(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hexanal

• ChemBase ID: 154042
• Molecular Formular: C12H22O10S
• Molecular Mass: 358.36208
• Monoisotopic Mass: 358.0933679
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)S[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)S[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C12H22O10S/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9-,10+,11+,12-/m0/s1
• InChIKey: VMEDEPBFFWJMMG-WELRSGGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hexanal
• IUPAC Traditional name: (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}hexanal
• Synonyms: 4-S-β-D-glucopyranosyl-4-thio-D-glucose; Thiocellobiose

Database IDs

• CAS Number: 80951-92-4
• MDL Number: MFCD00270082
• PubChem SID: 162248181
• PubChem CID: 196179

CALCULATED PROPERTIES

• Acid pKa: 12.069791
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -5.0280657
• LogD (pH = 7.4): -5.0280747
• Log P: -5.028065
• Molar Refractivity: 76.1097 cm^3
• Polarizability: 31.344275 Å^3
• Polar Surface Area: 188.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C12H22O10S

DETAILS

Sigma Aldrich - 19608

Application
Thiocellobiose is a glucose disaccharide linked via a β(1-4) thioether bond. Thiocellobiose is a cellulase inducer and inhibitor useful to identify, differentiate and characterize cellobiose-active β-glucosidase(s). Thiocellobiose is also used as a substrate to identify, differentiate and characterize cellobiose dehydrogenase(s).