A2388

N-Acetylneuraminic acid

≥98% (HPLC), from Escherichia coli

• Synonym(s): 5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Lactaminic acid, NAN, NANA, Sialic acid
• Empirical Formula (Hill Notation): C₁₁H₁₉NO₉
• CAS Number: 131-48-6
• Molecular Weight: 309.27
• UNSPSC Code: 12352201
• NACRES: NA.25
• PubChem Substance ID: 24890650
• EC Number: 205-023-1
• Beilstein/REAXYS Number: 1716283
• MDL number: MFCD00006620

Properties

• biological source: Escherichia coli
• Quality Segment: 300
• type: Type VI
• assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]20/D -34.0 to -30.0 °, c = 1% in water
• technique(s): HPLC: suitable
• color: white to off-white
• mp: 184-186 °C
• solubility: water: 50 mg/mL, clear, colorless
• application(s): advanced drug delivery
• storage temp.: −20°C
• SMILES string: 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
• 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
• InChI key: SQVRNKJHWKZAKO-PFQGKNLYSA-N

Description

Application

N-Acetylneuraminic acid (NANA, Neu5Ac) is a major component of glycoconjugates such as glycolipids, glycoproteins and proteoglycans (sialogylcoproteins) where it confers selective binding characteristics to the glycosylated component. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers.

Biochem/physiol Actions

Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H319
• pcodes: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)