N-acetyl neuraminic acid

(-)-5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid

CAS: 131-48-6 C11 H19 N O9 MW: 309.27223000

Identification

NameN-acetyl neuraminic acid
IUPAC(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CAS Number131-48-6
EINECS205-023-1
FDA UNIIGZP2782OP0
Molecular FormulaC11 H19 N O9
Molecular Weight309.27223000
MDL NumberMFCD00006620
Nikkaji NumberJ10.009I
Beilstein1716283

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesGRN 602

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 805.02 °C. @ 760.00 mm Hg (est)
Flash Point 825.00 °F. TCC ( 440.70 °C. ) (est)
logP (o/w) -1.897 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic ingredient for skin and hair conditioning
Recommendation for N-acetyl neuraminic acid usage levels up tonot for fragrance use.
Recommendation for N-acetyl neuraminic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

egg PMC milk PMC

Synonyms

(2S,4S,5R,6R)-5- acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid (-)-5- acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid N- acetyl-D-neuraminic acid N- acetyl-dextro-neuraminic acid N- acetylneuraminic acid neuraminic acid, N-acetyl- PubMed: Novel antibody-independent receptor-binding SPR-based assay for rapid measurement of influenza vaccine potency. PubMed: Establishment of a holistic and scientific protocol for the authentication and quality assurance of edible bird's nest. PubMed: Glycomic analysis of high density lipoprotein shows a highly sialylated particle. PubMed: The relationship between dietary vitamin A intake and the levels of sialic acid in the breast milk of lactating women. PubMed: Quantitative analysis of gangliosides in bovine milk and colostrum-based dairy products by ultrahigh performance liquid chromatography-tandem mass spectrometry. PubMed: Sugar-induced conformational change found in the HA-33/HA-17 trimer of the botulinum toxin complex. PubMed: LC-MS/MS quantification of N-acetylneuraminic acid, N-glycolylneuraminic acid and ketodeoxynonulosonic acid levels in the urine and potential relationship with dietary sialic acid intake and disease in 3- to 5-year-old children. PubMed: Effects of dietary sialic acid in n-3 fatty acid-deficient dams during pregnancy and lactation on the learning abilities of their pups after weaning. PubMed: Metabonomic analysis of urine from rats after low-dose exposure to 3-chloro-1,2-propanediol using UPLC-MS. PubMed: Catabolism of N-acetylneuraminic acid, a fitness function of the food-borne lactic acid bacterium Lactobacillus sakei, involves two newly characterized proteins. PubMed: Molecular evidence for the thriving of Campylobacter jejuni ST-4526 in Japan. PubMed: Gangliosides and sialic acid effects upon newborn pathogenic bacteria adhesion: an in vitro study. PubMed: Direct estimation of sialic acid in milk and milk products by fluorimetry and its application in detection of sweet whey adulteration in milk. PubMed: Short-term intra-nasal erythropoietin administration with low sialic acid content is without toxicity or erythropoietic effects. PubMed: Characterization of a novel N-acetylneuraminate lyase from Staphylococcus carnosus TM300 and its application to N-acetylneuraminic acid production. PubMed: Evidence for helical structure in a tetramer of α2-8 sialic acid: unveiling a structural antigen. PubMed: Metabolism of vertebrate amino sugars with N-glycolyl groups: mechanisms underlying gastrointestinal incorporation of the non-human sialic acid xeno-autoantigen N-glycolylneuraminic acid. PubMed: Loss of sialic acid binding domain redirects protein σ1 to enhance M cell-directed vaccination. PubMed: Identification and characterization of a lipopolysaccharide α,2,3-sialyltransferase from the human pathogen Helicobacter bizzozeronii. PubMed: Cooperative regulation of the Vibrio vulnificus nan gene cluster by NanR protein, cAMP receptor protein, and N-acetylmannosamine 6-phosphate. PubMed: The effect of stinging nettle (Urtica dioica) seed oil on experimental colitis in rats. PubMed: Are pathogenic bacteria just looking for food? Metabolism and microbial pathogenesis. PubMed: Effect of simulated gastrointestinal digestion on sialic acid and gangliosides present in human milk and infant formulas. PubMed: Chemical characterization of oligosaccharides in the milk of six species of New and Old World monkeys. PubMed: Protective potential of Royal Jelly against carbon tetrachloride induced-toxicity and changes in the serum sialic acid levels. PubMed: Absence of hematological side effects in acute and subacute nasal dosing of erythropoietin with a low content of sialic acid. PubMed: Involvement of sialic acid in transport of serotype C1 botulinum toxins through rat intestinal epithelial cells. PubMed: Effect of glycomacropeptide fractions on cholecystokinin and food intake. PubMed: Bovine Muc1 inhibits binding of enteric bacteria to Caco-2 cells. PubMed: Sialic acid-dependent binding and transcytosis of serotype D botulinum neurotoxin and toxin complex in rat intestinal epithelial cells. PubMed: Determination of sialic acid and gangliosides in biological samples and dairy products: a review. PubMed: Evaluation of the relationship between passive smoking and salivary electrolytes, protein, secretory IgA, sialic acid and amylase in young children. PubMed: Analyses of human colonic mucus obtained by an in vivo sampling technique. PubMed: Dietary selenium intake is negatively associated with serum sialic acid and