(2R,3S,5S)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

• ChemBase ID: 160666
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: [C@H]1([C@@H](C([C@@H]2OC1CO2)O)O)O
• Canonical SMILES: O[C@H]1[C@@H](O)C2CO[C@H](C1O)O2
• InChI: InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2?,3-,4-,5?,6-/m0/s1
• InChIKey: TWNIBLMWSKIRAT-DTUOTYQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5S)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• IUPAC Traditional name: (2R,3S,5S)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• Synonyms: 6,8-Dioxa-bicyclo[3.2.1]octane-2,3,4-triol; 1,6-Αnhydro-β-D-galactopyranose; D-Galactosan; Levogalactosan; 1,6-Anhydro-β-D-galactose

Database IDs

• CAS Number: 644-76-8
• PubChem SID: 162254801
• PubChem CID: 45038169

CALCULATED PROPERTIES

• Acid pKa: 12.212605
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.7708358
• LogD (pH = 7.4): -1.7708423
• Log P: -1.7708356
• Molar Refractivity: 32.4133 cm^3
• Polarizability: 13.814454 Å^3
• Polar Surface Area: 79.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Light Beige to Pale Yellow Solid
• Melting Point: 167-169°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A641000

1,6-Anhydro-β-D-glucopyranose is a carbohydrate contains in liquid smoke flavorings.

REFERENCES

• Kim, K., et al.: Agric. Biol. Chem., 38, 53 (1974)
• Guillen, M., et al.: Food Chem., 58, 97 (1974)
• Guillen, M., et al.: J. Agric. Food Chem., 46, 1276 (1974)