N-acetyl-dextro-glucosamine
N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
 
Notes:
the n-acetyl derivative of glucosamine. Monomer of Chitin. Also in the exopolysaccharide from blue-green alga Cyanospira capsulata (CCD) N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. (Wikipedia) All animals and plants dynamically attach and remove beta-N-acetylglucosamine at serine and threonine residues on myriad nuclear and cytoplasmic proteins. b-N-Acetylglucosamine cycling, which is tightly regulated by the concerted actions of two highly conserved enzymes, serves as a nutrient and stress sensor. On some proteins, b-N-Acetylglucosamine competes directly with phosphate for serine/threonine residues. b-N-Acetylglucosamine's subcellular localization in hepatocytes established that it is highly concentrated at the nuclear envelope, particularly at the nuclear pore complex, but is also abundant and widespread within chromatin. However, several cytosolic and cytoskeletal proteins are also found to be glycosylated with b-N-Acetylglucosamine. b-N-Acetylglucosamination is in many ways distinct from 'classical' protein glycosylation. First, it is found mostly within the cytoplasm or nucleoplasm. Second, unlike the extraordinarily complex array of glycans found on extracellular glycoproteins, b-N-Acetylglucosamine is not elongated or further modified. Third, b-N-Acetylglucosamine cycles by means of mechanisms and on a timescale similar to those of phosphorylation and quite different from the cycling of complex extracellular glycans. b-N-Acetylglucosamination is one of the most common post-translational modifications. In terms of high-energy compounds, the intracellular concentration of the direct donor for b-N-Acetylglucosamination, UDP-GlcNAc, is second only to that of ATP, with 2-5% of all glucose being used to generate this sugar nucleotide. b-N-Acetylglucosaminated proteins can be found in almost every intracellular compartment, and there are proteins in almost every functional class that are subject to b-N-Acetylglucosamination. (PMID: 17460662) [HMDB]
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CAS Number: 7512-17-6Picture of molecule3D/inchi
Other(deleted CASRN): 134-61-2
ECHA EINECS - REACH Pre-Reg: 231-368-2
FDA UNII: V956696549
Nikkaji Web: J81.413J
Beilstein Number: 1727589
MDL: MFCD00061615
XlogP3: -1.70 (est)
Molecular Weight: 221.20975000
Formula: C8 H15 N O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 595.35 °C. @ 760.00 mm Hg (est)
Flash Point: 597.00 °F. TCC ( 313.90 °C. ) (est)
logP (o/w): -2.314 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
AIDP
N-Acetyl D-Glucosamine NAG 98%-101%
BOC Sciences
For experimental / research use only.
N-Acetyl-D-glucosamine
Carbosynth
For experimental / research use only.
N-Acetyl-D-glucosamine
EMD Millipore
For experimental / research use only.
N-Acetyl-D-glucosamine
Glentham Life Sciences
N-Acetyl-D-glucosamine
Indis NV
For experimental / research use only.
N-Acetyl-D-Glucosamine
Jiangyin Healthway
N-Acetyl-D-Glucosamine
New functional food ingredients
Kingchem Laboratories
N-Acetyl Glucosamine
Nacalai USA
For experimental / research use only.
N-Acetyl-D-glucosamine
Penta International
N-ACETYL-D-GLUCOSAMINE
Santa Cruz Biotechnology
For experimental / research use only.
N-Acetyl-D-glucosamine ≥98%
Sarchem Laboratories
For experimental / research use only.
N-Acetyl-D-Glucosamine
Sigma-Aldrich: Sigma
For experimental / research use only.
N-Acetyl-D-glucosamine ≥99%
Synerzine
n-acetyl-d-glucosamine
TCI AMERICA
For experimental / research use only.
N-Acetyl-D-glucosamine >98.0%(HPLC)(N)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: pharmaceuticals / chemical synthisis
Recommendation for N-acetyl-dextro-glucosamine usage levels up to:
 not for fragrance use.
 
Recommendation for N-acetyl-dextro-glucosamine flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
Daily Med: search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
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Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 7512-17-6
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 24139
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Chemidplus: 0007512176
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References:
 N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 7512-17-6
Pubchem (cid): 24139
Pubchem (cas): 7512-17-6
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
Metabolomics Database: Search
KEGG (GenomeNet): C00140
HMDB (The Human Metabolome Database): HMDB00215
FooDB: FDB022253
YMDB (Yeast Metabolome Database): YMDB00294
Export Tariff Code: 2932.99.9010
VCF-Online: VCF Volatile Compounds in Food
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 peach
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Synonyms:
2-acetamido-2-deoxy-a-D-glucopyranose
2-acetamido-2-deoxy-D-glucose
N-acetyl-a-D-glucosamine
N-acetyl-D-glucosamine
2-acetylamino-2-deoxy-a-D-glucopyranose
2-(acetylamino)-2-deoxy-a-D-glucopyranose
2-(acetylamino)-2-deoxy-D-glucose
a-D-glucopyranose, 2-(acetylamino)-2-deoxy-
 glucosamine, N-acetyl-
N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
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