(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid
chenodeoxycholic acid
CAS: 474-25-9
Molecular Formula: C24H40O4
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Names and Identifiers
| Name | chenodeoxycholic acid |
| Synonyms | CDCA CHENODIOL Chenodiol chenodeoxycholic acid CHENODEOXYCHOLIC ACID CHENODESOXYCHOLIC ACID 5β-Cholanic acid-3α,7α-diol Chenodiol (5beta)-3,7-dihydroxycholan-24-oic acid 3alpha,7alpha-Dihydroxy-5beta-cholanic acid (3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid URSODEOXYCHOLOC ACID,3,7-dihydroxy-,(3-alpha,5-beta,7-alpha)-cholan-24-oicaci (R)-4-((3R,5S,7R,10S,13R)-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid (R)-4-((3R,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid |
| CAS | 474-25-9 |
| EINECS | 207-481-8 |
| InChI | InChI=1/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22?,23+,24-/m1/s1 |
| InChIKey | RUDATBOHQWOJDD-BSWAIDMHSA-N |
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Physico-chemical Properties
| Molecular Formula | C24H40O4 |
| Molar Mass | 392.57 |
| Density | 0.9985 (rough estimate) |
| Melting Point | 165-167 °C (lit.) |
| Boling Point | 437.26°C (rough estimate) |
| Specific Rotation(α) | 12 º (c=1, CHCl3) |
| Flash Point | 9℃ |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Solubility | Almost insoluble in water, easily soluble in ethanol, glacial acetic acid, slightly soluble in chloroform. |
| Appearance | White powder |
| Color | White to off-white |
| Merck | 13,2062 |
| BRN | 3219887 |
| pKa | pKa 4.34 (Uncertain) |
| Storage Condition | room temp |
| Sensitive | Sensitive to light |
| Refractive Index | 1.4460 (estimate) |
| MDL | MFCD00064142 |
| Physical and Chemical Properties | Melting point 167-171°C Specific Rotation 12 ° (c = 1, CHCl3) water-soluble PRACTICALLY INSOLUBLE |
| Use | Suitable for the prevention and treatment of cholesterol gallstones |
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 63 - Possible risk of harm to the unborn child |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 2 |
| RTECS | FZ1980000 |
| HS Code | 29181990 |
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Reference
| Reference Show more | 1. Chen Jiangning, single country, Zhao Qimiao, et al. Comparison of components of cholic acids and their antipyretic effects in different bile-derived gallstones [J]. Modern medicine and clinic 2017 32(004):567-571. 2. Zhao Qimiao, Shan Guoshun, Chen Jiangning, et al. A preliminary study on the quality evaluation method of the compound of gallbladder [J]. Chinese Journal of Experimental prescriptions, 2017, 26 (06):28-31. 3. Xi Xiaozhi, Li Jia, Guo Shosa, etc. Optimization of purification process of Chenodeoxycholic acid by macroporous resin and its Hypolipidemic activity [J]. Modern food science and technology, 2018, 034(008):123-129. 4. Chen Jiangning, single country, Liu Xiaoyu, etc. Component Analysis and heat-clearing effect of excipients of dananxing [J]. Modern Chinese medicine, 18 vol. 7,, pp. 837-840, ISTIC CA, 2016. 5. Chen, Yunyu, Hong Li, Wu, Hao et al. Effect of fermentation on bile acids and determination of three free bile acids in gallstone [J]. Chinese Journal of Traditional Chinese Medicine, 2018, 43(22):99-103. 6. Chen Yun, Chen Jinsong, Yu Hongli, etc. Identification of fermented products and mixed steamed products of dananxing [J]. World Traditional Chinese Medicine, 2019, v.14(02):42-45 50. 7. Cao Yan, Song Qingqing, Li Jun, etc. Analysis of chemical constituents of bile acids in yak bile [J]. Chinese Journal of Traditional Chinese Medicine, 44 Vol. 12,, pp. 2538-2543, MEDLINE ISTIC PKU CSCD CA BP, 2019. 8. Li Wei, Jiang Zhenzhen, Li Han, Tu Pengfei, Song Qingqing, Yu Juan, Song Yuelin. Using online pressurized solvent extraction-ultra performance liquid chromatography-ion trap-Time of flight-mass spectrometry for qualitative analysis of chemical composition and grouping [J]. Chromatography, 2021,39(05):478-487. 9. Cao Yan, Li Ting, Chang Anqi, Jiang Zhenzhen, Yu Juan, Tu Peng-fei, Song Yue-Lin. Analysis of chemical constituents of bile acids in snake bile [J]. Chinese Journal of Traditional Chinese Medicine, 2021,46(01):130-138. 