| Identification | More | [Name]
CHOLIC ACID METHYL ESTER | [CAS]
1448-36-8 | [Synonyms]
5(BETA)-CHOLAMIC ACID-3ALPHA,7ALPHA,12ALPHA-TRIOL METHYL ESTER
5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL METHYL ESTER
CHOLIC ACID METHYL ESTER
METHYL 4-(3,7,12-TRIHYDROXY-10,13-DIMETHYLPERHYDROCYCLOPENTA[A]PHENANTHREN-17-YL)PENTANOATE
METHYL CHOLATE
Methyl 4-(3,7,12-trihydroxy-10,13-dimethylperhydrocyclopenta[a]phenanthren-17-yl)pen
CHOLIC ACID METHYL ESTER(P)
Methyl cholate, 98+%
3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid methyl ester
3α,7α,12α-Triol-5β-24-cholanoic acid methyl ester
Cholic acid methyl | [EINECS(EC#)]
215-903-7 | [Molecular Formula]
C25H42O5 | [MDL Number]
MFCD00064934 | [Molecular Weight]
422.6 | [MOL File]
1448-36-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
155-156°C | [Boiling point ]
541.6±50.0 °C(Predicted) | [density ]
1.141±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
14?+-.0.70(Predicted) | [color ]
White to Off-White | [Water Solubility ]
Insoluble in water. Soluble in medium polarity organic solvents. | [Detection Methods]
TLC;HPLC;NMR | [Merck ]
14,2203 | [BRN ]
2226989 | [CAS DataBase Reference]
1448-36-8(CAS DataBase Reference) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Methanol-->Cholic acid-->Toluene-->(TRIMETHYLSILYL)DIAZOMETHANE | [Preparation Products]
Ursodeoxycholic acid-->Cholan-24-oic acid, 7,12-dihydroxy-3-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, (3α,5β,7α,12α)--->3,7-diketo, 12-hydroxy methyl ester of Cholic Acid-->(5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid-->(3β,5β,7α,12α)-3-(ForMyloxy)-7,12-dihydroxycholan-24-oic Acid Methyl Ester |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
A bile acid derivative as anti-inflammatory and antitumor agent. | [Uses]
Protected Cholic Acid | [Definition]
ChEBI: Cholic Acid Methyl Ester is a bile acid. | [Synthesis]
To a mixed toluene/methanol (30 ml, V/V=2:1) solution of cholic acid (2.0 g, 4.9 mmol) was added trimethylsilyl diazomethane (3.67 ml, 7.34 mmol), and the reaction was stirred for 2 h at 20 °C. The reaction was monitored by thin layer chromatography (TLC, spreader ratio of methanol/dichloromethane=1:10). The progress of the reaction was monitored by thin layer chromatography (TLC, spreading agent ratio methanol/dichloromethane=1:10) to confirm complete consumption of cholic acid and generation of new spots. Upon completion of the reaction, the reaction mixture was concentrated to afford (R)-methyl 4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthracen-17-yl)pentanoate (2.08 g, 100% yield) as a white foamy solid. Its hydrogen NMR spectrum (400MHz, CDCl3) data were as follows: δ 3.98(m, 1H, C12-H), 3.85(m, 1H, C7-H), 3.45(m, 1H, C3-H), 3.66(s, 3H, OCH3), 0.98(d, 3H, 21-Me), 0.89(s, 3H, 19-Me), 0.69 (s, 3H, 18-Me). | [References]
[1] Drug Metabolism and Disposition, 2017, vol. 45, # 7, p. 721 - 733
[2] Patent: WO2009/146218, 2009, A2. Location in patent: Page/Page column 141
[3] Tetrahedron Letters, 2010, vol. 51, # 1, p. 93 - 95
[4] Steroids, 2010, vol. 75, # 10, p. 701 - 709
[5] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7128 - 7131 |
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