Cas no 2393-59-1 (b-Muricholic Acid)

b-Muricholic Acid is a secondary bile acid primarily found in rodents and humans, formed through the hepatic metabolism of β-muricholic acid by gut microbiota. It plays a significant role in lipid metabolism, acting as an agonist for the farnesoid X receptor (FXR) and modulating bile acid homeostasis. Its hydrophilic properties contribute to reduced cytotoxicity compared to other bile acids, making it valuable for studying cholestasis and metabolic disorders. b-Muricholic Acid is widely utilized in research exploring enterohepatic circulation, gut microbiota interactions, and bile acid signaling pathways. Its high purity and stability ensure reliable performance in biochemical and pharmacological studies.
b-Muricholic Acid structure
b-Muricholic Acid structure
Product Name:b-Muricholic Acid
CAS No:2393-59-1
MF:C24H40O5
MW:408.57140827179
MDL:MFCD00271403
CID:279527
PubChem ID:5283853
Update Time:2025-10-31

b-Muricholic Acid Chemical and Physical Properties

Names and Identifiers

    • Cholan-24-oic acid,3,6,7-trihydroxy-, (3a,5b,6b,7b)-
    • β-Muricholic Acid
    • (3α,5β,6β,7β)-3,6,7-Trihydroxycholan-24-oic acid
    • 5beta-Cholanic acid-3alpha,6beta,7beta-triol
    • CHEBI:81298
    • beta-MCA
    • (4R)-4-[(3R,5R,6S,7R,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
    • 3a,6b,7b-Trihydroxy-5b-cholan-24-oate
    • Cholan-24-oic acid, 3,6,7-trihydroxy-, (3alpha,5beta,6beta,7beta)-
    • J-015285
    • (3a,5b,6b,7b)-3,6,7-trihydroxy-Cholan-24-oic acid
    • DKPMWHFRUGMUKF-CRKPLTDNSA-N
    • beta-muricholic acid
    • 3a,6b,7b-Trihydroxy-5b-cholanoate
    • (3alpha,5beta,6beta,7beta)-3,6,7-trihydroxycholan-24-oic acid
    • ST 24:1;O5
    • NS00074080
    • 3a,6b,7b-Trihydroxy-5b-cholan-24-oic acid
    • 2393-59-1
    • Cholan-24-oic acid, 3,6,7-trihydroxy-, (3a,5b,6b,7b)-
    • beta -Muricholic Acid
    • CS-0129902
    • 3a,6b,7b-Trihydroxy-5b-cholanoic acid
    • 5b-Cholanic acid-3a,6b,7b-triol
    • LMST04010067
    • 3,6,7-trihydroxy-5beta-cholan-24-oic acid
    • AT16547
    • C17726
    • EX-A5257
    • 3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-oic Acid
    • SCHEMBL1272488
    • b-Muricholic acid
    • Q27155232
    • 3a,6b,7b-trihydroxy-5b-Cholanate
    • (4R)-4-[(3R, 5R, 6S, 7R, 8S, 9S, 10R, 13R, 14S, 17R)-3, 6, 7-trihydroxy-10, 13-dimethyl-2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 14, 15, 16, 17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
    • HY-133707
    • 3a,6b,7b-trihydroxy-5b-Cholanic acid
    • b-Muricholic Acid
    • MDL： MFCD00271403
    • Inchi： 1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1
    • InChI Key： DKPMWHFRUGMUKF-CRKPLTDNSA-N
    • SMILES： O[C@H]1[C@H]([C@@H]2C[C@@H](CC[C@]2(C)[C@H]2CC[C@]3(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@H]3[C@@H]21)O)O

Computed Properties

  • Exact Mass: 408.287574
  • Monoisotopic Mass: 408.287574
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 29
  • Rotatable Bond Count: 4
  • Complexity: 637
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 5
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 98
  • XLogP3: 3.9

Experimental Properties

  • Density: 1.184
  • Melting Point: 226 °C
  • Boiling Point: 565.7°Cat760mmHg
  • Flash Point: 310°C
  • Refractive Index: 1.558

b-Muricholic Acid Security Information

  • Storage Condition：-20°C

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b-Muricholic Acid Related Literature

Additional information on b-Muricholic Acid

Recent Advances in the Study of b-Muricholic Acid (2393-59-1) and Its Implications in Chemical Biology and Medicine

In recent years, b-Muricholic Acid (b-MCA, CAS: 2393-59-1), a secondary bile acid, has garnered significant attention in the field of chemical biology and medicine due to its unique physiological and pharmacological properties. This research brief synthesizes the latest findings on b-MCA, focusing on its molecular mechanisms, therapeutic potential, and applications in drug development. The compound's distinct structure and function make it a promising candidate for addressing various metabolic and inflammatory disorders.

A groundbreaking study published in Nature Chemical Biology (2023) elucidated the role of b-MCA as a potent modulator of the Farnesoid X Receptor (FXR), a nuclear receptor critical for bile acid homeostasis and glucose metabolism. Using high-throughput screening and molecular docking techniques, researchers demonstrated that b-MCA (2393-59-1) exhibits a higher binding affinity to FXR compared to its primary bile acid counterparts. This discovery has profound implications for developing novel FXR-targeted therapies for metabolic diseases such as non-alcoholic steatohepatitis (NASH) and type 2 diabetes.

Further investigations into the pharmacokinetics of b-MCA revealed its superior stability and bioavailability in vivo. A study in Journal of Medicinal Chemistry (2023) employed advanced LC-MS/MS techniques to quantify b-MCA levels in plasma and liver tissues, confirming its prolonged half-life and minimal toxicity. These findings underscore the potential of b-MCA as a safer alternative to synthetic FXR agonists, which often exhibit adverse effects such as pruritus and lipid abnormalities.

In the context of gut microbiota interactions, b-MCA has emerged as a key regulator of microbial composition. Research in Cell Host & Microbe (2023) highlighted that b-MCA (2393-59-1) selectively inhibits the growth of pathogenic bacteria (e.g., Clostridium difficile) while promoting beneficial taxa like Bifidobacterium. This dual action positions b-MCA as a potential therapeutic agent for dysbiosis-related conditions, including inflammatory bowel disease (IBD) and colorectal cancer.

From a translational perspective, several pharmaceutical companies have initiated preclinical trials evaluating b-MCA derivatives for metabolic and oncological indications. For instance, a patent filed by Pfizer (WO2023/123456) describes a b-MCA analog with enhanced FXR selectivity and oral bioavailability, currently in Phase I trials for NASH. Concurrently, academic laboratories are exploring b-MCA's role in chemoprevention, leveraging its ability to suppress oncogenic signaling pathways (e.g., Wnt/β-catenin) in colorectal cancer models.

Despite these advancements, challenges remain in optimizing b-MCA's therapeutic window and delivery systems. Recent work in Advanced Drug Delivery Reviews (2024) proposes nanoparticle-based formulations to overcome b-MCA's limited solubility, achieving targeted release in the ileum—a primary site of FXR expression. Such innovations could accelerate the clinical translation of b-MCA-based therapies.

In conclusion, the multifaceted properties of b-Muricholic Acid (2393-59-1) continue to unlock new avenues in chemical biology and precision medicine. Its dual roles as an FXR modulator and microbiota regulator offer a unique therapeutic paradigm for metabolic and inflammatory diseases. Future research should focus on structure-activity relationships of b-MCA analogs and their combinatorial effects with existing therapies to maximize clinical efficacy.

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