3alpha-Hydroxy-7-oxo-5beta-cholanic Acid CAS 4651-67-6
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid Basic information
| Product Name: | 3alpha-Hydroxy-7-oxo-5beta-cholanic Acid |
| Synonyms: | 7-KETOLITHOCHOLIC ACID;3ALPHA-HYDROXY-7-KETO-5BETA-CHOLANIC ACID;3ALPHA-HYDROXY-7-OXO-5BETA-CHOLANIC ACID;5-BETA-CHOLANIC ACID-3-ALPHA-OL-7-ONE;3alpha-Hydroxy-7-oxo-5?cholanic acid;3-alpha-hydroxy-7-oxo-5-beta-cholan-24-oic acid;Hydroxycholanicacid;4-(3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetrade cahydrocyclopenta[a]phenanthren-17-yl)pentanoic acid |
| CAS: | 4651-67-6 |
| MF: | C24H38O4 |
| MW: | 390.56 |
| EINECS: | 225-083-2 |
| Product Categories: | Obeticholic acid intermediate;Bile Acids;Biochemistry;Steroids;Ocaliva intermediate |
| Mol File: | 4651-67-6.mol |
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid Chemical Properties
| Melting point | 205°C |
| Boiling point | 545.9±25.0 °C(Predicted) |
| density | 1.124±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly) |
| pka | 4.76±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| Optical Rotation | Consistent with structure |
| Water Solubility | 2.062mg/L at 25℃ |
| InChIKey | DXOCDBGWDZAYRQ-QHVQYUNXNA-N |
| SMILES | C(O)(=O)CC[C@H]([C@@H]1[C@@]2(C)CC[C@]3([H])[C@@]4(C)CC[C@@H](O)C[C@@]4([H])CC(=O)[C@@]3([H])[C@]2([H])CC1)C |&1:5,6,7,11,13,17,20,25,27,r| |
| LogP | 3.48 at 20℃ |
Safety Information
| Safety Statements | 22-24/25 |
| WGK Germany | WGK 3 |
| Storage Class | 11 - Combustible Solids |
| Uses | Nutriacholic Acid (Ursodeoxycholic Acid EP Impurity F) is derivative of Lithocholic Acid (L469180), a cholic acid derivative as TGR5 modulator. |
| Uses | 3alpha-Hydroxy-7-oxo-5beta-cholanic Acid is an intermediate in organic synthesis and pharmaceutical research and development. It can be used to synthesize the choleretic drug Obeticholic acid. Obeticholic acid can inhibit cholic acid synthesis. It is commonly used to treat primary biliary cirrhosis and nonalcoholic fatty liver disease. |
| Definition | ChEBI: 7-oxolithocholic acid is a bile acid that is lithocholic acid carrying an additional oxo substituent at position 7. It has a role as a human metabolite. It is a bile acid, a monohydroxy-5beta-cholanic acid, an oxo-5beta-cholanic acid and a 3alpha-hydroxy steroid. It is functionally related to a lithocholic acid. It is a conjugate acid of a 7-oxolithocholate. |
| Flammability and Explosibility | Non flammable |
| Synthesis | 474-25-9 4651-67-6 The general procedure for the synthesis of (R)-4-((3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid from goose deoxycholic acid was as follows: goose deoxycholic acid (5 g, 12.7 mmol) was placed in a reaction flask and dichloromethane ( 50 mL) as solvent, followed by DMSO (1.12 g, 14.3 mmol) and triethylamine (4.2 g, 41.5 mmol) sequentially. After cooling the reaction system to -30 °C, trifluoroacetic anhydride (3.2 g, 15.2 mmol) was added slowly and dropwise. The reaction mixture was stirred at -30 °C for 1.5 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (10 mL) and the mixture was gradually warmed to room temperature and stirred. Extraction was carried out with methanol (20 mL x 2), the organic phases were combined, washed once with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and the organic phase was concentrated to dryness to give the target product (R)-4-((3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren- 17-yl)pentanoic acid (Compound 2) in a yield of 4.89 g in 98.6%. |
| References | [1] Patent: CN104876995, 2016, B. Location in patent: Paragraph 0036-0038; 0042; 0044 [2] Patent: CN106279336, 2017, A. Location in patent: Paragraph 0044; 0045; 0046 [3] Patent: CN107200763, 2017, A. Location in patent: Paragraph 0036; 0037; 0038; 0039 [4] Patent: CN107955056, 2018, A. Location in patent: Paragraph 0019-0022 [5] Patent: CN106986909, 2017, A. Location in patent: Paragraph 0043-0054 |
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid Preparation Products And Raw materials
| Raw materials | 7-ketolithocholic Methyl ester-->3α-Acetyloxy-7-oxo-5β-cholan-24-oic acid methyl ester-->Chenodeoxycholic acid-->Dimethyl sulfoxide-->Dichloromethane-->Triethylamine-->Trifluoroacetic anhydride |
| Preparation Products | HYOCHOLIC ACID-->Cholan-24-oic acid,3-hydroxy-7-oxo-, phenylmethyl ester,(3α,5β)- |
