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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

5α-hydroxy-6-keto Cholesterol

Cayman Chemical Item Number 10007601

6-Oxo-3,5-diol; Cholestane-6-oxo-3β,5α-diol (CAS 13027-33-3)

5α-hydroxy-6-keto Cholesterol (CAS 13027-33-3)

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Description

Cholesterol is the most abundant neutral lipid present in the surfactant of the lung epithelial lining fluid. The double bond between carbons 5 and 6 of cholesterol is susceptible to attack by ozone within this surfactant environment. 5α-hydroxy-6-keto Cholesterol (6-oxo-3,5,-diol) is a major metabolite of cholesterol formed during exposure of lung epithelial cells to ozone, with formation of 5β,6β-epoxycholesterol as a predominant precursor.1 Exposure of C57BL/6J mice to 0.5-3 ppm ozone produced a dose-dependent formation of 6-oxo-3,5,-diol which was detectable in the bronchalveolar lavage fluid, lavaged cells, and lung homogenates.2 6-Oxo-3,5-diol is a potent inhibitor of cholesterol synthesis in human bronchial epithelial cells with an IC50 of 350 nM and exhibits significant cytotoxicity in the low µM range.1 Therefore, the toxic effects of ozone may be mediated by formation oxysterols of this type.

1 Pulfer, M.K., and Murphy, R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. J Biol Chem 279(25) 26331-26338 (2004).

2 Pulfer, M.K., Taube, C., Gelfand, E., et al. Ozone exposure in vivo and formation of biologically active oxysterols in the lung. J Pharmacol Exp Ther 312(1) 256-264 (2005).

Synonyms
  • 6-Oxo-3,5-diol
  • Cholestane-6-oxo-3β,5α-diol
Formal Name 3β,​5α-​dihydroxy-​cholestan-​6-​one
CAS Number 13027-33-3
Molecular Formula C27H46O3
Formula Weight 418.7
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C1[C@@]​2(O)​C[C@@H]​(O)​CC[C@]​2(C)​C3C(C(CCC4[C@H]​(C)​CCCC(C)​C)​[C@]​4(C)​CC3)​C1

Background Reading

Pulfer, M.K., and Murphy, R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. J Biol Chem 279(25) 26331-26338 (2004).

Pulfer, M.K., Taube, C., Gelfand, E., et al. Ozone exposure in vivo and formation of biologically active oxysterols in the lung. J Pharmacol Exp Ther 312(1) 256-264 (2005).

5α-hydroxy-6-keto Cholesterol is available in the following screening library:

Size Price Quantity Subtotal
1 mg $18.00 $0.00
5 mg $81.00 $0.00
10 mg $144.00 $0.00
50 mg $630.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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