N-Acetyl-D-Glucosamine Chemical Properties

Melting point:

211 °C (dec.) (lit.)

alpha 

42 º (c=2,water,2 hrs)

vapor pressure 

8Pa at 20℃

refractive index 

+39.0 to +42.0 ° (C=1, H2O)

storage temp. 

-20°C

solubility 

Soluble in concentrated hydrochloric acid, sulfuric acid, phosphoric acid and formic acid. Insoluble in water, dilute acids, dilute alkalis, concentrated alkalis and organic solvents.

Boiling point:

636.4±55.0 °C(Predicted)

Density 

1.54 g/cm3

pka

13.04±0.20(Predicted)

form 

saline suspension

color 

white to off-white

optical activity

Alpha type +75 → +41 Beta type -22 → +41.3

Water Solubility 

H2O: 50 mg/mL colorless to faint yellow solution, clear to very slightly hazy

Sensitive 

Hygroscopic

Merck 

14,4458

BRN 

1727589

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

OVRNDRQMDRJTHS-ROGOILFBSA-N

LogP

-2.2 at 23.7℃

CAS DataBase Reference

7512-17-6(CAS DataBase Reference)

EPA Substance Registry System

N-Acetylglucosamine (7512-17-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26-22

WGK Germany 

3

RTECS 

LZ6651000

F 

3-10

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29329985

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Acetyl-D-Glucosamine Usage And Synthesis

Description

N-Acetyl-D-Glucosamine is the N-acetyl derivative of glucosamine.Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate.
N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. It is also synthesized in the glycosylation pathway as uridine diphosphate (UDP-GlcNAc), which can then be released following degradation of glycosylated proteins.D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s). It is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.

Chemical Properties

White powder

Uses

N-Acetyl-D-glucosamine is used in the identification and characterization of N-acetyl-beta-D-hexoaminidase. It is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.

Uses

N-acetyl-D-Glucosamine (GlcNAc) is a monosaccharide derivative of glucose. It is released by the action of O-GlcNAcase, in mammalian systems from proteins that have been post-translationally modified with O-GlcNAc. Levels of O-GlcNAcylation proteins from Alzheimer’s disease brain extracts are decreased as compared to that in controls, suggesting that release of GlcNAc may contribute to pathogenesis.1 In E. coli, GlcNAc induces the expression of multidrug exporter genes, indicating that this sugar can alter gene expression.1 GlcNAc is also the monomeric unit of chitin, which is found in fungi and many invertebrates, including crustaceans, insects, and nematodes. For this reason, chemicals that inhibit the incorporation of GlcNAc into chitin are cytotoxic to these organisms.

1. Atypical microbial danger signal that acts as a new activator of NLRP3 inflammasome by dissociating the enzyme hexokinase from the mitochondria. D-GlcNAc inhibits purified hexokinase, which is also involved in the glucose metabolism and obesity in mM range. For hexokinase dissociation from the mitochondria much higher concentrations are needed.
2. Acceptor substrate for galactosyltransferases. Inhibits the lectin WGA and is used to identify, differentiate and characterize N-acetyl-β-D-hexosaminidase(s).
3. Used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Significantly enhances the prevention of joint damage and inhibits elastase activity and superoxide release from human polymorphonuclear leukocytes. Acts as a cytoprotective agent restoring the integrity and normal function of mucous membrane in humans.
4. D-GlcNAc enhances the proliferation and collagen expression of fibroblasts, reduces hyperpigmentation and is therefore considered a valuable ingredient in cosmetics for improving skin wrinkles and color.
5. Important substrate for the production of sialic acids.
6. Used in multiple other applications in drug development and food supplement, based on a newly described bio-wave model.

Definition

ChEBI: N-acetyl-D-glucosamine is the D isomer of N-acetylglucosamine. It has a role as a bacterial metabolite. It is a N-acetylglucosamine and a N-acetyl-D-hexosamine.

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.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

N-Acetylglucosamine (GlcNAc) oligomer may have the ability to initiate factors for canine polymorphonuclear cells (PMN) in vivo. It possesses wound healing and chemotactic activity. GlcNAc and its derivatives are usually employed in preparing dietary supplements and also used in therapeutic development.

N-Acetyl-D-Glucosamine(7512-17-6)Related Product Information

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