CN105481927A - Method for extracting cholic acid of ducks and chenodeoxycholic acid (CDCA) from bile of ducks - Google Patents
Method for extracting cholic acid of ducks and chenodeoxycholic acid (CDCA) from bile of ducks Download PDFInfo
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- CN105481927A CN105481927A CN201511000721.3A CN201511000721A CN105481927A CN 105481927 A CN105481927 A CN 105481927A CN 201511000721 A CN201511000721 A CN 201511000721A CN 105481927 A CN105481927 A CN 105481927A
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- duck
- acid
- chenodiol
- bile
- cholic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- 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
Abstract
The invention discloses a method for extracting cholic acid of ducks and chenodeoxycholic acid (CDCA) from bile of ducks. The method is used for directly extracting CDCA from the bile of ducks and is also used for extracting cholic acid of ducks. The preparation method is simple, is easy to operate and is suitable for industrial application. The preparation method can be used for preparing CDCA and cholic acid of ducks at the same time. The purity of the prepared CDCA and cholic acid of ducks is higher and is more than or equal to 95% and more than or equal to 90% respectively.
Description
Technical field
The present invention relates to the preparation method of Chenodiol, be specifically related to a kind of method extracting duck cholic acid and Chenodiol from duck bile.
Background technology
Chenodiol (Chenodeoxycholicacid is called for short CDCA), being a kind of natural cholic acid, is within 1848, extract first from goose bile to obtain.Chenodiol has the ability and other pharmacy functions of dissolving gallbladdergallstonecholetithiasis, is the natural good medicine for the treatment of gallbladdergallstonecholetithiasis, is again the raw material of synthesis ursodesoxycholic acid and other steroidal compounds simultaneously.
Due to the main component that Chenodiol is the poultry bile such as chicken, duck and goose, it can directly extract from the bile of bird.But by technical limitation, CDCA acid product in the market substantially extracts and obtains from Fel Gallus domesticus.The raising comparatively small amt of goose, is difficult to apply the raw material that its bile makes to extract Chenodiol.The number of animals raised of duck is huge, and compared with the moiety of Fel Gallus domesticus, the composition of duck bile is more complicated, can not apply the Chenodiol in the method extraction duck bile extracting Chenodiol from Fel Gallus domesticus.
Up to the present, traditional Chenodiol technique of extracting from the bile of chicken, duck and goose etc. comprises bile saponification, acidifying, except alcohol insoluble solids, grease removal, generation barium salt, takes off the steps such as barium, complex technical process, and yield is low, commercial application difficulty.Or employing calcium salt precipitation method, sedimentation speed is slow, and efficiency is low, and hydrogen peroxide and activated carbon decolorizing effect also undesirable.
Summary of the invention
[technical problem that will solve]
The object of the invention is the problem solving above-mentioned prior art, a kind of method extracting duck cholic acid and Chenodiol from duck bile is provided.The method is extracting directly Chenodiol and duck cholic acid from duck bile.The method step is simple, it is controlled to operate, and the purity of the Chenodiol obtained and duck cholic acid is higher.
[technical scheme]
In order to reach above-mentioned technique effect, the present invention takes following technical scheme:
From duck bile, extract a method for duck cholic acid and Chenodiol, it comprises the following steps:
A, the extraction of bile acide crude product
Get fresh duck bile, saponification, salt acid for adjusting pH are 2 ~ 3 acid precipitations, obtain black paste; Then after adding dissolve with methanol, then add sherwood oil grease removal, below 70 DEG C, vacuum concentration methanol layer obtains described bile acide crude product;
B, the preparation of duck cholic acid, Chenodiol
The bile acide crude product that steps A is obtained after esterification reaction of organic acid, acetonitrile crystallization, filtration, filtrate is concentrated obtains Chenodiol methyl esters compound, is then that 2 ~ 3 acid precipitations obtain chenodeoxycholic acid crude product by saponification reaction, salt acid for adjusting pH; Finally by the vacuum-drying below 60 DEG C of the chenodeoxycholic acid crude product that obtains to weight loss on drying≤3%, then obtain Chenodiol through chloroform crystal refining.
The filter residue of described filtration is duck Methyl cholate compound, its after drying, saponification, to add salt acid for adjusting pH be 2 ~ 3 acid precipitations, then filters to obtain duck cholic acid crude product; By described duck cholic acid crude product below 60 DEG C after vacuum-drying to weight loss on drying≤3%; Refine through methanol crystallization again and obtain duck cholic acid.
