CN1830996A - Method for preparing chenodeoxycholic acid - Google Patents
Method for preparing chenodeoxycholic acid Download PDFInfo
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- CN1830996A CN1830996A CN 200610031503 CN200610031503A CN1830996A CN 1830996 A CN1830996 A CN 1830996A CN 200610031503 CN200610031503 CN 200610031503 CN 200610031503 A CN200610031503 A CN 200610031503A CN 1830996 A CN1830996 A CN 1830996A
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Abstract
The invention relates to a method of distilling the chenodeoxychoilc acid from the offcuts which be gained by distilling the bilirubin from the bile of the pig. With the offcuts of the alkali saponification, the deposit is treated with the oxidation treatment by means of the hydrogen peroxide, the filtrate is treated by the dilute sulfuric acid and decolored by means of the active carbon and solved, crystaled using the ethyl acetate again and again; the coordinate production of the hyodeoxycholic acid is purified, the mother liquor is concentrated to the cream and melted using the alkali and have the salifying treatment with the chloride of barium, so the cholate is formed, the cholate is treated to take off barium when the cholate suspending the aqueous solution containing the sodium carbonate, then it is acidificated with the dilute sulfuric acid and is separated ,deposited and dried to gain the crude chenodeoxycholic acid which is decolored using the active carbon and is melted, rimed and dried using the ethyl acetate. Then the finished production of the chenodeoxycholic acid form.The whole technics has some merits of the abundant material, the amity of the environment, the safety and innocuity, producing many outputs from the single stuff and easy to the mass production. The invention is used for distilling the chenodeoxycholic acid.
Description
Technical field
The present invention relates to a kind of preparation method of Chenodiol, relate in particular to a kind of Fel Sus domestica that utilizes and extract the method that bilirubinic tankage extract Chenodiol.
Background technology
The effect of Chenodiol: have stronger anti-inflammatory, cough-relieving, go the effect of phlegm and dissolving calculus, except that pharmaceutical use itself, also can be used as the raw material of producing ursodesoxycholic acid, ursodesoxycholic acid is used for the treatment of various courage diseases and digestive tract diseases clinically.At present, extract Chenodiol, the one, from Fel Bovis seu Bubali or Fel Caprae seu Ovis, extract cholic acid, be that raw material carries out the chemosynthesis Chenodiol again with the cholic acid; The 2nd, from poultry bile, directly extract Chenodiol.With the Fel Bovis seu Bubali or Fel Caprae seu Ovis is that starting raw material carries out the chemosynthesis Chenodiol, and its process cycle is long, cost is high; With poultry bile is that raw material directly extracts Chenodiol, because poultry bladder is little, and easily collecting not, yield is lower, and raw material sources are restricted, and cost is also higher.Application number is the preparation method that 031514758 Chinese invention patent application discloses a kind of Chenodiol, when being the feedstock production Chenodiol with animal bile (comprising Fel Sus domestica) in this method, Hyodeoxycholic Acid product arranged side by side do not occur, this does not conform to production is actual.
Summary of the invention
Existing carry out chemosynthesis or directly extract long, defective such as cost is high or raw material sources are restricted of Chenodiol synthesis technique cycle in order to overcome, the invention provides that a kind of raw material is easy to get, utilization of waste material, a plurality of products of single raw material output, cost are lower, can form the preparation method of the Chenodiol that large-scale industrialization produces.
