CN106883281B - The method that chenodeoxycholic acid is extracted from duck bile - Google Patents
The method that chenodeoxycholic acid is extracted from duck bile Download PDFInfo
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- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
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Abstract
The invention discloses a kind of method that chenodeoxycholic acid is extracted in bile from duck, comprise the following steps：Step 1: reference state chenodeoxycholic acid is free；Step 2: in crude product aliphatic acid removal；Step 3: 3 α, 7 α, the removal of the β cholanic acids of 23 trihydroxy 5；Step 4: CDCA acid treating.The application passes through simple raw material and step, it becomes possible to obtains the chenodeoxycholic acid of higher degree, petroleum ether has only been used in method, it becomes possible to completes the removal of aliphatic acid, saves conventional methanol dissolving or the addition of water, reduce the generation of waste water.And the sequencing by adding water to cool, it becomes possible to effectively remove 3 α, 7 α, the β cholanic acids of 23 trihydroxy 5, saved cost.The larger acetonitrile and chloroform of toxicity is substituted using dichloromethane in addition, there is very big advantage in production.
Description
Technical field
The present invention relates to a kind of extracting method of chemical substance, and in particular to one kind extracts chenodeoxycholic acid from duck bile
Method.
Background technology
Chenodeoxycholic acid (chenodeoxycholic acid, abbreviation CDCA) chemistry entitled 3 α, 7-5 β of alpha-dihydroxy-courage
Alkanoic acid, molecular formula C24H40O4, molecular weight 392.58.It is to extract within 1848 to obtain from goose bile first.Chenodeoxycholic acid has
There are the ability of dissolving gall stone and other pharmacy functions, since last century the seventies, be clinically used as treating courage knot
The medicine of stone and other diseases in the liver and gallbladder.In recent years research is found, in terms of gall stone is dissolved, the isomer of chenodeoxycholic acid
The clinical application effect of urso is more preferable, and is free from side effects.Therefore, in the clinical practice side of dissolving gall stone medicine
Face, urso gradually instead of chenodeoxycholic acid.
Natural urso derives from bear gall juice, is to take courage or by bile water conservancy diversion art out of bear body by killing bear in the past
Extract bear gall juice and obtain.At present, this way is prohibited by country.Constantly increase with the demand of clinical practice
Add, natural urso far can not meet the market demand.Obtaining urso by chemical synthesis process becomes more next
It is more important.In recent years, using chenodeoxycholic acid as raw material, synthesis urso technical process greatly simplifies, and turns into synthesis bear deoxidation
The main path of cholic acid.
Chenodeoxycholic acid is the Main Ingredients and Appearance of the poultry bile such as chicken, duck and goose, directly can be extracted from poultry bile
Arrive.But by technology restriction, CDCA acid product in the market is substantially to extract what is obtained from chicken bile.The raising of goose
Negligible amounts, it is difficult to make the raw material of extraction chenodeoxycholic acid using its bile.The number of animals raised of duck is huge, with the composition of chicken bile into
Split-phase ratio, the composition of duck bile are more complicated, it is impossible to which application is extracted from chicken bile in the method extraction duck bile of chenodeoxycholic acid
Chenodeoxycholic acid.Up to the present, it is domestic also to be reported without using the industrialization that duck bile is raw material production chenodeoxycholic acid.
Competition between chenodeoxycholic acid manufacturing enterprise, promote to produce the raw material chicken gall bladder substantial appreciation of prices of chenodeoxycholic acid, its market price
From 4000 yuan/ton in 2008,6000 yuan/ton of rise to 2012 15000 yuan/ton of 2009.Cause using chicken bile as
The enterprise of raw material production chenodeoxycholic acid is not much profit substantially to earn.Discarded object of the duck gall bladder as duck Product processing enterprise
The current market price is 2000 yuan/ton or so, and acute with the continuous expansion of duck Product processing production scale of enterprise, gall bladder yield
Increase.A kind of method that chenodeoxycholic acid is produced using duck bile as raw material of this patent report.
