CAS 131-48-6 N-Acetyl-Neuraminic Acid (HCID 439197)

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Basic information

CAS: 131-48-6
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
Molecular formula: C11H19NO9
Average molar mass: 309.27 g/mol
Monoisotopic mass: 309.10598119

Overview

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.

Names & identifiers

Preferred 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
English name: N-Acetylneuraminic acid
Molecular formula: C11H19NO9
Molecular weight: 309.27

Names & synonyms

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

Show more names

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

Properties

Computed structural properties

XLogP: -3.5
Topological polar surface area: 177 Å²
Hydrogen bond donors: 7
Hydrogen bond acceptors: 9
Rotatable bonds: 5
Heavy atoms: 21
Formal charge: 0
Complexity: 403

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Monosaccharides and Derivatives

Physical DescriptionWhite crystals; [Sigma-Aldrich MSDS]

Collision Cross Section · 2 items

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)]

Physicochemical properties

Melting point: 184 · 184-186 °C
alpha: -32 · -32 º (c=2,water)
Boiling point: 449.56 °C · 449.56°C (rough estimate)
Density: 1.358 · 1.3580 (rough estimate)
refractive index: -32 ° · -32 ° (C=1, H2O)
storage temp.: -20 °C · -20°C
solubility: 50 g/L · 50 g/L (20°C)
pka: 2.41 · 2.41±0.54(Predicted)

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

Regulatory Information · 2 items

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%)

Safety data

F: 3-10-23
wgk: 3
tsca: TSCA listed
hs_code: 29329970
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H319
Hazard Classifications: Eye Irrit. 2

Chemistry & industry

Uses & manufacturing

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

Applications · 2 items

DescriptionN-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.

UsesN-Acetylneuraminic acid is an integral part of sialic acids (SAs), important functional sugars that play an important role in maintaining and improving brain health, detoxification, antibacterial, and immune enhancement. n-Acetylneuraminic acid is biologically useful for neurotransmission, leukocyte extravasation, viral or bacterial infection, and carbohydrate-protein recognition. n- Acetylneuraminic acid is used to study its biochemistry, metabolism and absorption in vivo and in vitro.