CN106883281A - The method that chenodeoxycholic acid is extracted from duck bile - Google Patents
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- C07J9/00—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
- 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
A kind of method the invention discloses chenodeoxycholic acid is extracted in bile from duck, comprises the following steps:Step one, dissociating with reference to state chenodeoxycholic acid;The removal of aliphatic acid in step 2, crude product;Step 3,3 α, 7 α, the removal of the β cholanic acids of 23 trihydroxy 5;Step 4, CDCA acid treating.The application is by simple raw material and step, it becomes possible to obtain the chenodeoxycholic acid of higher degree, petroleum ether has only been used in method, it becomes possible to complete the removal of aliphatic acid, saves conventional methanol dissolving or the addition of water, reduces the generation of waste water.And by the sequencing of the cooling that adds water, it becomes possible to effectively 3 α of removal, 7 α, the β cholanic acids of 23 trihydroxy 5 have 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 and other pharmacy functions of dissolving gall stone, 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 finds, in terms of gall stone is dissolved, the isomer of chenodeoxycholic acid
The clinical application effect of urso more preferably, 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 in the past to take courage or by bile water conservancy diversion art from bear body by killing bear
Extract bear gall juice and obtain.At present, this way is prohibited by country.Demand with clinical practice constantly increases
Plus, 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, with chenodeoxycholic acid as raw material, synthesis urso technical process is greatly simplified, as 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 to obtain from chicken bile.The raising of goose
Negligible amounts, it is difficult to which application its bile work extracts the raw material of chenodeoxycholic acid.The number of animals raised of duck is huge, with the composition of chicken bile into
Split-phase ratio, the composition of duck bile is more complicated, it is impossible to which application is extracted in the method extraction duck bile of chenodeoxycholic acid from chicken bile
Chenodeoxycholic acid.It is up to the present, domestic that also application duck bile is not the industrialization report of raw material production chenodeoxycholic acid.
Competition between chenodeoxycholic acid manufacturing enterprise, promotes to produce the raw material chicken gall bladder substantial appreciation of prices of chenodeoxycholic acid, its market price
From 4000 yuan/ton of 2008,6000 yuan/ton of 2009 rise to 15000 yuan/ton of 2012.Cause be with chicken bile
The enterprise of raw material production chenodeoxycholic acid is not much profit substantially can earn.Duck gall bladder as duck Product processing enterprise discarded object
The current market price is 2000 yuan/ton or so, and with the continuous expansion of duck Product processing production scale of enterprise, gall bladder yield is acute
Increase.A kind of method for producing chenodeoxycholic acid as raw material with duck bile of this patent report.
The content of the invention
A kind of method it is an object of the invention to provide 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 one, dissociating with reference to state chenodeoxycholic acid
Duck bile is put into reaction bulb by 1.1, adds NaOH, 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, is changed into chenodeoxycholic acid sodium salt;
After the completion of 1.2 question responses, 10~15 DEG C are cooled to, are slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjust pH value to 3~4, this
When, Cholic acids material forms Precipitation, and filtering removal waste water collects solid, obtains chenodeoxycholic acid crude product;
The removal of aliphatic acid in step 2, crude product
Chenodeoxycholic acid crude product pulverizer is ground into the powder less than 200 mesh, the throwing of chenodeoxycholic acid crude product powder is taken
Enter in reaction bulb, petroleum ether is added for the first time, petroleum ether consumption is 3 with the amount ratio of chenodeoxycholic acid crude product powder:1 to 5:
1mL/g, 20~30 DEG C of quick stirring reactions 1 hour, filtering;Filter cake puts into reaction bulb again, second addition petroleum ether, stone
Oily ether consumption is 1 with the amount ratio of chenodeoxycholic acid crude product powder:1 to 3:1mL/g, 20~30 DEG C of quick stirring reactions 0.5 are small
When, filtering;Filtration cakes torrefaction, obtains nonfatty solid;
Step 3,3 α, 7 α, the removal of -5 β of 23- trihydroxies-cholanic acid
3.1 extracting degreasing solids, add ethanol, and ethanol consumption is 4 with the amount ratio of nonfatty solid:1 to 6:1mL/g, stirring
Dissolving is complete, adds activated carbon, and activated carbon dosage is 1 with the amount ratio of nonfatty solid:60 to 1:40g/g, is warming up to 60~65
DEG C, carry out decoloring reaction 1~2 hour, filter, collect filtrate;
Under 3.2 normal pressures, heating recovery falls 80% amount of alcohol added;Surplus solution, under quick stirring, is slowly added dropwise water,
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 is 3 α, 7 α, -5 β of 23- trihydroxies-cholanic acid, and filtrate is mainly chenodeoxycholic acid, collects filtrate;
Under 3.3 quick stirrings, continue to being added dropwise 9 to 11 times of water of filtrate volume in filtrate, stirred crystallization 1~2 hour,
Filtering, collects filter cake, dries, and obtains chenodeoxycholic acid crude product;
Step 4, CDCA acid treating
The chenodeoxycholic acid crude product that step 3.3 is prepared is taken, dichloromethane, methylene chloride and CDCA is added
The amount ratio of acid crude is 9:1 to 11:1mL/g, heated up stirring, back flow reaction 0.5~1 hour, and slow cooling is stirred to 0~5 DEG C
Mix crystallization 1~2 hour, filter, obtain chenodeoxycholic acid fine work.
