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C6509

Sigma-Aldrich

Cholesteryl behenate

≥90% (HPLC; detection at 205 nm)

Synonym(s):

3β-Hydroxy-5-cholestene 3-docosanoate, 5-Cholesten-3β-ol 3-docosanoate, Cholesteryl docosanoate

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About This Item

Empirical Formula (Hill Notation):
C49H88O2
CAS Number:
Molecular Weight:
709.22
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

Assay

≥90% (HPLC; detection at 205 nm)

form

solid

functional group

ester

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C

InChI

1S/C49H88O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h30,39-40,42-46H,7-29,31-38H2,1-6H3/t40-,42+,43+,44-,45+,46+,48+,49-/m1/s1

InChI key

WBOQXYUYHINMOC-FTAWAYKBSA-N

Application

Cholesteryl behenate was used as standard in electrospray ionization tandem mass spectrometry for the analysis of cholesterol and cholesteryl esters.

Biochem/physiol Actions

Cholesteryl behenate is a cholesterol ester found associated with the neutral core of low density lipoprotein. Receptor-LDL complexes are taken up by lysosomes and hydrolyzed to release cholesterol from the esters. The enzyme acid cholesteryl ester hydrolase is responsible for the hydrolysis of cholesteryl esters; a defective enzyme can result in the formation of atherosclerotic lesions in humans.

Storage Class Code

13 - Non 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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G S Ginsburg et al.
Progress in lipid research, 23(3), 135-167 (1984-01-01)
Cholesteryl esters, the intracellular storage form and intravascular transport form of cholesterol, can exist in crystal, liquid crystal and liquid states. The physical state of cholesteryl esters at physiologic temperatures may be a determinant of their pathogenicity. This review has
Gerhard Liebisch et al.
Biochimica et biophysica acta, 1761(1), 121-128 (2006-02-07)
Analysis of free cholesterol (FC) is not well suited for electrospray ionization (ESI); however, cholesteryl ester (CE) form ammonium adducts in positive ion mode and generate a fragment ion of m/z 369 upon collision-induced fragmentation. In order to allow parallel
G S Ginsburg et al.
Biochimica et biophysica acta, 664(1), 98-107 (1981-04-23)
By polarizing microscopy and differential scanning calorimetry we observed that the relative stability of the smectic and cholesteric mesophases of cholesteryl esters of acyl chain length of 20 carbons or more depends on the length of the acyl chain and
W Guo et al.
Biochemistry, 32(35), 9038-9052 (1993-09-07)
Cholesteryl esters are a major lipid constituent of plasma lipoproteins and atherosclerotic lesions. Crystalline and liquid crystalline phases of several cholesteryl esters [oleate (C18:1, omega-9), erucate (C22:1, omega-9), hexanoate (C6:0), decanoate (C10:0), undecanoate (C11:0), myristate (C14:0), palmitate (C16:0), and stearate
Shobha Ghosh et al.
Vascular pharmacology, 52(1-2), 1-10 (2009-11-03)
Accumulation of cholesteryl esters (CE) stored as cytoplasmic lipid droplets is the main characteristic of macrophage foam cells that are central to the development of atherosclerotic plaques. Since only unesterified or free cholesterol (FC) can be effluxed from the cells

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