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284122

5-Cholesten-3β-ol-7-one

95%

Synonym(s):

3β-Hydroxy-5-cholesten-7-one, 7-Ketocholesterol

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About This Item

Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
566-28-9
Molecular Weight:
400.64
UNSPSC Code:
12352103
PubChem Substance ID:
329752905
MDL number:
MFCD00010474
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assay

95%

SMILES string

C[C@]12CC[C@@]([C@](CC[C@H](O)C3)(C)C3=CC4=O)([H])[C@]4([H])[C@]1([H])CC[C@]2([H])[C@]([H])(C)CCCC(C)C

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

InChI key

YIKKMWSQVKJCOP-ABXCMAEBSA-N

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
13308LR
11305EN
08616DT
08554DF
07021HN

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Jiahn-Dar Huang et al.
Biochimica et biophysica acta, 1821(4), 637-646 (2012-02-22)
Sterculic acid is a cyclopropene fatty acid with numerous biological activities. In this study we demonstrate that sterculic acid is a potent inhibitor of endoplasmic reticulum (ER) stress and related inflammation caused by 7-ketocholesterol (7KCh). 7KCh is a highly toxic
Luisa Tesoriere et al.
The British journal of nutrition, 110(2), 230-240 (2012-12-12)
7-Ketocholesterol (7-KC)-induced apoptosis of macrophages is considered a key event in the development of human atheromas. In the present study, the effect of indicaxanthin (Ind), a bioactive pigment from cactus pear fruit, on 7-KC-induced apoptosis of human monocyte/macrophage THP-1 cells
Vesa M Olkkonen
Current opinion in lipidology, 23(5), 462-470 (2012-07-21)
To offer a comprehensive review on the roles that oxysterols synthesized or engulfed by macrophages, or oxysterol-binding proteins in these cells, play in the development and progression of atherosclerotic lesions. Oxysterols abundant within the plaque have the capacity to potentiate
Brigitta Buttari et al.
Biochemical pharmacology, 86(1), 130-137 (2013-04-25)
Macrophages, the major cellular components of atherosclerotic plaques, consist of two main subsets: the pro-inflammatory, M1 or classically activated macrophages, and the anti-inflammatory, M2 or alternatively activated macrophages. The molecular and cellular mechanisms that orchestrate the macrophage polarization and activation
Dmitri Svistounov et al.
PloS one, 7(9), e46134-e46134 (2012-10-03)
Fenestrations are transcellular pores in endothelial cells that facilitate transfer of substrates between blood and the extravascular compartment. In order to understand the regulation and formation of fenestrations, the relationship between membrane rafts and fenestrations was investigated in liver sinusoidal
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