A quantitative analytical standard guaranteed to meet MaxSpec® identity, purity, stability, and concentration specifications
Features
  • Purpose built for quantitative mass spectrometry
  • Prepared gravimetrically as a solution with a defined concentration
  • Packaged in an ampule sealed under argon to maintain product integrity
  • Guaranteed to meet MaxSpec® identity, purity, stability, and concentration specifications
Related Products
Labeled Version(s)
31354Lithocholic Acid-d4 MaxSpec® Standard
Research Tool(s)
20253Lithocholic Acid
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Lithocholic Acid MaxSpec® Standard

Item No. 31353

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 solution in methanol at 100 µg/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
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    100 µg

    $75

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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 (Item No. 10011286) 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.4,2,5

    Lithocholic Acid MaxSpec® standard is a quantitative grade standard of Lithocholic Acid (Item No. 20253) that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This Lithocholic Acid MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

    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

    Qu, P., Rom, O., Li, K., et al. DT-109 ameliorates nonalcoholic steatohepatitis in nonhuman primates. Cell Metab. 35(5), 742-757 (2023).