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N-Acetyl-β-D-glucosamin

N-Acetyl-D-Glucosamine

HCID 439174
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Grundinformationen

CAS
7512-17-6
Standard-SMILES
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChIKey
OVRNDRQMDRJTHS-RTRLPJTCSA-N
Summenformel
C8H15NO6
Durchschnittliche Molmasse
221,21 g/mol
Monoisotopische Masse
221,0899372

Überblick

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

Namen und Bezeichner

Bevorzugter Name
N-Acetyl-D-Glucosamine
IUPAC
N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Lokaler Name
N-Acetyl-β-D-glucosamin
Englischer Name
N-Acetyl-D-Glucosamine
Summenformel
C8H15NO6
Molmasse
221.21

Namen und Synonyme

2-acetamido-2-deoxy-D-glucopyranoseGlcNAc2-Deoxy-2-Acetamido-D-Glucopyranosen-acetyl-glucosamine2-acetamido-2-deoxy-glucose2-Deoxy-2-Acetamido-Glucose2-Acetamido-2-Deoxy-Glucopyranose2-Deoxy-2-Acetamido-Glucopyranose2-acetamido-2-deoxy-glucopyranoside2-Deoxy-2-Acetamido-Glucopyranoside2-acetamido-2-deoxy-D-glucopyranoside2-Deoxy-2-Acetamido-D-Glucopyranoside
Weitere Namen anzeigen
N-ACETYLGLUCOSAMINEacetylglucosamineN-Acetyl-D-glucosaminN-Acetyl-beta-D-glucosamineNADGAcetyl chitin2-Acetamido-D-glucose
2-Acetamido-2-Deoxy-D-Glucose2-Deoxy-2-Acetamido-D-GlucoseD-GlcNAcGlcNAc (SNFG)N-Acetyl-D-GlucosamineSNFG:GlcNAcN-AcetylchitosamineN-Acetyl-D-glucosamine-Agarose

Datenbank-Bezeichner

CAS
7512-17-6
PubChem CID
439174
DTXSID
DTXSID901045903
ChEMBL
CHEMBL240524
ChEBI
CHEBI:506227
Nikkaji
J35.752I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,7
Polarare Oberfläche (TPSA)
119 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
2
Schwere Atome
15
Formalladung
0
Komplexität
235

Experimentelle und physikochemische Eigenschaften

LogP-2.1
Solubility · 2 Einträge

167 mg/mL

>33.2 [ug/mL] (The mean of the results at pH 7.4)

Melting Point210 °C
Physical DescriptionSolid
Collision Cross Section · 2 Einträge

147.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

160.36 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

Physikochemische Eigenschaften

Schmelzpunkt
211 °C · 211 °C (dec.) (lit.)
Dampfdruck
8 Pa · 8Pa at 20℃
Brechungsindex
39 to · +39.0 to +42.0 ° (C=1, H2O)
storage temp.
-20 °C · -20°C
Löslichkeit
Soluble in concentrated hydrochloric acid, sulfuric acid, phosphoric acid and formic acid. Insoluble in water, dilute acids, dilute alkalis, concentrated alkalis and organic solvents.
Siedepunkt
636.4 · 636.4±55.0 °C(Predicted)
Dichte
1.54 g/cm3 · 1.54 g/cm3
pka
13.04 · 13.04±0.20(Predicted)
Aggregatzustand
saline suspension
Farbe
white to off-white
Biologische Quelle
crab (red)
Wasserlöslichkeit
2 O: · H2O: 50 mg/mL colorless to faint yellow solution, clear to very slightly hazy
Merck
14 · 14,4458
BRN
1727589 · 1727589
Stabilität
Stable. Incompatible with strong oxidizing agents.
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
InChIKey
OVRNDRQMDRJTHS-ROGOILFBSA-N
SMILES
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
LogP
-2.2 at · -2.2 at 23.7℃
CAS Datenbank
7512 · 7512-17-6(CAS DataBase Reference)
EPA chemische Informationen
N-Acetylglucosamine (7512-17-6)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

F
3-10
wgk
3
tsca
TSCA listed
hs_code
29329985
RTECS-Nr.
LZ6651000
risk_code
36/37/38
hazard_code
Xi
hazard_note
Irritant
safety_code
24/25-36-26-22
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsIntestine
Cellular LocationsCytoplasm
Metabolite PathwaysAmino Sugar Metabolism
Anwendungen · 3 Einträge

BeschreibungN-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.

VerwendenN-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.

VerwendenN-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.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.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranosideGlucose

Ergänzende Hinweise

DefinitionChEBI: 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.

Zugehörige Reaktionen

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