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D6513

Sigma-Aldrich

Desmosterol

≥84% (GC)

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

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

General description

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Thomas Wisniewski et al.
Journal of Alzheimer's disease : JAD, 33(3), 881-888 (2012-10-09)
Desmosterol is a C27 sterol intermediate in cholesterol synthesis generated during the metabolic pathway that transforms lanosterol into cholesterol. It has become of particular interest in the pathogenesis of Alzheimer's disease (AD) because of the report that the activity of
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
Anna Meljon et al.
Journal of lipid research, 53(11), 2469-2483 (2012-08-15)
Unesterified cholesterol is a major component of plasma membranes. In the brain of the adult, it is mostly found in myelin sheaths, where it plays a major architectural role. In the newborn mouse, little myelination of neurons has occurred, and
Cholesterol Homeostatic Regulator SCAP-SREBP2 Integrates NLRP3 Inflammasome Activation and Cholesterol Biosynthetic Signaling in Macrophages
Guo C, et al.
Immunity, 49(5), 842-856 (2018)
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Articles

Cholesterol Biosynthesis

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

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