5α-hydroxy-6-keto Cholesterol
Item № 10007601
CAS № 13027-33-3
Purity ≥98%
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL $0.00
1 mg $25.00 $0.00
5 mg $119.00 $0.00
10 mg $225.00 $0.00

Pricing updated 2016-05-04. Prices are subject to change without notice.

Bulk Inquiry Form

X

Enter number, size, and select unit. Example: 2 x 500 mg

Please indicate any analytical testing requirements, special handling, packaging, or delivery requirements.

Description
Synonyms
  • 6-Oxo-3,5-diol
  • Cholestane-6-oxo-3β,5α-diol

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.

Download Product Insert Download Safety Data Sheet (SDS)

Related Products
View Related Product Categories
View Screening Libraries with 5α-hydroxy-6-keto Cholesterol
Technical Information
Formal Name 3β,5α-dihydroxy-cholestan-6-one
CAS Number 13027-33-3
Synonyms
  • 6-Oxo-3,5-diol
  • Cholestane-6-oxo-3β,5α-diol
Molecular Formula C27H46O3
Formula Weight 418.7
Purity ≥98%
Formulation A crystalline solid
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
InChI Code 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 SJZZRXMQSAXCFD-ZCBMJONGSA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Product Downloads & Resources
Product Downloads

Download Product Insert

Download Safety Data Sheet (SDS)

Download free InChI Key generation software

Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

Get Batch-Specific Data and Documents by Batch Number

Separate multiple batch numbers with commas

Inserts
QC Sheets
Certificates of Analysis
GCMS Data
References & Background Reading
Product Description References

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).

Technical Support
Contact Us
  • To streamline the process attach the appropriate questionnaire to your inquiry.

  • Toll Free Phone (USA and Canada Only): (888) 526-5351
  • Direct Phone: (734) 975-3888
Contract Research Services

We offer you the deep and diverse knowledge of more than 100 in-house scientists and the expertise that comes from more than three decades of designing and developing the tools to advance biomedical research.

Cayman is know as a partner to scientists worldwide, responding to your needs with services in:

Cayman Chemical

1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA

JOIN OUR SOCIAL NETWORK!