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49130

Sigma-Aldrich

D-(+)-Glucosamine hydrochloride

≥99.0% (HPLC)

Synonym(s):

2-Amino-2-deoxy-D-glucose hydrochloride, Chitosamine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H13NO5 · HCl
CAS Number:
66-84-2
Molecular Weight:
215.63
Beilstein:
4157370
EC Number:
200-638-1
MDL number:
MFCD00135831
UNSPSC Code:
12352201

Assay

≥99.0% (HPLC)

optical activity

[α]20/D +72.5±2°, 24 hr, c = 2% in H2O

ign. residue

≤0.05%

mp

190-194 °C (dec.) (lit.)
≥300 °C

solubility

H2O: 0.1 g/mL, clear, colorless

SMILES string

Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI

1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6?;/m1./s1

InChI key

QKPLRMLTKYXDST-NSEZLWDYSA-N

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Biochem/physiol Actions

Glucosamine, an amino sugar, is the precursor of the hexosamine biosynthetic pathway leading to the formation of UDP-N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. D-(+)-Glucosamine inhibits the coaggregation of Candida yeast species with the bacterial strain S. salivarius.

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Oshra Betzer et al.
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Metabolism: clinical and experimental, 64(3), 368-379 (2014-12-18)
This study investigated the potential of glucosamine (GlcN) to affect body weight gain and insulin sensitivity in mice normal and at risk for developing diabetes. Male C57BL/6J mice were fed either chow diet (CD) or a high fat diet (HFD)
Khadijeh Jamialahmadi et al.
Environmental toxicology and pharmacology, 38(1), 212-219 (2014-06-25)
Glucosamine (GlcN) is an important precursor in the biochemical synthesis of glycosylated proteins and lipids in human body. It gains importance because of its contribution to human health and its multiple biological and therapeutic effects. In this study, the in
Hiba Al-Hamidi et al.
Pharmaceutical development and technology, 20(1), 74-83 (2014-01-08)
The solid dispersion technique is one of the most effective methods for improving the dissolution rate of poorly water-soluble drugs; however this is reliant on a suitable carrier and solvent being selected. The work presented explores amino sugars (d-glucosamine HCl
Anna Maria Piras et al.
International journal of biological macromolecules, 67, 124-131 (2014-03-26)
A commercially available chitosan (CS) was employed in the formulation of nanoparticles loaded with lysozyme (LZ) as antimicrobial protein drug model. Due to the variability of commercially available batches of chitosans and to the strict dependence of their physical and
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