D-Mannose
Title: D-Mannose
CAS Registry Number: 3458-28-4
Additional Names: Seminose; carubinose
Molecular Formula: C6H12O6
Molecular Weight: 180.16
Percent Composition: C 40.00%, H 6.71%, O 53.28%
Literature References: Prepn of a-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 a- and b-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 Type: a-Form
Properties: Crystals from methanol, mp 133°. [a]D +29.3° ® +14.2° (water).
Melting point: mp 133°
Optical Rotation: [a]D +29.3° ® +14.2° (water)
 
Derivative Type: b-Form
Properties: Orthorhombic, bisphenoidal needles from alcohol or acetic acid, dec 132°. Sweet taste with bitter aftertaste. d20 1.54. Shows mutarotation. [a]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.
pKa: pKa (18°): 11.98
Optical Rotation: [a]D20 -17.0° ® +14.2° (c = 4)
Density: d20 1.54
 
Derivative Type: Phenylhydrazone
Molecular Formula: C12H18N2O5
Molecular Weight: 270.28
Percent Composition: C 53.33%, H 6.71%, N 10.36%, O 29.60%
Properties: Crystals from dil ethanol, mp 199-200°. [a]D20 +26.3° ® +33.8° (pyridine).
Melting point: mp 199-200°
Optical Rotation: [a]D20 +26.3° ® +33.8° (pyridine)
 
Derivative Type: CaCl2-addition compd tetrahydrate
Molecular Formula: C6H12O6.CaCl2.4H2O
Molecular Weight: 363.20
Percent Composition: C 19.84%, H 5.55%, O 44.05%, Ca 11.03%, Cl 19.52%
Properties: mp 101-102°. [a]D20 -31.3° ® +6.0° (c = 9).
Melting point: mp 101-102°
Optical Rotation: [a]D20 -31.3° ® +6.0° (c = 9)

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