10. [IF = 3.935] Ziying Liu et al."Promotion of classic neutral bilateral acids synthesis pathway is responsible for Cholester ol-opening effect of Si-miao-yong-an decection: Application of LC-MS/MS method to determine 6 major bile acids in rat liver and plasma."J Pharmaceut Bio 11. [IF=5.81] Li Peng et al."Detection of Vasodilators From Herbal Components by a Transcriptome-Based Functional Gene Module Reference Approach."Front Pharmacol. 2019 Oct;0:1144 12. [IF=5.81] Shujing Lv et al."The Study on the Mechanism of Hugan Tablets in Treating Drug-Induced Liver Injury Induced by Atorvastatin."Front Pharmacol. 2021; 12: 683707 13. [IF=5.396] Shiming Huang et al."A sulfated polysaccharide from Gracilaria Lemaneiformis regulates cholesterol and bile acid metabolism in high-fat diet mice."Food Funct. 2019 Jun;10(6):3224-3236 14. [IF=5.396] Cong Liang et al."Lactiplantibacillus plantarum H-87 prevents high-fat diet-induced obesity by regulating bile acid metabolism in C57BL/6J mice."Food Funct. 2021 May;12(10):4315-4324 15. [IF=5.34] Kaihui Zhang et al."A UPLC-MS/MS-based metabolomics analysis of the pharmacological mechanisms of rabdosia serra against cholestasis."Phytomedicine. 2021 Oct;91:153683 16. [IF=3.935] Song Lin et al."A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induced cholestatic liver injury in mice."J Pharmaceut Biomed. 2019 Jul;171:180 17. [IF=3.935] Song Lin et al."A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induced cholestatic liver injury in mice."J Pharmaceut Biomed. 2019 Jul;171:180 18. [IF=3.935] Runjing Zhang et al."Xiaoyan lidan formula ameliorates α-naphthylisothiocyanate-induced intrahepatic cholestatic liver injury in rats as revealed by non-targeted and targeted metabolomics."J Pharmaceut Biomed. 2020 Feb;179:112966 19. [IF=5.396] Juan Wu et al."Sargassum fusiforme polysaccharide is a potential auxiliary substance for metformin in the management of diabetes."Food Funct. 2022 Feb;: 20. [IF=6.558] Yan Cao et al."Widely quasi-quantitative analysis enables temporal bile acids-targeted metabolomics in rat after oral administration of ursodeoxycholic acid."ANALYTICA CHIMICA ACTA. 2022 Jun;1212:339885 |
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Nature
Open Data Verified Data
- This product is white or light yellow crystalline powder; Taste bitter, there are different odor. Soluble in ethanol, chloroform, acetic acid, almost insoluble in water. The melting point was 141-142 °c.
- This strain was extracted from the bile of chicken, duck, goose, etc. It is synthesized by cholesterol in the liver and is a free bile acid component in normal bile. Bile contains cholic acid and Chenodeoxycholic acid 30% ~ 40%, deoxycholic acid 10% ~ 20%, lithocholic acid and ursodeoxycholic acid less than 5%, in addition, there are lecithin, cholesterol and bilirubin and other excreta. It can reduce the synthesis and secretion of cholesterol, reduce the total cholesterol excretion of bile, improve the dissolving power of bile to cholesterol, and promote the dissociation of cholesterol from stones to achieve the effect of dissolving stones.
- the CDCA used in the clinic contains unbound cholic acid with different crystal forms, which dissolves quickly in the intestinal tract and is almost completely absorbed in the usual dosage after oral administration. The liver can effectively ingest and clear up, the first pass effect was 62%. A small part of the plasma protein binding, part of the biliary tract into the intestinal tract, the formation of enterohepatic circulation. Unabsorbed drugs are excreted or converted into ursodeoxycholic acid by feces, but most of them are decomposed into lithocholic acid (LCA) by the coliform flora, which is toxic to the liver and can cause bile duct hyperplasia, bile movement and liver fibrosis. About 1/5 of the normal human body is absorbed by the intestinal tract, but mainly in the liver and kidney sulfated into non-toxic substances, with CDCA, LCA in bile increased only 1% ~ 3%.
