Skip to Content
Merck
All Photos(2)

Documents

292710

Sigma-Aldrich

Phenyl β-D-glucopyranoside

≥95.0%

Synonym(s):

Phenyl beta-D-glucoside

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C12H16O6
CAS Number:
1464-44-4
Molecular Weight:
256.25
Beilstein:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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%)
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)
Synthesis of peptidomimetics based on iminosugar and ?-d-glucopyranoside scaffolds and inhibiton of HIV-protease.
Chery F, et al.
Tetrahedron, 60(31), 6597-6608 (2004)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service