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)
DMAP DMC DMMP DMPA DMPO

Mannose
Mannose structure.svg
D-Mannopyranose
DL-Mannose.svg
Fischer projections
Identifiers
CAS number 31103-86-3 YesY
PubChem 18950
UNII PHA4727WTP N
MeSH Mannose
ChEMBL CHEMBL469448 N
Properties
Molecular formula C6H12O6
Molar mass 180.16 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Mannose is a sugar monomer of the aldohexose series of carbohydrates. Mannose is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylation of certain proteins. Several congenital disorders of glycosylation are associated with mutations in enzymes involved in mannose metabolism.[1]