The content of the invention
It is an object of the invention to provide a kind of method that chenodeoxycholic acid is extracted in bile from duck.
What the present invention was realized in：
A kind of method that chenodeoxycholic acid is extracted in bile from duck, comprises the following steps：
Step 1: reference state chenodeoxycholic acid is free
Duck bile is put into reaction bulb by 1.1, adds sodium hydroxide, and sodium hydroxide concentration is 1 with duck bile amount ratio：15 to
1：After 25g/mL stirring and dissolvings, 90 to 110 DEG C are warming up to, keeping temperature carries out reaction 18~24 hours；Make ox sulphur CDCA
Sour ester linkage breaking, it is changed into chenodeoxycholic acid sodium salt；
After the completion of 1.2 question responses, 10~15 DEG C are cooled to, is slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjusts pH value to 3~4, this
When, Cholic acids material forms Precipitation, filters off except waste water, collects solid, obtain chenodeoxycholic acid crude product；
Step 2: in crude product aliphatic acid removal
Chenodeoxycholic acid crude product is ground into less than 200 mesh powders with pulverizer, takes chenodeoxycholic acid crude product powder to throw
Enter in reaction bulb, for the first time addition petroleum ether, the amount ratio of petroleum ether dosage and chenodeoxycholic acid crude product powder is 3：1 to 5：
1mL/g, 20~30 DEG C of quick stirring reactions 1 hour, filtering；Filter cake is put into reaction bulb again, second of addition petroleum ether, stone
The amount ratio of oily ether dosage and chenodeoxycholic acid crude product powder is 1：1 to 3：1mL/g, 20~30 DEG C of quick stirring reactions 0.5 are small
When, filtering；Filtration cakes torrefaction, obtain nonfatty solid；
Step 3: 3 α, 7 α, the removal of -5 β of 23- trihydroxies-cholanic acid
The amount ratio of 3.1 extracting degreasing solids, addition ethanol, ethanol consumption and nonfatty solid is 4：1 to 6：1mL/g, stirring
Dissolving is complete, addition activated carbon, and the amount ratio of activated carbon dosage and nonfatty solid is 1：60 to 1：40g/g, it is warming up to 60~65
DEG C, carry out decoloring reaction 1~2 hour, filtering, collect filtrate；
Under 3.2 normal pressures, heating recovery falls 80% amount of alcohol added；Surplus solution, under quick stirring, water is slowly added dropwise,
When solution bleaches, stop being added dropwise, maintain stirring slow cooling to 10~15 DEG C；Stirred crystallization 1~2 hour, filtering, through thin layer
Chromatography, filter cake are 3 α, and 7 α, -5 β of 23- trihydroxies-cholanic acid, filtrate is mainly chenodeoxycholic acid, collect filtrate；
Under 3.3 quick stirrings, continue that the water of 9 to 11 times of filtrate volumes is added dropwise into filtrate, stirred crystallization 1~2 hour,
Filtering, filter cake is collected, dry, obtain chenodeoxycholic acid crude product；
Step 4: CDCA acid treating
The chenodeoxycholic acid crude product that step 3.3 is prepared is taken, adds dichloromethane, methylene chloride and CDCA
The amount ratio of acid crude is 9：1 to 11：1mL/g, heating stirring, back flow reaction 0.5~1 hour, slow cooling stirs to 0~5 DEG C
Mix crystallization 1~2 hour, filter, obtain chenodeoxycholic acid fine work.
Further scheme is：
In step 1, sodium hydroxide concentration is 1 with duck bile amount ratio：20g/mL.
Further scheme is：
In step 2, petroleum ether is added for the first time, the amount ratio of petroleum ether dosage and chenodeoxycholic acid crude product powder is 4：
The amount ratio of 1mL/g, second of addition petroleum ether, petroleum ether dosage and chenodeoxycholic acid crude product powder is 2：1mL/g.
