CN109438208A - The purification process of xanthoxylin - Google Patents
The purification process of xanthoxylin Download PDFInfo
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- CN109438208A CN109438208A CN201811524992.2A CN201811524992A CN109438208A CN 109438208 A CN109438208 A CN 109438208A CN 201811524992 A CN201811524992 A CN 201811524992A CN 109438208 A CN109438208 A CN 109438208A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
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- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of purification process of xanthoxylin.A kind of purification process of xanthoxylin is comprising steps of provide xanthoxylin crude extract and xanthoxylin standard items；Silica gel column chromatography is carried out to xanthoxylin crude extract, xanthoxylin crude extract is eluted using mobile phase, is that a unit collects eluent with predetermined volume, obtains the eluent of multiple unit volumes, wherein, mobile phase is selected from least one of ethyl acetate and petroleum ether；It is compared using eluent and xanthoxylin standard items of the thin layer chromatography to each unit volume, merges the eluent of each unit volume containing xanthoxylin, obtain amalgamation liquid；Amalgamation liquid is concentrated, xanthoxylin crude product is obtained；Xanthoxylin crude product is dissolved in 60 DEG C~90 DEG C of organic solvent and being filtered, and the filtrate being obtained by filtration is subjected to crystallisation by cooling, obtains xanthoxylin.The experiment proved that the purity for the xanthoxylin that the purification process of above-mentioned xanthoxylin obtains is higher.
Description
Technical field
The present invention relates to pharmaceutical chemistry technical fields, more particularly to a kind of purification process of xanthoxylin.
Background technique
Xanthoxylin is one of the volatile oil component in Chinese prickly ash pericarp, it has effects that expelling parasite stops ascarid.In addition, Zanthoxylum essential oil
Element and its derivative also have the function of sterilization, it is antimicrobial and mould proof, to fleshes such as uterus caused by some drugs, intestines, bladders
Meat contraction has direct inhibiting effect.Xanthoxylin is generally extracted from Chinese prickly ash, then obtained crude extract is purified, but is passed
The purity for the xanthoxylin that the purification process of system obtains is lower.
Summary of the invention
Based on this, it is necessary to provide a kind of purification process that can obtain the higher xanthoxylin of purity.
A kind of purification process of xanthoxylin, comprising the following steps:
Xanthoxylin crude extract and xanthoxylin standard items are provided；
Silica gel column chromatography is carried out to the xanthoxylin crude extract, the xanthoxylin crude extract is carried out using mobile phase
Elution is that a unit collects eluent with predetermined volume, obtains the eluent of multiple unit volumes, wherein the mobile phase
Selected from least one of ethyl acetate and petroleum ether；
The eluent of each unit volume and the xanthoxylin standard items are compared using thin layer chromatography
Analysis merges the eluent containing each of xanthoxylin unit volume, obtains amalgamation liquid；
The amalgamation liquid is concentrated, xanthoxylin crude product is obtained；
Xanthoxylin crude product is dissolved in 60 DEG C~90 DEG C of organic solvent and being filtered, and by the filter being obtained by filtration
Liquid carry out crystallisation by cooling, obtain xanthoxylin, wherein the organic solvent in petroleum ether, ether and ethyl acetate extremely
Few one kind.
The purification process of above-mentioned xanthoxylin uses thin layer chromatography pair by the way that xanthoxylin is carried out silica gel column chromatography
The eluent of unit volume is compared, and obtains xanthoxylin crude product, then xanthoxylin crude product is carried out crystallisation by cooling, obtains
To xanthoxylin.The experiment proved that the purity for the xanthoxylin that the purification process of above-mentioned xanthoxylin obtains is higher.
The mobile phase is the mixed liquor of ethyl acetate and petroleum ether, the ethyl acetate in one of the embodiments,
Volume ratio with the petroleum ether is 1:9~1:15.
The described the step of xanthoxylin crude extract is eluted using mobile phase in one of the embodiments,
In, the temperature of the mobile phase is 70 DEG C~90 DEG C.
The described the step of filtrate being obtained by filtration is subjected to crystallisation by cooling in one of the embodiments, specifically:
The filtrate being obtained by filtration successively is carried out at 20 DEG C~30 DEG C, 2 DEG C~6 DEG C and -18 DEG C~-25 DEG C to the cooling knot of gradient
It is brilliant.
