For research use only. Not for therapeutic Use.
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-<wbr></wbr>hydroxy-<wbr></wbr>6-<wbr></wbr>keto Cholesterol (6-<wbr></wbr>oxo-<wbr></wbr>3,5,-<wbr></wbr>diol) is a major metabolite of cholesterol formed during exposure of lung epithelial cells to ozone, with formation of 5β,6β-<wbr></wbr>epoxycholesterol as a predominant precursor. Exposure of C57BL/6J mice to 0.5-<wbr></wbr>3 ppm ozone produced a dose-<wbr></wbr>dependent formation of 6-<wbr></wbr>oxo-<wbr></wbr>3,5,-<wbr></wbr>diol which was detectable in the bronchalveolar lavage fluid, lavaged cells, and lung homogenates. 6-<wbr></wbr>Oxo-<wbr></wbr>3,5-<wbr></wbr>diol is a potent inhibitor of cholesterol synthesis in human bronchial epithelial cells with an IC<sub>50</sub> of 350 nM and exhibits significant cytotoxicity in the low µM range. Therefore, the toxic effects of ozone may be mediated by formation oxysterols of this type.
| CAS Number | 13027-33-3 |
| Synonyms | 6-Oxo-3,5-diol;Cholestane-6-oxo-3β,5α-diol |
| Molecular Formula | C27H46O3 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | (3S,5R,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one |
| InChI | 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 |
| InChIKey | SJZZRXMQSAXCFD-ZCBMJONGSA-N |
| SMILES | CC(C)CCCC(C)C1CCC2C1(CCC3C2CC(=O)C4(C3(CCC(C4)O)C)O)C |