Further scheme is:
In step one, 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, petroleum ether consumption is 4 with the amount ratio of chenodeoxycholic acid crude product powder:
1mL/g, second addition petroleum ether, petroleum ether consumption is 2 with the amount ratio of chenodeoxycholic acid crude product powder:1mL/g.
Further scheme is:
In step 3, ethanol consumption is 5 with the amount ratio of nonfatty solid: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 to 10 times of water of filtrate volume of dropwise addition in filtrate.
Further scheme is:
In step 4, methylene chloride is 10 with the amount ratio of chenodeoxycholic acid crude product:1mL/g.
The application is by 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, conventional methanol dissolving or the addition of water are saved, reduce the product of waste water
It is raw.And by the sequencing of the cooling that adds water, it becomes possible to effectively removal 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.
Specific embodiment
Embodiment 1
A kind of method that chenodeoxycholic acid is extracted in bile from duck, comprises the following steps:
Step one, dissociating with reference to state chenodeoxycholic acid
1000mL ducks bile is put into reaction bulb by 1.1, adds NaOH 50g, after stirring and dissolving, is warming up to 100 DEG C, is protected
Holding temperature carries 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, are slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjust pH value to 3~4, this
When, Cholic acids material forms Precipitation, and filtering removal waste water collects solid, obtains 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 to combine state form, 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 to state.
The removal of aliphatic acid in step 2, crude product
Chenodeoxycholic acid crude product pulverizer is ground into the powder less than 200 mesh, is taken in 100g input reaction bulbs, added
Petroleum ether 400mL, 20~30 DEG C of quick stirring reactions 1 hour, filtering;Filter cake puts into reaction bulb again, adds petroleum ether
200mL, 20~30 DEG C of quick stirring reactions 0.5 hour, filtering;Filtration cakes torrefaction, obtains nonfatty solid 63.8g.
In this step, petroleum ether has only been used, it becomes possible to complete the removal of aliphatic acid, saved 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, add ethanol 250mL, and stirring and dissolving completely, adds activated carbon 1g, is warming up to 60~65
DEG C, carry out decoloring reaction 1~2 hour, filter, collect filtrate.
Under 3.2 normal pressures, heating recovery ethanol 200mL;Surplus solution, under quick stirring, is slowly added dropwise water, 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, 7 α, -5 β of 23- trihydroxies-cholanic acid, and filtrate is mainly chenodeoxycholic acid, collects filtrate.
Under 3.3 quick stirrings, continue to water 500mL is added dropwise in filtrate, filter cake is collected in stirred crystallization 1~2 hour, filtering,
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, dichloromethane 200mL is added, heat up stirring, backflow
Reaction 0.5~1 hour, to 0~5 DEG C, stirred crystallization 1~2 hour, filtering obtains chenodeoxycholic acid fine work 14.7g to slow cooling,
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 one, dissociating with reference to state chenodeoxycholic acid
1000mL ducks bile is put into reaction bulb by 1.1, adds NaOH 60g, after stirring and dissolving, is warming up to 110 DEG C, is protected
Holding temperature carries 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, are slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjust pH value to 3~4, this
When, Cholic acids material forms Precipitation, and filtering removal waste water collects solid, obtains 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 to combine state form, 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 to state.
The removal of aliphatic acid in step 2, crude product
Chenodeoxycholic acid crude product pulverizer is ground into the powder less than 200 mesh, is taken in 100g input reaction bulbs, added
Petroleum ether 420mL, 20~30 DEG C of quick stirring reactions 1 hour, filtering;Filter cake puts into reaction bulb again, adds petroleum ether
210mL, 20~30 DEG C of quick stirring reactions 0.5 hour, filtering;Filtration cakes torrefaction, obtains nonfatty solid 63.8g.
In this step, petroleum ether has only been used, it becomes possible to complete the removal of aliphatic acid, saved 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, add ethanol 280mL, and stirring and dissolving completely, adds activated carbon 1g, is warming up to 60~65
DEG C, carry out decoloring reaction 1~2 hour, filter, collect filtrate.
Under 3.2 normal pressures, heating recovery ethanol 230mL;Surplus solution, under quick stirring, is slowly added dropwise water, 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, 7 α, -5 β of 23- trihydroxies-cholanic acid, and filtrate is mainly chenodeoxycholic acid, collects filtrate.
