12L/h under the action of a gear pump; the primary separation pressure is 100 Pa, the temperature of the film evaporator is 160 ℃, and the cooling temperature of the cold trap is 10 ℃, so that a primary light component and a primary heavy component are obtained, and the primary light component is few; the first-stage heavy component enters secondary separation under the action of another gear pump, the pressure of the second-stage separation is 50 Pa, the temperature of molecular distillation is 215 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and the secondary heavy component is separated to obtain 20.1 kg of magnolol (the total phenol content is 99.1 percent, and the honokiol content is 0.6 percent) with the content of 98.5 percent as the second-stage light component, and 2.7 kg of honokiol (the total phenol content is 99.1 percent, and the magnolol content is 32.1 percent) with the content of 65.7 percent as the second-stage heavy component; the yield of the high-purity magnolol is 85.0%, the rest 15.0% is mainly in other different components, a small part of magnolol is condensed in a first-stage cold trap and a tail-end cold trap, and a small part of magnolol is taken away by a vacuum system.
22.3 kg of 87.6% honokiol (total phenol content is 97.4%, magnolol content is 8.8%) is put into a melting tank, melted into liquid at 90 ℃, and then enters first-stage separation at a flow rate of 10L/h under the action of a gear pump; the primary separation pressure is 100 Pa, the temperature of the film evaporator is 160 ℃, and the cooling temperature of the cold trap is 10 ℃ to obtain a primary light component and a primary heavy component, wherein the primary light component is very little; the first-stage heavy component enters secondary separation under the action of another gear pump, the pressure of the second-stage separation is 50 Pa, the temperature of molecular distillation is 215 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and the secondary light component is 1.7 kg of magnolol (the total phenol content is 98.2%, and the honokiol content is 10.3%) with the content of 87.9%, and the secondary heavy component is 20.6kg of honokiol (the total phenol content is 98.7%, and the magnolol content is 0.4%); the yield of the high-purity honokiol is 85.1%, the rest 14.9% of the honokiol is mainly in other different components, a small part of the honokiol is condensed in a first-stage cold trap and a tail-end cold trap, and a small part of the honokiol is taken away by a vacuum system.
And (3) detecting the magnolol and honokiol obtained in the second embodiment:
respectively and precisely weighing 5 mg of magnolol and honokiol sample obtained in example II, and dissolving the magnolol and honokiol sample in 1L of methanol by ultrasonic waves to obtain a sample solution of 5 mg/L. HPLC detection conditions are as follows: octadecylsilane chemically bonded silica is used as a filling agent; acetonitrile-water (80; the detection wavelength was 294 nm.
The invention has the beneficial effects that:
1. the invention can treat the magnolia bark extract without using solvents comprising water and organic solvents;
2. the process is safe and efficient, simple, pollution-free and suitable for industrial production, and the product quality is high.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes, which are made by the present specification, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (1)
1. A method for separating and purifying magnolol and honokiol in magnolia officinalis extract by molecular distillation is characterized by comprising the following steps: the method comprises the following steps:
(1) Taking cortex Magnolia officinalis extract with total phenol content of no less than 90% as raw material, melting at 90-95 deg.C;
(2) Performing primary separation on the extract, wherein the primary separation process conditions comprise a sample introduction flow rate of 10-12L/h, a pressure of 100-500 Pa, a temperature of a thin film evaporator of 150-160 ℃, a cooling temperature of a cold trap of 4-10 ℃, and mainly removing water and other low-boiling-point impurities contained in the extract to obtain a primary heavy component;
(3) Performing secondary separation on the primary heavy component, wherein the secondary separation process conditions comprise that the pressure is 30-50 Pa, the molecular distillation temperature is 210-215 ℃, the cooling temperature of a molecular distillation cold trap is 90 ℃, the temperature of a tail end cold trap is-20 ℃, and separating to obtain a secondary light component, namely, magnolol with the content of 90-92%, and a secondary heavy component, namely, honokiol with the content of 85-90%;
(4) In order to obtain magnolol with content of not less than 98%, the secondary light component (magnolol with content of 90-92%) is purified again for 1 time by the above method;
(5) In order to obtain honokiol with content not less than 98%, the heavy component (honokiol with content of 85-90%) is purified again for 1 time by the method.
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1362395A (en) * | 2001-12-27 | 2002-08-07 | 广州美晨药业有限公司 | Method of refining effective component of official magnolia |
CN113197935A (en) * | 2021-04-13 | 2021-08-03 | 开平健之源保健食品有限公司 | Extraction method of high-purity magnolia bark extract |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1362395A (en) * | 2001-12-27 | 2002-08-07 | 广州美晨药业有限公司 | Method of refining effective component of official magnolia |
CN113197935A (en) * | 2021-04-13 | 2021-08-03 | 开平健之源保健食品有限公司 | Extraction method of high-purity magnolia bark extract |
Non-Patent Citations (1)
Title |
---|
YUAN YU-JIE: "GC-MS Analysis of Cortex Magnolia Officinalis Oil Separated by Molecular Distillation", CHINESE JOURNAL OF NATURAL MEDICINES, vol. 8, no. 1, pages 47 - 50 * |
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