N-Acetyl-D-Glucosamine

Iupac Name：N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide

Molecular Weight：221.2078

Modify Date.: 2022-11-09 14:42

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: N-Acetyl-D-Glucosamine
1.2 Synonyms: 2-(acetylamino)-2-deoxy-α-D-glucopyranose 2-Acetamido-2-deoxy-a-D-glucopyranose 2-Acetamido-2-deoxy-alpga-D-glucopyranose 2-ACETAMIDO-2-DEOXY-D-GLUCOSE 2-Acetamido-2-deoxy-α-D-glucopyranose 2-acetamido-2-deoxy-α-Δ-glucopyranose 2-ACETAMIDO-2-DESOXY-D-GLUCOPYRANOSE, N-ACETYL-D-GLUCOSAMINE 2-acetylamino-2-deoxy-a-D-glucopyranose 2-acetylamino-2-deoxy-α-D-glucopyranose ACETYL-D-GLUCOSAMINE, N- D-GLCNAC D-Glucose, 2-acetamido-2-deoxy- EINECS 231-368-2 Glucosamine, N-acetyl- MFCD00136044 N-acetyl D-glucosamine N-ACETYL-DELTA-GLUCOSAMINE N-acetyl-Δ-glucosamine N-qcetyl-D-glucosamine α-D-GlcNAc α-D-Glucopyranose, 2-(acetylamino)-2-deoxy- α-GlcNAc α-N-Acetyl-D-glucosamine

1.3 CAS No.: 7512-17-6

1.4 CID: 439174

1.5 EINECS(EC#): 231-368-2

1.6 Molecular Formula: C8H15NO6 (isomer)

1.7 Inchi: 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

1.8 InChkey: MBLBDJOUHNCFQT-LXGUWJNJSA-N

1.9 Canonical Smiles: CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O

1.10 Isomers Smiles: O=CC(NC(=O)C)C(O)C(O)C(O)CO

2. Properties

2.1 Density: 1.423

2.1 Melting point: 201-204℃

2.1 Boiling point: 636.4°C at 760 mmHg

2.1 Refractive index: 1.541

2.1 Flash Point: 338.7°C

2.1 Precise Quality: 221.089935

2.1 PSA: 127.09000

2.1 logP: -2.1

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

2.2 Appearance: White to Almost white powder to crystal

2.3 Storage: Keep Cold. Hygroscopic. Store under Nitrogen.

2.4 Chemical Properties: White powder

2.5 Color/Form: Powder

2.6 pKa: 13.04±0.20(Predicted)

2.7 Water Solubility: >33.2 [ug/mL]

2.8 Stability: Stable. Incompatible with strong oxidizing agents.

2.9 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The pyranose form of N-acetyl-D-glucosamine. N-Acetyl-D-GlucosamineSupplier

3.2 Usage: A pharmaceutical and cosmetic compound.

4. Safety and Handling

4.1 Hazard Codes: Xi:;

4.1 Risk Statements: 36/37/38

4.1 Safety Statements: S24/25

4.1 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.2 RIDADR: NONH for all modes of transport

4.2 WGK Germany: 3

4.2 RTECS: LZ6651000

4.2 Sensitive: Hygroscopic

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

7512-17-6Total: 46 Synthesis Route

3006-60-8 24 Suppliers

7512-17-6 329 Suppliers

Literatures:
Kartha, K.P. Ravindranathan; Mukhopadhyay, Balaram; Field, Robert A. Carbohydrate Research, 2004 , vol. 339, # 3 p. 729 - 732
Yield: ~97%

4239-72-9 3 Suppliers

7512-17-6 329 Suppliers

Literatures:
Wang, Zhi-Guang; Zhang, XuFang; Live, David; Danishefsky, Samuel J. Angewandte Chemie (International Edition in English), 2000 , vol. 39, # 20 p. X3652-3656
Yield: ~59%

3068-34-6 31 Suppliers

7512-17-6 329 Suppliers

Literatures:
Journal of Medicinal Chemistry, , vol. 54, # 19 p. 6949 - 6955
Yield: null

View all

7. Precursor and Product

precursor:

13319-33-0

2776-93-4

4239-72-9

3459-18-5

13319-32-9

81749-53-3

81520-71-0

37067-30-4

3006-60-8

33289-65-5

3068-34-6

1398-61-4

14200-67-0

80265-04-9

22595-97-7

14131-63-6

7284-16-4

97055-07-7

View all

product :

63535-27-3

488-30-2

470-69-9

6838-16-0

3459-18-5

131-48-6

3946-01-8

6082-04-8

3646-68-2

583-50-6

122331-70-8

29024-90-6

19234-58-3

3615-17-6

132498-72-7

3006-60-8

473-81-4

131287-39-3

50787-09-2

10323-20-3

3068-34-6

3055-46-7

10293-57-9

2495-96-7

2495-95-6

70832-36-9

View all

8. Other Information

8.0 Usage: 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.

8.1 Merck: 14,4458

8.2 BRN: 1727589

8.3 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.

8.4 Chemical Properties: White powder

8.5 Uses: A pharmaceutical and cosmetic compound.

8.6 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.

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.
Acceptor substrate for galactosyltransferases. Inhibits the lectin WGA and is used to identify, differentiate and characterize N-acetyl-β-D-hexosaminidase(s).
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.
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.
Important substrate for the production of sialic acids.
Used in multiple other applications in drug development and food supplement, based on a newly described bio-wave model.

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8.7 Definition: ChEBI: The pyranose form of N-acetyl-D-glucosamine.

8.8 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.

9. Computational chemical data

Molecular Weight: 221.2078g/mol
Molecular Formula: C₈H₁₅NO₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 221.08993720
Monoisotopic Mass: 221.08993720
Complexity: 235
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 119
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccByOAAAAAAAAAAAAAAAAAAAAAAAAAAkAAAAAAAAAAAAAAAAHgAQCAAACDzxgAcCCALABgAIAAEQEAAAAAAAAAAAAIAIAAATEAIAgAAHQAAHFgCXAAHwcAcAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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99% N-Acetyl-D-glucosamine C8H15NO6