An oxidative metabolite of cholesterol
Related Products
Isomer(s)
200987α-hydroxy Cholesterol
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5β,6β-epoxy Cholestanol

Item No. 25603

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5β,6β-epoxy-cholestan-3β-ol
CAS Number
4025-59-6
Synonyms
  • Cholesterol β-Epoxide
  • 5β,6β-Epoxycholesterol
  • 5β,6β-Epoxycholestan-3β-ol
  • NSC 148940
Molecular Formula
C27H46O2
Formula Weight
402.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 0.1 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
SMILES
C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C[C@@H]4[C@]5(O4)C[C@@H](O)CC[C@]5(C)[C@@]3([H])CC[C@@]21C
InChi Code
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
InChi Key
PRYIJAGAEJZDBO-DTLXENBRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Product Description

    5β,6β-epoxy Cholestanol is an oxidative metabolite of cholesterol that is formed via radical and non-radical oxidation of cholesterol at the 5,6-double bond.1,2 It induces release of lactate dehydrogenase (LDH) and apoptosis in macrophage-differentiated U937 cells.3 5β,6β-epoxy Cholestanol has been found in human fatty streaks and advanced atherosclerotic lesions but is not present in normal aortic tissue.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Aringer, L., and Eneroth, P. Formation and metabolism in vitro of 5,6-epoxides of cholesterol and β-sitosterol. J. Lipid Res. 15(4), 389-398 (1974).

    3. Lordan, S., O'Brien, N.M., and Mackrill, J.J. The role of calcium in apoptosis induced by 7β-hydroxycholesterol and cholesterol-5β,6β-epoxide. J. Biochem. Mol. Toxicol. 23(5), 324-332 (2009).

    4. Garcia-Cruset, S., Carpenter, K.L., Guardiola, F., et al. Oxysterol profiles of normal human arteries, fatty streaks and advanced lesions. Free Radic. Res. 35(1), 31-41 (2001).