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C2800

Sigma-Aldrich

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
EC Number:
251-781-1
MDL number:
MFCD00021140
UNSPSC Code:
12352211
PubChem Substance ID:
24892533
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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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 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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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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