63266-91-1

Usage

Uses

Used in Digestive Health:
Cholic acid is used as a digestive aid for enhancing the emulsification and absorption of dietary fats in the small intestine. Its presence in bile is essential for the proper breakdown and assimilation of lipids, which are crucial for energy production and cellular function.
Used in Pharmaceutical Applications:
Cholic acid is utilized as a component in the formulation of drugs targeting metabolic diseases. Its role in lipid metabolism regulation makes it a potential therapeutic agent for conditions related to imbalances in fat processing and utilization.
Used in Cholesterol Management:
Due to its influence on lipid metabolism, cholic acid is used as a component in treatments aimed at managing cholesterol levels. It can potentially help in the development of therapies for hypercholesterolemia and other related conditions.
Used in Drug Delivery Systems:
Cholic acid can be employed in the development of novel drug delivery systems, particularly for enhancing the solubility and bioavailability of drugs with poor water solubility. Its amphiphilic nature allows it to interact with both hydrophilic and hydrophobic drug molecules, improving their delivery and efficacy.
Used in Research and Development:
Cholic acid is also used in the research and development of new pharmaceuticals and therapies. Its unique properties and role in metabolic processes make it a valuable tool for studying the mechanisms of various diseases and for designing targeted treatments.

InChI:InChI=1/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15?,16+,17-,18+,19+,20?,21?,23+,24-/m1/s1

Upstream product

• 91097-45-9 1β,3α,12α-trihydroxy-5β-cholan-24-oic acid methyl ester 
• 104839-75-0 (R)-methyl 4-((1R,3S,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1,3-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 104854-44-6 (R)-methyl 4-((1R,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 83-44-3 Deoxycholic acid 
• 104854-43-5 (R)-methyl 4-[(1S,2S,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1,2-epoxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate 
• 104839-67-0 methyl 12α-acetoxy-2β,4β-dibromo-3-oxo-5β-cholan-24-oate 
• 104881-54-1 methyl 12α-acetoxy-2β-bromo-3-oxo-5β-cholan-24-oate 
• 99598-09-1 (R)-4-((1S,2S,5R,8S,9S,10S,12S,13R,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-hexadecahydro-20-oxa-cyclopropa[1,2]cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 99598-21-7 2,4-dibromo-3-oxo deoxycholic acid methyl ester 
• 99598-05-7 (R)-4-((5R,8R,9S,10R,12S,13R,14S,17R)-12-Hydroxy-10,13-dimethyl-3-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 99598-13-7 (R)-4-((1R,5R,8S,9S,10S,12S,13R,14S,17R)-1,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 7753-75-5 (R)-methyl 4-((5R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 10538-58-6 methyl 12α-hydroxy-3-oxo-5β-cholan-24-oate 
• 3245-38-3 methyl deoxycholate 

Relevant academic research and scientific papers

CYP3A specifically catalyzes 1β-hydroxylation of deoxycholic acid: Characterization and enzymatic synthesis of a potential novel urinary biomarker for CYP3A activity

The endogenous bile acid metabolite 1β-hydroxy-deoxycholic acid (1β-OH-DCA) excreted in human urine may be used as a sensitive CYP3A biomarker in drug development reflecting in vivo CYP3A activity. An efficient and stereospecific enzymatic synthesis of 1β-OH-DCA was developed using a Bacillus megaterium (BM3) cytochrome P450 (P450) mutant, and its structure was confirmed by nuclear magnetic resonance (NMR) spectroscopy. A [2H4]-labeled analog of 1β-OH-DCA was also prepared. The major hydroxylated metabolite of deoxycholic acid (DCA) in human liver microsomal incubations was identified as 1β-OH-DCA by comparison with the synthesized reference analyzed by UPLC-HRMS. Its formation was strongly inhibited by CYP3A inhibitor ketoconazole. Screening of 21 recombinant human cytochrome P450 (P450) enzymes showed that, with the exception of extrahepatic CYP46A1, the most abundant liver P450 subfamily CYP3A, including CYP3A4, 3A5, and 3A7, specifically catalyzed 1β-OH-DCA formation. This indicated that 1β-hydroxylation of DCA may be a useful marker reaction for CYP3A activity in vitro. The metabolic pathways of DCA and 1β-OHDCA in human hepatocytes were predominantly via glycine and, to a lesser extent, via taurine and sulfate conjugation. The potential utility of 1β-hydroxylation of DCA as a urinary CYP3A biomarker was illustrated by comparing the ratio of 1β-OH-DCA:DCA in a pooled spot urine sample from six healthy control subjects to a sample from one patient treated with carbamazepine, a potent CYP3A inducer; 1β-OH-DCA:DCA was considerably higher in the patient versus controls (ratio 2.8 vs. 0.4). Our results highlight the potential of 1β-OH-DCA as a urinary biomarker in clinical CYP3A DDI studies.

Synthesis of 1β-hydroxydeoxycholic acid in H-2 and unlabeled forms

1β–hydroxydeoxycholic acid in unlabeled and stable isotope labeled forms was required for use as a biomarker for Cytochrome P450 3A4/5 activity. A lengthy synthesis was undertaken to deliver the unlabeled compound and in the process, to develop a route to the deuterium labeled compound. The synthesis of the unlabeled compound was completed but in a very low yield. Concurrent with the synthetic approach, a biosynthetic route was pursued and this approach proved to be much more rapid and afforded the compound in both unlabeled and deuterium labeled forms in a 1-step oxidation from deoxycholic acid and [D4]deoxycholic acid, respectively.