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28609

Sigma-Aldrich

Cholesterol β-D-glucoside

≥97% (TLC)

Synonym(s):

Cholesteryl β-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C33H56O6
CAS Number:
7073-61-2
Molecular Weight:
548.79
MDL number:
MFCD00273002
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
329753275
NACRES:
NA.25

Quality Level

100

Assay

≥97% (TLC)

form

solid

optical activity

[α]/D -49.0±3.0°, c = 0.5 in pyridine

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O

InChI

1S/C33H56O6/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(13-15-32(21,4)26(23)14-16-33(24,25)5)38-31-30(37)29(36)28(35)27(18-34)39-31/h9,19-20,22-31,34-37H,6-8,10-18H2,1-5H3/t20-,22+,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33-/m1/s1

InChI key

FSMCJUNYLQOAIM-UQBZCTSOSA-N

Biochem/physiol Actions

A lipid mediator in heat stress responses in animals, shows anti-ulcer effect.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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A possible mechanism of cholesteryl glucoside formation involved in heat shock response in the animal cell membrane.
Akiyama, H., et al.
Cytologia, 76, 19-25 (2011)
M Shimamura et al.
Current medicinal chemistry, 19(28), 4869-4874 (2012-09-01)
Steryl glycosides are derivatives of sterols where the 3β-hydroxy group is glycosylated. Some of them are further converted to steryl O-acyl glycosides. Steryl glycosides and their derivatives are widely distributed in plants, algae, and fungi, but are relatively rarely distributed
Shohko Kunimoto et al.
Cell structure and function, 28(3), 179-186 (2003-09-03)
The cytoprotective effect of heat shock proteins (HSPs) promises new therapeutic modalities for medical treatment. We examined the anti-ulcer effect of cholesteryl glucoside (1-O-cholesteryl-beta-D-glucopyranoside, CG) on cold-restraint stress-induced gastric ulcer in rats, in terms of its correlative ability to activate
B Steinbrueckner et al.
FEMS microbiology letters, 168(2), 209-212 (1998-12-03)
Helicobacter pullorum and Campylobacter lari are rarely isolated from humans with acute enteritis. Hitherto the two species could only be identified by genotypic techniques. Gas liquid chromatography of whole cell fatty acid extracts is described as the first phenotypic method
Yoshio Hirabayashi
Proceedings of the Japan Academy. Series B, Physical and biological sciences, 88(4), 129-143 (2012-04-14)
Glycosphingolipids (GSLs) are present on cell surface membranes and are particularly abundant in the brain. Since over 300-400 GSLs are synthesized from glucosylceramide (GlcCer), GlcCer is believed to only serve as the source of most GSLs, including sialic acid-containing GSLs
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