(2S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

• ChemBase ID: 177978
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: [C@@H]1([C@@H](C([C@@](OC1)(CO)O)O)O)O
• Canonical SMILES: OC[C@]1(O)OC[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5?,6+/m1/s1
• InChIKey: LKDRXBCSQODPBY-JTSAIASGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
• IUPAC Traditional name: (2S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
• Synonyms: D-lyxo-2-Hexulose; D-Tagatose

Database IDs

• CAS Number: 87-81-0
• PubChem SID: 164233888
• PubChem CID: 71752285

CALCULATED PROPERTIES

• Acid pKa: 10.291031
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.7580063
• LogD (pH = 7.4): -2.7585566
• Log P: -2.7579994
• Molar Refractivity: 36.3608 cm^3
• Polarizability: 15.155883 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T004850

A monosaccharide (hexose) that can be used as a low-calorie sweetener, as an intermediate for synthesis of other optically active compounds, and as an additive in detergent, cosmetic, and pharmaceutical formulation.

REFERENCES

• Oh, D. et al.: Appl. Microbiol. Biotech., 76, 76, 1 (2007)
• Lu, Y. et al.: Int. J. Cosm. Sci., 24, 225 (2007)
• Donner, T.W. et al.: Diab. Obes. Metab., 1, 285 (2007)