CN105418716A - Method for synthesizing chenodeoxycholic acid by using duck cholic acid extracted from duck bile - Google Patents
Method for synthesizing chenodeoxycholic acid by using duck cholic acid extracted from duck bile Download PDFInfo
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- CN105418716A CN105418716A CN201511000722.8A CN201511000722A CN105418716A CN 105418716 A CN105418716 A CN 105418716A CN 201511000722 A CN201511000722 A CN 201511000722A CN 105418716 A CN105418716 A CN 105418716A
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- duck
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- chenodiol
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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 synthesizing chenodeoxycholic acid by using duck cholic acid extracted from duck bile. The method is characterized in that a duck cholic acid crude product is extracted from the duck bile, then methyl esterification and acetylation are carried out on the duck cholic acid crude product, and then a Huang Minglong reduction is used for preparing chenodeoxycholic acid. The chenodeoxycholic acid obtained by the preparation method has the advantages of high yield and high purity which can basically reach about 95%. The preparation method is used for utilizing waste materials, reduces cost, has the advantages of simpleness and effectiveness, and is adapted to industrial application.
Description
Technical field
The present invention relates to a kind of preparation method of Chenodiol, being specifically related to a kind of method of the duck cholic acid synthesis Chenodiol with extracting in 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 to solve above-mentioned prior art problem, a kind of method of the duck cholic acid synthesis Chenodiol with extracting in duck bile is provided.The method by extracting duck cholic acid crude product from duck bile, then by duck cholic acid crude product after esterification acetylize, utilize Huang Min-lon reduction to react obtained Chenodiol, yield is good, purity is high; Be suitable for commercial application.
[technical scheme]
In order to reach above-mentioned technique effect, the present invention takes following technical scheme:
By a method for the duck cholic acid synthesis Chenodiol extracted in duck bile, it comprises the following steps:
I, the extraction of duck cholic acid
Get fresh duck bile, saponification, salt adding acid for adjusting pH are obtain black paste after 2 ~ 3 acidifyings; Then add methyl alcohol and dissolve black paste completely and after utilizing sherwood oil to remove grease, vacuum concentration methanol layer obtains bile acide crude product below 70 DEG C; Then add acetonitrile methanol mixed solution and dissolve bile acide crude product, and the absorption of upper silicagel column, gradient elution obtains described duck cholic acid crude product;
II, the synthesis of Chenodiol
Duck cholic acid crude product step I obtained obtains product A after esterification, acetylize, then is obtained by reacting described chenodeoxycholic acid crude product through Huang Min-lon reduction;
The chenodeoxycholic acid crude product this step obtained, through chloroform crystallization, obtains described Chenodiol.
According to the present invention's further technical scheme, in step I, described saponification is that 1:0.3 ~ 0.4 adds sodium hydroxide in fresh duck bile by the mass ratio of fresh duck bile and sodium hydroxide, and then sealing is warming up to 110 ~ 125 DEG C, stirring reaction 12 ~ 14h.
According to the present invention's further technical scheme, in step I, the described sherwood oil that utilizes removes grease process repetition 2 ~ 3 times.
According to the present invention's further technical scheme, in step I, described acetonitrile methanol mixing solutions be by acetonitrile and methyl alcohol by volume 72:25 mix; Described gradient elution is the acetonitrile methanol mixing solutions gradient elution of 72:25 ~ 60:40 with acetonitrile and methyl alcohol volume range.
According to the present invention's further technical scheme, in step I, after described gradient elution, confirm that Fractional Collections elutriant obtains duck cholic acid crude product with tlc (TLC) point sample.
According to the present invention's further technical scheme, in step II, described esterification is that after duck cholic acid crude product is added dissolve with methanol, the massfraction slowly adding duck cholic acid crude product quality 0.11 ~ 0.13 times is the sulfuric acid of 98%, esterification reaction of organic acid 4 ~ 5h under normal temperature; Then adding sodium hydroxide to reaction solution pH is 6 ~ 8, stops esterification reaction of organic acid; Filter and remove neutralized reaction product sodium sulfate, concentrated filtrate obtains duck Methyl cholate compound.