The mass ratio of the xanthoxylin crude extract and silica gel in the silicagel column is 1:30 in one of the embodiments,
~1:60.
The mesh number of the silica gel in the silicagel column is 100 mesh~200 mesh in one of the embodiments,.
In one of the embodiments, before described the step of carrying out silica gel column chromatography to the xanthoxylin crude extract,
Further include the steps that the xanthoxylin crude extract being dissolved in loading solvent, wherein the ingredient and the stream of the loading solvent
The ingredient of dynamic phase is identical.
The mass volume ratio of the xanthoxylin crude extract and the loading solvent is 1g in one of the embodiments:
5mL~1g:15mL.
It in one of the embodiments, further include the preparation step of the xanthoxylin crude extract, the xanthoxylin is thick
The preparation step of extract includes:
Chinese prickly ash and water are mixed, mixture is obtained；
The mixture is distilled and extracted simultaneously using extractant, obtains xanthoxylin crude extract, wherein described
Extractant is selected from least one of anhydrous ether, petroleum ether and hexamethylene.
The described the step of mixture is distilled and extracted simultaneously using extractant in one of the embodiments,
Specifically: under conditions of 50 DEG C~60 DEG C, the mixture is distilled and extracted simultaneously using extractant.
Specific embodiment
The invention can be realized in many different forms, however it is not limited to embodiment described herein.On the contrary, mentioning
Purpose for these embodiments is to make the disclosure of the present invention more thorough and comprehensive.
Unless otherwise defined, all technical and scientific terms used herein and belong to technical field of the invention
The normally understood meaning of technical staff is identical.Term as used herein in the specification of the present invention is intended merely to description tool
Body embodiment purpose, it is not intended that in limitation the present invention.
The purification process of the xanthoxylin of one embodiment, comprising the following steps:
Step S110: xanthoxylin crude extract and xanthoxylin standard items are provided.
Wherein, xanthoxylin crude extract can be by being commercially available.In the present embodiment, xanthoxylin crude extract is to pass through
It is prepared, the preparation step of xanthoxylin crude extract includes:
Step S111: Chinese prickly ash and water are mixed, mixture is obtained.
Wherein, the mass ratio of Chinese prickly ash and water is 1:10~1:15.
Step S112: mixture is distilled and is extracted simultaneously using extractant, obtains xanthoxylin crude extract.
Wherein, extractant is selected from least one of anhydrous ether, petroleum ether and hexamethylene.
Further, the step of mixture being distilled and is extracted simultaneously using extractant specifically: 50 DEG C~60
Under conditions of DEG C, mixture is distilled and extracted simultaneously using extractant.
Specifically, it while being distilled and the equipment that extracts is Likens-Nickerson SDE method.
Wherein, xanthoxylin standard items are purchased from Beijing Han Longda development in science and technology Co., Ltd, purity 99.2%.
Step S120: to xanthoxylin crude extract carry out silica gel column chromatography, using mobile phase to xanthoxylin crude extract into
Row elution is that a unit collects eluent with predetermined volume, obtains the eluent of multiple unit volumes.
Specifically, xanthoxylin crude extract and the mass ratio of silica gel in silicagel column are 1:30~1:60, to prevent because of silica gel
Column overload and so that the purification effect of xanthoxylin crude extract is deteriorated.
Specifically, the mesh number of silica gel is 100 mesh~200 mesh in silicagel column, preferably to purify to xanthoxylin crude extract.
Specifically, the diameter height of silicagel column compares for 1:20~1:40.
It should be noted that further including by Zanthoxylum essential oil before the step of carrying out silica gel column chromatography to xanthoxylin crude extract
Plain crude extract is dissolved in the step of loading solvent, wherein the ingredient of loading solvent and the ingredient of mobile phase are identical.Further, flower
The mass volume ratio of the plain crude extract of green pepper oil and loading solvent is 1g:5mL~1g:15mL.
Wherein, mobile phase is selected from least one of ethyl acetate and petroleum ether.Further, mobile phase is ethyl acetate
With the mixed liquor of petroleum ether, the volume ratio of ethyl acetate and petroleum ether is 1:9~1:15, with better to xanthoxylin crude extract
Elution, and then improve the purity of xanthoxylin.
