CN101215309A - Method for producing chenodeoxycholic acid from 98% of cholic acid of cattle and sheep - Google Patents
Method for producing chenodeoxycholic acid from 98% of cholic acid of cattle and sheep Download PDFInfo
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- CN101215309A CN101215309A CNA2008100100729A CN200810010072A CN101215309A CN 101215309 A CN101215309 A CN 101215309A CN A2008100100729 A CNA2008100100729 A CN A2008100100729A CN 200810010072 A CN200810010072 A CN 200810010072A CN 101215309 A CN101215309 A CN 101215309A
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Abstract
The invention relates to a process for producing anthrodsoxycholic acid by using 98% bovine and sheep cholic acid, which comprises esterifying, acetylating, oxygenizing and reducing bovine and sheep cholic acid transforming cholic acid with isomer into the structure of anthrodsoxycholic acid, thereby forming the compound of anthrodsoxycholic acid. The invention overcomes the limit that anthrodsoxycholic acid is only extracted from fowl galls, and the technology which transforms bovine and sheep cholic acid into anthrodsoxycholic acid has low production cost, and is suitable to be produced in mass production.
Description
Technical field
The present invention relates to a kind of method of producing Chenodiol, relate in particular to a kind of production method of cattle and sheep bile acid production Chenodiol of usefulness 98%.
Background technology
Chenodiol has solvency action to hepatobiliary calculus, liver cirrhosis, chronic hepatitis there is therapeutic action, also have simultaneously extremely strong effects such as promotion fat splitting, be usually used in treating hepatobiliary calculus clinically, primary biliary cirrhosis, primary sclerosing cholangitis, and be used for the treatment of " diseases such as intrahepatic cholestasis of pregnancy, gall-bladder fiber hepatopathy, alcoholic liver disease, non-alcohol fatty liver, viral hepatitis ".
At first in goose bile, found this effective constituent of Chenodiol as far back as 1848, in this title of nineteen twenty-four called after Chenodiol (CDCA).Since nineteen thirty-seven, someone attempts with the mixture dissolving gallbladdergallstonecholetithiasis that contains Chenodiol, found again afterwards that Chenodiol had the saturated bile effect of the cholesterol of correction, Britain has formally opened up the treatment of dissolving cholesterol calculus in 1972, correct the medicine of saturated bile and dissolving gallbladdergallstonecholetithiasis as first.
The chemical name of Chenodiol is 3 α, 7 alpha-dihydroxy-s-5 β-ursodeoxycholic acid, is white, needle-shaped crystals, and is tasteless, dissolves in methyl alcohol, ethanol, chloroform, acetone, Glacial acetic acid and sig water.Water insoluble, petroleum acid and benzene, fusing point 141-142 ℃ [α].+11.50°。
At present, the Chenodiol raw material always is to obtain Chenodiol through extraction, separation, purifying from poultry biles such as Fel Gallus domesticus, duck bile, goose bile, not high with the Chenodiol purity that obtains in the fowl courage, the highlyest can only reach 90%, and to separate with a lot of solvents, purifying, wasted a lot of solvents, cost is very high, and the source of fowl courage is less, can't satisfy people's requirement.
Summary of the invention
The present invention is directed to above-mentioned problems of the prior art,,, provide a kind of production method of cattle and sheep bile acid production Chenodiol of usefulness 98% by a large amount of groping and Test Summary according to the modern theory of extracting; Solved in the prior art and can only from the fowl courage, extract Chenodiol, and the low problem of extracting of Chenodiol purity, operation is simple for production method of the present invention simultaneously, reduced production cost, is fit to produce in enormous quantities.