According to the present invention's further technical scheme, in step II, described acetylize is that add acetic anhydride in described duck Methyl cholate compound after, acetylization reaction 4 ~ 5h at 135 ~ 145 DEG C, after reacting completely, below 120 DEG C, vacuum concentration obtains product A.
According to the present invention's further technical scheme, in step II, described Huang Min-lon reduction reaction be in product A, add ethylene glycol, massfraction be 85% hydrazine hydrate solution and potassium hydroxide, then reflux 4 ~ 5h, obtains described chenodeoxycholic acid crude product.
According to the present invention's further technical scheme, the mass ratio of described product A, ethylene glycol, hydrazine hydrate solution and potassium hydroxide is 1:3:1:5.
In step I, bile acide crude product, in the process of upper silicagel column gradient elution, also can elute chenodeoxycholic acid crude product, and this part crude product obtains Chenodiol fine work by chloroform crystallization.
The present invention will be explained below.
The present invention, by after saponification, acidifying, grease removal reaction, utilizes acetonitrile methanol mixing solutions that the bile acide crude product obtained is crossed silicagel column separation and purification, confirms that Fractional Collections elutriant obtains duck cholic acid crude product by tlc (TLC) point sample.After silicagel column separation and purification, the duck cholic acid crude product purity obtained is higher, thus ensures the high purity of the CDCA acid product that subsequent reactions obtains.When adding sherwood oil except grease, divide petroleum ether layer by siphon, inspissated oil ether layer can reclaim sherwood oil, enriched material is grease, abandons.
Described concentrated methanol layer refers to except the reacted methanol solution of grease, need below 70 DEG C vacuum concentration methanol layer because under normal pressure methyl alcohol be difficult to concentrated completely, and concentrated temperature is not easily too high, in order to avoid destroy reaction product.Utilizing acetonitrile methanol mixed solution gradient elution bile acide crude product, is different according to the matter chemistry polarity in its crude product and gradient elution obtains duck cholic acid crude product and chenodeoxycholic acid crude product.The duck cholic acid crude product obtained after wash-out is added methyl sulfateization reaction 3.8 ~ 4.2h that massfraction is 98%, reaction times can not be long or too short, reaction times is too short, duck cholic acid crude product can not esterification completely, long may causing again produces too much impurity, affects subsequent operations thus the final purity affecting Chenodiol.
[beneficial effect]
The present invention compared with prior art, has following beneficial effect:
The Chenodiol yield that preparation method of the present invention obtains is high, purity is high, substantially reaches about 95%.And utilize preparation method of the present invention, can be salvaged, reduce costs, simply effectively, and be suitable for commercial application.
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:
I, the extraction of duck cholic acid
First 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 adjust pH 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; Repeat to add sherwood oil except after grease process 3 times, collect methanol layer, and the acetonitrile methanol mixing solutions that vacuum concentration methanol layer obtains bile acide crude product 70g below 70 DEG C, adds 2 times amount acetonitriles, methyl alcohol volume ratio is 75:25, upper silicagel column absorption after normal-temperature dissolution; Then utilize acetonitrile, acetonitrile methanol mixing solutions gradient elution that methyl alcohol volume ratio is 75:25 ~ 60:40, confirm that Fractional Collections elutriant obtains duck cholic acid crude product 32g by TLC;
II, the synthesis of Chenodiol
Obtain adding 2 times amount methyl alcohol in duck cholic acid crude product to step I, stirring at normal temperature, to dissolving completely, slowly adds 0.12 times amount 98% sulfuric acid, carries out esterification reaction of organic acid 4 hours under normal temperature; Add appropriate solid sodium hydroxide neutralisation of sulphuric acid, make pH value be 6 ~ 8, cross and filter neutralized reaction product sodium sulfate, less than 70 DEG C vacuum concentrated filtrates, obtain duck Methyl cholate compound; Add duck cholic acid crude product 1.5 times amount acetic anhydride and at 140 DEG C, carry out acetylization reaction 4 hours, after reacting completely, less than the 120 DEG C above-mentioned solution of vacuum concentration obtain product A 39g altogether, then in product A, add 3 times amount ethylene glycol, 1 times amount 85% hydrazine hydrate solution, 5 times amount potassium hydroxide; Reflux 4 hours, generates chenodeoxycholic acid crude product 31.4g;
Finally will obtain the Chenodiol 27g that purity is 95.4% after chenodeoxycholic acid crude product chloroform crystal refining.