The present invention is technical scheme further, and in step, described saponification is that after sensing fresh duck bile adds the sodium hydroxide of its quality 0.3 ~ 0.4 times, sealing is warming up to 110 ~ 125 DEG C, stirs 12 ~ 13h; In stepb, the saponification of described Chenodiol methyl esters compound points to after Chenodiol methyl esters compound adds the sodium hydroxide of 0.9 ~ 1.1 times of water gaging of its quality and 0.3 ~ 0.4 times, and sealing is warming up to 110 ~ 125 DEG C, stirs 12 ~ 13h.
The present invention is technical scheme further, in step, after described dissolve with methanol refers to the methyl alcohol adding described black paste quality 3 ~ 4 times, is heated to 50 DEG C and is stirred to and dissolve completely.
The present invention is technical scheme further, in step, described in add sherwood oil grease removal process repeat 2 ~ 3 times.
The present invention is technical scheme further, in stepb, described esterification reaction of organic acid is after sensing bile acide crude product adds the anhydrous methanol dissolving of 2 ~ 3 times of its quality, the massfraction adding bile acide crude product quality 0.11 ~ 0.13 times is again the sulfuric acid of 98%, stirring at normal temperature 3.8 ~ 4.2h, then adding solid sodium hydroxide adjust ph is 6 ~ 8, stops esterification reaction of organic acid, filters and concentrated filtrate.
The present invention is technical scheme further, and in stepb, the acetonitrile adding its quality 1.5 ~ 2 times in described enriched product is pointed in described acetonitrile crystallization, is heated to backflow, dissolves slow cooling to 0 ~ 5 DEG C crystallization 5 ~ 6h completely.
The present invention is technical scheme further, and in stepb, the filtrate of described filtration is duck Methyl cholate compound, its after drying, saponification, to add salt acid for adjusting pH be 2 ~ 3 acid precipitations, then filters to obtain duck cholic acid crude product; Described duck cholic acid crude product below 60 DEG C vacuum-drying to weight loss on drying≤3%; Duck cholic acid is obtained finally by methanol crystallization is refining.
The present invention is technical scheme further, and the saponification of described duck Methyl cholate compound points to after duck Methyl cholate compound adds the sodium hydroxide of its quality 0.9 ~ 1.1 times of water gaging and 0.3 ~ 0.4 times, and sealing is warming up to 110 ~ 125 DEG C, stirs 12 ~ 13h.
The present invention is technical scheme further, and described methanol crystallization is that be slowly down to 0 ~ 5 DEG C, crystal refining obtains duck cholic acid by desciccate after methanol eddy dissolves.
The present invention will be explained below.
The present invention uses fresh duck bile extracting directly Chenodiol, can also extract duck cholic acid simultaneously.In preparation process, the process adding sherwood oil grease removal repeats 2 ~ 3 times, effectively can remove the grease in reactant, reduces the purity that impurity ensures Chenodiol and the duck cholic acid obtained further.When the esterification of step B, the add-on of anhydrous methanol is 2 ~ 3 times of bile acide crude product quality, and normal-temperature reaction 3.8 ~ 4.2h, be because the reaction times can not long can not be too short, ensure the esterification reaction of organic acid impurity of simultaneously avoiding reaction times long generation too much fully.Because the solubleness of Chenodiol in chloroform is relevant with temperature, therefore by after rising temperature for dissolving Chenodiol and slow cooling crystallization can go out Chenodiol effectively, and the Chenodiol purity obtained is higher.Utilize the principle of methanol crystallization duck cholic acid identical with it.
[beneficial effect]
The present invention compared with prior art, has following beneficial effect:
Preparation method of the present invention is simple, easy to operate, is suitable for commercial application.Preparation method of the present invention can prepare Chenodiol and duck cholic acid simultaneously, and the purity of the Chenodiol prepared and duck cholic acid is higher, and it is respectively more than 95% and 90%.
Embodiment
Below in conjunction with embodiments of the invention, the invention will be further elaborated.
N times amount in following embodiment refers to N times of quality, and wherein N represents the natural number of > 0.
