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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:
Molecular Weight:
653.12
Beilstein:
2068492
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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Autoxidation of cholesterol fatty acid esters in solid state and aqueous dispersion.
Korahani V, et al.
Lipids, 17(10), 703-708 (1982)
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)
Haiyang Feng et al.
Chemical biology & drug design, 90(5), 867-872 (2017-04-23)
In this study, rhein-SLNs were successfully produced by hot homogenization followed by ultrasonication. Precirol ATO5 in which rhein exhibited higher partition coefficient was selected for preparation of SLNs. In the dynamic light scattering, the rhein-SLNs showed a smaller size with
M Cabeza et al.
Proceedings of the Western Pharmacology Society, 40, 87-89 (1997-01-01)
We demonstrated for the first time that progesterone and 5 alpha-dihydroprogesterone stimulate [U-14C]glucose incorporation into lipids in gonadectomized female hamster flanking organs. We also found that cholesterol stearate is the major lipid synthesized female hamster flanking organs under progesterone and
J Robin Harris et al.
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

Articles

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

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