The technical solution adopted for the present invention to solve the technical problems is: extracting bilirubinic tankage (paste) with Fel Sus domestica is raw material, and the preparation method may further comprise the steps:
(1) separates Hyodeoxycholic Acid
Get Fel Sus domestica and extract bilirubinic tankage, with sodium hydroxide saponification tankage, the part by weight that feeds intake is: tankage: water: sodium hydroxide=1: 6～8: 1.1～1.3, by the part by weight blanking that feeds intake, water inlet earlier, again sodium hydroxide is dropped in the water and stir, treat to dissolve fully the back and drop into tankage, heating is protected and was boiled 24 hours, carries out saponification, need constantly to replenish vaporize water therebetween, after saponification reaction is finished, open water coolant it is cooled to room temperature, left standstill 12 hours, upper strata alkali lye is extracted out, and lower floor is a throw out.The throw out that saponification is produced carries out oxide treatment with hydrogen peroxide, the part by weight that feeds intake is: throw out: water: hydrogen peroxide=50: 190～210: 1～1.2, by the part by weight blanking that feeds intake, with water and throw out stirring and dissolving together, add hydrogen peroxide again, stir, carry out oxide treatment, leave standstill.Liquid material is filtered, and it is between 1.5～2 that filtrate adds 10% dilute sulphuric acid or hydrochloric acid to the pH value of solution, stirs, and the acid precipitation total cholic acid through acidification, obtains the paste total cholic acid.With the vacuum-drying of paste total cholic acid,, use activated carbon decolorizing with the dry thing of vinyl acetic monomer dissolving total cholic acid, the part by weight that feeds intake is: the dry thing of total cholic acid: vinyl acetic monomer: gac=10: 55～65: 1～1.2, and by the part by weight blanking that feeds intake, reflux is 30 minutes in conversion unit, the dissolving decolouring, filter, filtrate is concentrated into 1/5 o'clock of original volume, stop to concentrate, put cold crystallization, after treating sufficient crystallising, crystallisate and mother liquor are collected in the centrifugation crystallization.With crystallisate vacuum-drying, with the dissolving crystallized thing of vinyl acetic monomer, the part by weight that feeds intake is: crystallisate: vinyl acetic monomer=1: 7～9, by the part by weight blanking that feeds intake, mixed dissolution, filter, filtrate is concentrated into 1/5 o'clock of original volume, at 0～5 ℃ of refrigeration crystallization, fractional crystallization, vacuum-drying obtains the white Hyodeoxycholic Acid of fusing point more than 190 ℃.
(2) extract crude product Chenodiol (I)
The mother liquor that merges twice crystallization, with the mother liquor concentrating under reduced pressure, the evaporation of residual vinyl acetic monomer, to forming paste, paste is carried out salify to be handled, the part by weight that feeds intake is: paste: 10% aqueous sodium hydroxide solution: 20% barium chloride solution=10: 50～60: 3～3.5, by the part by weight blanking that feeds intake, with concentration is 10% aqueous sodium hydroxide solution dissolving paste, add concentration again and be 20% barium chloride solution, carry out salify and handle, generate yellow cholate, the centrifugation cholate.Salify is handled the cholate that obtains take off the barium processing, the part by weight that feeds intake is: cholate: 15% aqueous sodium carbonate=1: 4～6, by the part by weight blanking that feeds intake, it is in 15% the aqueous sodium carbonate that cholate is suspended in concentration, be heated to and boil, taking off barium handles, filter, in filtrate, add concentration and be 10% dilute sulphuric acid to the pH value of mixed solution between 1～2, carry out acidification, produce throw out, throw out is separated, vacuum-drying obtains crude product Chenodiol (I).
(3) crude product Chenodiol (I) is purified
The part by weight that crystallization for the first time feeds intake is: crude product Chenodiol (I): vinyl acetic monomer: gac=100: 470～520: 13～16, by the part by weight blanking that feeds intake, (I) dissolves with vinyl acetic monomer with the crude product Chenodiol, add gac processings of decolouring, filtration, filtrate is concentrated into 1/5 o'clock of original volume, in temperature is 0～5 ℃ of refrigeration crystallization, crystallisate is separated and press dry, vacuum-drying obtains crude product Chenodiol (II); The part by weight that recrystallization feeds intake is: crude product Chenodiol (II): vinyl acetic monomer=1: 7～9, by the part by weight blanking that feeds intake, (II) dissolves with vinyl acetic monomer with the crude product Chenodiol, filter, filtrate is concentrated into 1/5 o'clock of original volume, is 0～5 ℃ of refrigeration recrystallization in temperature, crystallisate is separated and press dry, in temperature is vacuum-drying in 80 ℃, obtains white Chenodiol finished product (HPLC content is greater than 95%).
The invention has the beneficial effects as follows that abundant raw material is easy to get, the pig courage is individual big, easily collecting, and yield is higher; Utilization of waste material, raw materials used for Fel Sus domestica extracts bilirubinic tankage, be sharp useless technology, be again deep processing technology, a plurality of products of single raw material output have extracted bilirubin, Hyodeoxycholic Acid and Chenodiol by Fel Sus domestica; Cost is low, and the present invention is raw materials used, and except that vinyl acetic monomer, other raw material prices are all lower, and vinyl acetic monomer is can be by distillation regenerated organic solvent; The present invention can form large-scale industrialization production, and technology is also uncomplicated, meets environmental protection requirement.
Embodiment
The invention will be further described below by specific embodiment.