Embodiment 1:
From duck bile, extract a method for duck cholic acid and Chenodiol, it comprises the following steps:
A, the extraction of bile acide crude product
Get 1000g fresh duck bile drop into reactor, 0.35 times amount sodium hydroxide continue drop into, sealing keep pressure be warming up to 120 DEG C, stirring reaction 12 hours, leave standstill be down to room temperature, add dilute hydrochloric acid be adjusted to pH value be 3 black paste 200g.In black paste, add 3 times amount methyl alcohol, be heated to 50 DEG C, be stirred to and dissolve completely; Continue to add 3 times amount petroleum ether and stirring 30 minutes, leave standstill, siphon divides petroleum ether layer; Continue to add 3 times amount sherwood oils, then repeat 2 times; Inspissated oil ether layer reclaims sherwood oil, and enriched material is grease, abandons.Less than 70 DEG C vacuum concentration methanol layers obtain bile acide crude product 70g.
B, the preparation of duck cholic acid, Chenodiol
Bile acide crude product 2 times amount anhydrous methanol is added in the bile acide crude product that steps A obtains, stirring at normal temperature is to dissolving completely, slowly add 0.12 times amount 98% vitriol oil, after stirring at normal temperature reacts 4 hours, add appropriate solid sodium hydroxide neutralisation of sulphuric acid, make pH value be 6 ~ 8, filter and remove neutralized reaction product sodium sulfate.Concentrated above-mentioned methanol solution obtains solid 65g, add enriched product 1.5 times amount acetonitrile, be heated to backflow, dissolve completely rear slow cooling to 0 ~ 5 DEG C crystallization 5 hours, filter, filter residue less than 90 DEG C warm air dryings obtain duck Methyl cholate compound 30g, and filtrate less than 90 DEG C vacuum concentration obtain Chenodiol methyl esters compound 35g.
1 times of water gaging is added to Chenodiol methyl esters compound, 0.35 times amount sodium hydroxide, sealing keeps pressure to be warming up to 120 DEG C, stirring reaction 12 hours, leave standstill and be down to room temperature, adding dilute hydrochloric acid, to be adjusted to pH value be 3, filters to obtain chenodeoxycholic acid crude product, crude product at 60 DEG C vacuum-drying to weight loss on drying less than 3%; Obtaining content with chloroform crystal refining is 95.8% Chenodiol 22.3g.
Add 1 times of water gaging to duck Methyl cholate compound, 0.35 times amount sodium hydroxide, sealing keeps pressure to be warming up to 120 DEG C, stirring reaction 12 hours, leave standstill near room temperature, adding dilute hydrochloric acid adjust ph is 3, filter to obtain duck cholic acid crude product, crude product at 60 DEG C vacuum-drying to weight loss on drying less than 3%; Obtain desciccate 29.3g, desciccate 0.5 times amount methanol eddy dissolves completely, and slow cooling to 0 ~ 5 DEG C, it is 91.2% duck cholic acid 25.1g that crystal refining obtains content.
Embodiment 2:
From duck bile, extract a method for duck cholic acid and Chenodiol, it comprises the following steps:
A, the extraction of bile acide crude product
Get fresh duck bile drop into reactor, 0.3 times amount sodium hydroxide continue drop into, sealing keep pressure be warming up to 125 DEG C, stirring reaction 12 hours, leave standstill be down to room temperature, add dilute hydrochloric acid be adjusted to pH value be 2.8 black paste.In black paste, add 4 times amount methyl alcohol, be heated to 50 DEG C, be stirred to and dissolve completely; Continue to add 3 times amount petroleum ether and stirring 30 minutes, leave standstill, siphon divides petroleum ether layer; Continue to add 3 times amount sherwood oils, then repeat 3 times; Inspissated oil ether layer reclaims sherwood oil, and enriched material is grease, abandons.Less than 70 DEG C vacuum concentration methanol layers obtain bile acide crude product.
B, the preparation of duck cholic acid, Chenodiol
Bile acide crude product 2 times amount anhydrous methanol is added in the bile acide crude product that steps A obtains, stirring at normal temperature is to dissolving completely, slowly add 0.11 times amount 98% vitriol oil, after stirring at normal temperature reacts 3.8 hours, add appropriate solid sodium hydroxide neutralisation of sulphuric acid, make pH value be 6 ~ 8, filter and remove neutralized reaction product sodium sulfate.Concentrated above-mentioned methanol solution obtains solid, adds enriched product 1.5 times amount acetonitrile, is heated to backflow, dissolve completely rear slow cooling to 0 ~ 5 DEG C crystallization 6 hours, filter, filter residue less than 90 DEG C warm air dryings obtain duck Methyl cholate compound, and filtrate less than 90 DEG C vacuum concentration obtain Chenodiol methyl esters compound.