Further scheme is：
In step 3, the amount ratio of ethanol consumption and nonfatty solid is 5：The use of 1mL/g, activated carbon dosage and nonfatty solid
Amount is than being 1：50g/g.
Further scheme is：
In step 3.3, continue that the water of 10 times of filtrate volumes is added dropwise into filtrate.
Further scheme is：
In step 4, the amount ratio of methylene chloride and chenodeoxycholic acid crude product is 10：1mL/g.
The application passes through simple raw material and step, it becomes possible to obtains the chenodeoxycholic acid of higher degree, only makes in method
With petroleum ether, it becomes possible to complete the removal of aliphatic acid, save conventional methanol dissolving or the addition of water, reduce the production of waste water
It is raw.And the sequencing by adding water to cool, it becomes possible to effectively remove 3 α, 7 α, -5 β of 23- trihydroxies-cholanic acid, save
Cost.The larger acetonitrile and chloroform of toxicity is substituted using dichloromethane in addition, there is very big advantage in production.
Embodiment
Embodiment 1
A kind of method that chenodeoxycholic acid is extracted in bile from duck, comprises the following steps：
Step 1: reference state chenodeoxycholic acid is free
1000mL ducks bile is put into reaction bulb by 1.1, adds sodium hydroxide 50g, after stirring and dissolving, is warming up to 100 DEG C, is protected
Hold temperature and carry out reaction 18~24 hours；Make Taurochenodeoxycholic Acid ester linkage breaking, be changed into chenodeoxycholic acid sodium salt；
After the completion of 1.2 question responses, 10~15 DEG C are cooled to, is slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjusts pH value to 3~4, this
When, Cholic acids material forms Precipitation, filters off except waste water, collects solid, obtain chenodeoxycholic acid crude product 192.6g.
In this step, because duck bile mainly contains 3 α, 7-5 β of alpha-dihydroxy-cholanic acid (being commonly called as chenodeoxycholic acid) and 3 α, 7
- 5 β of α, 23- trihydroxy-cholanic acid, they exist with taurine or Formation of glycine ester bond in the form of reference state, thus have
It is water-soluble.In order to extract chenodeoxycholic acid, it is necessary to it first is changed into free state from reference state.
Step 2: in crude product aliphatic acid removal
Chenodeoxycholic acid crude product is ground into less than 200 mesh powders with pulverizer, takes in 100g input reaction bulbs, adds
Petroleum ether 400mL, 20~30 DEG C of quick stirring reactions 1 hour, filtering；Filter cake is put into reaction bulb again, adds petroleum ether
200mL, 20~30 DEG C of quick stirring reactions 0.5 hour, filtering；Filtration cakes torrefaction, obtain nonfatty solid 63.8g.
In this step, petroleum ether has only been used, it becomes possible to complete the removal of aliphatic acid, save conventional methanol dissolving or water
Add, reduce the generation of waste water.
Step 3: 3 α, 7 α, the removal of -5 β of 23- trihydroxies-cholanic acid
3.1 extracting degreasing solid 50g, adding ethanol 250mL, stirring and dissolving is complete, adds activated carbon 1g, is warming up to 60~65
DEG C, carry out decoloring reaction 1~2 hour, filtering, collect filtrate.
Under 3.2 normal pressures, heating recovery ethanol 200mL；Surplus solution, under quick stirring, water is slowly added dropwise, treats that solution bleaches
When (about add 50~60mL), stop being added dropwise, maintain stirring slow cooling to 10~15 DEG C；Stirred crystallization 1~2 hour, filtering,
Through thin-layer chromatographic analysis, filter cake is 3 α, and 7 α, -5 β of 23- trihydroxies-cholanic acid, filtrate is mainly chenodeoxycholic acid, collects filtrate.
Under 3.3 quick stirrings, continue that water 500mL is added dropwise into filtrate, stirred crystallization 1~2 hour, filtering, collect filter cake,
Dry, obtain chenodeoxycholic acid crude product 27.6g, high performance liquid chromatography detection CDCA acid content 83.4%.
