Cas no 2276-94-0 (Allolithocholic acid)

Allolithocholic acid is a bile acid derivative and a secondary metabolite formed through the bacterial modification of lithocholic acid in the intestinal tract. It is structurally characterized by the epimerization of the 3α-hydroxyl group to a 3β-configuration. This compound is of interest in biochemical and pharmacological research due to its role in bile acid metabolism and potential interactions with nuclear receptors, such as the farnesoid X receptor (FXR). Allolithocholic acid serves as a valuable reference standard in analytical studies, particularly in investigations of gut microbiota-mediated bile acid transformations. Its well-defined structure and purity make it suitable for use in metabolic and enzymatic research applications.
Allolithocholic acid structure
Allolithocholic acid structure
Product Name:Allolithocholic acid
CAS No:2276-94-0
MF:C24H40O3
MW:376.57260799408
CID:274707
PubChem ID:5283803
Update Time:2025-07-22

Allolithocholic acid Chemical and Physical Properties

Names and Identifiers

    • Cholan-24-oic acid,3-hydroxy-, (3a,5a)-
    • (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-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
    • Allolithocholic acid
    • CHEBI:139131
    • LMST04010005
    • AC1NR32F
    • HY-143712
    • 3a-Hydroxy-5a-cholanoic acid
    • DTXSID90415285
    • CS-0374914
    • Q63399710
    • 2276-94-0
    • SCHEMBL15156767
    • 3alpha-Hydroxy-5alpha-cholan-24-oic Acid
    • Inchi: 1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17-,18+,19-,20+,21+,23+,24-/m1/s1
    • InChI Key: SMEROWZSTRWXGI-NWFSOSCSSA-N
    • SMILES: O[C@@H]1CC[C@@]2(C)[C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@H]21

Computed Properties

  • Exact Mass: 376.29774513g/mol
  • Monoisotopic Mass: 376.29774513g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 4
  • Complexity: 574
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 9
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 6.3
  • Topological Polar Surface Area: 57.5?2

Experimental Properties

  • Density: 1.073
  • Boiling Point: 511°Cat760mmHg
  • Flash Point: 276.9°C

Allolithocholic acid Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
A128920-10mg
Allolithocholic acid
2276-94-0
10mg
$ 155.00 2023-09-09
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1PlusChem
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Cholan-24-oic acid,3-hydroxy-, (3a,5a)-
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$126.00 2024-05-24
1PlusChem
1P007ODA-5mg
Cholan-24-oic acid,3-hydroxy-, (3a,5a)-
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1PlusChem
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Cholan-24-oic acid,3-hydroxy-, (3a,5a)-
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Allolithocholic acid Related Literature

Additional information on Allolithocholic acid

Cholan-24-oic acid, 3-hydroxy-, (3a,5a)

Cholan-24-oic acid, also known as 3-hydroxy-cholan-24-oic acid, is a unique bile acid derivative that has garnered significant attention in recent biomedical research. This compound belongs to the family of bile acids, which are naturally occurring organic molecules that play critical roles in digestion, absorption of fats and fat-soluble vitamins, and maintenance of overall liver health.

Bile acids, such as Cholan-24-oic acid, are synthesized in the liver and secreted into the bile ducts. They are composed of a steroid-like structure (referred to as the cholane skeleton) with various functional groups that confer specific biological activities. The hydroxyl group at position 3 (3-hydroxy) in this molecule is particularly significant, as it contributes to its unique pharmacological properties and interactions within the body.

Recent studies have highlighted the potential of Cholan-24-oic acid in various biomedical applications. One of the most promising areas of research is its role in gastrointestinal health. Bile acids are known to influence gut microbiota composition and function, which in turn can impact overall systemic health. Research has shown that 3-hydroxy-cholan-24-oic acid may exhibit selective effects on gut bacteria, promoting a balanced microbial environment that supports digestion and immune function.

Another area of intense investigation is the relationship between bile acids and inflammation. Emerging evidence suggests that certain bile acids, including Cholan-24-oic acid, may possess anti-inflammatory properties. These effects are thought to be mediated through interactions with membrane receptors such as the Takeda G-protein coupled receptor (TGR5) and the Farnesoid X receptor (FXR). These interactions can lead to downstream signaling pathways that modulate inflammatory responses, making this compound a potential candidate for therapeutic interventions in inflammatory diseases.

Beyond its role in digestion and inflammation, Cholan-24-oic acid has also been explored for its potential in metabolic regulation. Bile acids are known to influence energy metabolism, glucose homeostasis, and lipid metabolism. Preclinical studies have demonstrated that this specific bile acid derivative may improve insulin sensitivity and reduce hepatic fat accumulation, suggesting its potential utility in the management of metabolic disorders such as type 2 diabetes and non-alcoholic fatty liver disease (NAFLD).

The structural features of Cholan-24-oic acid, particularly its hydroxyl group at position 3, also make it a valuable tool for studying bile acid biosynthesis and transport. Researchers are investigating how this compound interacts with key enzymes and transporters involved in bile acid metabolism, such as bile acid synthase (BAS) and apical sodium-dependent bile acid transporter (ASBT). Understanding these interactions could provide new insights into the regulation of bile acid homeostasis and its implications for human health.

Furthermore, the study of Cholan-24-oic acid extends to its potential applications in cancer research. Certain bile acids have been shown to exhibit anti-cancerous properties by inducing apoptosis in cancer cells or by modulating signaling pathways that promote tumor growth and metastasis. Early-stage research on this compound suggests that it may possess cytotoxic effects against specific types of cancer cells, making it a promising candidate for further investigation in oncology.

Given the multifaceted biological activities of Cholan-24-oic acid, ongoing research is focused on elucidating its mechanisms of action and exploring its therapeutic potential across various disease states. Collaborative efforts between academic institutions, pharmaceutical companies, and biotechnology firms are essential to advance our understanding of this compound and bring its benefits to patients.

Overall, Cholan-24-oic acid represents a fascinating area of study within the field of bile acid research. Its unique structural features and diverse biological activities make it a valuable subject for exploring fundamental biological processes as well as developing novel therapeutic interventions. As our knowledge of this compound continues to expand, so too does its potential to contribute to advancements in medicine and healthcare.

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