A toxic secondary bile acid
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Lithocholic Acid

Item No. 20253

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β)-3-hydroxy-cholan-24-oic acid
CAS Number
434-13-9
Synonyms
  • 3α-hydroxy Cholanic Acid
  • LCA
  • Lithocholate
  • NSC 683770
Molecular Formula
C24H40O3
Formula Weight
376.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/ml
SMILES
C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C
InChi Code
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-HVATVPOCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 g

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    25 g

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    Cayman Chemical
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    Product Description

    Lithocholic acid is a secondary bile acid that has been shown to cause cholestasis in animal models and has also been implicated in carcinogenesis.1,2 It is produced from chenodeoxycholic acid by bacterial action in the colon and can be conjugated with glycine or taurine. Whereas in normal colonic epithelium lithocholic acid promotes apoptosis, it has been shown to suppress apoptosis in pre-malignant colonic epithelium in the presence of a carcinogen.3 Lithocholic acid can activate the pregnane X receptor and the vitamin D receptor, which may serve as a biological sensor to regulate lithocholic acid-induced toxicity.2,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Little, J.M., Zimniak, P., Shattuck, K.E., et al. Metabolism of lithocholic acid in the rat: Formation of lithocholic acid 3-O-glucuronide in vivo. J. Lipid. Res. 31(4), 615-622 (1990).

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

    3. Kozoni, V., Tsioulias, G., Shiff, S., et al. The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: Differential effect on apoptosis in the presence of a colon carcinogen. Carcinogenesis 21(5), 999-1005 (2000).

    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. Tan, K.P., Yang, M., and Ito, S. Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. Mol. Pharmacol. 72(5), 1380-1390 (2007).

    Product Citations

    Wei, W., Lyu, X., Markhard, A.L., et al. PTER is a N-acetyltaurine hydrolase that regulates feeding and obesity. Nature 633(8028), 182-188 (2023).