Technical scheme of the present invention is as follows:
Production method of the present invention comprises the steps:
Esterification:
Get methyl alcohol 20-60kg, add the cholic acid 5-30kg of content more than 98.0%, reflux 0.5-2 hour, be placed to crystallization under the room temperature and separated out, filter, use petroleum ether, 60-80 ℃ of following vacuum-drying, get Methyl cholate;
Acetylization reaction:
Get toluene 5-20kg, adding 1-4kg 4-lutidine adds above-mentioned crystalline Methyl cholate 1-4kg and at room temperature stirred 20-50 minute, add water 80-150kg then, stirred once more 20-50 minute, after leaving standstill 2-6 hour then, reclaim after isolating toluene, separate out crystallization, crystallization is 60-100 ℃ of following vacuum-drying; Crystallization gets 3 α, 7 α-diacetyl Methyl cholate with the sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get above-mentioned diacetyl Methyl cholate 0.5-4kg, add the 1-4kg sodium-acetate, adding 5-15kg methyl alcohol refluxed 20-40 minute, treat to add when temperature reaches 5-10 ℃ bromine liquid 0.5-2.5kg, continue to stir 2-5 hour, add then in the 80-120kg water, after-filtration to be crystallized, crystallization is 70-100 ℃ of following vacuum-drying; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 10-30kg and add ethylene glycol 100-250kg, hydrazine hydrate solvent 10-30kg was in 100-160 ℃ of backflow 12-18 hour, and then be warming up to 195-200 ℃ and refluxed again 2-4 hour, stop then heating up and be cooled to room temperature, add the dilution of 500-700kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 70-100 ℃ of vacuum-drying; Crystallization is content 98.5% Chenodiol.
Production method of the present invention comprises the steps:
Esterification:
Get methyl alcohol 40kg, add the cattle and sheep bile acid 15kg of content more than 98.0%, reflux 1 hour has been placed to crystallization under the room temperature and has separated out, and filters, and with the 90-120 petroleum ether, gets Methyl cholate 70 ℃ of following vacuum-dryings;
Acetylization reaction:
Get toluene 10kg, adding 2kg 4-lutidine adds above-mentioned crystalline Methyl cholate 2kg and at room temperature stirred 30 minutes, add water 100kg then, stirred once more 30 minutes, after leaving standstill 4 hours then, reclaim after isolating toluene, separate out crystallization, crystallization is 80 ℃ of following vacuum-dryings, and crystallization gets 3 α, 7 α-diacetyl Methyl cholate with 90-120 sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get the diacetyl Methyl cholate 1.5kg that above-mentioned crystallization goes out, add the 2kg sodium-acetate, add 10kg methyl alcohol and refluxed 30 minutes, treat to add bromine liquid 1kg when temperature reaches 8 ℃, continue to stir 4 hours, add then in the 100kg water, after-filtration to be crystallized, crystallization is 80 ℃ of vacuum-dryings; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 15kg and add ethylene glycol 150kg, hydrazine hydrate solvent 15kg with content 85% refluxed 15 hours in 130 ℃, and then be warming up to 200 ℃ and refluxed again 3 hours, stop then heating up and be cooled to room temperature, add the dilution of 600kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 80 ℃ of vacuum-dryings; Crystallization is content 98.5% Chenodiol.
Advantage of the present invention and beneficial effect are as follows:
The present invention adopts cattle and sheep bile acid through four steps such as over-churning, acetylize, oxidation, reduction; the cholic acid of isomers is changed into the structure of Chenodiol; formed the compound of Chenodiol; overcome the limitation that from the fowl courage, to extract Chenodiol; in addition, the bile of fowl courage is less, and the bile of cattle and sheep is big and more; the explained hereafter cost that changes into Chenodiol with cattle and sheep bile acid is low, is fit to produce in enormous quantities.
Simultaneously, process for machining and manufacturing of the present invention is simple, and flow process is short, and raw material sources are easy to get, and cost is low, and production and transport stores no any risk, has extensive market outlook.
Embodiment
Every technical indicator of the present invention and beneficial effect have carried out comprehensive and systematic check with reference to national standard, and its detected result is listed in the table below for ease of reference:
Detect data or testing data
| Test item (Items) | National standard (Specifications of country) | Detected result Results |
| The name of an article (Name) | Chenodiol (Chenodeoxycholic Acid) | Chenodiol (Chenodeoxycholic Acid) |
| Outward appearance (Appearance) | Light yellow crystalline powder (Tiny yellow crystalline powder) | Light yellow crystalline powder (Tiny yellow crystalline powder) |
| Differentiate (Identification) | Chemical process (Chemical method) | Comfirms |
| Detection method of content (Test method) | TLC | Comfirms |
| Specific optical rotation (Specific rotation) (°) | +11.0~13.0 | ?Comfirms |
| Residue on ignition (Residue on ignition) (%) | ＜0.2 | ?0.1 |
| Weight loss on drying (Loss on drying) (%) | ＜2.0 | ?1.5 |
| Muriate (Chloride) (%) | ＜0.016 | ?Confirms |
| Acidity (Acidity) | 0.5max | ?Confirms |
| Content (Assay) (%) | ≥98.0 | ?TLC98 |
Conclusion:
Comprehensive above-mentioned comparison and detection that every technical indicator of the present invention is undertaken by national standard as can be known, the equal conformance with standard of every technical indicator of the present invention.And fully prove Chenodiol purity height of the present invention, be fit to produce in batches.