1 times of water gaging is added to Chenodiol methyl esters compound, 0.3 times amount sodium hydroxide, sealing keeps pressure to be warming up to 125 DEG C, stirring reaction 12 hours, leave standstill and be down to room temperature, adding dilute hydrochloric acid, to be adjusted to pH value be 3, filters to obtain chenodeoxycholic acid crude product, crude product at 60 DEG C vacuum-drying to weight loss on drying less than 3%; Obtaining content with chloroform crystal refining is 95.1% Chenodiol.
Add 1 times of water gaging to duck Methyl cholate compound, 0.3 times amount sodium hydroxide, sealing keeps pressure to be warming up to 125 DEG C, stirring reaction 12 hours, leaves standstill near room temperature, and adding dilute hydrochloric acid, to be adjusted to pH value be 3, filter to obtain duck cholic acid crude product, crude product at 60 DEG C vacuum-drying to weight loss on drying less than 3%; Obtain desciccate, desciccate 0.5 times amount methanol eddy dissolves completely, and slow cooling to 0 ~ 5 DEG C, it is 90.8% duck cholic acid that crystal refining obtains content.
Embodiment 3:
From duck bile, extract a method for duck cholic acid and Chenodiol, it comprises the following steps:
A, the extraction of bile acide crude product
Get fresh duck bile drop into reactor, 0.4 times amount sodium hydroxide continue drop into, sealing keep pressure be warming up to 115 DEG C, stirring reaction 13 hours, leave standstill be down to room temperature, add dilute hydrochloric acid be adjusted to pH value be 2.8 black paste.In black paste, add 3 times amount methyl alcohol, be heated to 50 DEG C, be stirred to and dissolve completely; Continue to add 3 times amount petroleum ether and stirring 30 minutes, leave standstill, siphon divides petroleum ether layer; Continue to add 3 times amount sherwood oils, then repeat 2 times; Inspissated oil ether layer reclaims sherwood oil, and enriched material is grease, abandons.Less than 70 DEG C vacuum concentration methanol layers obtain bile acide crude product.
B, the preparation of duck cholic acid, Chenodiol
Bile acide crude product 3 times amount anhydrous methanol is added in the bile acide crude product that steps A obtains, stirring at normal temperature is to dissolving completely, slowly add 0.13 times amount 98% vitriol oil, after stirring at normal temperature reacts 4.2 hours, add appropriate solid sodium hydroxide neutralisation of sulphuric acid, make pH value be 6 ~ 8, filter and remove neutralized reaction product sodium sulfate.Concentrated above-mentioned methanol solution obtains solid, adds enriched product 1.5 times amount acetonitrile, is heated to backflow, dissolve completely rear slow cooling to 0 ~ 5 DEG C crystallization 6 hours, filter, filter residue less than 90 DEG C warm air dryings obtain duck Methyl cholate compound, and filtrate less than 90 DEG C vacuum concentration obtain Chenodiol methyl esters compound.
1 times of water gaging is added to Chenodiol methyl esters compound, 0.4 times amount sodium hydroxide, sealing keeps pressure to be warming up to 115 DEG C, stirring reaction 13 hours, leave standstill and be down to room temperature, adding dilute hydrochloric acid, to be adjusted to pH value be 3, filters to obtain chenodeoxycholic acid crude product, crude product at 60 DEG C vacuum-drying to weight loss on drying less than 3%; Obtaining content with chloroform crystal refining is 95.5% Chenodiol.
Add 1 times of water gaging to duck Methyl cholate compound, 0.4 times amount sodium hydroxide, sealing keeps pressure to be warming up to 115 DEG C, stirring reaction 13 hours, leaves standstill near room temperature, and adding dilute hydrochloric acid, to be adjusted to pH value be 3, filter to obtain duck cholic acid crude product, crude product at 60 DEG C vacuum-drying to weight loss on drying less than 3%; Obtain desciccate, desciccate 0.5 times amount methanol eddy dissolves completely, and slow cooling to 0 ~ 5 DEG C, it is 91% duck cholic acid that crystal refining obtains content.
In sum, the Chenodiol for preparing of preparation method of the present invention and duck cholic acid all have good purity.And the Chenodiol yield utilizing preparation method of the present invention to prepare is high.
