Phenylbeta-D-glucopyranoside

Phenyl b-D-glucopyranoside is a natural compound that is found in various plants. It inhibits the binding of an inhibitor to its substrate molecule by forming a covalent bond with the inhibitor through an ester linkage. Phenyl b-D-glucopyranoside has been shown to inhibit glucose transport and histochemical staining in rat liver tissues and has been used to study autoimmune diseases. Phenyl b-D-glucopyranoside is also used as a monoclonal antibody substrate molecule for tissue culture experiments. The analytical method for determining phenyl b-D-glucopyranoside's molecular weight is based on the ph of hydrolysis, which is optimum at pH 7.0. CAS Number 1464-44-4 Product Name Phenyl beta-D-glucopyranoside IUPAC Name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol Molecular Formula C12H16O6 Molecular Weight 256.25 g/mol InChI 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 SMILES C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O Synonyms phenyl beta-D-glucopyranoside, phenyl-beta-glucoside, phenylglucoside, phenylglucoside, (alpha-(D))-isomer, phenylglucoside, (alpha-(L))-isomer Canonical SMILES C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O Isomeric SMILES C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O CAS No: 1464-44-4 MDL No: MFCD00064089 Chemical Formula: C12H16O6 Molecular Weight: 256.25 COA: Product name : Phenyl-beta-D-glucopyranoside CAS: 1464-44-4 M.F. : C 12 H 16 O 6 M .W. : 256.25 Items Standards Results Appearance White crystal powder Complies Solubility Soluble in hot water, insoluble in ether Complies Identification IR and HPLC Complies Melting point 170 ? ~ 175 ?C 172 ? ~174 ? Specific rotation ( [?] 20/D , in H 2 O) -70 o ~ -74 o -72.5 o Any other impurity Max. 0.5% Complies Total impurity Max. 2% Complies Heavy metal Max. 20ppm Complies Residue on ignition Max. 0.5% 0.1% TLC One spot One spot Assay by HPLC Min. 98% 98.7% References: 1. Joniak D, Polakova M, J. Serb. Chem. Soc. 2001, Vol66, p81-86