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Documentos Principais

C6509

Sigma-Aldrich

Cholesteryl behenate

≥90% (HPLC; detection at 205 nm)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C49H88O2
Número CAS:
Peso molecular:
709.22
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:

Ensaio

≥90% (HPLC; detection at 205 nm)

Formulário

solid

grupo funcional

ester

Condições de expedição

ambient

temperatura de armazenamento

room temp

cadeia de caracteres SMILES

[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

chave InChI

WBOQXYUYHINMOC-FTAWAYKBSA-N

Aplicação

Cholesteryl behenate was used as standard in electrospray ionization tandem mass spectrometry for the analysis of cholesterol and cholesteryl esters.[1]

Ações bioquímicas/fisiológicas

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.[2] 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.[3]

Código de classe de armazenamento

13 - Non Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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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
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
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
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
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

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