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A0812

N-Acetylneuraminic acid

Name: N-Acetylneuraminic acid
Brand: SIGMA

≥95% anhydrous basis, synthetic

Synonym(s):

5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Lactaminic acid, NAN, NANA, Sialic acid

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₉NO₉

CAS Number:

131-48-6

Molecular Weight:

309.27

UNSPSC Code:

12352201

NACRES:

NA.25

PubChem Substance ID:

24890457

EC Number:

205-023-1

Beilstein/REAXYS Number:

1716283

MDL number:

MFCD00006620

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biological source

synthetic

Quality Level

200

type

Type IV-S

assay

≥95% anhydrous basis

form

powder

color

white to off-white

mp

184-186 °C

solubility

H₂O: ~50 mg/mL

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

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Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

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.

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)

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Certificates of Analysis (COA)

Lot/Batch Number

0000474172

0000474173

0000474170

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Glycan cross-feeding supports mutualism between Fusobacterium and the vaginal microbiota.

Kavita Agarwal et al.

PLoS biology, 18(8), e3000788-e3000788 (2020-08-26)

Women with bacterial vaginosis (BV), an imbalance of the vaginal microbiome, are more likely to be colonized by potential pathogens such as Fusobacterium nucleatum, a bacterium linked with intrauterine infection and preterm birth. However, the conditions and mechanisms supporting pathogen

Relative roles of GM1 ganglioside, N-acylneuraminic acids, and α2β1 integrin in mediating rotavirus infection.

Fiona E Fleming et al.

Journal of virology, 88(8), 4558-4571 (2014-02-07)

N-acetyl- and N-glycolylneuraminic acids (Sia) and α2β1 integrin are frequently used by rotaviruses as cellular receptors through recognition by virion spike protein VP4. The VP4 subunit VP8*, derived from Wa rotavirus, binds the internal N-acetylneuraminic acid on ganglioside GM1. Wa

Receptor binding by an H7N9 influenza virus from humans.

Xiaoli Xiong et al.

Nature, 499(7459), 496-499 (2013-06-22)

Of the 132 people known to have been infected with H7N9 influenza viruses in China, 37 died, and many were severely ill. Infection seems to have involved contact with infected poultry. We have examined the receptor-binding properties of this H7N9

Renal handling of free sialic acid in normal humans and patients with Salla disease or renal disease.

R Seppala et al.

Laboratory investigation; a journal of technical methods and pathology, 63(2), 197-203 (1990-08-01)

The renal handling of free sialic acid, a negatively charged sugar, was investigated in normal humans and in patients with impaired sialic acid metabolism or impaired renal function. A sensitive assay for sialic acid, based upon the specific degradation of

A novel synthetic receptor-based immunoassay for influenza vaccine quantification.

Anwar M Hashem et al.

PloS one, 8(2), e55428-e55428 (2013-02-21)

Vaccination is the most effective prophylactic method for preventing influenza. Quantification of influenza vaccine antigens is critically important before the vaccine is used for human immunization. Currently the vaccine antigen quantification relies on hemagglutinin content quantification, the key antigenic component

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Global Trade Item Number

SKU	GTIN
A0812-100MG	04061835365951
A0812-250MG	04061833334485
A0812-1G	04061833334478
A0812-25MG	04061833334492

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