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

• ChemBase ID: 134130
• Molecular Formular: C12H16O6
• Molecular Mass: 256.25184
• Monoisotopic Mass: 256.09468823
• SMILES: c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• 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-YBXAARCKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
• IUPAC Traditional name: phenylgalactoside
• Synonyms: P-Gal; Phenyl-β-D-galactopyranoside; Phenyl beta-D-galactopyranoside; Phenyl β-D-galactoside; Phenyl β-D-galactopyranoside; 苯基-β-D-半乳糖苷; 苯基±-D-呋喃乳糖苷; 苯基-β-D-呋喃乳糖苷

Database IDs

• CAS Number: 2818-58-8
• EC Number: 220-573-2
• MDL Number: MFCD00063258
• Beilstein Number: 87518
• PubChem SID: 162228407; 24887322; 24898771
• PubChem CID: 102336

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: ~150 °C; 152-156°C; 153-155 °C(lit.)
• Optical Rotation: [α]20/D -42±2°, c = 2.3% in H2O; [α]25/D -40°, c = 2.3 in H2O; -42 (c=2 in water)

Safety Information

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

Product Information

• Purity: ≥98% (TLC); ≥99.0% (HPLC); 98%; 99%
• Empirical Formula (Hill Notation): C12H16O6

DETAILS

Sigma Aldrich - P6501

包装
1, 5 g in poly bottle
Substrates
Noninducing β-galactosidase substrate.
Application
Phenyl-β-D-galactopyranoside is used as a substrate for detecting beta-galactosidase enzymatic activity.

Sigma Aldrich - 78552

Other Notes
Acceptor substrate in fucosyltransferase detection1