Title: Glucosamine
CAS Registry Number: 3416-24-8
CAS Name: 2-Amino-2-deoxy-D-glucose
Synonyms: chitosamine
Molecular Formula: C6H13NO5
Molecular Weight: 179.17
Percent Composition: C 40.22%, H 7.31%, N 7.82%, O 44.65%
Literature References: Found in chitin, in mucoproteins, and in mucopolysaccharides. Isoln from chitin: Ledderhose,
Z. Physiol. Chem. 2, 213 (1878); Hackman,
Aust. J. Biol. Sci. 7, 168 (1954). Synthesis: Fischer, Leuchs,
Ber. 35, 3787 (1902);
36, 24 (1903). Separation of a- and b-forms: Westphal, Holzmann,
ibid. 75B, 1274 (1942). Structure: Haworth
et al., J. Chem. Soc. 1939, 271; Cutler, Peat,
ibid. 782; Cox, Jeffrey,
Nature 143, 894 (1939). Pharmacokinetics in dog and man: I. Setnikar
et al., Arzneim.-Forsch. 36, 729 (1986). Clinical trials in arthrosis: Y. Vajarudal,
Clin. Ther. 3, 336 (1981); M. J. Tapadinhas
et al., Pharmatherapeutica 3, 157 (1982).
Review: Foster, Stacey, "The Chemistry of the 2-Amino Sugars" in C. S. Hudson
et al., Advan. Carbohyd. Chem. vol. 7 (Academic Press, New York, 1952) pp 247-288. Review of pharmacology, toxicology and clinical efficacy: J. W. Anderson
et al.,
Food Chem. Toxicol. 43, 187-201 (2005).
Derivative Type: a-Form
CAS Registry Number: 28905-11-5
Properties: Crystals, mp 88°. [a]D20 +100° changing to +47.5° after 30 min (water).
Melting point: mp 88°
Optical Rotation: [a]D20 +100° changing to +47.5° after 30 min (water)
Derivative Type: b-Form
CAS Registry Number: 28905-10-4
Properties: Needles from methanol, dec 110°. [a]D20 +28° changing to +47.5° after 30 min (water). Very sol in water, sol in about 38 parts boiling methanol; sparingly sol in cold methanol or ethanol. Practically insol in ether, chloroform.
Optical Rotation: [a]D20 +28° changing to +47.5° after 30 min (water)
Derivative Type: N-Acetylglucosamine
CAS Registry Number: 7512-17-6
Molecular Formula: C8H15NO6
Molecular Weight: 221.21
Percent Composition: C 43.44%, H 6.83%, N 6.33%, O 43.40%
Properties: Needles from methanol + ether, mp 205°. [a]D18 +64° changing to +40.9° (in water).
Melting point: mp 205°
Optical Rotation: [a]D18 +64° changing to +40.9° (in water)
Derivative Type: Sulfate salt
CAS Registry Number: 29031-19-4
Trademarks: Dona (Rottapharm)
Line Formula: C6H13NO5.xH2SO4
Use: Pharmaceutic aid.
Therap-Cat: Antiarthritic.
Keywords: Antiarthritic/Antirheumatic.
