4-Aminophenylbeta-D-glucopyranoside

4-Aminophenyl b-D-glucopyranoside 4-Aminophenyl b-D-glucopyranoside is a membrane transport inhibitor that prevents the uptake of glucose by inhibiting the enzyme hexose transporter. It is used in biological treatment and has been shown to be effective against glutamicum. 4-Aminophenyl b-D-glucopyranoside can also be used in assays to identify bacteria based on their surface antigens. This compound was isolated from corynebacterium glutamicum and its metabolic pathway has been elucidated. 4-Aminophenyl b-D-glucopyranoside has also been shown to inhibit enzymatic activity, which may be due to inhibition of the enzyme dihydroorotate dehydrogenase. CAS Number 20818-25-1 Product Name (2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol IUPAC Name (2S,3R,4S,5S,6R)-2-(4-aminophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol Molecular Formula C12H17NO6 Molecular Weight 271.27 g/mol InChI InChI=1S/C12H17NO6/c13-6-1-3-7(4-2-6)18-12-11(17)10(16)9(15)8(5-14)19-12/h1-4,8-12,14-17H,5,13H2/t8-,9-,10+,11-,12-/m1/s1 InChI Key MIAKOEWBCMPCQR-RMPHRYRLSA-N SMILES C1=CC(=CC=C1N)OC2C(C(C(C(O2)CO)O)O)O Synonyms 4-aminophenyl glucoside, 4-aminophenyl glucoside, (alpha-D)-isomer, 4-aminophenyl-beta-D-glucopyranoside, p-aminophenyl-beta-D-glucoside, PAPB-DG Canonical SMILES C1=CC(=CC=C1N)OC2C(C(C(C(O2)CO)O)O)O Isomeric SMILES C1=CC(=CC=C1N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O CAS No: 20818-25-1 MDL No: MFCD00067365 Chemical Formula: C12H17NO6 Molecular Weight: 271.27 COA: Name : 4-Aminophenyl ?-D-glucopyranoside CAS : 20818-25-1 M.F. : C 12 H 17 NO 6 M .W. : 271.27 Items Standards Results Appearance White or slightly yellowish crystalline power Positive Solubility Soluble in water and insoluble in ether Positive NMR and MS Should comply Complies Identification IR and TLC Positive M.P. 150 ? ~ 160 ? 155 ? ~158 ? [a] D [in H 2 O] -54 o ~ -66 o -55.2 o Loss Weight On Dryness Max. 1% Complies Alpha-Isomer Max. 0.5% 0 TLC (15%H 2 SO 4 -C 2 H 5 OH) One spot Complies Assay Min. 98% 99.2% References: 1. Lee W-C, Hsiao C-C, Chu R, Russ. J. Chem. Tech. Biotech. 4, 1, p66