28609
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:
Molecular Weight:
548.79
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.25
MDL number:
Quality Level
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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