An active metabolite of cholesterol-5,6-epoxides
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5α-hydroxy-6-keto Cholesterol

Item No. 10007601

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β,5α-dihydroxy-cholestan-6-one
CAS Number
13027-33-3
Synonyms
  • 6-Oxo-3,5-diol
  • Cholestane-6-oxo-3β,5α-diol
  • OCDO
  • ​Oncosterone
Molecular Formula
C27H46O3
Formula Weight
418.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 0.5 mg/mlEthanol: 5 mg/ml
SMILES
O=C1[C@@]2(O)C[C@@H](O)CC[C@]2(C)[C@]3([H])[C@@]([C@@](CC[C@]4([H])[C@H](C)CCCC(C)C)([H])[C@]4(C)CC3)([H])C1
InChi Code
InChI=1S/C27H46O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-23,28,30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,25-,26-,27+/m1/s1
InChi Key
SJZZRXMQSAXCFD-ZCBMJONGSA-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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    Product Description

    5α-hydroxy-6-keto Cholesterol (OCDO) is an oxysterol and active metabolite of cholesterol-5,6-epoxides.1 Cholesterol-5,6-epoxides are hydrolyzed by cholesterol epoxide hydrolase (ChEH) into cholestane-3β,5α,6β-triol, which is then dehydrogenated by 11β-hydroxysteroid dehydrogenase 2 (11β-HSD2) into OCDO. OCDO inhibits cholesterol synthesis in 16HBE cells (IC50 = 350 nM).2 It increases the proliferation of MDA-MB-231 and MDA-MB-468 cells when used at concentrations of 2 and 5 µM.3 In vivo, OCDO (50 µg/kg) increases tumor volume in MCF-7, MDA-MB-231, EO771, and MDA-MB-468 breast cancer mouse xenograft models.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Poirot, M., Soules, R., Maillinger, A., et al. Chemistry, biochemistry, metabolic fate and mechanism of action of 6-oxo-cholestan-3β,5α-diol (OCDO), a tumor promoter and cholesterol metabolite. Biochimie 153, 139-149 (2018).

    2. Pulfer, M.K., and Murphy, R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. The Journal of Biological Chemisty 279(25), 26331-26338 (2004).

    3. Voisin, M., de Medina, P., Mallinger, A., et al. Identification of a tumor-promoter cholesterol metabolite in human breast cancers acting through the glucocorticoid receptor. Proc. Natl. Acad. Sci. USA 114(44), E9346-E9355 (2017).