Last Update：2024-01-02 23:10:35
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Preparation Method
Open Data Verified Data
take fresh or frozen chicken (or duck, goose) bile, add 1/10 amount of industrial sodium hydroxide, heat and boil for 20~24h, and constantly replenish the amount of water evaporated, cooling, and then hydrochloric acid to adjust the pH value of 2~3, the appearance of black paste. After the mixture was allowed to stand and layered, the paste was taken out and washed with water until neutral to obtain total bile acid. Add 2 times the amount of total bile acid 95% ethanol and 10% activated carbon, heating reflux 2~3H, while hot filtration. The filtrate was cooled, then extracted with equal volume of 1 20# gasoline for 3 times for degreasing, left to stand and layered, and the lower liquid was separated and compressed to obtain paste. A large amount of water was added to the paste to precipitate a precipitate, which was washed with water until colorless. The precipitate was then adjusted to pH 95% by adding 2-fold amounts of 8.5 ethanol and 5% sodium hydroxide solution and heated to reflux for 2H. Then add barium chloride in an amount of 150 grams per liter, heat and reflux for 2H, filter while hot, concentrate the filtrate to appear crystal film or turbidity, let it cool, precipitate crystals, suction filter, wash with water, drying under reduced pressure, white Chenodeoxycholic acid barium salt crystals can be obtained. Then the barium salt is dissolved with water, and sodium carbonate of about 12% of the barium salt is added, heated and stirred, filtered, and the barium carbonate precipitate is discarded. The filtrate is adjusted to pH 2-3 with hydrochloric acid to precipitate and filter, filter cake water to neutral, dry, available Chenodeoxycholic acid product. If necessary, it can be recrystallized with ethyl acetate for 1 to 2 times. There are also methods of extraction using calcium chloride salts.
Last Update：2022-01-01 11:14:06
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Introduction
Chenodeoxycholic acid is a hydrophobic primary bile acid capable of activating the nuclear receptor FXR, which is involved in cholesterol metabolism.
Last Update：2022-10-16 17:25:21
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Use
Open Data Verified Data
- gallstone dissolving drug.
- usage and dose of oral administration, 0. 25~0.5g, 2~3 times a day.
Last Update：2022-01-01 11:14:06
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Safety
Open Data Verified Data
- had a mild Diarrhea (due to inhibition of absorption of water and electrolytes in the colon) and elevated cholesterol. Liver toxicity occurs in 3% of patients with elevated transaminases. Pregnant women, severe hepatitis and biliary obstruction disabled.
- store in a cool and dry place.
Last Update：2022-01-01 11:14:07
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Biological activity
Chenodeoxycolic Acid is a hydrophobic primary bile Acid capable of activating the nuclear receptor FXR, which is involved in cholesterol metabolism. Both Chenodeoxycholic acid (CDCA) and deoxycholic acid (DCA) inhibited 11 beta HSD2 with IC50 values of 22mm and 38mm, respectively, and caused cortisol-dependent nuclear translocation and increased mineralocorticoid receptor (MR). The transcriptional activity. Chenodeoxycholic acid can stimulate the growth of Ishikawa cells by activating the membrane G protein coupled receptor (TGR5)-dependent pathway, inducing a significant increase in the expression of cyclin d1 protein and mRNA. Chenodeoxycholic acid (CDCA) induces approximately 4-fold low-density lipoprotein receptor mRNA levels and 2-fold high-density lipoprotein-CoA reductase and high-density lipoprotein-CoA synthetase mRNA levels in the cultured human hepatoblastoma cell line hepg2. Chlorodeoxycholic acid-induced ISC(≥ 67%) was cftrinh-172 inhibited by bumetanide, Bacl2, and cystic fibrosis transmembrane conductance regulator (CFTR) inhibitors. The adenylate cyclase inhibitor MDL12330A reduces by 43% the Chenodeoxycholic acid-stimulated ISC, which increases the intracellular cAMP concentration. Chenodeoxycholic acid treatment activates c/ebp as shown by its increased phosphorylation, nuclear accumulation and expression in hepg2 cells. Chenodeoxyolic acid enhances the transcription of the luciferase gene in constructs containing the -1.65-kb GSTA2 promoter, which contains the C / EBP response element (pGL-1651). Chenodeoxycholic acid treatment activates AMP-activated protein kinase (AMPK), leading to activation of extracellular signal-regulated kinase 1/2(ERK1/2), experimental results demonstrate the use of dominant negative mutants and chemical inhibitors of ampkα.
