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97617

Sigma-Aldrich

Cholesterol α-D-glucoside

≥98% (TLC)

Synonym(s):

αCG, Cholesteryl α-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C33H56O6
CAS Number:
40653-08-5
Molecular Weight:
548.79
UNSPSC Code:
12352211
PubChem Substance ID:
329770549

assay

≥98% (TLC)

form

powder

optical activity

[α]/D 67.0±3.0°, c = 1 in pyridine

suitability

conforms to structure for Infrared spectrum

SMILES string

O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H](C2)CC[C@@]3(C)C2=CC[C@]4([H])[C@]3([H])CC[C@@]5(C)[C@@]4([H])CC[C@@]5([C@H](C)CCCC(C)C)[H]

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-QIFAGWPJSA-N

Biochem/physiol Actions

Cholesteryl α-glucoside plays a critical role in H. pylori-mediated gastric inflammation and precancerous atrophic gastritis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
STBF1081V

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Yuki Ito et al.
PloS one, 8(12), e78191-e78191 (2013-12-07)
Approximately 10-15% of individuals infected with Helicobacter pylori will develop ulcer disease (gastric or duodenal ulcer), while most people infected with H. pylori will be asymptomatic. The majority of infected individuals remain asymptomatic partly due to the inhibition of synthesis
Hitomi Hoshino et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 59(1), 98-105 (2010-09-30)
Helicobacter pylori (H. pylori) is the causative pathogen underlying gastric diseases such as chronic gastritis and gastric cancer. Previously, the authors revealed that α1,4-linked N-acetylglucosamine-capped O-glycan (αGlcNAc) found in gland mucin suppresses H. pylori growth and motility by inhibiting catalytic
Masatomo Kawakubo et al.
Science (New York, N.Y.), 305(5686), 1003-1006 (2004-08-18)
Helicobacter pylori infects the stomachs of nearly a half the human population, yet most infected individuals remain asymptomatic, which suggests that there is a host defense against this bacterium. Because H. pylori is rarely found in deeper portions of the
Y Hirai et al.
Journal of bacteriology, 177(18), 5327-5333 (1995-09-01)
A chloroform-methanol-extracted lipid of Helicobacter pylori was studied. Three kinds of glycolipids, accounting for about 25% (wt/wt) of the total lipid, were detected and identified to be cholesteryl glucosides. The structures of two of them were determined to be cholesteryl-alpha-D-glucopyranoside
Christian Wunder et al.
Nature medicine, 12(9), 1030-1038 (2006-09-05)
Helicobacter pylori infection causes gastric pathology such as ulcer and carcinoma. Because H. pylori is auxotrophic for cholesterol, we have explored the assimilation of cholesterol by H. pylori in infection. Here we show that H. pylori follows a cholesterol gradient
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