Under 3.3 quick stirrings, continue to water 580mL is added dropwise in filtrate, filter cake is collected in stirred crystallization 1~2 hour, filtering,
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, dichloromethane 220mL is added, heat up stirring, backflow
Reaction 0.5~1 hour, to 0~5 DEG C, stirred crystallization 1~2 hour, filtering obtains chenodeoxycholic acid fine work 15.0g to slow cooling,
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 preferably implementation method, 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 modification and implementation methods, and these modifications and implementation method will fall in principle disclosed in the present application
Within scope and spirit.
Claims (6)
1. a kind of method that chenodeoxycholic acid is extracted in bile from duck, it is characterised in that comprise the following steps:
Step one, dissociating with reference to state chenodeoxycholic acid
Duck bile is put into reaction bulb by 1.1, adds NaOH, 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, is changed into chenodeoxycholic acid sodium salt;
After the completion of 1.2 question responses, 10~15 DEG C are cooled to, are slowly added dropwise watery hydrochloric acid or dilute sulfuric acid, adjust pH value to 3~4, now,
Cholic acids material forms Precipitation, and filtering removal waste water collects solid, obtains chenodeoxycholic acid crude product;
The removal of aliphatic acid in step 2, crude product
Chenodeoxycholic acid crude product pulverizer is ground into the powder less than 200 mesh, chenodeoxycholic acid crude product powder input is taken anti-
Answer in bottle, petroleum ether is added for the first time, petroleum ether consumption is 3 with the amount ratio of chenodeoxycholic acid crude product powder: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 addition petroleum ether, petroleum ether is used
Amount is 1 with the amount ratio of chenodeoxycholic acid crude product powder:1 to 3:1mL/g, 20~30 DEG C of quick stirring reactions 0.5 hour, mistake
Filter;Filtration cakes torrefaction, obtains nonfatty solid;
Step 3,3 α, 7 α, the removal of -5 β of 23- trihydroxies-cholanic acid
3.1 extracting degreasing solids, add ethanol, and ethanol consumption is 4 with the amount ratio of nonfatty solid:1 to 6:1mL/g, stirring and dissolving
Completely, activated carbon is added, activated carbon dosage is 1 with the amount ratio of nonfatty solid:60 to 1:40g/g, is warming up to 60~65 DEG C, enters
Filtrate is collected in row decoloring reaction 1~2 hour, filtering;
Under 3.2 normal pressures, heating recovery falls 80% amount of alcohol added;Surplus solution, under quick stirring, is slowly added dropwise water, 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, 7 α, -5 β of 23- trihydroxies-cholanic acid, and filtrate is mainly chenodeoxycholic acid, collects filtrate;
Under 3.3 quick stirrings, continue to 9 to 11 times of water of filtrate volume of dropwise addition, stirred crystallization 1~2 hour, mistake in filtrate
Filter, collects filter cake, dries, and obtains chenodeoxycholic acid crude product;
Step 4, CDCA acid treating
The chenodeoxycholic acid crude product that step 3.3 is prepared is taken, dichloromethane is added, methylene chloride is thick with chenodeoxycholic acid
The amount ratio of product is 9:1 to 11:1mL/g, heat up stirring, back flow reaction 0.5~1 hour, and slow cooling to 0~5 DEG C, tie by stirring
Brilliant 1~2 hour, filtering obtains chenodeoxycholic acid fine work.
2. the method for extracting chenodeoxycholic acid from duck bile according to claim 1, it is characterised in that:
In step one, sodium hydroxide concentration is 1 with duck bile amount ratio:20g/mL.
3. the method for extracting chenodeoxycholic acid from duck bile according to claim 1, it is characterised in that:
In step 2, petroleum ether is added for the first time, petroleum ether consumption is 4 with the amount ratio of chenodeoxycholic acid crude product powder:1mL/
G, second addition petroleum ether, petroleum ether consumption is 2 with the amount ratio of chenodeoxycholic acid crude product powder:1mL/g.
4. the method for extracting chenodeoxycholic acid from duck bile according to claim 1, it is characterised in that:
In step 3, ethanol consumption is 5 with the amount ratio of nonfatty solid:The amount ratio of 1mL/g, activated carbon dosage and nonfatty solid
It is 1:50g/g.
5. the method for extracting chenodeoxycholic acid from duck bile according to claim 1, it is characterised in that:
In step 3.3, continue to 10 times of water of filtrate volume of dropwise addition in filtrate.
6. the method for extracting chenodeoxycholic acid from duck bile according to claim 1, it is characterised in that:
In step 4, methylene chloride is 10 with the amount ratio of chenodeoxycholic acid crude product:1mL/g.
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