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28609

Sigma-Aldrich

Cholesterol β-D-glucoside

≥97% (TLC)

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Synonym(s):
Cholesteryl β-D-glucopyranoside
Empirical Formula (Hill Notation):
C33H56O6
CAS Number:
Molecular Weight:
548.79
MDL number:
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.25

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

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This Item
104477C9523D5394
Cholesterol β-D-glucoside ≥97% (TLC)

28609

Cholesterol β-D-glucoside

1-Thio-β-D-glucose tetraacetate 97%

104477

1-Thio-β-D-glucose tetraacetate

Sodium cholesteryl sulfate

C9523

Sodium cholesteryl sulfate

Decyl β-D-glucopyranoside ≥98% (GC)

D5394

Decyl β-D-glucopyranoside

form

solid

form

solid

form

powder

form

powder

optical activity

[α]/D -49.0±3.0°, c = 0.5 in pyridine

optical activity

[α]20/D +5.8°, c = 2.2 in chloroform

optical activity

-

optical activity

-

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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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Carbohydrate research, 345(17), 2438-2449 (2010-10-15)
Cholesterol amphiphiles containing positively charged groups (pyridinium, N-methylimidazolium, N-methylmorpholinium, and N-methylpiperidinium) linked via β-glucosyl spacer were prepared by alkylation of the corresponding bases with 6-О-mesyl-β-D-cholesteryl glucopyranoside. IC(50) values were in the range 20-35μM for the series of compounds and liposomal

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