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4651-67-6

4651-67-6 Structure

4651-67-6 Structure
IdentificationBack 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 PropertiesBack 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℃
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H302
[Precautionary statements ]

P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
[Safety Statements ]

22-24/25
[WGK Germany ]

WGK 3
[REACH Registrations]

Active
[Storage Class]

11 - Combustible Solids
Hazard InformationBack 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]

Chenodeoxycholic acid

474-25-9

3alpha-Hydroxy-7-oxo-5beta-cholanic Acid

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%.

[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
Spectrum DetailBack Directory
[Spectrum Detail]

3alpha-Hydroxy-7-oxo-5beta-cholanic Acid(4651-67-6)MS
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid(4651-67-6)1HNMR
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid(4651-67-6)13CNMR
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid(4651-67-6)IR1
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid(4651-67-6)IR2
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