N-Acetylneuraminsure

N-Acetyl-Neuraminic Acid

HCID 439197CAS 131-48-6

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Grundinformationen

Standard-SMILES: CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(O)(C(=O)O)C[C@@H]1O
InChIKey: SQVRNKJHWKZAKO-LUWBGTNYSA-N
Summenformel: C11H19NO9
Durchschnittliche Molmasse: 309,27 g/mol
Monoisotopische Masse: 309,10598119

Überblick

N-acetylneuraminic acid is an N-acylneuraminic acid where the N-acyl group is specified as acetyl. It has a role as an antioxidant, an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor, a mouse metabolite, a bacterial metabolite and a human metabolite. It is a conjugate acid of a N-acetylneuraminate.

Namen und Bezeichner

Bevorzugter Name: N-Acetyl-Neuraminic Acid
IUPAC: (4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Lokaler Name: N-Acetylneuraminsure
Englischer Name: N-Acetylneuraminic acid
Summenformel: C11H19NO9
Molmasse: 309.27

Namen und Synonyme

N-acetylneuraminic acidNeu5AcN-Acetyl-neuraminic acidAcidium aceneuramicum5-n-acetyl-neuraminic acidDTXSID4013771095-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acidAcid, SialicSNFG:Neu5AcN Acetylneuraminic AcidNeu5Ac (SNFG)Acid, N-Acetylneuraminic

Weitere Namen anzeigen

SIALIC ACIDNANNANAAcetylneuraminic acidNeuAcLACTAMINIC ACID(-)-N-ACETYLNEURAMINIC ACID(2S,4S,5R,6R)-5-AcetaMido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acidN-AcetyIneuraminic acid

GlyTouCan:G81533KYRefChem:1113556G81533KY5-(Acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulopyranosonic Acid5-(Acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-non-2-nonulosonic Acid5-(Acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic AcidD-glycero-5-acetamido-3,5-dideoxy-D-galacto-Non-2-ulo-pyranosonic Acid2,4-dihydroxy-5-((1-hydroxyethylidene)amino)-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid; 4,6,7,8,9-pentahydroxy-5-((1-hydroxyethylidene)amino)-2-oxononanoic acid

Datenbank-Bezeichner

CAS: 131-48-6
PubChem CID: 439197
DTXSID: DTXSID401377109
ChEMBL: CHEMBL4280954
ChEBI: CHEBI:17012
EC Number: 205-023-1
Nikkaji: J1.219.302E

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -3,5
Polarare Oberfläche (TPSA): 177 Å²
H-Brücken-Donoren: 7
H-Brücken-Akzeptoren: 9
Frei drehbare Bindungen: 5
Schwere Atome: 21
Formalladung: 0
Komplexität: 403

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Monosaccharides and Derivatives

Physical DescriptionWhite crystals; [Sigma-Aldrich MSDS]

Collision Cross Section · 2 Einträge

168.6 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

168.7 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

Physikochemische Eigenschaften

Schmelzpunkt: 184 · 184-186 °C
Siedepunkt: 449.56 °C · 449.56°C (rough estimate)
Dichte: 1.358 · 1.3580 (rough estimate)
Brechungsindex: -32 ° · -32 ° (C=1, H2O)
storage temp.: -20 °C · -20°C
Löslichkeit: 50 g/L · 50 g/L (20°C)
pka: 2.41 · 2.41±0.54(Predicted)
Aggregatzustand: synthetic, crystalline
Farbe: White to Off-White
Biologische Quelle: synthetic
Wasserlöslichkeit: 50 g/L · 50 g/L (20 ºC)
Merck: 14 · 14,8484
BRN: 1716283 · 1716283
Stabilität: Stable. Incompatible with strong oxidizing agents.
Major Application: food and beverages
Kosmetik-Inhaltsstoffe Funktionen: SKIN CONDITIONINGSKIN PROTECTING
InChI: 1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
InChIKey: SQVRNKJHWKZAKO-PFQGKNLYSA-N
SMILES: O[C@@]1(O[C@@]([C@@H]([C@H](C1)O)NC(C)=O)([H])[C@@H]([C@@H](CO)O)O)C(O)=O
LogP: -1.897 · -1.897 (est)
CAS Datenbank: 131 · 131-48-6(CAS DataBase Reference)
EPA chemische Informationen: Neuraminic acid, N-acetyl- (131-48-6)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 78.6% (44 of 56) of all reports.

Warning

H319 (21.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 56 reports by companies from 5 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Regulation (EC) No 258/1997

Neuraminic acid, N-acetyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn eye irritant; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesEye Irrit. 2A (21.4%)

Sicherheitsdaten

F: 3-10-23
wgk: 3
tsca: TSCA listed
hs_code: 29329970
risk_code: 36/37/38
hazard_code: Xi
hazard_note: Irritant
safety_code: 22-24/25-36-26
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2

Chemie und Industrie

Verwendung und Herstellung

UsesAn N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. [ChemIDplus]

General Manufacturing InformationNeuraminic acid, N-acetyl-: ACTIVE

Anwendungen · 1 Eintrag

BeschreibungN-acetylneuraminic acid is an N-acyl derivative of neuraminic or acid amino sugar derivative, derived from N-acetylmannosamine and pyruvic acid. It is an important constituent of glycoproteins and glycolipids. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria.