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C79409

Sigma-Aldrich

Cholesteryl stearate

96%

Synonym(s):

5-Cholesten-3β-yl octadecanoate

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About This Item

Empirical Formula (Hill Notation):
C45H80O2
CAS Number:
35602-69-8
Molecular Weight:
653.12
Beilstein:
2068492
EC Number:
252-637-0
MDL number:
MFCD00003639
UNSPSC Code:
12352108
PubChem Substance ID:
24892584
NACRES:
NA.22

Quality Level

100

Assay

96%

form

powder

optical activity

[α]25/D −21°, c = 2 in chloroform

mp

79-83 °C (lit.)

transition temp

cholesteric phase to smectic phase 75.5 °C
isotropic phase to cholesteric phase 79.5 °C
crystalline phase to isotropic phase 83 °C

SMILES string

CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C

InChI

1S/C45H80O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h26,35-36,38-42H,7-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1

InChI key

XHRPOTDGOASDJS-XNTGVSEISA-N

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General description

Cholesteryl stearate is a stearic acid ester of cholesterol. In solid-state, its autoxidation is higher than its free form.

Application

It can be used as a reference standard during the determination of tocopherols and sterols in vegetable oils by GC.

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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Determination of tocopherols and sterols in vegetable oils by solid-phase extraction and subsequent capillary gas chromatographic analysis.
Lechner M, et al.
Journal of Chromatography A, 857(1), 231-238 (1999)
Autoxidation of cholesterol fatty acid esters in solid state and aqueous dispersion.
Korahani V, et al.
Lipids, 17(10), 703-708 (1982)
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Journal of structural biology, 139(2), 122-135 (2002-10-31)
The Vibrio cholerae cytolysin (VCC) 63-kDa monomer has been shown to interact in aqueous suspension with cholesterol microcystals to produce a ring/pore-like heptameric oligomer approximately 8 nm in outer diameter. Transmission electron microscopy data were produced from cholesterol samples adsorbed
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Articles

Cholesterol Esterification

Cholesterol undergoes esterification to improve transport. Cholesterol esters are more easily packaged into the interior of lipoproteins - increasing the quantity that can be readily transported in the blood stream.

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