Embodiment 2:
I, the extraction of duck cholic acid
First get fresh duck bile drop into reactor, 0.3 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 adjust pH be 3 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; Repeat to add sherwood oil except after grease process 2 times, collect methanol layer, and the acetonitrile methanol mixing solutions that vacuum concentration methanol layer obtains bile acide crude product below 70 DEG C, adds 2 times amount acetonitriles, methyl alcohol volume ratio is 75:25, upper silicagel column absorption after normal-temperature dissolution; Then utilize acetonitrile, acetonitrile methanol mixing solutions gradient elution that methyl alcohol volume ratio is 75:25 ~ 60:40, confirm that Fractional Collections elutriant obtains duck cholic acid crude product by TLC;
II, the synthesis of Chenodiol
Obtain adding 2 times amount methyl alcohol in duck cholic acid crude product to step I, stirring at normal temperature, to dissolving completely, slowly adds 0.12 times amount 98% sulfuric acid, carries out esterification reaction of organic acid 3.8 hours under normal temperature; Add appropriate solid sodium hydroxide neutralisation of sulphuric acid, make pH value be 6 ~ 8, cross and filter neutralized reaction product sodium sulfate, less than 70 DEG C vacuum concentrated filtrates, obtain duck Methyl cholate compound; Add duck cholic acid crude product 1.5 times amount acetic anhydride and at 140 DEG C, carry out acetylization reaction 4 hours, after reacting completely, less than the 120 DEG C above-mentioned solution of vacuum concentration obtain product A, then in product A, add 3 times amount ethylene glycol, 1 times amount 85% hydrazine hydrate solution, 5 times amount potassium hydroxide; Reflux 4 hours, generates chenodeoxycholic acid crude product;
Finally obtain after chenodeoxycholic acid crude product chloroform crystal refining the Chenodiol that purity is 94.9%.
Embodiment 3:
I, the extraction of duck cholic acid
First get fresh duck bile drop into reactor, 0.4 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 adjust pH be 2.5 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; Repeat to add sherwood oil except after grease process 3 times, collect methanol layer, and the acetonitrile methanol mixing solutions that vacuum concentration methanol layer obtains bile acide crude product below 70 DEG C, adds 2 times amount acetonitriles, methyl alcohol volume ratio is 75:25, upper silicagel column absorption after normal-temperature dissolution; Then utilize acetonitrile, acetonitrile methanol mixing solutions gradient elution that methyl alcohol volume ratio is 75:25 ~ 60:40, confirm that Fractional Collections elutriant obtains duck cholic acid crude product by TLC;
II, the synthesis of Chenodiol
Obtain adding 2 times amount methyl alcohol in duck cholic acid crude product to step I, stirring at normal temperature, to dissolving completely, slowly adds 0.12 times amount 98% sulfuric acid, carries out esterification reaction of organic acid 4.2 hours under normal temperature; Add appropriate solid sodium hydroxide neutralisation of sulphuric acid, make pH value be 6 ~ 8, cross and filter neutralized reaction product sodium sulfate, less than 70 DEG C vacuum concentrated filtrates, obtain duck Methyl cholate compound; Add duck cholic acid crude product 1.5 times amount acetic anhydride and at 140 DEG C, carry out acetylization reaction 4 hours, after reacting completely, less than the 120 DEG C above-mentioned solution of vacuum concentration obtain product A, then in product A, add 3 times amount ethylene glycol, 1 times amount 85% hydrazine hydrate solution, 5 times amount potassium hydroxide; Reflux 4 hours, generates chenodeoxycholic acid crude product;
Finally obtain after chenodeoxycholic acid crude product chloroform crystal refining the Chenodiol that purity is 95%.
In sum, Chenodiol preparation method cost of the present invention is low, purity is high, simple to operate, can be suitable for commercial application.
