Selective Oxidation with N-Bromosuccinimide. I. Cholic Acid

Fieser, Louis; Rajagopalan, S.

doi:10.1021/ja01180a015

Cited by 130 publications

(42 citation statements)

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“…10 7-Ketodeoxycholic acid was prepared through selective oxidation of cholic acid with N-bromosuccinimide. 11 -MCA was prepared from 3 ␣-and 6 ␣-dihydroxy-7-keto-5 ␤-cholanoic acid through reduction of a tetrahydropyranyl ether derivative with metal sodium and saponification. 3 ␣-and 6␣-Dihydroxy-7-keto-5 ␤-cholanoic acid was obtained by alkaline hydrolysis of methyl 3 ␣-acetoxy-6-bromo-7-keto-5 ␤-cholanoic acid synthesized from CDCA.…”

Section: Methodsmentioning

confidence: 99%

A Paucity of Unusual Trihydroxy Bile Acids in the Urine of Patients With Severe Liver Diseases

et al. 1999

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To clarify the relationship between the occurrence of unusual trihydroxy bile acids, namely hyocholic acid, ursocholic acid (UCA), and ω‐muricholic acid (ω‐MCA) in urine and liver disease severity, urinary bile acids were analyzed by gas‐liquid chromatography in acute and late phases of acute hepatitis and before and after ursodeoxycholic acid (UDCA) loading in healthy adults and liver cirrhosis patients. In 11 patients with acute hepatitis, the occurrence rates and amounts of unusual trihydroxy bile acids were increased in the late (recovery) phase, as compared with those in the early phase. In 10 patients with severe acute hepatitis who had prothrombin times exceeding 16 seconds, these bile acids had completely disappeared from the urine in the early phase but reappeared in the late phase in those who had a good outcome, though never in a patient who died. After UDCA administration for a week, the amounts of unusual bile acids, especially UCA and ω‐MCA, which are thought to be synthesized through 12 α‐ and 6 α‐hydroxylations, respectively, from UDCA, were clearly increased in 10 healthy adults but only slightly changed in 10 patients with liver cirrhosis. In conclusion, hepatic hydroxylations of dihydroxy bile acids as a detoxification reaction were impaired in severe liver diseases, which may play a role in the intensification and perpetuation of hepatocellular injuries.

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Section: Methodsmentioning

confidence: 99%

A Paucity of Unusual Trihydroxy Bile Acids in the Urine of Patients With Severe Liver Diseases

et al. 1999

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“…3a, 12~Dihydroxy-7-oxo-So-cholan-24-oic acid was prepared as described by Fieser and Rajiagopalan [8], 7a, 12a-dihydroxy-30x0~S/3-cholan-24-oic acid respectively by Sihn [9], 3a, 70, 12a-trihydroxySpcholan-24.oic acid by Samuelsson [ lo] ,3a, 12~ dihydroxy-5&chol-6-en-24-oic acid by Kagan and Jacques [ 111.…”

Section: Clostridium Bifermentans Sd 10 Was Cultivated Inmentioning

confidence: 99%

Activity on bile acids of a Clostridium bifermentans cell‐free extract

Ferrari

Beretta

1977

FEBS Letters

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“…153-155°C (ref. [23] Methyl 3α,12α-Diacetoxy-7α-hydroxy-5β-cholan-24-oate (5): Acetic anhydride (3.75 mL, 39.7 mmol) and anhyd. potassium acetate (5.0 g, 50.9 mmol) were added to a stirred solution of compound 4 (5.0 g, 11.8 mmol) in dry toluene (40 mL).…”

Section: Methodsmentioning

confidence: 99%

First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α‐Hydroxycholic Acid

Nonappa

Maitra

2007

Eur J Org Chem

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The first chemical synthesis of pythocholic acid, a major component of python's bile, and 3α,7α,12α,16α-tetrahydroxy-5β-cholan-24-oic acid (16α-hydroxycholic acid), a minor component in Shoebill stork's bile, was achieved starting from readily available cholic acid in overall yields of 5 % and 5.5 %, respectively, through a common intermediate. A biomimetic template-directed remote functionalization strategy was uti-

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Selective Oxidation with N-Bromosuccinimide. I. Cholic Acid

Cited by 130 publications

References 0 publications

A Paucity of Unusual Trihydroxy Bile Acids in the Urine of Patients With Severe Liver Diseases

A Paucity of Unusual Trihydroxy Bile Acids in the Urine of Patients With Severe Liver Diseases

Activity on bile acids of a Clostridium bifermentans cell‐free extract

First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α‐Hydroxycholic Acid

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