An intermediate in the synthesis of ursodeoxycholic acid and chenodeoxycholic acid
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12-keto Chenodeoxycholic Acid

Item No. 30838

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β,7α)-3,7-dihydroxy-12-oxo-cholan-24-oic acid
CAS Number
2458-08-4
Synonyms
  • 12-keto CDCA
  • 12-oxo CDCA
  • 12-oxo Chenodeoxycholic Acid
  • 3α,7α-Dihydroxy-12-keto-5β-cholanic acid
Molecular Formula
C24H38O5
Formula Weight
406.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
[H][C@@]12CC[C@@]([C@@H](CCC(O)=O)C)([H])[C@]1(C(C[C@]3([C@]2([C@@H](C[C@]4([C@@]3(CC[C@H](C4)O)C)[H])O)[H])[H])=O)C
InChi Code
InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1
InChi Key
MIHNUBCEFJLAGN-DMMBONCOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    12-keto Chenodeoxycholic acid (12-keto CDCA) is an intermediate in the semisynthetic synthesis of ursodeoxycholic acid (Item Nos. 31016 | 15121) and chenodeoxycholic acid (Item Nos. 10011286 | 35346) from the primary bile acid cholic acid (Item No. 20250).1,2 12-keto CDCA has been found in the gastric tissues of C57BL/6J mice, KM mice, Sprague-Dawley rats, New Zealand white rabbits, and JX black pigs.3 Fecal levels of 12-keto CDCA are increased in children with hepatic glycogen storage disease.4 The sodium salt of 12-keto CDCA, known as 12-monoketocholic acid (12-MKA), increases brain uptake of quinine (Item No. 23958), the analgesic effect of morphine in the hot plate test, and pentobarbital-induced sleeping time in rats when administered at a dose of 2 mg/kg.5 It also promotes nasal absorption of insulin and increases the duration of local anesthesia induced by lidocaine in rats.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sutherland, J.D., Macdonald, I.A., and Forrest, T.P. The enzymic and chemical synthesis of ursodeoxycholic and chenodeoxycholic acid from cholic acid. Prep. Biochem. 12(4), 307-321 (1982).

    2. Hofmann, A.F. The preparation of chenodeoxycholic acid and Its glycine and taurine conjugates. Acta Chemica Scand. 17, 173-186 (1963).

    3. Zhao, A., Wang, S., Chen, W., et al. Increased levels of conjugated bile acids are associated with human bile reflux gastritis. Sci. Rep. 10(1), 11601 (2020).

    4. Wang, Y., Liu, H., Dong, F., et al. Altered gut microbiota and microbial metabolism in children with hepatic glycogen storage disease: a case-control study. Transl. Pediatr. 12(4), 572-586 (2023).

    5. Mikov, M., Kevresan, S., Kuhajda, K., et al. 3α,7α-dihydroxy-12-oxo-5β-cholanate as blood-brain barrier permeator. Pol. J. Pharmacol. 56(3), 367-371 (2004).

    6. Poša, M., Kevrešan, S., Mikov, M., et al. Effect of cholic acid and its keto derivatives on the analgesic action of lidocaine and associated biochemical parameters in rats. Eur. J. Drug Metab. Pharmacokinet. 32(2), 109-117 (2007).