Embodiment 1
Get cattle and sheep bile acid 15kg, add methyl alcohol 40kg, after the reflux 1 hour, be placed to the generation crystallization under the room temperature, filter, crystallization is washed with sherwood oil (model 90-120), 70 ℃ of following vacuum-drying crystallizations promptly, get dry product 2kg then, get toluene 10kg, get 4-dimethylbenzene pyridine 2kg and put into retort together, at room temperature stirred 30 minutes, add 100kg water then and stirred once more 30 minutes, leave standstill 4 hours then after, isolate toluene and reclaim, separate out crystallization, crystallization with sherwood oil (model 90-120) repeated multiple times wash 3 α, 7 α-diacetyl Methyl cholate 80 ℃ of vacuum-dryings, get dry product 1.5kg and add the 2kg sodium-acetate, getting 10kg methyl alcohol then puts into retort together and refluxed together 30 minutes, cool the temperature to 5-10 ℃ then and add bromine liquid 1kg, continue to stir 4 hours, add water 100kg then, continue to stir after 30 minutes, separate out crystallization, filter, crystallization is 80 ℃ of vacuum-dryings.Get above-mentioned dry product 15kg and add ethylene glycol 150kg, hydrazine hydrate solution 15kg with content 85% refluxed 15 hours in 130 ℃, and then be warming up to 195-200 ℃ and refluxed again 3 hours, stop then adding the dilution of 600kg water again after intensification is cooled to room temperature, transfer PH3.0 crystallization and filtration to be separated out with dilute sulphuric acid then, crystallization is 80 ℃ of vacuum-dryings, and crystallization is the Chenodiol (CDCA) of content more than 98%.
Embodiment 2
Production method of the present invention comprises the steps:
Esterification:
Get methyl alcohol 20kg, add the cattle and sheep bile acid 5kg of content more than 98.0%, reflux 0.5 hour has been placed to crystallization under the room temperature and has separated out, and filters, and with the 90-120 petroleum ether, 60 ℃ of following vacuum-dryings, gets Methyl cholate;
Acetylization reaction:
Get toluene 5kg, adding 1kg 4-lutidine adds above-mentioned crystalline Methyl cholate 1kg and at room temperature stirred 20 minutes, adds water 80kg then, stirred once more 20 minutes, leave standstill 2 hours then after, reclaim after isolating toluene, separate out crystallization, crystallization is 60 ℃ of following vacuum-dryings; Crystallization gets 3 α, 7 α-diacetyl Methyl cholate with 90-120 sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get above-mentioned diacetyl Methyl cholate 0.5kg, add the 1kg sodium-acetate, add 5kg methyl alcohol and refluxed 20 minutes, treat to add bromine liquid 0.5kg when temperature reaches 5 ℃, continue to stir 2 hours, add then in the 80kg water, after-filtration to be crystallized, crystallization is 70 ℃ of following vacuum-dryings; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 10-30kg and add ethylene glycol 100kg, the hydrazine hydrate solvent 10kg of content 85% refluxed 12 hours in 100 ℃, and then be warming up to 195 ℃ and refluxed again 2 hours, stop then heating up and be cooled to room temperature, add the dilution of 500kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 70 ℃ of vacuum-dryings; Crystallization is content 98.5% Chenodiol.
Embodiment 3
Production method of the present invention comprises the steps:
Esterification:
Get methyl alcohol 60kg, add the cattle and sheep bile acid 30kg of content more than 98.0%, reflux 2 hours has been placed to crystallization under the room temperature and has separated out, and filters, and with the 90-120 petroleum ether, 80 ℃ of following vacuum-dryings, gets Methyl cholate;
Acetylization reaction:
Get toluene 20kg, adding 4kg 4-lutidine adds above-mentioned crystalline Methyl cholate 4kg and at room temperature stirred 50 minutes, adds water 150kg then, stirred once more 50 minutes, leave standstill 6 hours then after, reclaim after isolating toluene, separate out crystallization, crystallization is 100 ℃ of following vacuum-dryings; Crystallization gets 3 α, 7 α-diacetyl Methyl cholate with 90-120 sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get above-mentioned diacetyl Methyl cholate 4kg, add the 4kg sodium-acetate, add 15kg methyl alcohol and refluxed 40 minutes, treat to add bromine liquid 2.5kg when temperature reaches 10 ℃, continue to stir 5 hours, add then in the 120kg water, after-filtration to be crystallized, crystallization is 100 ℃ of following vacuum-dryings; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 30kg and add ethylene glycol 250kg, hydrazine hydrate solvent 30kg with content 85% refluxed 18 hours in 160 ℃, and then be warming up to 200 ℃ and refluxed again 4 hours, stop then heating up and be cooled to room temperature, add the dilution of 700kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 100 ℃ of vacuum-dryings; Crystallization is content 98.5% Chenodiol.
