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C2800

Sigma-Aldrich

Cholesteryl phenylacetate

≥98% (HPLC; detection at 258 nm)

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Synonym(s):
3β-Hydroxy-5-cholestene 3-phenylacetate, 5-Cholesten-3β-ol 3-phenylacetate
Empirical Formula (Hill Notation):
C35H52O2
CAS Number:
Molecular Weight:
504.79
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (HPLC; detection at 258 nm)

form

crystalline powder

functional group

ester

shipped in

ambient

storage temp.

−20°C

SMILES string

O=C(O[C@@H]1CC2=CC[C@]3([H])[C@@](CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C)C)([H])[C@@]2(C)CC1)CC5=CC=CC=C5

InChI

1S/C35H52O2/c1-24(2)10-9-11-25(3)30-16-17-31-29-15-14-27-23-28(37-33(36)22-26-12-7-6-8-13-26)18-20-34(27,4)32(29)19-21-35(30,31)5/h6-8,12-14,24-25,28-32H,9-11,15-23H2,1-5H3/t25-,28?,29?,30?,31?,32?,34?,35?/m1/s1

InChI key

JHFRODPXYCPTCM-ZTUKSAGPSA-N

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Show Differences

1 of 4

This Item
C9253C0289C6013
vibrant-m

C2800

Cholesteryl phenylacetate

vibrant-m

C9253

Cholesteryl oleate

vibrant-m

C0289

Cholesteryl linoleate

vibrant-m

C6013

Cholesteryl hemisuccinate tris salt

assay

≥98% (HPLC; detection at 258 nm)

assay

≥98% (HPLC; detection at 205 nm)

assay

≥98% (HPLC; detection at 205 nm)

assay

≥98% (TLC)

functional group

ester

functional group

ester

functional group

ester

functional group

ester

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

form

crystalline powder

form

powder

form

powder

form

powder

Biochem/physiol Actions

Cholesteryl phenylacetate 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.

Preparation Note

Cholesteryl phenylacetate yields clear, colorless solution in chloroform at 50 mg/ml.

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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Pieter H E Groot et al.
Journal of lipid research, 46(10), 2182-2191 (2005-07-19)
Liver X receptor (LXR) nuclear receptors regulate the expression of genes involved in whole body cholesterol trafficking, including absorption, excretion, catabolism, and cellular efflux, and possess both anti-inflammatory and antidiabetic actions. Accordingly, LXR is considered an appealing drug target for
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
Replacement of endogenous cholesteryl esters of low density lipoprotein with exogenous cholesteryl linoleate. Reconstitution of a biologically active lipoprotein particle.
M Krieger et al.
The Journal of biological chemistry, 253(12), 4093-4101 (1978-06-25)

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