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292710

Sigma-Aldrich

Phenyl β-D-glucopyranoside

≥95.0%

Synonym(s):

Phenyl beta-D-glucoside

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About This Item

Empirical Formula (Hill Notation):
C12H16O6
CAS Number:
1464-44-4
Molecular Weight:
256.25
Beilstein/REAXYS Number:
87517
EC Number:
215-978-6
MDL number:
MFCD00064089
UNSPSC Code:
12352201
PubChem Substance ID:
24857607
NACRES:
NA.22

assay

≥95.0%

form

powder

optical activity

[α]25/D −70°, c = 1 in H2O

mp

176-178 °C (lit.)

SMILES string

OC[C@H]1O[C@@H](Oc2ccccc2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1

InChI key

NEZJDVYDSZTRFS-RMPHRYRLSA-N

Application

Phenyl β-D-glucopyranoside can be used:
  • As a starting material for the synthesis of various derivatives of β-D-glucopyranosides with potential application as anti-HIV agents.
  • As a model for glycosides in the gas phase for their spectroscopic investigation.
  • As an internal standard in GC and GC-MS quantitative analyses.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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4-(Arylamino)phenyl alpha-D-glucopyranosides as potential anti-HIV agents.
J C Briggs et al.
Carbohydrate research, 282(2), 293-298 (1996-03-18)
Sugars in the gas phase: the spectroscopy and structure of jet-cooled phenyl ?-D-glucopyranoside.
Talbot FO and Simons JP
Physical Chemistry Chemical Physics, 4(15), 3562-3565 (2002)
Ying Na et al.
Bioorganic chemistry, 39(3), 111-113 (2011-03-26)
The spontaneous hydrolysis of glycosylamines, where the aglycone is either a primary amine or ammonia, is over a hundred million-times faster than that of O- or S-glycosides. The reason for this (as pointed out by Capon and Connett in 1965)
Chunyan Bao et al.
Carbohydrate research, 339(7), 1311-1316 (2004-04-29)
A new hydrogel based on a substituted phenyl glucoside with a Schiff base in the aglycon was synthesized, and the self-assembling characteristics was studied. FTIR spectra, UV-vis absorption spectra and X-ray diffraction (XRD) revealed that pi-pi interactions between the Schiff
Udayanath Aich et al.
Carbohydrate research, 341(1), 19-28 (2005-11-26)
Reported is an attractive and environmentally friendly method for the synthesis of the title compounds in moderate yield using inexpensive 1,2,3,4,6-penta-O-acetyl-beta-D-gluco- and galactopyranoses as sugar donors, five different phenols as acceptors and H-beta zeolite as the catalyst. The yield (23-28%)
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