Embodiment 4
Production method of the present invention comprises the steps:
Esterification:
Get methyl alcohol 20kg, add the cattle and sheep bile acid 30kg of content more than 98.0%, reflux 2 hours has been placed to crystallization under the room temperature and has separated out, and filters, and with the 90-120 petroleum ether, 60 ℃ of following vacuum-dryings, gets Methyl cholate;
Acetylization reaction:
Get toluene 5kg, adding 1kg 4-lutidine adds above-mentioned crystalline Methyl cholate 4kg and at room temperature stirred 50 minutes, adds water 80kg then, stirred once more 20 minutes, leave standstill 6 hours then after, reclaim after isolating toluene, separate out crystallization, crystallization is 100 ℃ of following vacuum-dryings; Crystallization gets 3 α, 7 α-diacetyl Methyl cholate with 90-120 sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get above-mentioned diacetyl Methyl cholate 0.5kg, add the 4kg sodium-acetate, add 5kg methyl alcohol and refluxed 40 minutes, treat to add bromine liquid 0.5kg when temperature reaches 10 ℃, continue to stir 5 hours, add then in the 80kg water, after-filtration to be crystallized, crystallization is 100 ℃ of following vacuum-dryings; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 10kg and add ethylene glycol 100kg, refluxed 18 hours in 100 ℃ with content hydrazine hydrate solvent 30kg, and then be warming up to 195 ℃ and refluxed again 2 hours, stop then heating up and be cooled to room temperature, add the dilution of 500kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 70 ℃ of vacuum-dryings; Crystallization is content 98.5% Chenodiol.
Claims (4)
1. a production method of producing Chenodiol with 98% cattle and sheep bile acid is characterized in that comprising the steps:
Esterification:
Get methyl alcohol 20-60kg, add the cholic acid 5-30kg of content more than 98.0%, reflux 0.5-2 hour, be placed to crystallization under the room temperature and separated out, filter, use petroleum ether, 60-80 ℃ of following vacuum-drying, get Methyl cholate;
Acetylization reaction:
Get toluene 5-20kg, adding 1-4kg 4-lutidine adds above-mentioned crystalline Methyl cholate 1-4kg and at room temperature stirred 20-50 minute, add water 80-150kg then, stirred once more 20-50 minute, after leaving standstill 2-6 hour then, reclaim after isolating toluene, separate out crystallization, crystallization is 60-100 ℃ of following vacuum-drying; Crystallization gets 3 α, 7 α-diacetyl Methyl cholate with the sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get above-mentioned diacetyl Methyl cholate 0.5-4kg, add the 1-4kg sodium-acetate, adding 5-15kg methyl alcohol refluxed 20-40 minute, treat to add when temperature reaches 5-10 ℃ bromine liquid 0.5-2.5kg, continue to stir 2-5 hour, add then in the 80-120kg water, after-filtration to be crystallized, crystallization is 70-100 ℃ of following vacuum-drying; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 10-30kg and add ethylene glycol 100-250kg, hydrazine hydrate solvent 10-30kg was in 100-160 ℃ of backflow 12-18 hour, and then be warming up to 195-200 ℃ and refluxed again 2-4 hour, stop then heating up and be cooled to room temperature, add the dilution of 500-700kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 70-100 ℃ of vacuum-drying; Crystallization is content 98.5% Chenodiol.
