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7-Ketocholesterol

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Category	Natural Sterols
Catalog NO.	BPG-3288
Product Name	7-Ketocholesterol
CAS	566-28-9
Molecular Formula	C27H44O2
Molecular Weight	400.64

Scheme Design
Custom Synthesis
cGMP Manufacturing
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Product Information
Application
References
Documents
Reviews

Product Information

Description	7-Ketocholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL. It is also a metabolite of Cholesterol.
Synonyms	(3β)-3-Hydroxycholest-5-en-7-one; 3β-Hydroxycholest-5-en-7-one; 7-Oxocholesterol; Cholest-5-en-3β-ol-7-one; 7-Oxocholesterol; 7-oxo-cholesterol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)O)C)C
InChI	InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
InChIKey	YIKKMWSQVKJCOP-ABXCMAEBSA-N
Boiling Point	516.7°C at 760 mmHg
Melting Point	168-170°C
Purity	> 95%
Density	1.0 g/cm3
Solubility	Soluble in Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
Appearance	White to Pale Beige Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	400.334
Hygroscopic	No
Light Sensitive	Yes
Percent Composition	C 80.94%, H 11.07%, O 7.99%

References

1. Hutchinson SA, Lianto P, Roberg-Larsen H, Battaglia S, Hughes TA, Thorne JL. ER-Negative Breast Cancer Is Highly Responsive to Cholesterol Metabolite Signalling. Nutrients. 2019 Nov 1;11(11). pii: E2618. doi: 10.3390/nu11112618. PubMed ID: 31683867.
2. Rudd-Schmidt JA, Hodel AW, Noori T, Lopez JA, Cho HJ, Verschoor S, Ciccone A, Trapani JA, Hoogenboom BW, Voskoboinik I. Lipid order and charge protect killer T cells from accidental death. Nat Commun. 2019 Nov 27;10(1):5396. doi: 10.1038/s41467-019-13385-x. PubMed ID: 31776337.
3. Rossin D, Barbosa-Pereira L, Iaia N, Testa G, Sottero B, Poli G, Zeppa G, Biasi F. A Dietary Mixture of Oxysterols Induces In Vitro Intestinal Inflammation through TLR2/4 Activation: The Protective Effect of Cocoa Bean Shells. Antioxidants (Basel). 2019 May 31;8(6). pii: E151. doi: 10.3390/antiox8060151. PubMed ID: 31151323.
4. Fidalgo Rodríguez JL, Dynarowicz-Latka P, Minones Conde J. Interactions of cholesterol and 7‑ketocholesterol with unsaturated fatty acids of different unsaturation degree - The monolayer study. Biochim Biophys Acta Biomembr. 2019 Aug 1;1861(8):1428-1436. doi: 10.1016/j.bbamem.2019.06.002. Epub 2019 Jun 9. PubMed ID: 31189076.
5. Tajima N, Xiaoyan L, Taniguchi M, Kato N. 24S-hydroxycholesterol alters activity of large-conductance Ca2+-dependent K+ (slo1 BK) channel through intercalation into plasma membrane. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 May 25. pii: S1388-1981(19)30085-X. doi: 10.1016/j.bbalip.2019.05.010. [Epub ahead of print]...PubMed ID: 31136842.
6. Rossin D, Dias IHK, Solej M, Milic I, Pitt AR, Iaia N, Scoppapietra L, Devitt A, Nano M, Degiuli M, Volante M, Caccia C, Leoni V, Griffiths HR, Spickett CM, Poli G, Biasi F. Increased production of 27-hydroxycholesterol in human colorectal cancer advanced stage: Possible contribution to cancer cell survival and infiltration. Free Radic Biol Med. 2019 Mar 23;136:35-44. doi: 10.1016/j.freeradbiomed.2019.03.020. [Epub ahead of print]...PubMed ID: 30910555.
7. Fidalgo Rodríguez JL, Dynarowicz-Latka P, Miñones Conde J. Effects of saturated and polyunsaturated fatty acids on interactions with cholesterol versus 7-ketocholesterol in Langmuir monolayers and their potential biological implications. Colloids Surf B Biointerfaces. 2019 Feb 1;174:189-198. doi: 10.1016/j.colsurfb.2018.08.052. Epub 2018 Aug 25. PubMed ID: 30463048.
8. Wang X, Sun J, Zhao XE, Xu Y, Sun L, Zhu S, You J, Wang X. Stable isotope labeling derivatization coupled with magnetic dispersive solid phase extraction for the determination of hydroxyl-containing cholesterol and metabolites by in vivo microdialysis and ultra-high performance liquid chromatography tandem mass spectrometry. J Chromatogr A. 2019 Feb 14. pii: S0021-9673(19)30151-7. doi: 10.1016/j.chroma.2019.02.021. [Epub ahead of print]...PubMed ID: 30797576.

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