Step 4: CDCA acid treating
The chenodeoxycholic acid crude product 20g that step 3.3 is prepared is taken, adds dichloromethane 200mL, heating stirring, backflow
Reaction 0.5~1 hour, slow cooling stirred crystallization 1~2 hour, filtering, obtain chenodeoxycholic acid fine work 14.7g to 0~5 DEG C,
High performance liquid chromatography detection CDCA acid content 96.6%.
Embodiment 2
A kind of method that chenodeoxycholic acid is extracted in bile from duck, comprises the following steps：
Step 1: reference state chenodeoxycholic acid is free
1000mL ducks bile is put into reaction bulb by 1.1, adds sodium hydroxide 60g, after stirring and dissolving, is warming up to 110 DEG C, is protected
Hold temperature and carry out reaction 18~24 hours；Make Taurochenodeoxycholic Acid ester linkage breaking, be changed into chenodeoxycholic acid sodium salt；
After the completion of 1.2 question responses, 10~15 DEG C are cooled to, is slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjusts pH value to 3~4, this
When, Cholic acids material forms Precipitation, filters off except waste water, collects solid, obtain chenodeoxycholic acid crude product 190.3g.
In this step, because duck bile mainly contains 3 α, 7-5 β of alpha-dihydroxy-cholanic acid (being commonly called as chenodeoxycholic acid) and 3 α, 7
- 5 β of α, 23- trihydroxy-cholanic acid, they exist with taurine or Formation of glycine ester bond in the form of reference state, thus have
It is water-soluble.In order to extract chenodeoxycholic acid, it is necessary to it first is changed into free state from reference state.
Step 2: in crude product aliphatic acid removal
Chenodeoxycholic acid crude product is ground into less than 200 mesh powders with pulverizer, takes in 100g input reaction bulbs, adds
Petroleum ether 420mL, 20~30 DEG C of quick stirring reactions 1 hour, filtering；Filter cake is put into reaction bulb again, adds petroleum ether
210mL, 20~30 DEG C of quick stirring reactions 0.5 hour, filtering；Filtration cakes torrefaction, obtain nonfatty solid 63.8g.
In this step, petroleum ether has only been used, it becomes possible to complete the removal of aliphatic acid, save conventional methanol dissolving or water
Add, reduce the generation of waste water.
Step 3: 3 α, 7 α, the removal of -5 β of 23- trihydroxies-cholanic acid
3.1 extracting degreasing solid 50g, ethanol 280mL is added, stirring and dissolving is complete, adds activated carbon 1g, is warming up to 60~65
DEG C, carry out decoloring reaction 1~2 hour, filtering, collect filtrate.
Under 3.2 normal pressures, heating recovery ethanol 230mL；Surplus solution, under quick stirring, water is slowly added dropwise, treats that solution bleaches
When (about add 50~60mL), stop being added dropwise, maintain stirring slow cooling to 10~15 DEG C；Stirred crystallization 1~2 hour, filtering,
Through thin-layer chromatographic analysis, filter cake is 3 α, and 7 α, -5 β of 23- trihydroxies-cholanic acid, filtrate is mainly chenodeoxycholic acid, collects filtrate.
Under 3.3 quick stirrings, continue that water 580mL is added dropwise into filtrate, stirred crystallization 1~2 hour, filtering, collect filter cake,
Dry, obtain chenodeoxycholic acid crude product 25.7g, high performance liquid chromatography detection CDCA acid content 82.5%.
Step 4: CDCA acid treating
The chenodeoxycholic acid crude product 20g that step 3.3 is prepared is taken, adds dichloromethane 220mL, heating stirring, backflow
Reaction 0.5~1 hour, slow cooling stirred crystallization 1~2 hour, filtering, obtain chenodeoxycholic acid fine work 15.0g to 0~5 DEG C,
High performance liquid chromatography detection CDCA acid content 96.1%.
