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Merck

D6513

Desmosterol

≥84% (GC), cholesterol synthesis intermediate, powder

Synonym(s):

24-Dehydrocholesterol, 3β-Hydroxy-5,24-cholestadiene, 5,24-Cholestadien-3β-ol

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
313-04-2
Molecular Weight:
384.64
NACRES:
NA.77
PubChem Substance ID:
24894033
UNSPSC Code:
12352200
EC Number:
206-236-2
MDL number:
MFCD00056432

Product Name

Desmosterol, ≥84% (GC)

Quality Level

200

InChI

1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

AVSXSVCZWQODGV-DPAQBDIFSA-N

SMILES string

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCC=C(C)C

assay

≥84% (GC)

form

powder

storage temp.

−20°C

Related Categories

Application

Desmosterol has been used as a standard for the estimation of the concentrations of cholesterol and plant sterols. It has also been used to suppress nigericin-induced sterol regulatory element-binding proteins 2 (SREBP2) maturation.

General description

Desmosterol is a C27 sterol intermediate in cholesterol synthesis. It may be associated with the pathogenesis of Alzheimer′s disease (AD).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000497894
0000497894
0000481103
0000481102
0000481102

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Arjan Boerke et al.
Biology of reproduction, 88(1), 21-21 (2012-11-02)
This study demonstrates for the first time that porcine and mouse sperm incubated in capacitation media supplemented with bicarbonate produce oxysterols. The production is dependent on a reactive oxygen species (ROS) signaling pathway that is activated by bicarbonate and can
Clare L Beasley et al.
Bipolar disorders, 7(5), 449-455 (2005-09-24)
Cholesterol forms an integral part of cell membranes and is a major component of myelin. Furthermore, cholesterol also plays a vital role in the development, function and stability of synapses. While low serum cholesterol has previously been associated with mood
Ana Rita Lima et al.
Metabolites, 8(1) (2018-03-23)
Prostate cancer (PCa) is an important health problem worldwide. Diagnosis and management of PCa is very complex because the detection of serum prostate specific antigen (PSA) has several drawbacks. Metabolomics brings promise for cancer biomarker discovery and for better understanding
Anti-atherogenic effects of phytosteryl oleates in apo-E deficient mice
Moghadasian MH, et al
Journal of functional foods, 21, 97-103 (2016)
Tim Vanmierlo et al.
Plant foods for human nutrition (Dordrecht, Netherlands), 66(2), 149-156 (2011-03-25)
Plant sterols such as sitosterol and campesterol are frequently applied as functional food in the prevention of atherosclerosis. Recently, it became clear that plasma derived plant sterols accumulate in murine brains. We questioned whether plant sterols in the brain are
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Articles

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

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