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

• ChemBase编号: 154058
• 分子式: C12H16O5S
• 平均质量: 272.31744
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(phenylsulfanyl)oxane-3,4,5-triol
• IUPAC传统名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(phenylsulfanyl)oxane-3,4,5-triol
• 别名: Phenyl β-D-thioglucoside; Phenyl 1-thio-β-D-glucopyranoside; Phenyl β-D-thioglucopyranoside

登记号

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

理论计算性质

• Acid pKa: 12.466729
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -0.2005381
• LogD (pH = 7.4): -0.20054176
• Log P: -0.20053805
• 摩尔折射率: 66.72 cm^3
• 极化性: 26.935785 Å^3
• 极化表面积: 90.15 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 比旋光度: [α]/D +48.5±2.0°, c = 1 in ethanol

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

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

详细说明

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