2. the cattle and sheep bile acid of usefulness 98% according to claim 1 is produced the production method of Chenodiol, it is characterized in that comprising the steps:
Esterification:
Get methyl alcohol 40kg, add the cattle and sheep bile acid 15kg of content more than 98.0%, reflux 1 hour has been placed to crystallization under the room temperature and has separated out, and filters, and with the 90-120 petroleum ether, gets Methyl cholate 70 ℃ of following vacuum-dryings;
Acetylization reaction:
Get toluene 10kg, adding 2kg 4-lutidine adds above-mentioned crystalline Methyl cholate 2kg and at room temperature stirred 30 minutes, add water 100kg then, stirred once more 30 minutes, after leaving standstill 4 hours then, reclaim after isolating toluene, separate out crystallization, crystallization is 80 ℃ of following vacuum-dryings, and crystallization gets 3 α, 7 α-diacetyl Methyl cholate with 90-120 sherwood oil repetitive scrubbing;
Oxidizing reaction:
Get the diacetyl Methyl cholate 1.5kg that above-mentioned crystallization goes out, add the 2kg sodium-acetate, add 10kg methyl alcohol and refluxed 30 minutes, treat to add bromine liquid 1kg when temperature reaches 8 ℃, continue to stir 4 hours, add then in the 100kg water, after-filtration to be crystallized, crystallization is 80 ℃ of vacuum-dryings; Crystallization is 3 α-7 α-diacetoxy-12-ketone group ursodeoxycholic acid methyl esters;
Reduction reaction:
Get 3 α-7 α-diacetoxy-12-ketone 15kg and add ethylene glycol 150kg, the hydrazine hydrate solvent 15kg of content 85% refluxed 15 hours in 130 ℃, and then be warming up to 200 ℃ and refluxed again 3 hours, stop then heating up and be cooled to room temperature, add the dilution of 600kg water again, regulate PH3.0 with dilute sulphuric acid then, crystallization to be separated out, filter, crystallization is 80 ℃ of vacuum-dryings; Crystallization is content 98.5% Chenodiol.
3. the cattle and sheep bile acid of usefulness 98% according to claim 1 is produced the production method of Chenodiol, it is characterized in that described sherwood oil is the 90-120 sherwood oil.
4. the cattle and sheep bile acid of usefulness 98% according to claim 1 is produced the production method of Chenodiol, it is characterized in that the hydrazine hydrate solvent that described hydrazine hydrate solvent is a content 85%.
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| CNA2008100100729A CN101215309A (en) | 2008-01-10 | 2008-01-10 | Method for producing chenodeoxycholic acid from 98% of cholic acid of cattle and sheep |
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| CNA2008100100729A CN101215309A (en) | 2008-01-10 | 2008-01-10 | Method for producing chenodeoxycholic acid from 98% of cholic acid of cattle and sheep |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102224935A (en) * | 2011-05-16 | 2011-10-26 | 常德云港生物科技有限公司 | Duck gall powder and preparation method thereof |
| CN101830956B (en) * | 2008-11-19 | 2012-11-21 | 毕小升 | Preparation method for separating and purifying chenodeoxycholic acid in porcine bile paste or leftovers |
| CN102964416A (en) * | 2012-12-10 | 2013-03-13 | 辽宁百凤生物药业有限公司 | Method for producing chenodeoxycholic acid by using 98.5% sodium cholate |
| CN103012532A (en) * | 2012-12-10 | 2013-04-03 | 辽宁百凤生物药业有限公司 | Method for producing ursodesoxycholic acid with 98.5 percent sodium cholate |
| CN104523703A (en) * | 2014-12-24 | 2015-04-22 | 聂飚 | Application of free fatty acid translocator small-molecule inhibitor |
-
2008
- 2008-01-10 CN CNA2008100100729A patent/CN101215309A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830956B (en) * | 2008-11-19 | 2012-11-21 | 毕小升 | Preparation method for separating and purifying chenodeoxycholic acid in porcine bile paste or leftovers |
| CN102224935A (en) * | 2011-05-16 | 2011-10-26 | 常德云港生物科技有限公司 | Duck gall powder and preparation method thereof |
| CN102224935B (en) * | 2011-05-16 | 2012-10-24 | 常德云港生物科技有限公司 | Duck gall powder and preparation method thereof |
| CN102964416A (en) * | 2012-12-10 | 2013-03-13 | 辽宁百凤生物药业有限公司 | Method for producing chenodeoxycholic acid by using 98.5% sodium cholate |
| CN103012532A (en) * | 2012-12-10 | 2013-04-03 | 辽宁百凤生物药业有限公司 | Method for producing ursodesoxycholic acid with 98.5 percent sodium cholate |
| CN104523703A (en) * | 2014-12-24 | 2015-04-22 | 聂飚 | Application of free fatty acid translocator small-molecule inhibitor |
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