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7512-17-6

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7512-17-6 Usage

Description

N-Acetyl-D-Glucosamine (GlcNAc) is a monosaccharide derivative of glucose, playing a crucial role in various biological processes and possessing significant therapeutic potential. It is a component of heterogenous polysaccharides, such as murein and hyaluronic acid, and is involved in post-translational protein modification. GlcNAc exhibits anti-inflammatory properties and is considered a potential drug for treating osteoarthritis.

Uses

Used in Pharmaceutical Applications:
N-Acetyl-D-Glucosamine is used as a pharmaceutical compound for the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. It acts as a cytoprotective agent, restoring the integrity and normal function of mucous membranes in humans.
Used in Cosmetic Applications:
GlcNAc is used as a valuable ingredient in cosmetics for improving skin wrinkles and color. It enhances the proliferation and collagen expression of fibroblasts and reduces hyperpigmentation.
Used in Drug Development Research:
N-Acetyl-D-Glucosamine is used as a substrate in sialic acid production and serves as an acceptor substrate for galactosyltransferases. It is also used to identify, differentiate, and characterize N-acetyl-β-D-hexoaminidase(s) and in the development of novel drug delivery systems.
Used in Food Supplement Applications:
GlcNAc is used in multiple applications, including drug development and as a component of food supplements, based on a newly described bio-wave model.
Used in the Identification and Characterization of Enzymes:
N-Acetyl-D-glucosamine is used to identify, differentiate, and characterize N-acetyl-beta-D-hexoaminidase, which is involved in various biological processes.
Used in the Production of Sialic Acids:
GlcNAc is an important substrate for the production of sialic acids, which are essential components of many biological molecules.
Used in the Study of Alzheimer's Disease:
Levels of O-GlcNAcylation proteins from Alzheimer's disease brain extracts are decreased compared to controls, suggesting that the release of GlcNAc may contribute to the pathogenesis of the disease.
Used in the Regulation of Gene Expression:
In E. coli, GlcNAc induces the expression of multidrug exporter genes, indicating that this sugar can alter gene expression.
Used in the Treatment of Microbial Infections:
GlcNAc is a valuable component in the development of chemicals that inhibit the incorporation of GlcNAc into chitin, which is found in fungi and many invertebrates. These chemicals are cytotoxic to these organisms, making them potential treatments for various infections.
Used in the Study of Metabolic Disorders:
D-GlcNAc inhibits purified hexokinase, which is involved in glucose metabolism and obesity, suggesting its potential use in studying and treating metabolic disorders.

Flammability and Explosibility

Notclassified

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.

Check Digit Verification of cas no

The CAS Registry Mumber 7512-17-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,1 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 7512-17:
(6*7)+(5*5)+(4*1)+(3*2)+(2*1)+(1*7)=86
86 % 10 = 6
So 7512-17-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)

7512-17-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A13047)  N-Acetyl-D-glucosamine, 98+%   

  • 7512-17-6

  • 10g

  • 185.0CNY

  • Detail
  • Alfa Aesar

  • (A13047)  N-Acetyl-D-glucosamine, 98+%   

  • 7512-17-6

  • 50g

  • 591.0CNY

  • Detail
  • Alfa Aesar

  • (A13047)  N-Acetyl-D-glucosamine, 98+%   

  • 7512-17-6

  • 100g

  • 1065.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1432)  N-Acetylglucosamine  pharmaceutical secondary standard; traceable to USP

  • 7512-17-6

  • PHR1432-1G

  • 791.15CNY

  • Detail
  • USP

  • (1010022)  N-Acetylglucosamine  United States Pharmacopeia (USP) Reference Standard

  • 7512-17-6

  • 1010022-200MG

  • 4,647.24CNY

  • Detail

7512-17-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-acetyl-D-glucosamine

1.2 Other means of identification

Product number -
Other names N-Acetyl-D-glucosamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7512-17-6 SDS

