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Merck
CN

C2800

Cholesteryl phenylacetate

≥98% (HPLC; detection at 258 nm)

Synonym(s):

3β-Hydroxy-5-cholestene 3-phenylacetate, 5-Cholesten-3β-ol 3-phenylacetate

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About This Item

Empirical Formula (Hill Notation):
C35H52O2
CAS Number:
33998-26-4
Molecular Weight:
504.79
NACRES:
NA.77
PubChem Substance ID:
24892533
UNSPSC Code:
12352211
EC Number:
251-781-1
MDL number:
MFCD00021140

Key Documents

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Product Name

Cholesteryl phenylacetate, ≥98% (HPLC; detection at 258 nm)

InChI key

JHFRODPXYCPTCM-ZTUKSAGPSA-N

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

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

biological source

synthetic (organic)

assay

≥98% (HPLC; detection at 258 nm)

form

crystalline powder

functional group

ester

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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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

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
0000493577
0000493577
0000402680
0000382686
0000382686

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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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