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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)

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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Michio Shimamura
Archivum immunologiae et therapiae experimentalis, 60(5), 351-359 (2012-09-01)
Steryl glycosides, sterols glycosylated at the 3β-hydroxy group, have been widely found in plants, algae, and fungi, but are rare in bacteria and animals. Glycosylation of sterols is known to modify properties of the cell membrane and confer resistance against
Hung-Jung Wang et al.
Molecular microbiology, 83(1), 67-84 (2011-11-08)
Helicobacter pylori infection is an aetiological cause of gastric disorders worldwide. H. pylori has been shown to assimilate and convert host cholesterol into cholesteryl glucosides (CGs) by cholesterol-α-glucosyltransferase encoded by capJ. Here, we show that CapJ-deficient (ΔcapJ) H. pylori resulted
W Abraham et al.
Journal of lipid research, 28(4), 446-449 (1987-04-01)
The structures of two classes of glycolipids, acylglucosylsterol and glucosylsterol, from snake epidermis have been determined by chemical, spectroscopic, and gas-liquid chromatographic methods. The acylglucosylsterol consists of a glucose molecule attached to cholesterol and an ester-linked fatty acid on carbon
Alexander Panov et al.
The Journal of membrane biology, 237(2-3), 71-77 (2010-10-13)
The cluster of neurodegenerative disorders in the western Pacific termed amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC) has been repeatedly linked to the use of seeds of various species of cycad. Identification and chemical synthesis of the most toxic compounds in
Ryan A Davis et al.
Chemical communications (Cambridge, England), 48(72), 9083-9085 (2012-08-03)
In a three-step protocol involving regioselective enzymatic acylation, per-O-trimethylsilylation, and a one-pot α-glycosidation-deprotection sequence, cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside (α-CAG) of Helicobacter pylori is afforded starting from glucose in an overall yield of 45%. The production of CAG can be scaled to make purified
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