Specifically, the temperature of mobile phase is 70 DEG C~90 DEG C, preferably to elute xanthoxylin crude extract, and then improves flower
The purity of green pepper oil element.
Specifically, the flow velocity of mobile phase is 0.5mL/min~1mL/min.
Step S130: it is compared using eluent and xanthoxylin standard items of the thin layer chromatography to each unit volume
Analysis merges the eluent of each unit volume containing xanthoxylin, obtains amalgamation liquid.
Wherein, the point sample on lamellae by the eluent of each unit volume and xanthoxylin standard items, reuses expansion
Agent is unfolded, and the Rf value of the eluent of unit volume is compared with the Rf value of xanthoxylin standard items, and judgement is every
Whether contain xanthoxylin in the eluent of a unit volume.
Step S140: amalgamation liquid is concentrated, and obtains xanthoxylin crude product.
Wherein, the temperature of concentration is 40 DEG C~60 DEG C.
Step S150: xanthoxylin crude product is dissolved in 60 DEG C~90 DEG C of organic solvent and is filtered, and will filtered
The filtrate arrived carries out crystallisation by cooling, obtains xanthoxylin.
Wherein, organic solvent is selected from least one of petroleum ether, ether and ethyl acetate.
Specifically, the step of filtrate being obtained by filtration being subjected to crystallisation by cooling specifically: successively by the filtrate being obtained by filtration
Gradient crystallisation by cooling is carried out at 20 DEG C~30 DEG C, 2 DEG C~6 DEG C and -18 DEG C~-25 DEG C, so that the purity of xanthoxylin is higher,
Crystal form is more preferable.
More specifically, by the filtrate being obtained by filtration carry out crystallisation by cooling the step of specifically: by the filtrate being obtained by filtration according to
It is secondary in 20 DEG C~30 DEG C crystallisation by cooling 2h~3h, 2 DEG C~6 DEG C crystallisation by cooling 2h~3h and -18 DEG C~-25 DEG C crystallisation by cooling 12h
~for 24 hours.
The purification process of above-mentioned xanthoxylin uses thin layer chromatography pair by the way that xanthoxylin is carried out silica gel column chromatography
The eluent of unit volume is compared, and obtains xanthoxylin crude product, then xanthoxylin crude product is carried out crystallisation by cooling, obtains
To xanthoxylin.The experiment proved that the purity for the xanthoxylin that the purification process of above-mentioned xanthoxylin obtains is higher.
The purification process of above-mentioned xanthoxylin is simple and easy, is suitable for industrialized production.
The following are specific embodiment parts:
Embodiment 1
The purification step of the xanthoxylin of the present embodiment is as follows:
1) xanthoxylin crude extract is dissolved in loading solvent, then carries out silica gel column chromatography, using 80 DEG C of mobile phase pair
Xanthoxylin crude extract is eluted, and is that a unit collects eluent with 20mL, is obtained the eluent of multiple unit volumes,
In, loading solvent and mobile phase are the mixed liquor of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:
10, the mass volume ratio of xanthoxylin crude extract and loading solvent is 1g:10mL, silica gel in xanthoxylin crude extract and silicagel column
Mass ratio be 1:45, the length 400mm of silicagel column, diameter 23mm, the mesh number of silica gel is 100 mesh~200 mesh, the stream of mobile phase
Speed is 0.8mL/min.
2) eluent and xanthoxylin standard items of each unit volume are compared using thin layer chromatography, are closed
And the eluent of each unit volume containing xanthoxylin, obtain amalgamation liquid.
3) amalgamation liquid is concentrated, obtains xanthoxylin crude product.
4) xanthoxylin crude product is dissolved in 60 DEG C~90 DEG C of petroleum ether and being filtered, and by the filtrate being obtained by filtration according to
It is secondary to obtain Chinese prickly ash by 3 recrystallizations in 25 DEG C of crystallisation by cooling 2.5h, 4 DEG C of crystallisation by cooling 2.5h and -22 DEG C of crystallisation by cooling 18h
Oily element.