Although reference be made herein to invention has been described for explanatory embodiment of the invention, and above-described embodiment is only this hair
Bright preferable embodiment, embodiments of the present invention are simultaneously not restricted to the described embodiments, it should be appreciated that people in the art
Member can be designed that a lot of other modifications and embodiment, and these modifications and embodiment will fall in principle disclosed in the present application
Within scope and spirit.
Claims (6)
1. the method for chenodeoxycholic acid is extracted in a kind of bile from duck, it is characterised in that comprise the following steps：
Step 1: reference state chenodeoxycholic acid is free
Duck bile is put into reaction bulb by 1.1, adds sodium hydroxide, and sodium hydroxide concentration is 1 with duck bile amount ratio：15 to 1：
After 25g/ml stirring and dissolvings, 90 to 110 DEG C are warming up to, keeping temperature carries out reaction 18~24 hours；Make Taurochenodeoxycholic Acid
Ester linkage breaking, it is changed into chenodeoxycholic acid sodium salt；
After the completion of 1.2 question responses, 10~15 DEG C are cooled to, is slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjusts pH value to 3~4, now,
Cholic acids material forms Precipitation, filters off except waste water, collects solid, obtain chenodeoxycholic acid crude product；
Step 2: in crude product aliphatic acid removal
Chenodeoxycholic acid crude product is ground into less than 200 mesh powders with pulverizer, takes chenodeoxycholic acid crude product powder input anti-
Answer in bottle, for the first time addition petroleum ether, the amount ratio of petroleum ether dosage and chenodeoxycholic acid crude product powder is 3：1 to 5：1ml/g,
20~30 DEG C of quick stirring reactions 1 hour, filtering；Filter cake is put into reaction bulb again, and second of addition petroleum ether, petroleum ether is used
The amount ratio of amount and chenodeoxycholic acid crude product powder is 1：1 to 3：1ml/g, 20~30 DEG C of quick stirring reactions 0.5 hour, mistake
Filter；Filtration cakes torrefaction, obtain nonfatty solid；
Step 3: 3 α, 7 α, the removal of -5 β of 23- trihydroxies-cholanic acid
The amount ratio of 3.1 extracting degreasing solids, addition ethanol, ethanol consumption and nonfatty solid is 4：1 to 6：1ml/g, stirring and dissolving
Completely, the amount ratio of addition activated carbon, activated carbon dosage and nonfatty solid is 1：60 to 1：40g/g, 60~65 DEG C are warming up to, is entered
Row decoloring reaction 1~2 hour, filtering, collect filtrate；
Under 3.2 normal pressures, heating recovery falls 80% amount of alcohol added；Surplus solution, under quick stirring, water is slowly added dropwise, treats molten
When liquid bleaches, stop being added dropwise, maintain stirring slow cooling to 10~15 DEG C；Stirred crystallization 1~2 hour, filtering, through thin-layer chromatography
Analysis, filter cake is 3 α, and 7 α, -5 β of 23- trihydroxies-cholanic acid, filtrate is mainly chenodeoxycholic acid, collects filtrate；
Under 3.3 quick stirrings, continue that the water of 9 to 11 times of filtrate volumes, stirred crystallization 1~2 hour, mistake are added dropwise into filtrate
Filter, filter cake is collected, dry, obtain chenodeoxycholic acid crude product；
Step 4: CDCA acid treating
The chenodeoxycholic acid crude product that step 3.3 is prepared is taken, adds dichloromethane, methylene chloride is thick with chenodeoxycholic acid
The amount ratio of product is 9：1 to 11：1ml/g, heating stirring, back flow reaction 0.5~1 hour, slow cooling is to 0~5 DEG C, stirring knot
It is brilliant 1~2 hour, filtering, obtain chenodeoxycholic acid fine work.
