(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol

• ChemBase ID: 102883
• Molecular Formular: C12H16O6
• Molecular Mass: 256.25184
• Monoisotopic Mass: 256.09468823
• SMILES: O(c1ccccc1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
• 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
• InChIKey: NEZJDVYDSZTRFS-RMPHRYRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
• IUPAC Traditional name: phenyl β-D-glucoside
• Synonyms: Phenyl-β-D-glucopyranoside; PHENYL-β-D-GLUCOSIDE; Phenyl β-D-glucopyranoside; 苯基-β-D-吡喃葡萄糖苷

Database IDs

• CAS Number: 1464-44-4
• EC Number: 215-978-6
• MDL Number: MFCD00064089
• Beilstein Number: 87517
• PubChem SID: 24887323; 162089082; 24857607
• PubChem CID: 65080

CALCULATED PROPERTIES

• Acid pKa: 12.200142
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.59838766
• LogD (pH = 7.4): -0.59839445
• Log P: -0.5983876
• Molar Refractivity: 60.1833 cm^3
• Polarizability: 24.608507 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 174-176 °C; 176-178 °C(lit.)
• Optical Rotation: [α]20/D -73±2°, c = 1% in H2O; [α]25/D -70°, c = 1 in H2O

Safety Information

• Storage Condition: 0°C
• RTECS: LZ5985510
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); 97%
• Empirical Formula (Hill Notation): C12H16O6

DETAILS

MP Biomedicals - 02104894

Crystalline
Substrate for β-glucosidase.

Sigma Aldrich - 292710

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 78554

Other Notes
Substrate for β-D-glucosidase1