Identification | Back Directory | [Name]
3ALPHA-HYDROXY-7-OXO-5BETA-CHOLANIC ACID | [CAS]
4651-67-6 | [Synonyms]
OCA-A Nsc226118 Nutriacholic acid Hydroxycholanicacid 7-oxolithocholicaci Ursodiol Impurity F 7-Oxolithocholic acid 7-KETOLITHOCHOLIC ACID Emtricitabine Impurity 33 ursodeoxycholic acid oxide 7-Ketochenodeoxycholic acid 3-Hydoxy-7-ketocholanic acid 5β-CHOLANIC acid-3α-OL-7-ONE Obeticholic Acid impurity 01 5β-CHOLANIC ACID-3α-OL-7-ONE 3α-Hydroxy-7-ketocholanic acid obeticholic acid intermediate 1 3α-Hydroxy-7-oxo-5β-cholic acid Chenodeoxycholic Acid Impurity 6 3Α--hydroxy-7-oxo -5Β- bile acid 3ɑ-Hydroxy-7-Oxo-5β-Cholanic Acid 3α-Hydroxy-7-oxo-5β-cholanic acid 3-Hydroxy-7-oxocholan-24-oic acid 3a-Hydroxy-7-oxo-5b-cholanic acid 3α-Hydroxy-7-oxo-5β-cholanic acid Ursodeoxycholic Acid EP Impurity F 3α-hydroxy-7-oxo-5β-cholanoic acid 3α-Hydroxy-7-keto-5β-cholanic Acid 3α-Hydroxy-7-keto-5β-cholanic Acid 3α-Hydroxy-7-oxo-5β-cholanicAcid> Urosodeoxycholic Acid EP Impurity F Chenodeoxycholic acid EP Impurity F 3alpha-Hydroxy-7-oxo-5?cholanic acid 5-BETA-CHOLANIC ACID-3-ALPHA-OL-7-ONE alpha-Hydroxy-7-oxo-5beta-cholic acid 3-hydroxy -7- oxo -5beta- cholic acid 3α-hydroxy-7-oxo-5β-cholan-24-oicacid 3α-Hydroxy-7-oxo-5b-cholanic acid, 98% 3α-Hydroxy-7-oxo-5β-cholan-24-oic acid 3alpha-Hydroxy-7-oxo-5beta-cholic acid 7-Oxo-3α-hydroxy-5β-cholan-24-oic acid ALPHA-HYDROXY-7-OXO-5BETA-CHOLANIC ACID 3ALPHA-HYDROXY-7-OXO-5BETA-CHOLANIC ACID 3ALFA-HYDROXI-7KETO-5BETA-CHOLAN-24-ACID 3ALPHA-HYDROXY-7-KETO-5BETA-CHOLANIC ACID 3-ALPHA-HYDROXY-7-OXO-5-BETA-CHOLANOICACID (3α,5β)-3-Hydroxy-7-oxo-Cholan-24-oic acid 3-alpha-hydroxy-7-oxo-5-beta-cholan-24-oic 3ALPHA-HYDROXY-7-OXO-5BETA-CHOLANIC ACID 97+% Cholan-24-oic acid, 3-hydroxy-7-oxo-, (3α,5β)- 3-alpha-hydroxy-7-oxo-5-beta-cholan-24-oic acid 3ALPHA-HYDROXY-7-OXO-5BETA-CHOLANIC ACID USP/EP/BP 7-Ketolithocholic acid (Ursodeoxycholic Acid Impurity) Cholan-24-oic acid,6-ethyl-3,7-dihydroxy-,(3α,5β,6β,7β)- Cholan-24-oic acid, 3-hydroxy-7-oxo-, (3.alpha.,5.beta.)- Ursodeoxycholic Acid EP Impurity F(7-Ketolithocholic Acid) 7-Ketolithocholic acid (3alpha-hydroxy-7-oxo-5beta-Cholanic acid) Ursodeoxycholic Acid Impurity 6(Ursodeoxycholic Acid EP Impurity F) Urosodeoxycholic Acid EP Impurity F(Obeticholic Acid Intermediate 1) Chenodeoxycholic Acid Impurity 6(Chenodeoxycholic Acid EP Impurity F) Ursodeoxycholic Acid EP Impurity F,3α-hydroxy-7-oxo-5β-cholan-24-oic acid 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 (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 Ursodeoxycholic Acid EP Impurity F (Chenodeoxycholic Acid EP Impurity F/ 7-Oxo Ursodeoxycholic Acid/ 7-Oxo Chenodeoxycholic Acid) Chenodeoxycholic Acid EP Impurity F (Ursodeoxycholic Acid EP Impurity F/ 7-Oxo Ursodeoxycholic Acid/ 7-Oxo Chenodeoxycholic Acid) | [EINECS(EC#)]
225-083-2 | [Molecular Formula]
C24H38O4 | [MDL Number]
MFCD00271393 | [MOL File]
4651-67-6.mol | [Molecular Weight]
390.56 |
Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
4.76±0.10(Predicted) | [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℃ |
Hazard Information | Back Directory | [Uses]
Nutriacholic Acid (Ursodeoxycholic Acid EP Impurity F) is derivative of Lithocholic Acid (L469180), a cholic acid derivative as TGR5 modulator. | [Definition]
ChEBI: A bile acid that is lithocholic acid carrying an additional oxo substituent at position 7. | [Flammability and Explosibility]
Nonflammable | [Synthesis]
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%. | [storage]
Store at -20°C | [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 |
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