2. the method for chenodeoxycholic acid is extracted from duck bile according to claim 1, it is characterised in that：
In step 1, sodium hydroxide concentration is 1 with duck bile amount ratio：20g/ml.
3. the method for chenodeoxycholic acid is extracted from duck bile according to claim 1, it is characterised in that：
In step 2, petroleum ether is added for the first time, the amount ratio of petroleum ether dosage and chenodeoxycholic acid crude product powder is 4：1ml/
The amount ratio of g, second of addition petroleum ether, petroleum ether dosage and chenodeoxycholic acid crude product powder is 2：1ml/g.
4. the method for chenodeoxycholic acid is extracted from duck bile according to claim 1, it is characterised in that：
In step 3, the amount ratio of ethanol consumption and nonfatty solid is 5：The amount ratio of 1ml/g, activated carbon dosage and nonfatty solid
For 1：50g/g.
5. the method for chenodeoxycholic acid is extracted from duck bile according to claim 1, it is characterised in that：
In step 3.3, continue that the water of 10 times of filtrate volumes is added dropwise into filtrate.
6. the method for chenodeoxycholic acid is extracted from duck bile according to claim 1, it is characterised in that：
In step 4, the amount ratio of methylene chloride and chenodeoxycholic acid crude product is 10：1ml/g.
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| CN112334476B (en) * | 2019-09-09 | 2022-03-15 | 邦泰生物工程(深圳)有限公司 | Method for synthesizing chenodeoxycholic acid and application thereof |
| CN110627857A (en) * | 2019-10-18 | 2019-12-31 | 河南利伟生物药业股份有限公司 | Environment-friendly method for removing oil in animal bile |
| CN110845564B (en) * | 2019-11-14 | 2022-09-16 | 湖南九典制药股份有限公司 | Method for extracting chenodeoxycholic acid from chicken gall paste |
| CN112300237A (en) * | 2020-04-13 | 2021-02-02 | 苏州恩泰新材料科技有限公司 | Preparation method and application of seal cholic acid |
| CN113234115A (en) * | 2021-05-31 | 2021-08-10 | 山东海钰生物技术股份有限公司 | Production process for extracting chenodeoxycholic acid from chicken bile |
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| CN102453069A (en) * | 2010-10-20 | 2012-05-16 | 曾科 | Method for extracting chenodeoxycholic acid from goose and duck bile |
| CN102911234A (en) * | 2011-08-01 | 2013-02-06 | 天津科技大学 | Method for producing chenodeoxycholic acid by using chicken bile as raw material |
| CN102703556B (en) * | 2012-05-30 | 2013-08-21 | 绵阳劲柏生物科技有限责任公司 | Method for separating chenodeoxycholic acid from duck bile by using macroporous resin |
| CN102827234B (en) * | 2012-08-30 | 2014-07-16 | 苏州天绿生物制药有限公司 | Method for separating and purifying chenodeoxycholic acid from duck gall |
| CN103113447A (en) * | 2013-03-21 | 2013-05-22 | 天津纽伟仕生物医药技术有限公司 | Method for extracting chenodeoxycholic acid in duck bile by adopting calcium salt process |
| CN103360454B (en) * | 2013-05-06 | 2015-12-09 | 广西大学 | A kind of method of separating-purifying Chenodiol from goose bile |
| CN105884847A (en) * | 2014-09-17 | 2016-08-24 | 常德云港生物科技有限公司 | Chenodeoxycholic acid extraction method |
| CN105481927B (en) * | 2015-12-25 | 2018-08-24 | 成都市新功生物科技有限公司 | A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile |
| CN105481926A (en) * | 2015-12-25 | 2016-04-13 | 成都市新功生物科技有限公司 | Method for directly preparing chenodeoxycholic acid from duck bile |
| CN105418716B (en) * | 2015-12-25 | 2017-11-17 | 成都市新功生物科技有限公司 | A kind of method of the duck cholic acid synthesis chenodeoxycholic acid extracted in the bile with duck |
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