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PHR1432

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N-Acetylglucosamine

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):

N-Acetyl-D-glucosamine, 2-Acetamido-2-deoxy-D-glucose, D-GlcNAc

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About This Item

Empirical Formula (Hill Notation):
C8H15NO6
CAS Number:
Molecular Weight:
221.21
Beilstein:
1727589
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

Agency

traceable to USP 1010022

API family

glucosamine

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

211 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°C

SMILES string

CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI

1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1

InChI key

OVRNDRQMDRJTHS-RTRLPJTCSA-N

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General description

N-Acetylglucosamine (GlcNAc) is a monosaccharide, derived from glucose and undergoes linear polymerization by (1,4)-β-linkages to form the polymer chitin. It is also a component of heterogenous polysaccharides, such as murein and hyaluronic acid. N-acetylglucosamine exhibits anti-inflammatory properties and is considered as a potential drug in the treatment of osteoarthritis. Its antiarthritic mode of mechanism involves the suppression of IL-1β (Interleuken-1β)-induced NO (nitric oxide), cyclooxygenase-2 (COX-2), and IL-6 production by inhibition of expression of iNOS (inducible nitric oxide synthase) protein and mRNA.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Application

N-Acetylglucosamine may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by spectrophotometric, chromatographic, and electrophoretic techniques.
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAC3267 in the slot below. This is an example certificate only and may not be the lot that you receive.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Capillary electrophoretic determination of glucosamine in osteoarthritis tablets via microwave-accelerated dansylation
Qi L, et al.
Journal of Pharmaceutical and Biomedical Analysis, 41(5), 1620-1624 (2006)
N-acetylglucosamine prevents IL-β-mediated activation of human chondrocytes
Shikhman AR, et al.
Journal of Immunology, 166(8), 5155-5160 (2001)
Determination of N-acetylglucosamine in cosmetic formulations and skin test samples by hydrophilic interaction liquid chromatography and UV detection
Pedrali A, et al.
Journal of Pharmaceutical and Biomedical Analysis, 107(8), 125-130 (2015)
A Cassone et al.
Microbiologica, 8(1), 85-99 (1985-01-01)
N-acetylglucosamine is a morphogenic effector in the human pathogenic yeast Candida albicans. Depending on temperature, N-acetylglucosamine induces yeast-mycelial conversion or chlamydospore formation. N-acetylglucosamine is also a carbon source for growth in the yeast form. Germ-tube formation, i.e. the intermediary of
Victor M Darley-Usmar et al.
Journal of molecular and cellular cardiology, 52(3), 538-549 (2011-09-01)
The post-translational modification of serine and threonine residues of nuclear and cytoplasmic proteins by the O-linked attachment of the monosaccharide β-N-acetyl-glucosamine (O-GlcNAc) is emerging as an important mechanism for the regulation of numerous biological processes critical for normal cell function.

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