(1) separates Hyodeoxycholic Acid.Get Fel Sus domestica and extract bilirubinic tankage (paste), with sodium hydroxide saponification tankage, the part by weight that feeds intake is: tankage: water: sodium hydroxide=1: 7: 1.2, by the part by weight blanking that feeds intake, water inlet earlier, again sodium hydroxide is dropped in the water and stir, treat to dissolve fully the back and drop into tankage, heating is protected and was boiled 24 hours, carries out saponification, need constantly to replenish vaporize water therebetween, after saponification reaction is finished, open water coolant it is cooled to room temperature, left standstill 12 hours, upper strata alkali lye is extracted out, and lower floor is a throw out.The throw out that saponification is produced carries out oxide treatment with hydrogen peroxide, and the part by weight that feeds intake is: throw out: water: hydrogen peroxide=50: 200: 1, by the part by weight blanking that feeds intake, with water and throw out stirring and dissolving together, add hydrogen peroxide again, stir, carry out oxide treatment, leave standstill.Liquid material is filtered, and it is between 1.5～2 that filtrate adds 10% dilute sulphuric acid to the pH value of solution, stirs, and the acid precipitation total cholic acid through acidification, obtains the paste total cholic acid.With the vacuum-drying of paste total cholic acid,, use activated carbon decolorizing with the dry thing of vinyl acetic monomer dissolving total cholic acid, the part by weight that feeds intake is: the dry thing of total cholic acid: vinyl acetic monomer: gac=10: 60: 1, and by the part by weight blanking that feeds intake, reflux is 30 minutes in conversion unit, dissolving, decolouring is filtered, filtrate is concentrated into 1/5 o'clock of original volume, stop to concentrate, put cold crystallization, treat sufficient crystallising after, crystallisate and mother liquor are collected in the centrifugation crystallization.With crystallisate vacuum-drying, with the dissolving crystallized thing of vinyl acetic monomer, the part by weight that feeds intake is: crystallisate: vinyl acetic monomer=1: 8, by the part by weight blanking that feeds intake, mixed dissolution, filter, filtrate is concentrated into 1/5 o'clock of original volume, at 0～5 ℃ of refrigeration crystallization, fractional crystallization, vacuum-drying obtains the white Hyodeoxycholic Acid of fusing point more than 190 ℃.
(2) extract crude product Chenodiol (I).The mother liquor that merges twice crystallization, with the mother liquor concentrating under reduced pressure, the evaporation of residual vinyl acetic monomer is to forming paste, paste is carried out salify to be handled, the part by weight that feeds intake is: paste: 10% aqueous sodium hydroxide solution: 20% barium chloride solution=10: 50: 3 by the part by weight blanking that feeds intake, is 10% an aqueous sodium hydroxide solution dissolving paste with concentration, add concentration again and be 20% barium chloride solution, carry out salify and handle, generate yellow cholate, the centrifugation cholate.Cholate is taken off barium to be handled, the part by weight that feeds intake is: cholate: 15% aqueous sodium carbonate=1: 5, and by the part by weight blanking that feeds intake, it is in 15% the aqueous sodium carbonate that cholate is suspended in concentration, be heated to and boil, take off barium and handle, filter, in filtrate, add concentration and be 10% dilute sulphuric acid to the pH value of mixed solution between 1～2, carry out acidification, produce throw out,, obtain crude product Chenodiol (I) throw out separation, vacuum-drying.
(3) crude product Chenodiol (I) is purified, the part by weight that crystallization for the first time feeds intake is: crude product Chenodiol (I): vinyl acetic monomer: gac=100: 500: 15, by the part by weight blanking that feeds intake, crude product Chenodiol (I) with vinyl acetic monomer dissolving, is added the gac processing of decolouring, filter, filtrate is concentrated into 1/5 o'clock of original volume, is 0～5 ℃ of refrigeration crystallization in temperature, crystallisate is separated and press dry, vacuum-drying obtains crude product Chenodiol (II).The part by weight that recrystallization feeds intake is: crude product Chenodiol (II): vinyl acetic monomer=1: 8, by the part by weight blanking that feeds intake, (II) dissolves with vinyl acetic monomer with the crude product Chenodiol, filter, filtrate is concentrated into 1/5 o'clock of original volume, is 0～5 ℃ of refrigeration recrystallization in temperature, crystallisate is separated and press dry, in temperature is vacuum-drying in 80 ℃, obtains white Chenodiol finished product (HPLC content is greater than 95%).
