A major metabolite of lithocholic acid
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Parent Compound(s)
20253Lithocholic Acid 44907Lithocholic Acid (CRM)
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Dehydrolithocholic Acid

Item No. 29544

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-3-oxo-cholan-24-oic acid
CAS Number
1553-56-6
Synonyms
  • 3-keto LCA
  • 3-keto Lithocholate
  • 3-keto Lithocholic Acid
  • 3-KLCA
  • 3-oxo LCA
  • 3-oxo Lithocholate
  • 3-oxo Lithocholic Acid
Molecular Formula
C24H38O3
Formula Weight
374.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:4): 0.20 mg/mlDMSO: 15 mg/mlEthanol: 10 mg/ml
SMILES
C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
InChi Code
InChI=1S/C24H38O3/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/h15-16,18-21H,4-14H2,1-3H3,(H,26,27)/t15-,16-,18+,19-,20+,21+,23+,24-/m1/s1
InChi Key
KIQFUORWRVZTHT-OPTMKGCMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 mg

    $36

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    50 mg

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    100 mg

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    250 mg

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    Product Description

    Dehydrolithocholic acid is a major metabolite of lithocholic acid (LCA; Item No. 20253).1 It is formed from LCA by the cytochrome P450 (CYP) isoform CYP3A4. Dehydrolithocholic acid is an agonist of G protein-coupled bile acid activated receptor 1 (GP-BAR1/TGR5; EC50 = 0.27 μM), vitamin D receptor (VDR; EC50 = 3 μM), and farnesoid X receptor (FXR) in cell-based reporter assays.2,3 It also binds to the human pregnane X receptor (PXR; IC50 = 15 μM) and activates mouse and human PXRs in cell-based reporter assays when used at a concentration of 100 μM.4 Dehydrolithocholic acid binds to retinoic acid receptor-related orphan receptor γt (RORγt; Kd = 1.13 μM for the recombinant human ligand-binding domain) and decreases its activity in a cell-based reporter assay when used at a concentration of 10 μM.5 It inhibits the differentiation of T helper cells that express IL-17a (TH17 cells) when used at a concentration of 20 μM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Deo, A.K., and Bandiera, S.M. 3-Ketocholanoic acid is the major in vitro human hepatic microsomal metabolite of lithocholic acid. Drug Metab. Dispos. 37(9), 1938-1947 (2009).

    2. Sato, H., Macchiarulo, A., Thomas, C., et al. Novel potent and selective bile acid derivatives as TGR5 agonists: Biological screening, structure-activity relationships, and molecular modeling studies. J. Med. Chem. 51(6), 1831-1841 (2008).

    3. Makishima, M., Lu, T.T., Xie, W., et al. Vitamin D receptor as an intestinal bile acid sensor. Science 296(5571), 1313-1316 (2002).

    4. Staudinger, J.L., Goodwin, B., Jones, S.A., et al. The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity. Proc. Natl. Acad. Sci. USA 98(6), 3369-3374 (2000).

    5. Hang, S., Paik, D., Yao, L., et al. Bile acid metabolites control TH17 and Treg cell differentiation. Nature 576(7785), 143-148 (2019).