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

• ChemBase ID: 153974
• Molecular Formular: C8H16O5S
• Molecular Mass: 224.27464
• Monoisotopic Mass: 224.07184461
• SMILES: CCS[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: CCS[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C8H16O5S/c1-2-14-8-7(12)6(11)5(10)4(3-9)13-8/h4-12H,2-3H2,1H3/t4-,5+,6+,7-,8+/m1/s1
• InChIKey: CHAHFVCHPSPXOE-HNEXDWKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-(ethylsulfanyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-2-(ethylsulfanyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Ethyl β-D-thiogalactoside; Ethyl-1-thio-β-D-Gal; Ethyl-1-thio-β-D-galactopyranoside; Ethyl-β-D-thiogalactopyranoside; Ethyl 1-Thio-β-D-galactopyranoside; Ethyl 1-Deoxy-1-thio-β-D-galactopyranoside; Ethyl β-D-Thiogalactopyranoside

Database IDs

• CAS Number: 56245-60-4
• MDL Number: MFCD00798395
• PubChem SID: 162248113
• PubChem CID: 10466198

CALCULATED PROPERTIES

• Acid pKa: 12.482076
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.3253915
• LogD (pH = 7.4): -1.3253951
• Log P: -1.3253915
• Molar Refractivity: 51.5926 cm^3
• Polarizability: 21.124384 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Crystalline Solid
• Melting Point: 119-120°C

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: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C8H16O5S

DETAILS

Sigma Aldrich - 92320

Application
Ethyl-β-D-thiogalactopyranoside is a derivitized thiogalactopyranoside structurally related to the gene expression inducer isopropyl-1-thio-β-D-galactopyranoside (IPTG).