5?-hydroxy-6-keto Cholesterol

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Cat No: 10007601

Biochemicals - Lipids

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-ket...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

3?,5?-dihydroxy-cholestan-6-one

Correlated keywords:

atherosclerosis cholesterols ozonolysis cytotoxicity metabolites ozone-oxidized lipids surfactants lungs epithelials lining fluids exposures cells bronchalveoalar lavaged homogenates inhibits inhibitors synthesis bronchial cytotoxicity toxic oxysterols hydroxycholesterol

Product Overview:
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.{13448} 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.{13449} 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.{13448} Therefore, the toxic effects of ozone may be mediated by formation oxysterols of this type.

Size	1 mg
Shipping	dry ice
CAS Number	13027-33-3
Molecular Formula	C₂₇H₄₆O₃
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
Molecular Weight	418,7
Formulation	A crystalline solid
Purity	≥98%
Custom Code	2932.99
UNSPSC code	12352100

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Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

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