An intermediate in the synthesis of ursodeoxycholic acid
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7-keto Lithocholic Acid

Item No. 29546

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β)-3-hydroxy-7-oxo-cholan-24-oic acid
CAS Number
4651-67-6
Synonyms
  • 7-KLCA
  • 7-keto LCA
  • 7-oxo LCA
  • 7-keto Lithocholate
  • 7-oxo Lithocholate
  • 7-oxo Lithocholic Acid
  • NSC 226118
Molecular Formula
C24H38O4
Formula Weight
390.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C(C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
InChi Code
InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,22+,23+,24-/m1/s1
InChi Key
DXOCDBGWDZAYRQ-AURDAFMXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

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    Product Description

    7-keto Lithocholic acid is an intermediate in the synthesis of the secondary bile acid ursodeoxycholic acid (Item No. 15121) by intestinal bacteria in humans.1,2 It is formed from chenodeoxycholic acid (Item No. 10011286) in B. intestinalis isolated from human feces.1 Venous infusion of 7-keto lithocholic acid (1.2 µmol/min per 100 g body weight) increases the bile flow rate and the concentration of bile bicarbonate in rats.3 7-keto Lithocholic acid levels are decreased in rat feces in a model of adenine-induced chronic renal failure.4 Fecal levels are also reduced in patients with liver cirrhosis or hepatocellular carcinoma.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fukiya, S., Arata, M., Kawashima, H., et al. Conversion of cholic acid and chenodeoxycholic acid into their 7-oxo derivatives by Bacteroides intestinalis AM-1 isolated from human feces. FEMS Microbiol. Lett. 293(2), 263-270 (2009).

    2. Fromm, H., Carlson, G.L., Hofmann, A.F., et al. Metabolism in man of 7-ketolithocholic acid: Precursor of cheno- and ursodeoxycholic acids. Am. J. Physiol. 239(3), G161-G166 (1980).

    3. Kanai, S., Sato, Y., Nokubo, M., et al. Hepatic biotransformation and choleretic effect of 7-ketolithocholic acid in the rat. Lipids 24(10), 859–865 (1989).

    4. Zhao, Y.Y., Cheng, X.L., Wei, F., et al. Application of faecal metabonomics on an experimental model of tubulointerstitial fibrosis by ultra performance liquid chromatography/high-sensitivity mass spectrometry with MSE data collection technique. Biomarkers 17(8), 721-729 (2012).

    5. Cao, H., Huang, H., Xu, W., et al. Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal. Chim. Acta. 691(1-2), 68-75 (2011).