Claims (4)
1, a kind of preparation method of Chenodiol, extracting bilirubinic tankage with Fel Sus domestica is raw material, technological process comprises sodium hydroxide saponification tankage, hydrogen peroxide and activated carbon decolorizing, it is characterized in that, the preparation method may further comprise the steps: (1) separates Hyodeoxycholic Acid, with sodium hydroxide saponification tankage, the part by weight that feeds intake is: tankage: water: sodium hydroxide=1: 6～8: 1.1～1.3; The throw out that saponification is produced carries out oxide treatment with hydrogen peroxide, and the part by weight that feeds intake is: throw out: water: hydrogen peroxide=50: 190～210: 1～1.2; It is between 1.5～2 that the filtrate that oxide treatment is obtained adds 10% dilute sulphuric acid or hydrochloric acid to the pH value of solution, carry out acidification, obtain the paste total cholic acid, dry, with the dry thing of vinyl acetic monomer dissolving total cholic acid, use activated carbon decolorizing, the part by weight that feeds intake is: the dry thing of total cholic acid: vinyl acetic monomer: gac=10: 55～65: 1～1.2; Filtrate is concentrated into 1/5 o'clock of original volume puts cold crystallization, with the dissolving crystallized thing of vinyl acetic monomer, the part by weight that feeds intake is: crystallisate: Methane Carboxylic Acid=1: 7～9, filtrate is concentrated into refrigeration crystallization in 1/5 o'clock of original volume, and obtain Hyodeoxycholic Acid; (2) extract crude product Chenodiol (I), the mother liquor that merges twice crystallization, be concentrated into the formation paste, paste carried out salify handle, the part by weight that feeds intake is: paste: 10% aqueous sodium hydroxide solution: 20% barium chloride solution=10: 50～60: 3～3.5; Salify is handled the cholate that obtains take off the barium processing, the heavily reason ratio that feeds intake is: cholate: 15% aqueous sodium carbonate=1: 4～6; In filtrate filtered, add 10% dilute sulphuric acid to the pH value of mixed solution between 1～2, carry out acidification, sediment separate out is also done bath, obtains crude product Chenodiol (I); (3) crude product Chenodiol (I) is purified, the part by weight that crystallization for the first time feeds intake is: crude product Chenodiol (I): vinyl acetic monomer: gac=100: 470～520: 13～16; Obtain crude product Chenodiol (II); The part by weight that recrystallization feeds intake is: crude product Chenodiol (II): vinyl acetic monomer=1: 7～9; Crystallisate is separated, and vacuum-drying obtains white Chenodiol finished product.
2, preparation method according to claim 1 is characterized in that, in separating the Hyodeoxycholic Acid process, with sodium hydroxide saponification tankage, the part by weight that feeds intake is: tankage: water: sodium hydroxide=1: 7: 1.2; The throw out that saponification is produced carries out oxide treatment with hydrogen peroxide, and the part by weight that feeds intake is: throw out: water: hydrogen peroxide=50: 200: 1; With the dry thing of vinyl acetic monomer dissolving total cholic acid, use activated carbon decolorizing, the part by weight that feeds intake is: the dry thing of total cholic acid: vinyl acetic monomer: gac=10: 60: 1, with the dissolving crystallized thing of vinyl acetic monomer, the part by weight that feeds intake is: crystallisate: vinyl acetic monomer=1: 8.
3, preparation method according to claim 1, it is characterized in that, in extracting crude product Chenodiol (I) process, paste is carried out salify handle, the part by weight that feeds intake is: paste: 10% aqueous sodium hydroxide solution: 20% barium chloride solution=10: 50: 3; Cholate is taken off barium handle, the part by weight that feeds intake is: cholate: 15% aqueous sodium carbonate=1: 5.
4, preparation method according to claim 1, its row is levied and is, crude product Chenodiol (I) is purified, and the part by weight that crystallization for the first time feeds intake is: crude product Chenodiol (I): vinyl acetic monomer: gac=100: 500: 15; The part by weight that recrystallization feeds intake is: crude product Chenodiol (II): vinyl acetic monomer=1: 8.
