2-(4-aminophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 133569
• Molecular Formular: C12H17NO6
• Molecular Mass: 271.26648
• Monoisotopic Mass: 271.10558727
• SMILES: c1cc(ccc1N)OC1C(C(C(C(O1)CO)O)O)O
• Canonical SMILES: OCC1OC(Oc2ccc(cc2)N)C(C(C1O)O)O
• 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
• InChIKey: MIAKOEWBCMPCQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-aminophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: glucopyranoside,4-aminophenyl
• Synonyms: 4-Aminophenyl α-D-mannopyranoside; 4-Aminophenyl β-D-galactopyranoside; 4-Aminophenyl β-D-glucopyranoside

Database IDs

• CAS Number: 5094-33-7; 34213-86-0; 20818-25-1
• MDL Number: MFCD00067362; MFCD00067365; MFCD00067366
• PubChem SID: 24890539; 24891470; 162227846; 24890520
• PubChem CID: 1685

CALCULATED PROPERTIES

• Acid pKa: 12.200142
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.4968417
• LogD (pH = 7.4): -1.4282696
• Log P: -1.4273136
• Molar Refractivity: 64.8837 cm^3
• Polarizability: 25.775139 Å^3
• Polar Surface Area: 125.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C12H17NO6

DETAILS

Sigma Aldrich - A1269

Application
P-Aminophenyl β-D-glucopyranoside is used to create derivitized agarose beads useful for the analysis of the surfaces of cancer cells. 4-Aminophenyl β-D-glucopyranoside is used to derivatize biocompatible single-crystalline gold tabular nanoparticles, nanoprisms (NPRs) to improve their stability and cellular uptake.

Sigma Aldrich - A9545

Application
4-Aminophenyl β-D-galactopyranoside (PAPG) is used as a substrate for the detection, identification, differentiation and characterization of β-galactosidase(s) using electrochemical detection methods..

Sigma Aldrich - A1394

Application
4-Aminophenyl α-D-mannopyranoside is used to modify the surface of liposomes to increase uptake kinetics.