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

3416-24-8 , 2-Amino-2-deoxy-D-glucose,
D-Glucosamine ,
CAS:3416-24-8
C6H13NO5 / 179.17
MFCD01631140

D-葡萄糖胺, D-Glucosamine

Title: Glucosamine

CAS Registry Number: 3416-24-8

CAS Name: 2-Amino-2-deoxy-D-glucose

Additional Names: 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.

CAS Number	3416-24-8
Product Name	D-Glucosamine
IUPAC Name	(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Molecular Formula	C6H13NO5
Molecular Weight	179.17 g/mol
InChI	InChI=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/s1
InChI Key	MSWZFWKMSRAUBD-IVMDWMLBSA-N
SMILES	C(C1C(C(C(C(O1)O)N)O)O)O
Solubility	In water, 1X10+6 mg/l at 25 °C (est) 330 mg/mL
Synonyms	2 Amino 2 Deoxyglucose, 2-Amino-2-Deoxyglucose, Dona, Dona S, Glucosamine, Glucosamine Sulfate, Hespercorbin, Sulfate, Glucosamine, Xicil
Canonical SMILES	C(C1C(C(C(C(O1)O)N)O)O)O
Isomeric SMILES	C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)N)O)O)O

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