Although with reference to explanatory embodiment of the present invention, invention has been described here, above-described embodiment is only the present invention's preferably embodiment, embodiments of the present invention are not restricted to the described embodiments, should be appreciated that, those skilled in the art can design a lot of other amendment and embodiment, these amendments and embodiment will drop within spirit disclosed in the present application and spirit.
Claims (8)
1. from duck bile, extract a method for duck cholic acid and Chenodiol, it is characterized in that it comprises the following steps:
A, the extraction of bile acide crude product
Get fresh duck bile, saponification, salt acid for adjusting pH are 2 ~ 3 acid precipitations, obtain black paste; Then after adding dissolve with methanol, then add sherwood oil grease removal, below 70 DEG C, vacuum concentration methanol layer obtains described bile acide crude product;
B, the preparation of duck cholic acid, Chenodiol
The bile acide crude product that steps A is obtained after esterification reaction of organic acid, acetonitrile crystallization, filtration, filtrate is concentrated obtains Chenodiol methyl esters compound, is then that 2 ~ 3 acid precipitations obtain chenodeoxycholic acid crude product by saponification reaction, salt acid for adjusting pH; Finally by the vacuum-drying below 60 DEG C of the chenodeoxycholic acid crude product that obtains to weight loss on drying≤3%, then obtain Chenodiol through chloroform crystal refining;
The filter residue of described filtration is duck Methyl cholate compound, its after drying, saponification, to add salt acid for adjusting pH be 2 ~ 3 acid precipitations, then filters to obtain duck cholic acid crude product; By described duck cholic acid crude product below 60 DEG C after vacuum-drying to weight loss on drying≤3%; Refine through methanol crystallization again and obtain duck cholic acid.
2. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 1, it is characterized in that in step, described saponification is that after sensing fresh duck bile adds the sodium hydroxide of its quality 0.3 ~ 0.4 times, sealing is warming up to 110 ~ 125 DEG C, stirs 12 ~ 13h; In stepb, the saponification of described Chenodiol methyl esters compound points to after Chenodiol methyl esters compound adds the sodium hydroxide of 0.9 ~ 1.1 times of water gaging of its quality and 0.3 ~ 0.4 times, and sealing is warming up to 110 ~ 125 DEG C, stirs 12 ~ 13h.
3. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 1, it is characterized in that in step, after described dissolve with methanol refers to the methyl alcohol adding described black paste quality 3 ~ 4 times, be heated to 50 DEG C and be stirred to and dissolve completely.
4. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 1, is characterized in that in step, described in add sherwood oil grease removal process repeat 2 ~ 3 times.
5. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 1, it is characterized in that in stepb, described esterification reaction of organic acid is after sensing bile acide crude product adds the anhydrous methanol dissolving of 2 ~ 3 times of its quality, the massfraction adding bile acide crude product quality 0.11 ~ 0.13 times is again the sulfuric acid of 98%, stirring at normal temperature 3.8 ~ 4.2h, then adding solid sodium hydroxide adjust ph is 6 ~ 8, stops esterification reaction of organic acid, filters and concentrated filtrate.
6. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 5, it is characterized in that in stepb, the acetonitrile adding its quality 1.5 ~ 2 times in described enriched product is pointed in described acetonitrile crystallization, be heated to backflow, dissolve slow cooling to 0 ~ 5 DEG C crystallization 5 ~ 6h completely.
7. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 1, it is characterized in that in stepb, the saponification of described duck Methyl cholate compound points to after duck Methyl cholate compound adds the sodium hydroxide of its quality 0.9 ~ 1.1 times of water gaging and 0.3 ~ 0.4 times, sealing is warming up to 110 ~ 125 DEG C, stirs 12 ~ 13h.
8. the method extracting duck cholic acid and Chenodiol from duck bile according to claim 1, is characterized in that in stepb, and described methanol crystallization is that be slowly down to 0 ~ 5 DEG C, crystal refining obtains duck cholic acid by desciccate after methanol eddy dissolves.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106883281A (en) * | 2017-03-08 | 2017-06-23 | 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 |
CN112898370A (en) * | 2021-01-25 | 2021-06-04 | 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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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106883281A (en) * | 2017-03-08 | 2017-06-23 | 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 |
CN112898370A (en) * | 2021-01-25 | 2021-06-04 | 中山百灵生物技术股份有限公司 | Method for extracting allochenodeoxycholic acid from duck bile |
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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