7512-17-6Synthetic route

chitosan (deacetylation degree, 93%)

chitosan (deacetylation degree, 93%)

sodium acetate
127-09-3

sodium acetate

A

chitosan oligosaccharides

chitosan oligosaccharides

B

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

D

Low molecular weight chitosan

Low molecular weight chitosan

Conditions
ConditionsYield
With chitosanase In water at 40℃; for 20h; pH=4.5; Product distribution; Further Variations:; Reagents; pH-values; Enzymatic reaction;A 46.3%
B n/a
C n/a
D 44.6%
pyridine
110-86-1

pyridine

N-acetyl-D-mannosamine
14131-64-7

N-acetyl-D-mannosamine

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
at 100℃;
Ketene
463-51-4

Ketene

D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol; triethylamine
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

acetic anhydride
108-24-7

acetic anhydride

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol
In methanol; N,N-dimethyl-formamide
acetic anhydride
108-24-7

acetic anhydride

D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol; basic ion exchanger; water
With methanol; silver(I) acetate
Stage #1: D-(+)-glucosamine hydrochloride In water Industry scale;
Stage #2: acetic anhydride With sodium carbonate In water at 20 - 25℃; pH=4 - 6; Product distribution / selectivity; Industry scale;
Conditions
ConditionsYield
With ammonia
acetic anhydride
108-24-7

acetic anhydride

2-amino-2-deoxy-D-glucose hydrazone
77045-60-4

2-amino-2-deoxy-D-glucose hydrazone

A

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

B

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine
97055-07-7

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine

Conditions
ConditionsYield
With Amberlite IR-120 (H+) and IRA-400 (AcO-); sodium acetate In methanol; water
With sodium acetate In methanol; water for 1h; Ambient temperature;
1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine
97055-07-7

1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With Amberlite IR-120 (H+)
methyl 2-amino-2-deoxy-β-D-glucopyranoside
3867-92-3

methyl 2-amino-2-deoxy-β-D-glucopyranoside

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With methanol; acetic anhydride Ambient temperature;
N-acetyl-D-mannosamine
14131-64-7

N-acetyl-D-mannosamine

diluted aqueous solution

diluted aqueous solution

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
pH 11;
methanol
67-56-1

methanol

ammonia
7664-41-7

ammonia

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride
5432-46-2, 10034-19-2, 10034-20-5, 34948-62-4, 110253-00-4

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
Behandeln des Hydrochlorids;
glycolchitin

glycolchitin

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
With sodium acetate buffer; Tulipa bakeri chitinase-1 In water at 37℃; for 0.25h; pH=5.0; Enzyme kinetics; Further Variations:; Reagents;
D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrazine hydrate / overnight
2: CH3COONa / methanol; H2O / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: hydrazine hydrate / overnight
2: CH3COONa / methanol; H2O / 1 h / Ambient temperature
3: Amberlite IR-120 (H+)
View Scheme
2-amino-2-deoxy-D-glucose hydrazone
77045-60-4

2-amino-2-deoxy-D-glucose hydrazone

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH3COONa / methanol; H2O / 1 h / Ambient temperature
2: Amberlite IR-120 (H+)
View Scheme

7512-17-6Relevant articles and documents

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Cao, Lian-Gong,Cao, Zhi-Ling,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Lu, Xing,Shao, Zhong-Bai,Shi, Da-Hua,Wang, Lei,Wang, You-Xian

, p. 359 - 364 (2020/12/28)

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation

Andreeva, Olga V.,Garifullin, Bulat F.,Sharipova, Radmila R.,Strobykina, Irina Yu.,Sapunova, Anastasiya S.,Voloshina, Alexandra D.,Belenok, Mayya G.,Dobrynin, Alexey B.,Khabibulina, Leysan R.,Kataev, Vladimir E.

, p. 2367 - 2380 (2020/08/28)

Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.

Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

Cao, Zhi-Ling,Liu, Shu-Hao,Liu, Wei-Wei,Ren, Shu-Ting,Shi, Da-Hua,Wang, Lei,Wang, You-Xian,Wu, Yu-Ran

, p. 363 - 366 (2020/02/05)

Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.

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