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Acetylglucosamine

HCID 178781404
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Grundinformationen

CAS
98632-70-3
Standard-SMILES
CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
InChIKey
MBLBDJOUHNCFQT-LXGUWJNJSA-N
Summenformel
C8H15NO6
Durchschnittliche Molmasse
221,21 g/mol

Überblick

Aldehydo-N-acetyl-D-glucosamine is the open-chain form of N-acetyl-D-glucosamine. It has a role as a human metabolite.

Namen und Bezeichner

Bevorzugter Name
Acetylglucosamine
IUPAC
N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide
Englischer Name
N-Acetyl-beta-D-glucosamine
Summenformel
C8H15NO6
Molmasse
221.21

Namen und Synonyme

Marine SweetGreenNAGBio-NAGDTXSID3045855N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamideacetyl glucosamineN-((2R,3R,4S,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide2-Acetamido-2-deoxyglucoseD-Glucose, 2-(acetylamino)-2-deoxy-2 Acetamido 2 DeoxyglucoseN-ACETYL GLUCOSAMINE D-2 Acetamido 2 Deoxy D Glucose
Weitere Namen anzeigen
shrimp shellChitooctaose Octahydrochloride
DTXCID5032369D-Glucose, 2-acetamido-2-deoxy-Glucopyranose, 2-acetamido-2-deoxy-V956696549N acetylglucosamineNSC-400525NSC-524344Glucosamine, Acetyl

Datenbank-Bezeichner

CAS
98632-70-3
ChEMBL
CHEMBL4303483、CHEMBL447878
ChEBI
CHEBI:17411
UNII
V956696549
EC Number
231-368-2
Nikkaji
J81.413J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-3,4
Polarare Oberfläche (TPSA)
127 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
6
Schwere Atome
15
Formalladung
0
Komplexität
221

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Monosaccharides and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsCosmetic ingredients (Acetyl Glucosamine) -> CIR (Cosmetic Ingredient Review)
Physical DescriptionSolid; [Merck Index] Beige powder; [Sigma-Aldrich MSDS]

Physikochemische Eigenschaften

Löslichkeit
DMSO (Slightly), Water (Slightly)
Aggregatzustand
Solid
Farbe
White to Pale Yellow
Stabilität
Hygroscopic

Sicherheit und Regulatorisches

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

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 100% (50 of 50) of all reports.

Not Classified

Aggregated GHS information provided per 50 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: D-Glucose, 2-(acetylamino)-2-deoxy-

Status: Active Update: 03-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33451

D-Glucose, 2-(acetylamino)-2-deoxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses changes in liver weight, leukocyte counts, and sodium in 13-week oral studies of rats; [RTECS ]May cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified

Toxikologische Informationen

Toxicity Summary · 2 Einträge

The Expert Panel for Cosmetic Ingredient Safety concluded that Acetyl Glucosamine is safe in cosmetics in the present practices of use and concentration described in this safety assessment when formulated to be non-irritating.

Safe for use in cosmetics, with qualifications

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

The mechanism of action in relieving arthritic pain and in repair of cartilage is a matter of speculation. Biochemically, glucosamine is involved in glycoprotein metabolism. Glycoproteins, known as proteoglycans, form the ground substance in the extra-cellular matrix of connective tissue. Proteoglycans are polyanionic substances of high-molecular weight and contain many different types of heteropolysaccharide side-chains covalently linked to a polypeptide-chain backbone. These polysaccharides make up to 95% of the proteoglycan structure. In fact, chemically, proteoglycans resemble polysaccharides more than they do proteins. The polysaccharide groups in proteoglycans are called glycosaminoglycans (GAGs). GAGs include hyaluronic acid, chondroitin sulfate, dermatan sulfate, keratan sulfate, heparin and heparan sulfate. All of the GAGs contain derivatives of glucosamine or galactosamine. Glucosamine derivatives are found in hyaluronic acid, keratan sulfate and heparan sulfate. Chondroitin sulfate contains derivatives of galactosamine. The glucosamine-containing glycosaminoglycan hyaluronic acid is vital for the function of articular cartilage. GAG chains are fundamental components of aggrecan found in articular cartilage. Aggrecan confers upon articular cartilage shock-absorbing properties. It does this by providing cartilage with a swelling pressure that is restrained by the tensile forces of collagen fibers. This balance confers upon articular cartilage the deformable resilience vital to its function. In the early stages of degenerative joint disease, aggrecan biosynthesis is increased. However, in later stages, aggrecan synthesis is decreased, leading eventually to the loss of cartilage resiliency and to most of the symptoms that accompany osteoarthritis. During the progression of osteoarthritis, exogenous glucosamine may have a beneficial role. It is known that, in vitro, chondrocytes do synthesize more aggregan when the culture medium is supplemented with glucosamine. N-acetylglucosamine is found to be less effective in these in vitro studies. Glucosamine has also been found to have antioxidant activity and to be beneficial in animal models of experimental arthritis. The counter anion of the glucosamine salt (i.e. chloride or sulfate) is unlikely to play any role in the action or pharmacokinetics of glucosamine. Further, the sulfate in glucosamine sulfate supplements should not be confused with the glucosamine sulfate found in such GAGs as keratan sulfate and heparan sulfate. In the case of the supplement, sulfate is the anion of the salt. In the case of the above GAGs, sulfate is present as an ester. Also, there is no glucosamine sulfate in chondroitin sulfate (source: PDRhealth).

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Metabolism/MetabolitesA significant fraction of ingested glucosamine is catabolized by first-pass metabolism in the liver.
Absorption, Distribution and ExcretionApproximately 90% of orally administered glucosamine (salt form) gets absorbed from the small intestine.

Verwendung und Herstellung

Uses · 2 Einträge

CIR ingredient: Acetyl Glucosamine

Used as an anti-arthritic drug; [Merck Index]

Household ProductsInformation on 11 consumer products that contain Acetylglucosamine in the following categories is provided:
General Manufacturing InformationD-Glucose, 2-(acetylamino)-2-deoxy-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenChitooctaose Octahydrochloride is a chitin oligosaccharide created from the exoskeleton of crustaceans. Potential biomedical uses of chitin include gauze dressings displaying antibacterial activity, and as hemostatic agents. Also used in polymer coatings for automobiles as it remedies scratches via sunlight induced chemical bonding.