CN105566428A - Method for removing hyocholic acid from chenodeoxycholic acid - Google Patents
Method for removing hyocholic acid from chenodeoxycholic acid Download PDFInfo
- Publication number
- CN105566428A CN105566428A CN201610036122.5A CN201610036122A CN105566428A CN 105566428 A CN105566428 A CN 105566428A CN 201610036122 A CN201610036122 A CN 201610036122A CN 105566428 A CN105566428 A CN 105566428A
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- CN
- China
- Prior art keywords
- acid
- chenodiol
- butylacetate
- add
- crude product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 title claims abstract description 76
- 229960001091 chenodeoxycholic acid Drugs 0.000 title claims abstract description 60
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 18
- DKPMWHFRUGMUKF-UHFFFAOYSA-N (3alpha,5alpha,6alpha,7alpha)-3,6,7-Trihydroxycholan-24-oic acid Natural products OC1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DKPMWHFRUGMUKF-UHFFFAOYSA-N 0.000 title abstract 3
- JOYGXTIHTHBSOA-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-thiophen-2-ylprop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C=CC1=CC=CS1 JOYGXTIHTHBSOA-UHFFFAOYSA-N 0.000 title abstract 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 36
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000001035 drying Methods 0.000 claims abstract description 18
- 239000012452 mother liquor Substances 0.000 claims abstract description 12
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims abstract description 10
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000000536 complexating effect Effects 0.000 claims abstract description 4
- 229940043232 butyl acetate Drugs 0.000 claims description 34
- 239000000047 product Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- DKPMWHFRUGMUKF-KWXDGCAGSA-N hyocholic acid Chemical compound C([C@H]1[C@@H](O)[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DKPMWHFRUGMUKF-KWXDGCAGSA-N 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000012043 crude product Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 15
- 239000002244 precipitate Substances 0.000 claims description 13
- 150000003863 ammonium salts Chemical class 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000006166 lysate Substances 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 10
- 238000005119 centrifugation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 238000004945 emulsification Methods 0.000 claims description 8
- 241000282894 Sus scrofa domesticus Species 0.000 claims description 7
- 210000000941 bile Anatomy 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 238000010306 acid treatment Methods 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 230000011218 segmentation Effects 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002893 slag Substances 0.000 claims description 2
- 230000008719 thickening Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 8
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 abstract description 5
- 239000003613 bile acid Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 description 9
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 description 8
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- -1 CDCA amine Chemical class 0.000 description 6
- DGABKXLVXPYZII-UHFFFAOYSA-N Hyodeoxycholic acid Natural products C1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DGABKXLVXPYZII-UHFFFAOYSA-N 0.000 description 6
- DGABKXLVXPYZII-SIBKNCMHSA-N hyodeoxycholic acid Chemical compound C([C@H]1[C@@H](O)C2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DGABKXLVXPYZII-SIBKNCMHSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 206010013786 Dry skin Diseases 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 description 3
- 229960001661 ursodiol Drugs 0.000 description 3
- 239000003292 glue Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Lot number | Chenodiol | Iocholic acid | Hyodeoxycholic Acid | Lithocholic acid | Weight loss on drying |
Example one (20150501) | 61.3% | 5.8% | 0.37% | ≤1.0% | 2.5% |
Example two (20150502) | 59.7% | 5.1% | 0.47% | ≤1.0% | 2.8% |
Example three (20150503) | 63.3% | 4.9% | 0.35% | ≤1.0% | 2.1% |
Lot number | Chenodiol | Iocholic acid | Hyodeoxycholic Acid | Lithocholic acid | Weight loss on drying 3--> |
Example one (20150501) | 92.1% | 0.85% | 0.34% | ≤0.2% | 1.3% |
Example two (20150502) | 92.4% | 0.89% | 0.41% | ≤0.2% | 0.9% |
Example three (20150503) | 93.8% | 0.66% | 0.27% | ≤0.2% | 0.77% |
Lot number | Chenodiol | Iocholic acid | Other TOTAL BILE ACID |
Example one (20150501) | 6.5% | 21.09% | 11% |
Example two (20150502) | 5.7% | 23.2% | 10.9% |
Example three (20150503) | 6.1% | 20.8% | 13.2% |
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610036122.5A CN105566428B (en) | 2016-01-20 | 2016-01-20 | A kind of method that hyocholic acid is removed from chenodeoxycholic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610036122.5A CN105566428B (en) | 2016-01-20 | 2016-01-20 | A kind of method that hyocholic acid is removed from chenodeoxycholic acid |
Publications (2)
Publication Number | Publication Date |
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CN105566428A true CN105566428A (en) | 2016-05-11 |
CN105566428B CN105566428B (en) | 2017-06-09 |
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CN201610036122.5A Active CN105566428B (en) | 2016-01-20 | 2016-01-20 | A kind of method that hyocholic acid is removed from chenodeoxycholic acid |
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CN (1) | CN105566428B (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108299538A (en) * | 2018-03-09 | 2018-07-20 | 常德云港生物科技有限公司 | A method of removing different ursodesoxycholic acid in duck bile |
CN109810159A (en) * | 2019-01-22 | 2019-05-28 | 常德云港生物科技有限公司 | A kind of method that allocholic acid yield can be improved from duck 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 |
CN112062802A (en) * | 2019-06-11 | 2020-12-11 | 四川澄华生物科技有限公司 | Chenodeoxycholic acid butyl acetate extracting solution and preparation method thereof, and chenodeoxycholic acid ammonium salt and chenodeoxycholic acid preparation method |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1432579A (en) * | 2002-12-27 | 2003-07-30 | 贵州省生物技术研究开发基地 | Refining process of chenodeoxcholic acid |
CN1869044A (en) * | 2006-06-09 | 2006-11-29 | 沈阳化工学院 | Separation purification preparation method of chenodeoxycholic acid in pig's bile |
CN101948496A (en) * | 2010-09-21 | 2011-01-19 | 湖南凯勒迪化学科技有限公司 | Method for extracting chenodeoxycholic acid from bile of fowl |
CN102766185A (en) * | 2012-08-02 | 2012-11-07 | 苏州天绿生物制药有限公司 | Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor |
-
2016
- 2016-01-20 CN CN201610036122.5A patent/CN105566428B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1432579A (en) * | 2002-12-27 | 2003-07-30 | 贵州省生物技术研究开发基地 | Refining process of chenodeoxcholic acid |
CN1869044A (en) * | 2006-06-09 | 2006-11-29 | 沈阳化工学院 | Separation purification preparation method of chenodeoxycholic acid in pig's bile |
CN101948496A (en) * | 2010-09-21 | 2011-01-19 | 湖南凯勒迪化学科技有限公司 | Method for extracting chenodeoxycholic acid from bile of fowl |
CN102766185A (en) * | 2012-08-02 | 2012-11-07 | 苏州天绿生物制药有限公司 | Method for respectively recovering ursodesoxycholic acid and chenodeoxycholic acid from ursodesoxycholic acid waste mother liquor |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108299538A (en) * | 2018-03-09 | 2018-07-20 | 常德云港生物科技有限公司 | A method of removing different ursodesoxycholic acid in duck bile |
CN109810159A (en) * | 2019-01-22 | 2019-05-28 | 常德云港生物科技有限公司 | A kind of method that allocholic acid yield can be improved from duck bile |
CN112062802A (en) * | 2019-06-11 | 2020-12-11 | 四川澄华生物科技有限公司 | Chenodeoxycholic acid butyl acetate extracting solution and preparation method thereof, and chenodeoxycholic acid ammonium salt and chenodeoxycholic acid preparation method |
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 |
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