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glucosamine

Glucosamine Sulfate

Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of the polysaccharides chitosan and chitin, which compose the exoskeletons of crustaceans and other arthropods, as well as the cell walls of fungi and many higher organisms. Glucosamine is one of the most abundant monosaccharides.[1] It is produced commercially by the hydrolysis of crustacean exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. Glucosamine appears to be safe for use as a dietary supplement; effectiveness has not been established for any condition. In the US it is one of the most common non-vitamin, non-mineral, dietary supplements used by adults.[2]

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Product Description


IUPAC name

(3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
Other names

2-Amino-2-deoxy-glucose
Chitosamine

CAS Number
3416-24-8
Beilstein Reference
1723616
ChEBI CHEBI:5417
ChEMBL ChEMBL181132
ChemSpider 388352
DrugBank DB01296
EC Number 222-311-2
Gmelin Reference
720725
Jmol interactive 3D Image
KEGG D04334
MeSH Glucosamine
PubChem 439213
UNII N08U5BOQ1K
InChI[show]
SMILES[show]

Chemical formula
C6H13NO5
Molar mass 179.17 g·mol−1
Density 1.563 g/mL
Melting point 150 °C (302 °F; 423 K)
log P -2.175
Acidity (pKa) 12.273
Basicity (pKb) 1.724

Pharmacology
ATC code M01AX05