Last Update：2023-08-16 21:32:38
(3alpha,5beta,7alpha,8xi,9xi,14xi)-3,7-dihydroxycholan-24-oic acid - Reference Information
| LogP | 3.05 at 20℃ |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | dissolving gallstone drugs. It is used to prevent and treat cholesterol gallstones and hyperlipidemia, and has certain curative effect on bile pigment stones and mixed stones. For patients with mild symptoms, good gallbladder function and no obstruction of biliary tract, the curative effect is better. Long-term use has mild diarrhea, a small number of patients may have itching, dizziness, nausea and abdominal distension, individual patients can induce biliary colic and temporary transaminase elevation. Pregnant women, women of childbearing age, pancreatitis, liver cirrhosis, gastric and duodenal ulcers, hepatitis and biliary obstruction are prohibited. This product is a dissolving agent for cholesterol gallstones. Mainly used to prevent and treat cholesterol cholelithiasis. Mainly used as an intermediate of ursodeoxycholic acid. Biochemical research; used for the synthesis of ursodeoxycholic acid; gallstone dissolving agent, used for stones, biliary tract inflammation and cholecystitis caused by high cholesterol. A bile acid synthesized by cholesterol in the liver, and a selective DD2 inhibitor. suitable for the prevention and treatment of cholesterol gallstones |
| production method | the process of preparing deoxygenated goose cholic acid from goose (chicken) bile: goose (chicken) bile is hydrolyzed by NaOH to obtain hydrolysate, and then HCI acidification to obtain total bile acid, degreased with defatted gasoline and ethanol to obtain deoxygenated goose cholic acid crude product in ethanol and barium chloride salt to obtain deoxygenated goose cholic acid barium salt with ethyl acetate and HCI debarium crystals, washed and dried with ethyl acetate to obtain deoxygenated goose cholic acid. The total yield (for chicken or goose bile) was 1.92%. method 1. preparation of total bile acid by barium chloride salt method fresh or frozen chicken (or duck, goose) bile, add 1/10 times the amount of industrial sodium hydroxide, heat and boil for 20-24 hours, continuously supplement the evaporated water volume, cool, add equal volume of hydrochloric acid, adjust the pH2-3, appear black paste, take out, wash with water to nearly neutral, and obtain total bile acid. Chicken (goose, duck) bile [NaOH, boiling] → saponification solution [HCl, pH2]→ preparation of total bile acid CDCA barium salt take the total bile acid, add 2 times the amount of 95% ethanol, add 50-100g/L activated carbon, heat and reflux for 2 hours, filter while hot, cool the filtrate, add equal volume of 120# gasoline for extraction for 2-3 times, stand for stratification, lower layer concentration and decompression, and recover ethanol, get a paste. Increase the amount of water, precipitate precipitate, wash the precipitate with water until the washing solution is nearly colorless, add 2 times the amount of ethanol, add 50g/L sodium hydroxide alcohol solution, heat reflux for 1-2h, adjust the pH8-8.5, add 2 times the amount of 150g/L barium chloride solution of paste, heat reflux for 2h, filter while hot, distill the filtrate to recover ethanol, stop heating, release cooling, and precipitate needle crystals, after the crystal is complete, filter by suction to obtain white CDCA barium salt crystallization, washing with water, recrystallization with 65%-70% ethanol if necessary, and drying under reduced pressure to obtain CDCA barium salt. Total bile acid [ethanol] →[120# gasoline] CDCA crude product [BaCl2, pH8]→ preparation of CDCA barium salt CDCA finished product CDCA barium salt is finely grinded, suspended with 15 times the amount of water, slightly excess sodium carbonate is added, heated and refluxed, filtered while hot, cooled, filtered again once, the filtrate is pH2-3 by adding hydrochloric acid to adjust, precipitate precipitate, filter, precipitate is washed to near neutral with water, and vacuum dried, get CDCA boutique. Add ethyl acetate and recrystallize 1-2 times to obtain CDCA crystallization and vacuum drying to obtain CDCA finished product. CDCA barium salt [Na2CO3, HCl]→ CDCA fine product [ethyl acetate] CDCA crystal [drying] → CDCA finished product method 2. calcium chloride method preparation of total cholic acid calcium salt fresh chicken (or duck, goose) bile 100kg, placed in a stainless steel pot, added sodium hydroxide solid according to the amount of bile 100g/L, stirred and dissolved, heated and boiled for 24 hours to obtain saponified liquid, stirred and added 12kg of calcium chloride, precipitated, centrifuged, and collected precipitated, get the total bile acid calcium salt. Chicken (duck, goose)[NaOH]→ [boiling for 24 hours] saponification solution [CaCl2]→ preparation and separation of total bile acid calcium salt CDCA fine product, refined total bile acid calcium salt is dissolved in water, water insoluble substance is discarded, water solution is added with 6mol/L hydrochloric acid to adjust pH3, chenodeoxycholic acid precipitation is precipitated, filtration, concentration, crystallization, vacuum drying at 80 ℃ to obtain CDCA fine product. Total bile acid calcium salt [water] → chenodeoxycholic acid calcium salt [HCl, ethyl acetate] →[pH3]CDCA boutique. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 4000 mg/kg; Oral-mouse LD50: 3000 mg/kg |
| flammability hazard characteristics | thermal decomposition spicy stimulation smoke |
| storage and transportation characteristics | warehouse low temperature ventilation and drying |
| fire extinguishing agent | water, carbon dioxide, foam, dry powder |
Last Update：2024-04-09 20:49:11
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