CN105481927B - A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile - Google Patents
A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile Download PDFInfo
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- CN105481927B CN105481927B CN201511000721.3A CN201511000721A CN105481927B CN 105481927 B CN105481927 B CN 105481927B CN 201511000721 A CN201511000721 A CN 201511000721A CN 105481927 B CN105481927 B CN 105481927B
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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
The invention discloses a kind of methods that duck cholic acid and chenodeoxycholic acid are extracted in bile from duck.This method directly extracts chenodeoxycholic acid from duck bile, while being also extracted duck cholic acid.The preparation method of the present invention is simple, easy to operate, is suitable for commercial application.The purity for the chenodeoxycholic acid and duck cholic acid that the preparation method of the present invention can prepare chenodeoxycholic acid and duck cholic acid, and prepare simultaneously is higher, is respectively 95% and 90% or more.
Description
Technical field
The present invention relates to the preparation methods of chenodeoxycholic acid, and in particular to one kind extracting duck cholic acid from duck bile and goose goes
The method of oxycholic acid.
Background technology
Chenodeoxycholic acid (Chenodeoxycholic acid, abbreviation CDCA), is a kind of natural cholic acid, is 1848
Extraction obtains from goose bile for the first time.Chenodeoxycholic acid has the function of to dissolve the ability of gall stone and other pharmacy, is treatment
The natural good medicine of gall stone, while being the raw material for synthesizing ursodesoxycholic acid and other steroidal compounds again.
It, can be directly from the bile of birds since chenodeoxycholic acid is the main component of the poultry bile such as chicken, duck and goose
Extraction.But by technology restriction, chenodeoxycholic acid product currently on the market is substantially to extract to obtain from chicken bile.
The feeding quantity of goose is less, 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 chicken bile
Constituent compare, the ingredient of duck bile is more complex, cannot apply from chicken bile extract chenodeoxycholic acid method extraction
Chenodeoxycholic acid in duck bile.
Up to the present, it is traditional from the bile of chicken, duck and goose etc. extract chenodeoxycholic acid technique include bile saponification,
Acidification, except alcohol-insoluble substances, grease removal, generate barium salt, de- barium, complex technical process, yield is low, commercial application is difficult.
Or calcium salt precipitation method is used, settling velocity is slow, and efficiency is low, and hydrogen peroxide and activated carbon decolorizing effect are also undesirable.
Invention content
[technical problems to be solved]
Present invention aim to address above-mentioned problem of the prior art, provide one kind and extracting duck cholic acid and goose from duck bile
The method of deoxycholic aicd.This method directly extracts chenodeoxycholic acid and duck cholic acid from duck bile.This method step is simple, operates
Controllably, and the obtained purity of chenodeoxycholic acid and duck cholic acid is higher.
[technical solution]
In order to reach above-mentioned technique effect, the present invention takes following technical scheme：
A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile, it includes the following steps：
A, the extraction of bile acid crude
Fresh duck bile is taken, saponification, salt acid for adjusting pH are 2~3 acid precipitations, obtain black paste；Then first is added
After alcohol dissolving, petroleum ether grease removal is added, methanol layer is concentrated in vacuo at 70 DEG C or less and obtains the bile acid crude；
B, the preparation of duck cholic acid, chenodeoxycholic acid
After esterification reaction of organic acid, acetonitrile crystallization, filtering, filtrate are concentrated to give goose and go the bile acid crude that step A is obtained
Then oxycholic acid methyl esters compound is that 2~3 acid precipitations obtain chenodeoxycholic acid crude product by saponification, salt acid for adjusting pH；Most
Afterwards by obtained chenodeoxycholic acid crude product 60 DEG C it is below be dried under vacuum to loss on drying≤3% after, then through chloroform crystallize essence
Chenodeoxycholic acid is made.
The filter residue of the filtering is duck Methyl cholate compound, and after drying, salt acid for adjusting pH is added as 2~3 acid in saponification
Change precipitation, then filters to obtain duck cholic acid crude product；The duck cholic acid crude product is dried under vacuum to loss on drying≤3% at 60 DEG C or less
Afterwards；Again duck cholic acid is refining to obtain through methanol crystallization.
The further technical solution of the present invention, in step, the saponification is directed to fresh duck bile and its quality is added
After 0.3~0.4 times of sodium hydroxide, sealing is warming up to 110~125 DEG C, stirs 12~13h；In stepb, the goose deoxidation
The saponification of Methyl cholate compound be directed to chenodeoxycholic acid methyl esters compound be added 0.9~1.1 times of its quality amount water and 0.3~
After 0.4 times of sodium hydroxide, sealing is warming up to 110~125 DEG C, stirs 12~13h.
