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Cayman is a manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research. Analytical testing services and custom synthesis are also available.

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

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5α-hydroxy-6-keto Cholesterol

Cayman Chemical Item Number 10007601

Cholestane-6-oxo-3β,5α-diol; 6-Oxo-3,5-diol (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
  • Cholestane-6-oxo-3β,5α-diol
  • 6-Oxo-3,5-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)​[C@]​3([H]​)​[C@@]​([C@@]​(CC[C@]​4([H]​)​[C@H]​(C)​CCCC(C)​C)​([H]​)​[C@]​4(C)​CC3)​([H]​)​C1
InCHI Code
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​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
InCHI Key
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SJZZRXMQSAXCFD-ZCBMJONGSA-N

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

Size Price Quantity Subtotal
1 mg $25.00 $0.00
5 mg $119.00 $0.00
10 mg $225.00 $0.00
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Cart Total $0.00

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Pricing updated 2015-03-04. Prices are subject to change without notice.

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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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