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

• ChemBase ID: 154058
• Molecular Formular: C12H16O5S
• Molecular Mass: 272.31744
• Monoisotopic Mass: 272.07184461
• SMILES: c1ccc(cc1)S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Sc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H16O5S/c13-6-8-9(14)10(15)11(16)12(17-8)18-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12+/m1/s1
• InChIKey: OVLYAISOYPJBLU-ZIQFBCGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(phenylsulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(phenylsulfanyl)oxane-3,4,5-triol
• Synonyms: Phenyl β-D-thioglucoside; Phenyl 1-thio-β-D-glucopyranoside; Phenyl β-D-thioglucopyranoside

Database IDs

• CAS Number: 2936-70-1
• MDL Number: MFCD00064097
• PubChem SID: 162248197
• PubChem CID: 10934592

CALCULATED PROPERTIES

• Acid pKa: 12.466729
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.2005381
• LogD (pH = 7.4): -0.20054176
• Log P: -0.20053805
• Molar Refractivity: 66.72 cm^3
• Polarizability: 26.935785 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +48.5±2.0°, c = 1 in ethanol

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Impurities: 11.1-12.4% sulfur content
• Empirical Formula (Hill Notation): C12H16O5S

DETAILS

Sigma Aldrich - 04846

Application
Inhibition studies of a broad-specificity β-D-glucosidase2
Biochem/physiol Actions
Phenyl β-D-thioglucopyranoside was shown to inhibit the activity of sodium-D-glucose cotransporter (SGLT) 1 and 2 by a competitive inhibition mechanism. Phenyl β-D-thioglucopyranoside had a stronger inhibitory effect on SGLT2 than 1. 1