D6513

Desmosterol

Name: Desmosterol
Brand: SIGMA
Price: 94.8 USD
Availability: InStock

≥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

EC Number:

206-236-2

MDL number:

MFCD00056432

UNSPSC Code:

12352200

PubChem Substance ID:

24894033

NACRES:

NA.77

Key Documents

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Product Name

Desmosterol, ≥84% (GC)

Quality Level

200

assay

≥84% (GC)

form

powder

storage temp.

−20°C

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

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

Related Categories

Bioactive Small Molecules

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Show Differences

1 of 4

This Item	F5379	L5768	30800
Sigma-Aldrich D6513 Desmosterol	Sigma-Aldrich F5379 Fucosterol	Sigma-Aldrich L5768 Lanosterol	Sigma-Aldrich 30800 7-Dehydrocholesterol
assay ≥84% (GC)	assay ≥93%	assay ≥93%	assay ≥95.0% (HPLC)
form powder	form -	form powder	form powder or crystals
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 100
storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. −20°C

General description

Desmosterol is a C27 sterol intermediate in cholesterol synthesis. It may be associated with the pathogenesis of Alzheimer′s disease (AD).[1]

Application

Desmosterol has been used as a standard for the estimation of the concentrations of cholesterol and plant sterols.[2][3] It has also been used to suppress nigericin-induced sterol regulatory element-binding proteins 2 (SREBP2) maturation.[4]

Storage Class

11 - Combustible Solids

wgk_germany

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

0000481103

0000481102

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Involvement of bicarbonate-induced radical signaling in oxysterol formation and sterol depletion of capacitating mammalian sperm during in vitro fertilization.

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

Cerebral accumulation of dietary derivable plant sterols does not interfere with memory and anxiety related behavior in Abcg5-/- mice.

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

Anti-atherogenic effects of phytosteryl oleates in apo-E deficient mice

Moghadasian MH, et al

Journal of functional foods, 21, 97-103 (2016)

Reductions in cholesterol and synaptic markers in association cortex in mood disorders.

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

GC-MS-Based Endometabolome Analysis Differentiates Prostate Cancer from Normal Prostate Cells.

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

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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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Desmosterol