4-nitrophenyl-alpha-D-glucopyranoside

4-Nitrophenyl a-D-glucopyranoside CAS No: 3767-28-0 MDL No: MFCD00064088 Chemical Formula: C12H15NO8 Molecular Weight: 301.25 4-Nitrophenyl-alpha-D-glucopyranoside is a chemical compound that belongs to the class of nitrophenols. It is an anti-infective agent and has been used as a substrate in vitro for the study of enzyme activities. 4-Nitrophenyl-alpha-D-glucopyranoside has been shown to inhibit the growth of colorectal adenocarcinoma cells, both in vivo and in vitro, at low concentrations. This compound also inhibits bacterial growth by blocking the synthesis of proteins and nucleic acids. When ingested, 4-Nitrophenyl-alpha-D-glucopyranoside can be hydrolyzed into nitrite, which is toxic to bacteria. CAS Number 3767-28-0 Product Name 4-Nitrophenyl alpha-D-glucopyranoside IUPAC Name (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol Molecular Formula C12H15NO8 Molecular Weight 301.25 g/mol InChI InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11-,12+/m1/s1 InChI Key IFBHRQDFSNCLOZ-ZIQFBCGOSA-N SMILES C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O Synonyms 4-nitrophenyl alpha-glucoside, 4-nitrophenyl-alpha-D-glucopyranoside, p-nitrophenyl alpha-D-glucopyranoside, p-nitrophenyl-alpha-D-glucopyranoside, p-nitrophenyl-glucopyranoside, para-nitrophenyl alpha-glucoside, PNP-alpha-Glu Canonical SMILES C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O Isomeric SMILES C1=CC(=CC=C1[N+](=O)[O-])O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O COA: Product name : 4-Nitrophenyl-alpha-D-glucopyranoside CAS: 3767-28-0 M.F. : C 12 H 15 NO 8 M .W. : 301.25 Batch No : 20120201 Quantity :28g Items Standards Results Appearance White crystal powder Complies Solubility Soluble in DMF, insoluble in ether Complies Identification IR and HPLC Complies Melting point 210 ? ~ 220?C 215 ? ~217 ? Specific rotation ( [?] 20/D , in H 2 O) 218 o ~ 220 o 218.5 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% 99.1% Substrate for the assay of a-glucosidases. References: 1. Halvorson H, Methods Enzymol. 1966, 8, 559-62