2-Amino-2-deoxy-D-glucose, D-Glucosamine, CAS:3416-24-8

D-Glucosamine?Title:?GlucosamineCAS Registry Number:?3416-24-8CAS Name:?2-Amino-2-deoxy-D-glucoseAdditional Names:?chitosamineMolecular Formula:?C6H13NO5Molecular Weight:?179.17Percent 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-FormCAS Registry Number:?28905-11-5Properties:?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-FormCAS Registry Number:?28905-10-4Properties:?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-AcetylglucosamineCAS Registry Number:?7512-17-6Molecular Formula:?C8H15NO6Molecular Weight:?221.21Percent 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 saltCAS Registry Number:?29031-19-4Trademarks:?Dona (Rottapharm)Line Formula:?C6H13NO5.xH2SO4?Use:?Pharmaceutic aid.Therap-Cat:?Antiarthritic.Keywords:?Antiarthritic/Antirheumatic.CAS Number3416-24-8Product NameD-GlucosamineIUPAC Name(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triolMolecular FormulaC6H13NO5Molecular Weight179.17 g/molInChIInChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1InChI KeyMSWZFWKMSRAUBD-IVMDWMLBSA-NSMILESC(C1C(C(C(C(O1)O)N)O)O)OSolubilityIn water, 1X10+6 mg/l at 25 ?C (est) 330 mg/mLSynonyms2 Amino 2 Deoxyglucose, 2-Amino-2-Deoxyglucose, Dona, Dona S, Glucosamine, Glucosamine Sulfate, Hespercorbin, Sulfate, Glucosamine, XicilCanonical SMILESC(C1C(C(C(C(O1)O)N)O)O)OIsomeric SMILESC([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)N)O)O)O