alpha-Methylglucoside

Title: a-Methylglucoside
CAS Registry Number: 97-30-3
CAS Name: Methyl-a-D-glucopyranoside
Molecular Formula: C7H14O6
Molecular Weight: 194.18
Percent Composition: C 43.30%, H 7.27%, O 49.44%
Literature References: Prepd by refluxing finely powdered glucose with methanol-HCl: Fischer, Ber. 26, 2405; 27, 2987; 28, 1151 (1895); Helferich, Schäfer, Org. Synth. coll. vol. I, (2nd ed., 1941) 364. Enzymatic synthesis by means of a-glucosidase from yeast: Bourquelot et al., Compt. Rend. 156, 491 (1913). Prepd industrially by reacting glucose with methanol in the presence of a cation exchange material: Chem. Eng. News 33, 4592 (1955). Monograph: G. N. Bollenback, Methyl Glucoside, Preparation, Physical Constants, Derivatives (Academic Press, New York, 1958).
Properties: Orthorhombic bisphenoidal crystals, d430 1.46. mp 168°. bp0.2 200°. [a]D20 +158.9° (p = 10). pKa (25°): 13.71. Soly at 17° in water 63% (w/w); in 80% alcohol 7.3%; in 90% alcohol 1.6%. Practically insol in ether. Soly also reported at 20° as 108 g/100 g H2O and as 5.2 g/100 g methanol.
Melting point: mp 168°
Boiling point: bp0.2 200°
pKa: pKa (25°): 13.71
Optical Rotation: [a]D20 +158.9° (p = 10)
Density: d430 1.46
Use: Manuf reconstituted and upgraded drying oils; tall oil esters and varnishes; fatty acid esters; plasticizers; nonionic surface active agents; fast and hard drying alkyd resins, and so-called plasticizing alkyds. In making glucoside hydroxypropyl ethers for polyurethan foam production.
alpha-Methyl-m-tyrosine alpha-Methyltryptamine alphaMNP alpha-Naphtholphthalein alpha-Peltatin