5747. d-Mannose
Nomenclature
CAS number: 3458-28-4
Seminose; carubinose. C6H12O6; mol wt 180.16.
C 40.00%, H 6.71%, O 53.28%.
Description and references
Prepn of α-form by treating ivory nut shavings with H2SO4: Isbell, J. Res. Natl. Bur. Stand. 26, 47 (1941); Isbell, Frush in Methods in Carbohydrate Chemistry, R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 145-147. Prepn and stability of α- and β-forms: Reeves, J. Am. Chem. Soc. 72, 1499 (1950); J. Sowden in The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) pp 94-95.
Derivative
α-Form.Properties
Crystals from methanol, mp 133°. [α]D +29.3° → +14.2° (water).Derivative
β-Form.Properties
Orthorhombic, bisphenoidal needles from alcohol or acetic acid, dec 132°. Sweet taste with bitter aftertaste. d20 1.54. Shows mutarotation. [α]D20 -17.0° → +14.2° (c = 4). One gram dissolves in 0.4 ml water, 120 ml methanol, 250 ml abs ethanol, 3.5 ml pyridine. pKa (18°): 11.98. Reduces Fehling's soln; is fermented by yeast.Derivative
Phenylhydrazone.C12H18N2O5; mol wt 270.28.
C 53.33%, H 6.71%, N 10.36%, O 29.60%.
Properties
Crystals from dil ethanol, mp 199-200°. [α]D20 +26.3° → +33.8° (pyridine).Derivative
CaCl2-addition compd tetrahydrate.C6H12O6.CaCl2.4H2O; mol wt 363.20.
C 19.84%, H 5.55%, O 44.05%, Ca 11.03%, Cl 19.52%.