(2R,4S,5S)-2-[(1,3-dihydroxypropan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 169678
• Molecular Formular: C9H18O8
• Molecular Mass: 254.23442
• Monoisotopic Mass: 254.10016754
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)OC(CO)CO)O)O)O
• Canonical SMILES: OCC(O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)CO
• InChI: InChI=1S/C9H18O8/c10-1-4(2-11)16-9-8(15)7(14)6(13)5(3-12)17-9/h4-15H,1-3H2/t5?,6-,7+,8?,9-/m1/s1
• InChIKey: AQTKXCPRNZDOJU-WUSGRAFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5S)-2-[(1,3-dihydroxypropan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5S)-2-[(1,3-dihydroxypropan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 2-Hydroxy-1-(hydroxymethyl)ethyl-β-D-glucopyranoside; β-D-2-Hydroxy-1-(hydroxymethyl)ethyl Glucopyranoside; Lilioside B; β-Glucosylglycerol; 2-(β-Glucosyl)glycerol

Database IDs

• CAS Number: 10588-30-4
• PubChem SID: 162263810
• PubChem CID: 70640512

CALCULATED PROPERTIES

• Acid pKa: 12.2067995
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.6098497
• LogD (pH = 7.4): -3.6098564
• Log P: -3.6098497
• Molar Refractivity: 52.9294 cm^3
• Polarizability: 22.045732 Å^3
• Polar Surface Area: 139.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - G596825

A component contained in cosmetic formulation. Diesters of glycosylglycerols are active in cancer chemo-prevention.

REFERENCES

• Joyard, J., et al.: Eur. J. Biochem., 199, 489 (1991)
• Colombo, D., et al.: Bioorg. Med. Chem. Lett., 6, 1187 (1991)
• Colombo, D., et al.: Bioorg. Med. Chem., 7, 1867 (1991)
• Colombo, D., et al.: Cancer Lett., 161, 201 (1991)