The further technical solution of the present invention, in step, the methanol dissolving refers to that the black paste is added
After the methanol that 3~4 times of quality, it is heated to 50 DEG C and stirs to being completely dissolved.
The further technical solution of the present invention, in step, the process that petroleum ether grease removal is added repeat 2~3
It is secondary.
The further technical solution of the present invention, in stepb, the esterification reaction of organic acid are directed to the addition of bile acid crude
After 2~3 times of the absolute methanol dissolving of its quality, the mass fraction for adding 0.11~0.13 times of bile acid crude product quality is
98% sulfuric acid, 3.8~4.2h of stirring at normal temperature, it is 6~8 that solid sodium hydroxide, which is then added, and adjusts pH value, and it is anti-to terminate esterification
It answers, filter and concentrates filtrate.
The further technical solution of the present invention, in stepb, the acetonitrile crystallization are directed to add in the enriched product
The acetonitrile for entering 1.5~2 times of its quality, is heated to flowing back, and dissolves completely rear slow cooling to 0~5 DEG C of 5~6h of crystallization.
The further technical solution of the present invention, in stepb, the filtrate of the filtering is duck Methyl cholate compound,
Its after drying, saponification, addition salt acid for adjusting pH be 2~3 acid precipitations, then filter to obtain duck cholic acid crude product；The duck cholic acid
Crude product is dried under vacuum to loss on drying≤3% at 60 DEG C or less；Most duck cholic acid is refining to obtain through methanol crystallization afterwards.
The saponification of the further technical solution of the present invention, the duck Methyl cholate compound is directed to duck Methyl cholate compound
After 0.9~1.1 times of amount water of its quality and 0.3~0.4 times of sodium hydroxide is added, sealing is warming up to 110~125 DEG C, stirring 12
~13h.
The further technical solution of the present invention, the methanol crystallization are delayed by desciccate after methanol eddy dissolves
Slowly it is down to 0~5 DEG C, crystal refining obtains duck cholic acid.
It will be described in detail the present invention below.
The present invention directly extracts chenodeoxycholic acid using fresh duck bile, while can also extract duck cholic acid.It was preparing
Cheng Zhong, the process that petroleum ether grease removal is added repeat 2~3 times, can effectively remove the grease in reactant, reduce impurity into one
Step ensures the purity of obtained chenodeoxycholic acid and duck cholic acid.In the esterification of step B, the addition of absolute methanol is courage
2~3 times of juice acid crude quality, and 3.8~4.2h of normal-temperature reaction, be because the reaction time cannot it is long can not be too short,
Ensure the impurity for avoiding reaction time long generation excessive while esterification reaction of organic acid is abundant.Since chenodeoxycholic acid is in chloroform
Solubility it is related with temperature, therefore by after rising temperature for dissolving chenodeoxycholic acid and slow cooling can effectively crystallize out goose
Oxycholic acid, and obtained chenodeoxycholic acid purity is higher.Principle using methanol crystallization duck cholic acid is same.
[advantageous effect]
Compared with prior art, the present invention having advantageous effect below：
The preparation method of the present invention is simple, easy to operate, is suitable for commercial application.The preparation method of the present invention can be made simultaneously
It is standby go out chenodeoxycholic acid and duck cholic acid, and the purity for the chenodeoxycholic acid and duck cholic acid prepared is higher, is respectively 95%
With 90% or more.
Specific implementation mode
With reference to the embodiment of the present invention, the invention will be further elaborated.
N times of amount in following embodiments refers to N times of quality, and wherein N indicates the natural number of ＞ 0.
Embodiment 1：
A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile, it includes the following steps：
A, the extraction of bile acid crude
1000g fresh duck bile is taken to put into reaction kettle, 0.35 times of amount sodium hydroxide continues to put into, and sealing keeps pressure heating
It to 120 DEG C, is stirred to react 12 hours, standing is down to room temperature, and addition dilute hydrochloric acid is adjusted to pH value and obtains black paste 200g for 3.To
3 times of amount methanol are added in black paste, are heated to 50 DEG C, stirring is complete to dissolving；Continuously add 3 times of amount petroleum ether and stirrings 30
Minute, it stands, petroleum ether layer is removed in siphon point；3 times of amount petroleum ethers are continuously added, are repeated twice；Inspissated oil ether layer recycles oil
Ether, concentrate are grease, are abandoned.70 DEG C or less are concentrated in vacuo methanol layer and obtain bile acid crude 70g.
