Cholesterol 5beta,6beta-epoxide  (Synonyms: Cholesterol beta-epoxide)

Cholesterol 5beta,6beta-epoxide is an oxidative metabolite of cholesterol formed by free-radical and non-radical oxidation of cholesterol at the 5,6 double bond. Induces lactate dehydrogenase (LDH) release and apoptosis in macrophage-differentiated U937 cells. Cholesterol 5beta,6beta-epoxide has been found in human fatty streaks and advanced atherosclerotic lesions, but not in normal aortic tissue^[1][2][3].

402.65

C₂₇H₄₆O₂

4025-59-6

Solid

White to off-white

C[C@]12[C@@]3(C[C@H](CC2)O)[C@](C[C@]4([H])[C@]1([H])CC[C@]5([C@@]4([H])CC[C@]5([H])[C@H](C)CCCC(C)C)C)([H])O3

Room temperature in continental US; may vary elsewhere.

• [1]. Pulfer M K, et al. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant[J]. Journal of Biological Chemistry, 2004, 279(25): 26331-26338.

  [2]. Aringer L, et al. Formation and metabolism in vitro of 5, 6-epoxides of cholesterol and 尾-sitosterol[J]. Journal of Lipid Research, 1974, 15(4): 389-398.

  [3]. Garcia-Cruset S, et al. Oxysterol profiles of normal human arteries, fatty streaks and advanced lesions. Free Radic Res. 2001 Jul;35(1):31-41.  [Content Brief]