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 (9)
1., by a method for the duck cholic acid synthesis Chenodiol extracted in duck bile, it is characterized in that it comprises the following steps:
I, the extraction of duck cholic acid
Get fresh duck bile, saponification, salt adding acid for adjusting pH are obtain black paste after 2 ~ 3 acidifyings; Then add methyl alcohol and dissolve black paste completely and after utilizing sherwood oil to remove grease, vacuum concentration methanol layer obtains bile acide crude product below 70 DEG C; Then add acetonitrile methanol mixed solution and dissolve bile acide crude product, and the absorption of upper silicagel column, gradient elution obtains described duck cholic acid crude product;
II, the synthesis of Chenodiol
Duck cholic acid crude product step I obtained obtains product A after esterification, acetylize, then is obtained by reacting described chenodeoxycholic acid crude product through Huang Min-lon reduction;
The chenodeoxycholic acid crude product this step obtained, through chloroform crystallization, obtains described Chenodiol.
2. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 1, it is characterized in that in step I, described saponification is that 1:0.3 ~ 0.4 adds sodium hydroxide in fresh duck bile by the mass ratio of fresh duck bile and sodium hydroxide, then sealing is warming up to 110 ~ 125 DEG C, stirring reaction 12 ~ 14h.
3. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 1, is characterized in that in step I, and the described sherwood oil that utilizes removes grease process repetition 2 ~ 3 times.
4. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 1, is characterized in that in step I, described acetonitrile methanol mixing solutions be by acetonitrile and methyl alcohol by volume 72:25 mix; Described gradient elution is the acetonitrile methanol mixing solutions gradient elution of 72:25 ~ 60:40 with acetonitrile and methyl alcohol volume range.
5. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 1, is characterized in that in step I, confirms that Fractional Collections elutriant obtains duck cholic acid crude product after described gradient elution with tlc point sample.
6. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 1, it is characterized in that in step II, described esterification is after duck cholic acid crude product is added dissolve with methanol, the massfraction slowly adding duck cholic acid crude product quality 0.11 ~ 0.13 times is the sulfuric acid of 98%, esterification reaction of organic acid 3.8 ~ 4.2h under normal temperature; Then adding sodium hydroxide to reaction solution pH is 6 ~ 8, stops esterification reaction of organic acid; Filter and remove neutralized reaction product sodium sulfate, concentrated filtrate obtains duck Methyl cholate compound.
7. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 6; it is characterized in that in step II; described acetylize is add acetic anhydride in described duck Methyl cholate compound after; acetylization reaction 4 ~ 5h at 135 ~ 145 DEG C; after reacting completely, below 120 DEG C, vacuum concentration obtains product A.
8. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 1, it is characterized in that in step II, described Huang Min-lon reduction reaction be in product A, add ethylene glycol, massfraction be 85% hydrazine hydrate solution and potassium hydroxide, then reflux 4 ~ 5h, obtains described chenodeoxycholic acid crude product.
9. the method for the duck cholic acid synthesis Chenodiol with extracting in duck bile according to claim 8, is characterized in that the mass ratio of described product A, ethylene glycol, hydrazine hydrate solution and potassium hydroxide is 1:3:1:5.
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Cited By (6)
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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 |
| CN109825547A (en) * | 2019-03-18 | 2019-05-31 | 常德云港生物科技有限公司 | A method of passing through half enzymatic clarification ursodesoxycholic acid by raw material of cholic acid |
| CN111995652A (en) * | 2020-08-12 | 2020-11-27 | 山东省药学科学院 | Method for separating chenodeoxycholic acid 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 |
| CN112321665A (en) * | 2020-12-01 | 2021-02-05 | 江西邦泰绿色生物合成生态产业园发展有限公司 | Method for synthesizing 3 alpha, 7 alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid |
| CN112341512A (en) * | 2020-04-13 | 2021-02-09 | 苏州恩泰新材料科技有限公司 | Method for preparing chenodeoxycholic acid from seal cholic acid |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN112341512A (en) * | 2020-04-13 | 2021-02-09 | 苏州恩泰新材料科技有限公司 | Method for preparing chenodeoxycholic acid from seal cholic acid |
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| CN111995652B (en) * | 2020-08-12 | 2023-06-27 | 山东省药学科学院 | Method for separating chenodeoxycholic acid from duck bile |
| CN112321665A (en) * | 2020-12-01 | 2021-02-05 | 江西邦泰绿色生物合成生态产业园发展有限公司 | Method for synthesizing 3 alpha, 7 alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid |
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