B, the preparation of duck cholic acid, chenodeoxycholic acid
It is added 2 times of amount absolute methanols of bile acid crude in the bile acid crude obtained to step A, stirring at normal temperature is to having dissolved
Entirely, 0.12 times of 98% concentrated sulfuric acid of amount is slowly added to be added in appropriate solid sodium hydroxide and sulphur after stirring at normal temperature is reacted 4 hours
Acid, it is 6~8 to make pH value, filtering removal neutralized reaction product sodium sulphate.It concentrates above-mentioned methanol solution and obtains solid 65g, enriched product is added
1.5 times amount acetonitriles, be heated to flowing back, dissolve completely after slow cooling to 0~5 DEG C crystallize 5 hours, filtering, 90 DEG C of filter residue or less
Heated-air drying obtains duck Methyl cholate compound 30g, and 90 DEG C of filtrate or less is concentrated in vacuo to obtain chenodeoxycholic acid methyl esters compound 35g.
1 times of amount water, 0.35 times of amount sodium hydroxide is added to chenodeoxycholic acid methyl esters compound, sealing keeps pressure to be warming up to
It 120 DEG C, being stirred to react 12 hours, standing is down to room temperature, and it is 3 that dilute hydrochloric acid, which is added, and is adjusted to pH value, filters to obtain chenodeoxycholic acid crude product,
Crude product is dried under vacuum to 3% or less loss on drying at 60 DEG C；It is 95.8% chenodeoxycholic acid to obtain content with chloroform crystal refining
22.3g。
1 times of amount water, 0.35 times of amount sodium hydroxide is added to duck Methyl cholate compound, sealing keeps pressure to be warming up to 120 DEG C,
It is stirred to react 12 hours, stands near room temperature, it is 3 that dilute hydrochloric acid, which is added, and adjusts pH value, filters to obtain duck cholic acid crude product, crude product is at 60 DEG C
Under be dried under vacuum to 3% or less loss on drying；Desciccate 29.3g is obtained, desciccate is complete with 0.5 times of amount methanol eddy dissolving
Afterwards, for slow cooling to 0~5 DEG C, it is 91.2% duck cholic acid 25.1g that crystal refining, which obtains content,.
Embodiment 2：
A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile, it includes the following steps：
A, the extraction of bile acid crude
Fresh duck bile is taken to put into reaction kettle, 0.3 times of amount sodium hydroxide continues to put into, and sealing keeps pressure to be warming up to 125
DEG C, it is stirred to react 12 hours, standing is down to room temperature, and addition dilute hydrochloric acid is adjusted to pH value and obtains black paste for 2.8.To black paste
4 times of amount methanol are added in object, are heated to 50 DEG C, stirring is complete to dissolving；It continuously adds 3 times and measures petroleum ether and stirring 30 minutes, it is quiet
It sets, petroleum ether layer is removed in siphon point；3 times of amount petroleum ethers are continuously added, are repeated 3 times；Inspissated oil ether layer recycles petroleum ether, concentration
Object is grease, is abandoned.70 DEG C or less are concentrated in vacuo methanol layer and obtain bile acid crude.
B, the preparation of duck cholic acid, chenodeoxycholic acid
It is added 2 times of amount absolute methanols of bile acid crude in the bile acid crude obtained to step A, stirring at normal temperature is to having dissolved
Entirely, it is slowly added to 0.11 times of 98% concentrated sulfuric acid of amount, after stirring at normal temperature is reacted 3.8 hours, appropriate solid sodium hydroxide is added and neutralizes
Sulfuric acid, it is 6~8 to make pH value, filtering removal neutralized reaction product sodium sulphate.It concentrates above-mentioned methanol solution and obtains solid, enriched product is added
1.5 times amount acetonitriles, be heated to flowing back, dissolve completely after slow cooling to 0~5 DEG C crystallize 6 hours, filtering, 90 DEG C of filter residue or less
Heated-air drying obtains duck Methyl cholate compound, and 90 DEG C of filtrate or less is concentrated in vacuo to obtain chenodeoxycholic acid methyl esters compound.
1 times of amount water, 0.3 times of amount sodium hydroxide is added to chenodeoxycholic acid methyl esters compound, sealing keeps pressure to be warming up to 125
DEG C, it is stirred to react 12 hours, standing is down to room temperature, and it is 3 that dilute hydrochloric acid, which is added, and is adjusted to pH value, filters to obtain chenodeoxycholic acid crude product, slightly
Product are dried under vacuum to 3% or less loss on drying at 60 DEG C；It is 95.1% chenodeoxycholic acid to obtain content with chloroform crystal refining.
