(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester

Product Name: (3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester
CAS No.: 10538-65-5
Chemical Name: (3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester
Synonyms: METHYL 7-KETOCHOLATE;Cholic acid Impurity 67;Methyl-7-keto-3a,12a-dihydroxy-5b-cholanoate;3α,12α-diol-7-oxo-5β-24-cholanoic acid methyl ester, methyl;(3α,5β,12α)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester;(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester;Cholan-24-oic acid, 3,12-dihydroxy-7-oxo-, methyl ester, (3α,5β,12α)-;(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester;(R)-Methyl 4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate;methyl (R)-4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
CBNumber: CB62509989
Molecular Formula: C25H40O5
Formula Weight: 420.58
MOL File: 10538-65-5.mol

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(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester Property

Boiling point:: 540.0±50.0 °C(Predicted)
Density: 1.137
storage temp.: 2-8°C
pka: 14.70±0.70(Predicted)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Matrix Scientific

Product number: 098698
Product name: Methyl-7-keto-3a,12a-dihydroxy-5b-cholanoate
Purity: 95+%
Packaging: 250mg
Price: $84
Updated: 2021/12/16

Matrix Scientific

Product number: 098698
Product name: Methyl-7-keto-3a,12a-dihydroxy-5b-cholanoate
Purity: 95+%
Packaging: 500mg
Price: $129
Updated: 2021/12/16

AK Scientific

Product number: 1237AA
Product name: Methyl-7-keto-3a,12a-dihydroxy-5b-cholanoate
Packaging: 250mg
Price: $163
Updated: 2021/12/16

Matrix Scientific

Product number: 098698
Product name: Methyl-7-keto-3a,12a-dihydroxy-5b-cholanoate
Purity: 95+%
Packaging: 1g
Price: $198
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FD145354
Product name: (3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester
Packaging: 2g
Price: $280
Updated: 2021/12/16

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(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester Chemical Properties,Usage,Production

Synthesis

1448-36-8

15073-97-9

Using (R)-methyl 4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthracenecarbonyl17-yl)valerate as a starting material, the methyl ester (2) was first obtained by protection of the hydroxyl group of the cholate. Subsequently, the methyl ester (2) was oxidized to the corresponding ketone (3) using N-bromosuccinimide (NBS). Next, the ketone (3) was protected as diacetate (4) and converted to the key intermediate bromide (5) by reaction with molecular bromine. Afterwards, the bromide (5) was hydrolyzed to produce the hydroxyketone (6). Finally, the target product (R)-4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid methyl ester (7) was obtained by reduction of acetate and methyl ester portions and full deprotection.

References

[1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2821 - 2828
[2] Journal of the Chemical Society, Chemical Communications, 1993, # 19, p. 1469 - 1471
[3] Patent: WO2011/22838, 2011, A1. Location in patent: Page/Page column 37
[4] Journal of Biological Chemistry, 1943, vol. 147, p. 131,133
[5] Steroids, 1993, vol. 58, # 2, p. 52 - 58

(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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10538-65-5, (3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl esterRelated Search:

12-(Acetyloxy)-3,6,7-trihydroxycholan-24-oic acid methyl ester 3α,12α-Diacetoxy-7-oxo-5β-cholan-24-oic acid methyl ester 12-(Acetyloxy)-3,6-dihydroxy-7-oxocholan-24-oic acid methyl ester 7-KETODEOXYCHOLIC ACID (3alpha,5beta,6alpha,12alpha)-3,12-Bis(acetyloxy)-6-bromo-7-oxocholan-24-oic acid methyl ester

(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester

(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester

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methyl (R)-4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

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(3α,5β,12α)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester

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(R)-Methyl 4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Cholic acid Impurity 67

10538-65-5