Embodiment 2
The purification step of the xanthoxylin of the present embodiment is as follows:
1) xanthoxylin crude extract is dissolved in loading solvent, then carries out silica gel column chromatography, using 70 DEG C of mobile phase pair
Xanthoxylin crude extract is eluted, and is that a unit collects eluent with 20mL, is obtained the eluent of multiple unit volumes,
In, loading solvent and mobile phase are the mixed liquor of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:
9, the mass volume ratio of xanthoxylin crude extract and loading solvent is 1g:5mL, silica gel in xanthoxylin crude extract and silicagel column
Mass ratio is 1:30, the length 400mm of silicagel column, diameter 23mm, and the mesh number of silica gel is 100 mesh~200 mesh, the flow velocity of mobile phase
For 0.5mL/min.
2) eluent and xanthoxylin standard items of each unit volume are compared using thin layer chromatography, are closed
And the eluent of each unit volume containing xanthoxylin, obtain amalgamation liquid.
3) amalgamation liquid is concentrated, obtains xanthoxylin crude product.
4) xanthoxylin crude product is dissolved in 60 DEG C of petroleum ether and is filtered, and by the filtrate being obtained by filtration successively 20
DEG C crystallisation by cooling 2h, 2 DEG C of crystallisation by cooling 2h and -18 DEG C of crystallisation by cooling 12h recrystallize by 3 times, obtain xanthoxylin.
Embodiment 3
The purification step of the xanthoxylin of the present embodiment is as follows:
1) xanthoxylin crude extract is dissolved in loading solvent, then carries out silica gel column chromatography, using 90 DEG C of mobile phase pair
Xanthoxylin crude extract is eluted, and is that a unit collects eluent with 20mL, is obtained the eluent of multiple unit volumes,
In, loading solvent and mobile phase are the mixed liquor of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:
15, the mass volume ratio of xanthoxylin crude extract and loading solvent is 1g:15mL, silica gel in xanthoxylin crude extract and silicagel column
Mass ratio be 1:60, the length 400mm of silicagel column, diameter 23mm, the mesh number of silica gel is 100 mesh~200 mesh, the stream of mobile phase
Speed is 1mL/min.
2) eluent and xanthoxylin standard items of each unit volume are compared using thin layer chromatography, are closed
And the eluent of each unit volume containing xanthoxylin, obtain amalgamation liquid.
3) amalgamation liquid is concentrated, obtains xanthoxylin crude product.
4) xanthoxylin crude product is dissolved in 90 DEG C of petroleum ether and is filtered, and by the filtrate being obtained by filtration successively 30
DEG C crystallisation by cooling 3h, 6 DEG C of crystallisation by cooling 3h and -25 DEG C of crystallisation by cooling for 24 hours, recrystallize by 3 times, obtain xanthoxylin.
Comparative example 1
The purification step of the xanthoxylin of this comparative example is as follows:
Xanthoxylin crude product is added in beaker, then 60 DEG C of petroleum ether is added into beaker, until solid is completely dissolved.It is fast
Speed filters while hot, and filtrate is in being stored at room temperature Slow cooling 2h, then is placed in the cooling 2h of 4 DEG C of refrigerators, is finally placed in -20 DEG C of refrigerator mistakes
Night；Crystallizing system separates mother liquor and crystal, collects crystal by filtering；Residue is also collected in mother liquor, then recrystallizes receipts
Collect crystal, collect xanthoxylin to greatest extent, is recrystallized by 3 times, obtain xanthoxylin.
Test:
The purity of xanthoxylin in Examples 1 to 3 and comparative example 1 is detected respectively, and the results are shown in Table 1.
The purity of xanthoxylin in 1 Examples 1 to 3 of table and comparative example 1
| Embodiment | The purity of xanthoxylin |
| Embodiment 1 | 98.9 |
| Embodiment 2 | 98.3 |
| Embodiment 3 | 98.1 |
| Comparative example 1 | 91.2 |
As it can be seen from table 1 compared with comparative example 1, the purity of the xanthoxylin in Examples 1 to 3 98.1% or more,
Illustrate that the purity for the xanthoxylin that the purification process of the xanthoxylin of Examples 1 to 3 obtains is higher.