1 times of amount water, 0.3 times of amount sodium hydroxide is added to duck Methyl cholate compound, sealing keeps pressure to be warming up to 125 DEG C,
It is stirred to react 12 hours, stands near room temperature, it is 3 that dilute hydrochloric acid, which is added, and is adjusted to pH value, filters to obtain duck cholic acid crude product, crude product is at 60 DEG C
Under be dried under vacuum to 3% or less loss on drying；Desciccate is obtained after 0.5 times of amount methanol eddy dissolving completely of desciccate to delay
Slow to be cooled to 0~5 DEG C, it is 90.8% duck cholic acid that crystal refining, which obtains content,.
Embodiment 3：
A method of extracting duck cholic acid and chenodeoxycholic acid from duck bile, it includes the following steps：
A, the extraction of bile acid crude
Fresh duck bile is taken to put into reaction kettle, 0.4 times of amount sodium hydroxide continues to put into, and sealing keeps pressure to be warming up to 115
DEG C, it is stirred to react 13 hours, standing is down to room temperature, and addition dilute hydrochloric acid is adjusted to pH value and obtains black paste for 2.8.To black paste
3 times of amount methanol are added in object, are heated to 50 DEG C, stirring is complete to dissolving；It continuously adds 3 times and measures petroleum ether and stirring 30 minutes, it is quiet
It sets, petroleum ether layer is removed in siphon point；3 times of amount petroleum ethers are continuously added, are repeated twice；Inspissated oil ether layer recycles petroleum ether, concentration
Object is grease, is abandoned.70 DEG C or less are concentrated in vacuo methanol layer and obtain bile acid crude.
B, the preparation of duck cholic acid, chenodeoxycholic acid
It is added 3 times of amount absolute methanols of bile acid crude in the bile acid crude obtained to step A, stirring at normal temperature is to having dissolved
Entirely, it is slowly added to 0.13 times of 98% concentrated sulfuric acid of amount, after stirring at normal temperature is reacted 4.2 hours, appropriate solid sodium hydroxide is added and neutralizes
Sulfuric acid, it is 6~8 to make pH value, filtering removal neutralized reaction product sodium sulphate.It concentrates above-mentioned methanol solution and obtains solid, enriched product is added
1.5 times amount acetonitriles, be heated to flowing back, dissolve completely after slow cooling to 0~5 DEG C crystallize 6 hours, filtering, 90 DEG C of filter residue or less
Heated-air drying obtains duck Methyl cholate compound, and 90 DEG C of filtrate or less is concentrated in vacuo to obtain chenodeoxycholic acid methyl esters compound.
1 times of amount water, 0.4 times of amount sodium hydroxide is added to chenodeoxycholic acid methyl esters compound, sealing keeps pressure to be warming up to 115
DEG C, it is stirred to react 13 hours, standing is down to room temperature, and it is 3 that dilute hydrochloric acid, which is added, and is adjusted to pH value, filters to obtain chenodeoxycholic acid crude product, slightly
Product are dried under vacuum to 3% or less loss on drying at 60 DEG C；It is 95.5% chenodeoxycholic acid to obtain content with chloroform crystal refining.
1 times of amount water, 0.4 times of amount sodium hydroxide is added to duck Methyl cholate compound, sealing keeps pressure to be warming up to 115 DEG C,
It is stirred to react 13 hours, stands near room temperature, it is 3 that dilute hydrochloric acid, which is added, and is adjusted to pH value, filters to obtain duck cholic acid crude product, crude product is at 60 DEG C
Under be dried under vacuum to 3% or less loss on drying；Desciccate is obtained after 0.5 times of amount methanol eddy dissolving completely of desciccate to delay
Slow to be cooled to 0~5 DEG C, it is 91% duck cholic acid that crystal refining, which obtains content,.
In conclusion the chenodeoxycholic acid that is prepared of preparation method and duck cholic acid of the present invention all have it is preferable pure
Degree.And it is high using the chenodeoxycholic acid yield that the preparation method of the present invention is prepared.
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, embodiment of the present invention are not limited by the above embodiments, it should be appreciated that people in the art
Member can be designed that a lot of other modification and implementations, these modifications and implementations will be fallen in principle disclosed in the present application
Within scope and spirit.
