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PHR1432

N-Acetylglucosamine

Name: N-Acetylglucosamine
Brand: SIAL

Pharmaceutical Secondary Standard; Certified Reference Material

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₈H₁₅NO₆

CAS Number:

7512-17-6

Molecular Weight:

221.21

Beilstein:

1727589

MDL number:

MFCD00061615

PubChem Substance ID:

329822596

NACRES:

NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

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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Analytical Reference Standards

Certified Reference Materials

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.

related product

Product No.

Description

Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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N-acetylglucosamine prevents IL-β-mediated activation of human chondrocytes

Shikhman AR, et al.

Journal of Immunology, 166(8), 5155-5160 (2001)

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)

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 role for N-acetylglucosamine as a nutrient sensor and mediator of insulin resistance.

L Wells et al.

Cellular and molecular life sciences : CMLS, 60(2), 222-228 (2003-04-08)

The ability to regulate energy balance at both the cellular and whole body level is an essential process of life. As western society has shifted to a higher caloric diet and more sedentary lifestyle, the incidence of type 2 diabetes

O-GlcNAc reports ambient temperature and confers heat resistance on ectotherm development.

Pablo T Radermacher et al.

Proceedings of the National Academy of Sciences of the United States of America, 111(15), 5592-5597 (2014-04-08)

Effects of temperature on biological processes are complex. Diffusion is less affected than the diverse enzymatic reactions that have distinct individual temperature profiles. Hence thermal fluctuations pose a formidable challenge to ectothermic organisms in which body temperature is largely dictated

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