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
1. a kind of purification process of xanthoxylin, which comprises the following steps:
Xanthoxylin crude extract and xanthoxylin standard items are provided；
Silica gel column chromatography is carried out to the xanthoxylin crude extract, the xanthoxylin crude extract is washed using mobile phase
It is de-, it is that a unit collects eluent with predetermined volume, obtains the eluent of multiple unit volumes, wherein the mobile phase choosing
From at least one of ethyl acetate and petroleum ether；
The eluent of each unit volume and the xanthoxylin standard items are compared using thin layer chromatography,
Merge the eluent containing each of xanthoxylin unit volume, obtains amalgamation liquid；
The amalgamation liquid is concentrated, xanthoxylin crude product is obtained；
Xanthoxylin crude product is dissolved in 60 DEG C~90 DEG C of organic solvent and being filtered, and by the filtrate being obtained by filtration into
Row crystallisation by cooling, obtains xanthoxylin, wherein the organic solvent in petroleum ether, ether and ethyl acetate at least one
Kind.
2. the purification process of xanthoxylin according to claim 1, which is characterized in that the mobile phase be ethyl acetate and
The volume ratio of the mixed liquor of petroleum ether, the ethyl acetate and the petroleum ether is 1:9~1:15.
3. the purification process of xanthoxylin according to claim 1, which is characterized in that described to use mobile phase to the flower
In the step of plain crude extract of green pepper oil is eluted, the temperature of the mobile phase is 70 DEG C~90 DEG C.
4. the purification process of xanthoxylin according to claim 1, which is characterized in that described by the filter being obtained by filtration
Liquid carries out the step of crystallisation by cooling specifically: by the filtrate being obtained by filtration successively at 20 DEG C~30 DEG C, 2 DEG C~6 DEG C and -18
DEG C~-25 DEG C at carry out gradient crystallisation by cooling.
5. the purification process of xanthoxylin according to claim 1, which is characterized in that the xanthoxylin crude extract and institute
The mass ratio for stating silica gel in silicagel column is 1:30~1:60.
6. the purification process of xanthoxylin according to claim 1, which is characterized in that the mesh of the silica gel in the silicagel column
Number is 100 mesh~200 mesh.
7. the purification process of xanthoxylin according to claim 1, which is characterized in that described slightly to be mentioned to the xanthoxylin
Before object carries out the step of silica gel column chromatography, further include the steps that the xanthoxylin crude extract being dissolved in loading solvent, wherein
The ingredient of the loading solvent is identical as the ingredient of the mobile phase.
8. the purification process of xanthoxylin according to claim 7, which is characterized in that the xanthoxylin crude extract and institute
The mass volume ratio for stating loading solvent is 1g:5mL~1g:15mL.
9. the purification process of xanthoxylin according to claim 1, which is characterized in that further include that the xanthoxylin slightly mentions
The preparation step of the preparation step of object, the xanthoxylin crude extract includes:
Chinese prickly ash and water are mixed, mixture is obtained；
The mixture is distilled and extracted simultaneously using extractant, obtains xanthoxylin crude extract, wherein the extraction
Agent is selected from least one of anhydrous ether, petroleum ether and hexamethylene.
10. the purification process of xanthoxylin according to claim 9, which is characterized in that described to use extractant to described
The step of mixture is distilled and is extracted simultaneously specifically: under conditions of 50 DEG C~60 DEG C, using extractant to described mixed
Object is closed to be distilled and extracted simultaneously.
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| CN201811524992.2A CN109438208A (en) | 2018-12-13 | 2018-12-13 | The purification process of xanthoxylin |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114404612A (en) * | 2020-10-28 | 2022-04-29 | 西南交通大学 | Zanthoxylum bungeanum oleosin cyclodextrin inclusion compound and preparation method thereof |
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| CN102070430A (en) * | 2010-12-31 | 2011-05-25 | 昆明理工大学 | Method for preparing xanthoxylin |
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| CN102070430A (en) * | 2010-12-31 | 2011-05-25 | 昆明理工大学 | Method for preparing xanthoxylin |
| CN102701939A (en) * | 2012-06-06 | 2012-10-03 | 深圳海王药业有限公司 | Method for preparing xanthoxyline from natural blumea balsamifera powder |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114404612A (en) * | 2020-10-28 | 2022-04-29 | 西南交通大学 | Zanthoxylum bungeanum oleosin cyclodextrin inclusion compound and preparation method thereof |
| CN114404612B (en) * | 2020-10-28 | 2024-03-29 | 西南交通大学 | Zanthoxylum oil cyclodextrin inclusion compound and preparation method thereof |
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