Claims (4)
1. a kind of method for extracting duck cholic acid and chenodeoxycholic acid in bile from duck, it is characterised in that it includes the following steps：
A, the extraction of bile acid crude
Fresh duck bile is taken, saponification, salt acid for adjusting pH are 2~3 acid precipitations, obtain black paste；Then it is molten that methanol is added
Xie Hou adds petroleum ether grease removal, and methanol layer is concentrated in vacuo at 70 DEG C or less and obtains the bile acid crude；
B, the preparation of duck cholic acid, chenodeoxycholic acid
For the bile acid crude that step A is obtained after esterification reaction of organic acid, acetonitrile crystallization, filtering, filtrate are concentrated to give chenodeoxycholic
Then sour methyl esters compound is that 2~3 acid precipitations obtain chenodeoxycholic acid crude product by saponification, salt acid for adjusting pH；Finally will
Obtained chenodeoxycholic acid crude product 60 DEG C it is below be dried under vacuum to loss on drying≤3% after, then obtain through chloroform crystal refining
To chenodeoxycholic acid；
The filter residue of the filtering is duck Methyl cholate compound, and after drying, saponification is added salt acid for adjusting pH and is acidified for 2~3 and sunk
It forms sediment, then filters to obtain duck cholic acid crude product；By the duck cholic acid crude product after 60 DEG C or less are dried under vacuum to loss on drying≤3%；
Again duck cholic acid is refining to obtain through methanol crystallization；
In step, the methanol dissolving refers to after the methanol of 3~4 times of the black paste quality is added, being heated to 50 DEG C
And it stirs to being completely dissolved；
In step, the process that petroleum ether grease removal is added repeats 2~3 times；
In stepb, the esterification reaction of organic acid is directed to 2~3 times of the absolute methanol dissolving that its quality is added in bile acid crude
Afterwards, add 0.11~0.13 times of bile acid crude product quality mass fraction be 98% sulfuric acid, 3.8~4.2h of stirring at normal temperature,
Then it is 6~8 that solid sodium hydroxide, which is added, and adjusts pH value, terminates esterification reaction of organic acid, filters and concentrate filtrate；
In step, the saponification is directed to after the sodium hydroxide of 0.3~0.4 times of its quality is added in fresh duck bile, and sealing rises
Temperature stirs 12~13h to 110~125 DEG C；In stepb, the saponification of the chenodeoxycholic acid methyl esters compound is directed to goose deoxidation
After 0.9~1.1 times of amount water and 0.3~0.4 times of the sodium hydroxide of its quality is added in Methyl cholate compound, sealing is warming up to 110
~125 DEG C, stir 12~13h.
2. the method for extracting duck cholic acid and chenodeoxycholic acid in the bile according to claim 1 from duck, it is characterised in that
In step B, the acetonitrile crystallization is directed to that the acetonitrile of 1.5~2 times of its quality is added in the enriched product, is heated to flowing back,
Completely rear slow cooling is dissolved to 0~5 DEG C of 5~6h of crystallization.
3. the method for extracting duck cholic acid and chenodeoxycholic acid in the bile according to claim 1 from duck, it is characterised in that
In step B, the saponification of the duck Methyl cholate compound is directed to duck Methyl cholate compound and 0.9~1.1 times of amount water of its quality is added
After 0.3~0.4 times of sodium hydroxide, sealing is warming up to 110~125 DEG C, stirs 12~13h.
4. the method for extracting duck cholic acid and chenodeoxycholic acid in the bile according to claim 1 from duck, it is characterised in that
In step B, the methanol crystallization is to be slowly dropped to 0~5 DEG C, crystal refining obtains by desciccate after methanol eddy dissolves
Duck cholic acid.
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| CN106883281B (en) * | 2017-03-08 | 2017-12-22 | 眉山市新功生物科技有限公司 | The method that chenodeoxycholic acid is extracted from duck bile |
| 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 |
| CN112898370B (en) * | 2021-01-25 | 2022-04-12 | 中山百灵生物技术股份有限公司 | Method for extracting allochenodeoxycholic acid from duck 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 |
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| CN102453069A (en) * | 2010-10-20 | 2012-05-16 | 曾科 | Method for extracting chenodeoxycholic acid from goose and duck bile |
Non-Patent Citations (2)
| Title |
|---|
| 鸭胆汁中胆甾酸成分的研究;龙康侯;《中山大学学报（自然科学版）》;19940430;第33卷(第2期);86-90 * |
| 鸭胆膏中鹅去氧胆酸的提取工艺;刘雁红;《天津科技大学学报》;20090630;第24卷(第3期);43-45 * |
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Address after: 610014 No. 218, 6th floor, Unit 2, Building 27, Qinglong Street, Qingyang District, Chengdu City, Sichuan Province Patentee after: Sichuan Xin Gong biological science and Technology Group Co.,Ltd. Address before: 610000 No. 610, 6 floors, 3 units, 1 building, 17 Jielou Street, Qingyang District, Chengdu City, Sichuan Province Patentee before: CHENGDU XINGONG BIOTECHNOLOGY Co.,Ltd. |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180824 Termination date: 20211225 |