(3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol

• ChemBase ID: 134096
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2OC(O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11?,12-/m1/s1
• InChIKey: DLRVVLDZNNYCBX-CQUJWQHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
• IUPAC Traditional name: gentobiose
• Synonyms: 6-O-β-D-Glucopyranosyl-D-glucose; Amygdalose; β-Gentiobiose

Database IDs

• CAS Number: 554-91-6
• EC Number: 209-074-0
• MDL Number: MFCD00198056
• Beilstein Number: 93354
• PubChem SID: 24895110; 162228373
• PubChem CID: 5460026

CALCULATED PROPERTIES

• Acid pKa: 11.2481985
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.703376
• LogD (pH = 7.4): -4.7034364
• Log P: -4.703375
• Molar Refractivity: 68.3367 cm^3
• Polarizability: 28.969793 Å^3
• Polar Surface Area: 189.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 195-197 °C (dec.)
• Optical Rotation: [α]20/D +9.5±1°, c = 2% in H2O

Safety Information

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

Product Information

• Purity: ≥85% (remainder primarily α-anomer); ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C12H22O11