CN105566428A - 一种从鹅去氧胆酸中清除猪胆酸的方法 - Google Patents
一种从鹅去氧胆酸中清除猪胆酸的方法 Download PDFInfo
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- 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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- chenodiol
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
Description
批号 | 鹅去氧胆酸 | 猪胆酸 | 猪去氧胆酸 | 石胆酸 | 干燥失重 |
实例一(20150501) | 61.3% | 5.8% | 0.37% | ≤1.0% | 2.5% |
实例二(20150502) | 59.7% | 5.1% | 0.47% | ≤1.0% | 2.8% |
实例三(20150503) | 63.3% | 4.9% | 0.35% | ≤1.0% | 2.1% |
批号 | 鹅去氧胆酸 | 猪胆酸 | 猪去氧胆酸 | 石胆酸 | 干燥失重3 --> |
实例一(20150501) | 92.1% | 0.85% | 0.34% | ≤0.2% | 1.3% |
实例二(20150502) | 92.4% | 0.89% | 0.41% | ≤0.2% | 0.9% |
实例三(20150503) | 93.8% | 0.66% | 0.27% | ≤0.2% | 0.77% |
批号 | 鹅去氧胆酸 | 猪胆酸 | 其它总胆汁酸 |
实例一(20150501) | 6.5% | 21.09% | 11% |
实例二(20150502) | 5.7% | 23.2% | 10.9% |
实例三(20150503) | 6.1% | 20.8% | 13.2% |
Claims (1)
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108299538A (zh) * | 2018-03-09 | 2018-07-20 | 常德云港生物科技有限公司 | 一种清除鸭胆汁中异熊去氧胆酸的方法 |
CN109810159A (zh) * | 2019-01-22 | 2019-05-28 | 常德云港生物科技有限公司 | 一种能从鸭胆汁中提高别胆酸收率的方法 |
CN110256517A (zh) * | 2019-07-19 | 2019-09-20 | 中山百灵生物技术有限公司 | 一种从猪胆汁或下脚料中生产高纯度鹅去氧胆酸的方法 |
CN110790805A (zh) * | 2019-11-14 | 2020-02-14 | 湖南九典制药股份有限公司 | 一种从猪胆膏中提取鹅去氧胆酸的方法 |
CN112062802A (zh) * | 2019-06-11 | 2020-12-11 | 四川澄华生物科技有限公司 | 鹅去氧胆酸乙酸丁酯提取液和制备方法、以及鹅去氧胆酸铵盐和鹅去氧胆酸的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1432579A (zh) * | 2002-12-27 | 2003-07-30 | 贵州省生物技术研究开发基地 | 一种鹅去氧胆酸粗品的精制方法 |
CN1869044A (zh) * | 2006-06-09 | 2006-11-29 | 沈阳化工学院 | 猪胆汁中鹅去氧胆酸的分离纯化制备方法 |
CN101948496A (zh) * | 2010-09-21 | 2011-01-19 | 湖南凯勒迪化学科技有限公司 | 一种从家禽胆汁中提取鹅去氧胆酸的方法 |
CN102766185A (zh) * | 2012-08-02 | 2012-11-07 | 苏州天绿生物制药有限公司 | 一种从熊去氧胆酸废母液中分别回收熊去氧胆酸和鹅去氧胆酸的方法 |
-
2016
- 2016-01-20 CN CN201610036122.5A patent/CN105566428B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1432579A (zh) * | 2002-12-27 | 2003-07-30 | 贵州省生物技术研究开发基地 | 一种鹅去氧胆酸粗品的精制方法 |
CN1869044A (zh) * | 2006-06-09 | 2006-11-29 | 沈阳化工学院 | 猪胆汁中鹅去氧胆酸的分离纯化制备方法 |
CN101948496A (zh) * | 2010-09-21 | 2011-01-19 | 湖南凯勒迪化学科技有限公司 | 一种从家禽胆汁中提取鹅去氧胆酸的方法 |
CN102766185A (zh) * | 2012-08-02 | 2012-11-07 | 苏州天绿生物制药有限公司 | 一种从熊去氧胆酸废母液中分别回收熊去氧胆酸和鹅去氧胆酸的方法 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108299538A (zh) * | 2018-03-09 | 2018-07-20 | 常德云港生物科技有限公司 | 一种清除鸭胆汁中异熊去氧胆酸的方法 |
CN109810159A (zh) * | 2019-01-22 | 2019-05-28 | 常德云港生物科技有限公司 | 一种能从鸭胆汁中提高别胆酸收率的方法 |
CN112062802A (zh) * | 2019-06-11 | 2020-12-11 | 四川澄华生物科技有限公司 | 鹅去氧胆酸乙酸丁酯提取液和制备方法、以及鹅去氧胆酸铵盐和鹅去氧胆酸的制备方法 |
CN110256517A (zh) * | 2019-07-19 | 2019-09-20 | 中山百灵生物技术有限公司 | 一种从猪胆汁或下脚料中生产高纯度鹅去氧胆酸的方法 |
CN110256517B (zh) * | 2019-07-19 | 2021-03-09 | 中山百灵生物技术股份有限公司 | 一种从猪胆汁或下脚料中生产高纯度鹅去氧胆酸的方法 |
CN110790805A (zh) * | 2019-11-14 | 2020-02-14 | 湖南九典制药股份有限公司 | 一种从猪胆膏中提取鹅去氧胆酸的方法 |
CN110790805B (zh) * | 2019-11-14 | 2022-08-30 | 湖南九典制药股份有限公司 | 一种从猪胆膏中提取鹅去氧胆酸的方法 |
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Denomination of invention: A method for removing swine bile acid from chenodeoxycholic acid Effective date of registration: 20230217 Granted publication date: 20170609 Pledgee: Changde Finance Guarantee Co.,Ltd. Pledgor: Changdeyungang Biotechnology Co.,Ltd. Registration number: Y2023980032871 |
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Granted publication date: 20170609 Pledgee: Changde Finance Guarantee Co.,Ltd. Pledgor: Changdeyungang Biotechnology Co.,Ltd. Registration number: Y2023980032871 |
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