ChemicalBook > CAS DataBase List > N-Acetyl-D-Glucosamine

N-Acetyl-D-Glucosamine

Product Name
N-Acetyl-D-Glucosamine
CAS No.
7512-17-6
Chemical Name
N-Acetyl-D-Glucosamine
Synonyms
N-ACETYLGLUCOSAMINE;D-GLCNAC;acetylglucosamine;2-Acetamido-2-deoxy-D-glucopyranose;Acetyl chitin;N-Acetyl-D-glucosamin;N-ACETYL-D-GLUCOSAMINIDE;N-Acetyl-beta-D-glucosamine;2-ACETAMIDO-2-DEOXY-D-GLUCOSE;NADG
CBNumber
CB0320700
Molecular Formula
C8H15NO6
Formula Weight
221.21
MOL File
7512-17-6.mol
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N-Acetyl-D-Glucosamine Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A3286
Product name
N-Acetyl-D-glucosamine
Purity
suitable for cell culture, BioReagent
Packaging
5g
Price
$36.1
Updated
2024/03/01
Sigma-Aldrich
Product number
1010022
Product name
N-Acetyl-D-glucosamine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$383
Updated
2024/03/01
TCI Chemical
Product number
A0092
Product name
N-Acetyl-D-glucosamine
Purity
>98.0%(HPLC)(N)
Packaging
25g
Price
$37
Updated
2024/03/01
TCI Chemical
Product number
A0092
Product name
N-Acetyl-D-glucosamine
Purity
>98.0%(HPLC)(N)
Packaging
100g
Price
$106
Updated
2024/03/01
Alfa Aesar
Product number
A13047
Product name
N-Acetyl-D-glucosamine, 98+%
Packaging
10g
Price
$28.8
Updated
2023/06/20
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N-Acetyl-D-Glucosamine Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-Acetyl-D-Glucosamine manufacturers

Watson Biotechnology Co.,Ltd
Product
N-Acetyl-D-Glucosamine 7512-17-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
20MT
Release date
2024-07-29
HebeiShuoshengImportandExportco.,Ltd
Product
2-Acetamido-2-deoxy-D-glucose 7512-17-6
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-09
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
N-Acetyl-D-Glucosamine 7512-17-6
Price
US $85.00-35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-21

7512-17-6, N-Acetyl-D-GlucosamineRelated Search:

Glucosamine D-Glucose monohydrate Acetylacetone Acetyl chloride D(+)-Glucose D-Glucosamine hydrochloride Acetaminophen Acetoacetamide Acesulfame potassium L-Tyrosine N-ACETYLMURAMIC ACID N,N',N''-TRIACETYLCHITOTRIOSE ACETYL-D-GLUCOSAMINE, N-[GLUCOSAMINE-1-14C] N-ACETYLGLUCOSAMINE 6-SULFATE SODIUM SALT N,N'-Diacetylchitobiose Chitin SIALYL LEWIS X N-ACETYL-D-GLUCOSAMINE, [ACETYL-3H] N-Acetylglucosamine

  • N-Acetyl-D-glucosaMine, 98.0%(LC&N
  • N-qcetyl-D-glucosamine
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  • D-GLCNAC
  • ACETYL-D-GLUCOSAMINE, N-
  • N-ACETYL-DELTA-GLUCOSAMINE
  • 2-ACETAMIDO-2-DESOXY-D-GLUCOPYRANOSE, N-ACETYL-D-GLUCOSAMINE
  • 2-ACETAMIDO-2-DEOXY-D-GLUCOSE
  • 2-AcetaMido-2-deoxy-D-glucopyranose, 98% 10GR
  • N-ACETYL-D-GLUCOSAMINE 80 MESH
  • N-ACETYL-D-GLUCOSAMINE CELL CULTURETESTE D
  • N-Acetyl-D-Glucosamine97.5-102.5%
  • N-Acetylglucosamine,USP28:97,5-102,5%HPLC
  • NSC 52434
  • D-Glucose, 2-(acetylamino)-2-deoxy-
  • N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
  • N-ACETYL-D-GLUCOSAMINE COSMETIC GRADE
  • 2-Acetamido-2-deoxy-D-glucopyranose
  • N-Acetyl-beta-D-glucosamine
  • 2-Acetamido-2-deoxy-D-glucopyranose, N-Acetyl-D-glucosamine
  • N-((1R,2R,3S,4R)-1-FORMYL-2,3,4,5-TETRAHYDROXY-PENTYL)-ACETAMIDE
  • N-ACETYL-D-GLUCOSAMINE, IMMOBILIZED ON DIVINYLSULFONE-ACTIVATED AGAROSE 6B
  • N-ACETYL-D-GLUCOSAMINIDE
  • N-ACETYLGLUCOSAMINE
  • 2-(acetylamino)-2-deoxy-d-glucos
  • N-Acety-D-GlucosaMine
  • N-ACETYLGLUCOSAMINE (13C6, 99%)
  • NADG
  • ACEN-001
  • N-Acetyl-D-glucosamine - plant source
  • Glucosamine Impurity A
  • 2-Acetamido-2-deoxy-D-glucose 95%
  • N-Acetyl-D-glucosamine - CAS 7512-17-6 - Calbiochem
  • N-Acetyl-D-glucosamin
  • Gastrodin Impurity 9
  • N-((1S,2R,3R,4R)-2,3,6-trihydroxy
  • N-Acetylglucosamine (200 mg)
  • N-Acetyl-D-glucosamine (NADG)
  • N- acetyl -D- glucosamine (N- acetylglucosamine)
  • 2-Acetamido-2-deoxy-D-glucose 2-Acetamido-2-deoxy-D-glucopyranose N-Acetyl-D-glucosamine N-[2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]acetamide D-GlcNAc
  • acetylglucosamine
  • 2-Acetanido-2-deoxy-α-D-glucopyranose
  • N-Acetamideo-2-deoxy-D-glucose
  • N-acetyl-D-glucosamine;2-Acetanido-2-deoxy-α-D-glucopyranose;N-Acetamideo-2-deoxy-D-glucose;D-GlcNAc
  • 2-Acetamido-2-deoxy-D-glucoseN-Acetyl-beta-D-glucosamine
  • N-Acetyl-D-glucosamine, N-[(1R,2R,3S,4R)-1-Formyl-2,3,4,5-tetrahydroxypentyl]acetamide
  • NSC 524344
  • N-Acetyl-D-glucosamine, 98+%
  • 2-Acetamido-2-deoxy-alpha-glucopyranose
  • N-ACETYL-D-GLUCOSAMINE extrapure AR for biochemistry
  • 2-Acetamido-2-deoxy-D-glucose, D-GlcNAc
  • 2-Acetamido-2-deoxyglucose
  • 2-Acetamido-D-glucose
  • D-N-Acetylglucosamine
  • 2-(acetylamino)-2-deoxy-D-Glucose
  • 2-Acetamido-2-deoxy-D-glucopyranose,98%
  • N-Acetyl-D-glucosamine
  • ACETYL-DL-GLUCOSAMINE, N-(P)