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

• ChemBase ID: 172540
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: O1[C@H](O[C@@H]2C(O[C@H]([C@H](O)C2O)O)CO)[C@H](O)C([C@@H](C1CO)O)O
• Canonical SMILES: OCC1O[C@@H](O)[C@@H](C([C@@H]1O[C@H]1OC(CO)[C@H](C([C@H]1O)O)O)O)O
• InChI: InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3?,4?,5-,6?,7?,8-,9-,10-,11-,12-/m1/s1
• InChIKey: GUBGYTABKSRVRQ-BEQFSKIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5R,6R)-2-(hydroxymethyl)-6-{[(3S,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
• IUPAC Traditional name: (3S,5R,6R)-2-(hydroxymethyl)-6-{[(3S,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
• Synonyms: 4-O-α-D-Mannopyranosyl-D-mannopyrannose; α-D-Man-[1-4]D-man; 4-O-α-Mannobiose; Man-α-1,4-Man; 4-O-α-D-Mannopyranosyl-D-mannose

Database IDs

• CAS Number: 35438-40-5
• PubChem SID: 164228450
• PubChem CID: 45039681

CALCULATED PROPERTIES

• Acid pKa: 11.2543745
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.703376
• LogD (pH = 7.4): -4.7034354
• 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

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 105-108°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M166345

4-O-α-D-Mannopyranosyl-D-mannose is used in the preparation of immunostimulants, useful as materials for foods as well.

REFERENCES

• Imamura, L., et al.: Biol. Pharm. Bull., 17, 596 (1994)
• ,Perrin, S., et al.: J. Appl. Microbiol., 90, 859 (1994)
• Olano-Martin, E., et al.: J. Appl. Microbiol., 93, 505 (1994)
• Gibson, G., et al.: J. Food Sci., 69, 141 (1994)