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| CN 200610031503 CN1830996A (en) | 2006-04-17 | 2006-04-17 | Method for preparing chenodeoxycholic acid |
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| CN 200610031503 CN1830996A (en) | 2006-04-17 | 2006-04-17 | Method for preparing chenodeoxycholic acid |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101215308B (en) * | 2007-01-04 | 2010-05-12 | 苏州天绿生物制药有限公司 | Method for producing ursodeoxycholic acid by using swine bladder as raw material |
| CN102443033A (en) * | 2010-10-08 | 2012-05-09 | 娄倩倩 | Method for extracting bile acid from bilirubin leftovers |
| 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 |
| CN102838647A (en) * | 2011-06-23 | 2012-12-26 | 福建省仙游县南丰生化有限公司 | Hyodeoxycholic acid |
| CN103012534A (en) * | 2012-12-19 | 2013-04-03 | 四川大熊生物技术有限公司 | Method for extracting hyodeoxycholic acid from pig bile |
| CN104152387A (en) * | 2014-08-21 | 2014-11-19 | 曹国华 | Bile salt, preparation method thereof, and application of the bile salt in production of dry powder bacterium culture medium |
| CN106977573A (en) * | 2017-06-06 | 2017-07-25 | 福建省仙游县南丰生化有限公司 | Hyodesoxycholic acid, the joint generation of chenodeoxycholic acid, purification process |
| CN107098945A (en) * | 2017-06-09 | 2017-08-29 | 湖南迪博制药有限公司 | The method that cholic acid is extracted from cholic acid leftover bits and pieces |
| CN107337703A (en) * | 2017-07-07 | 2017-11-10 | 赵厚发 | A kind of isolation and purification method of Chenodeoxvcholic Acid from Pig Bile |
| CN110256517A (en) * | 2019-07-19 | 2019-09-20 | 中山百灵生物技术有限公司 | A method of producing high-purity chenodeoxy cholic acid from pig's bile or leftover bits and pieces |
| CN110790805A (en) * | 2019-11-14 | 2020-02-14 | 湖南九典制药股份有限公司 | Method for extracting chenodeoxycholic acid from pig bile paste |
| CN114478676A (en) * | 2022-02-18 | 2022-05-13 | 国药集团化学试剂有限公司 | Preparation method of high-purity sodium deoxycholate |
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2006
- 2006-04-17 CN CN 200610031503 patent/CN1830996A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101215308B (en) * | 2007-01-04 | 2010-05-12 | 苏州天绿生物制药有限公司 | Method for producing ursodeoxycholic acid by using swine bladder as raw material |
| 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 |
| CN102443033A (en) * | 2010-10-08 | 2012-05-09 | 娄倩倩 | Method for extracting bile acid from bilirubin leftovers |
| CN102838647A (en) * | 2011-06-23 | 2012-12-26 | 福建省仙游县南丰生化有限公司 | Hyodeoxycholic acid |
| CN103012534A (en) * | 2012-12-19 | 2013-04-03 | 四川大熊生物技术有限公司 | Method for extracting hyodeoxycholic acid from pig bile |
| CN103012534B (en) * | 2012-12-19 | 2015-03-18 | 四川大熊生物技术有限公司 | Method for extracting hyodeoxycholic acid from pig bile |
| CN104152387A (en) * | 2014-08-21 | 2014-11-19 | 曹国华 | Bile salt, preparation method thereof, and application of the bile salt in production of dry powder bacterium culture medium |
| CN106977573A (en) * | 2017-06-06 | 2017-07-25 | 福建省仙游县南丰生化有限公司 | Hyodesoxycholic acid, the joint generation of chenodeoxycholic acid, purification process |
| CN107098945A (en) * | 2017-06-09 | 2017-08-29 | 湖南迪博制药有限公司 | The method that cholic acid is extracted from cholic acid leftover bits and pieces |
| CN107098945B (en) * | 2017-06-09 | 2019-04-26 | 湖南迪博制药有限公司 | The method of cholic acid is extracted from cholic acid leftover bits and pieces |
| CN107337703A (en) * | 2017-07-07 | 2017-11-10 | 赵厚发 | A kind of isolation and purification method of Chenodeoxvcholic Acid from Pig Bile |
| CN110256517A (en) * | 2019-07-19 | 2019-09-20 | 中山百灵生物技术有限公司 | A method of producing high-purity chenodeoxy cholic acid from pig's bile or leftover bits and pieces |
| CN110256517B (en) * | 2019-07-19 | 2021-03-09 | 中山百灵生物技术股份有限公司 | Method for producing high-purity chenodeoxycholic acid from pig bile or leftovers |
| CN110790805A (en) * | 2019-11-14 | 2020-02-14 | 湖南九典制药股份有限公司 | Method for extracting chenodeoxycholic acid from pig bile paste |
| CN110790805B (en) * | 2019-11-14 | 2022-08-30 | 湖南九典制药股份有限公司 | Method for extracting chenodeoxycholic acid from pig bile paste |
| CN114478676A (en) * | 2022-02-18 | 2022-05-13 | 国药集团化学试剂有限公司 | Preparation method of high-purity sodium deoxycholate |
| CN114478676B (en) * | 2022-02-18 | 2024-05-10 | 国药集团化学试剂有限公司 | Preparation method of sodium deoxycholate |
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