(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol

• ChemBase ID: 155148
• Molecular Formular: C7H14O6
• Molecular Mass: 194.18246
• Monoisotopic Mass: 194.07903817
• SMILES: CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: CO[C@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4+,5+,6-,7+/m1/s1
• InChIKey: HOVAGTYPODGVJG-PZRMXXKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• IUPAC Traditional name: methyl α-galactoside
• Synonyms: Methyl α-D-galactoside; Methyl α-D-galactopyranoside; (2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol; 1-O-Methyl-α-D-galactopyranoside; Methyl α-Galactopyranoside; NSC 33684; Methyl α-D-Galactopyranoside

Database IDs

• CAS Number: 3396-99-4
• EC Number: 222-251-7
• MDL Number: MFCD00064085
• Beilstein Number: 81570
• PubChem SID: 24896637; 24885022; 162249286
• PubChem CID: 76935

CALCULATED PROPERTIES

• Acid pKa: 12.211393
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.2894127
• LogD (pH = 7.4): -2.2894194
• Log P: -2.2894127
• Molar Refractivity: 40.6746 cm^3
• Polarizability: 17.016506 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Clear Colourless Solution at 400 mg Plus 4 ml of Water
• Apperance: White Powder
• Melting Point: 116-117 °C(lit.); 79-101°C
• Optical Rotation: [α]20/D +169±3°, c = 1.5% in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); 95+%
• Grade: purum
• Impurities: ~8.5% water
• Empirical Formula (Hill Notation): C7H14O6

DETAILS

Toronto Research Chemicals - M305500

Methyl α-D-Galactopyranoside shows the most potent inhibitory activities toward the Debaryomyces hansenii UFV-1.

REFERENCES

• McCarter, J., et al.: Biochem. J., 286, 721 (1992)
• Namchuk, M., et al.: Biochemistry, 34, 16194 (1992)
• Viana, P., et al.: Food Chem., 103, 331 (1992)