metabolic syndrome features in healthy young adults. PubMed: Chemical characterization of oligosaccharides in chimpanzee, bonobo, gorilla, orangutan, and siamang milk or colostrum. PubMed: Clostridium botulinum serotype D neurotoxin and toxin complex bind to bovine aortic endothelial cells via sialic acid. PubMed: Analysis of major proteins and fat fractions associated with mare's milk fat globules. PubMed: Bacterial CMP-sialic acid synthetases: production, properties, and applications. PubMed: Genetic engineering of Escherichia coli for the economical production of sialylated oligosaccharides. PubMed: Architectural adaptation and protein expression patterns of Salmonella enterica serovar Enteritidis biofilms under laminar flow conditions. PubMed: The structure of Clostridium perfringens NanI sialidase and its catalytic intermediates. PubMed: Daily variations in oligosaccharides of human milk determined by microfluidic chips and mass spectrometry. PubMed: New role of antinutritional factors, phytic acid and catechin in the treatment of CCl4 intoxication. PubMed: Influence of distillery effluent on germination and growth of mung bean (Vigna radiata) seeds. PubMed: Detection of sialylated phosphorylated kappa-casein glycomacropeptide electrophoresed on polyacrylamide gels and cellulose acetate strips by the thiobarbituric acid and malachite green dye reactions. PubMed: Application of a sensitive fluorometric HPLC assay to determine the sialic acid content of infant formulas. PubMed: Anti-inflammatory and lysosomal stability actions of Cleome gynandra L. studied in adjuvant induced arthritic rats. PubMed: A liquid chromatography/tandem mass spectrometric approach for the determination of gangliosides GD3 and GM3 in bovine milk and infant formulae. PubMed: Relationships between biochemical bone turnover markers, season, and inflammatory status indices in prepubertal Gambian boys. PubMed: Efficient enzymatic synthesis of 4-methylumbelliferyl N-acetyllactosaminide and 4-methylumbelliferyl sialyl N-acetyllactosaminides employing beta-D-galactosidase and sialyltransferases. PubMed: Sialic acid-containing milk proteins show differential immunomodulatory activities independent of sialic acid. PubMed: Polysulfated sialic acid derivatives as anti-human immunodeficiency virus. PubMed: Analysis of sialyl oligosaccharides by high-performance liquid chromatography-electrospray ionisation-mass spectrometry with differentiation of alpha2-3 and alpha2-6 sialyl linkages. PubMed: Effects of a combination of niacin and chromium(III)-chloride on the skin and lungs of hyperlipemic rats. PubMed: Sialic Acid metabolism and systemic pasteurellosis. PubMed: Distribution of sialic acids in the milk of spanish mothers of full term infants during lactation. PubMed: Glycopeptide derived from hen egg ovomucin has the ability to bind enterohemorrhagic Escherichia coli O157:H7. PubMed: Optimization of carbohydrate silylation for gas chromatography. PubMed: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. PubMed: Chemical composition of chicken eggshell and shell membranes. PubMed: Characterization and biological activity of gangliosides in buffalo milk. PubMed: Purification of kappa-casien glycomacropeptide from sweet whey with undetectable level of phenylalanine. PubMed: Isolation and analysis of kappa-casein glycomacropeptide from goat sweet whey. PubMed: Influence of the length of the lipooligosaccharide alpha chain on its sialylation in Neisseria meningitidis. PubMed: Proposed biomolecular theory of fasting during fevers due to infection. PubMed: Concentration and distribution of sialic acid in human milk and infant formulas. PubMed: A longitudinal study of salivary sialic acid in preterm infants: Comparison of human milk-fed versus formula-fed infants. PubMed: Flu epidemic: shots, new treatments available. PubMed: A high molecular mass constituent of cranberry juice inhibits helicobacter pylori adhesion to human gastric mucus. PubMed: Use of an enzyme-linked lectinsorbent assay to monitor the shift in polysaccharide composition in bacterial biofilms. PubMed: Variation of the ganglioside compositions of human milk, cow's milk and infant formulas. PubMed: The innate immune response and type 2 diabetes: evidence that leptin is associated with a stress-related (acute-phase) reaction. PubMed: Determination of sialic acid by the thiobarbituric acid reaction in sweet whey and its fractions. PubMed: Changes in the level of sialic acid in plasma, brain and liver of inherently scorbutic rats during vitamin C and E deficiencies. PubMed: Sialic acid content of infant saliva: comparison of breast fed with formula fed infants. PubMed: Possible involvement of radical reactions in desialylation of LDL. PubMed: Experimental milk formulae with reduced protein content and desialylated milk proteins: influence on the faecal flora and the growth of term newborn infants. PubMed: A critical analysis of total sialic acid and sialoglycoconjugate contents of bovine milk-based infant formulas. PubMed: A total synthesis of glycononaosyl ceramide with a sialyl dimeric Le(x) sequence. PubMed: Quantitative detection of whey cream in sweet cream and butter. PubMed: [Sialic acid in breast milk and infant formula food]. PubMed: Characterization of high and low molecular weight forms of amphiregulin that differ in glycosylation and peptide core length. Evidence that the NH2-terminal region is not critical for bioactivity. PubMed: Inhibition of adhesion of S-fimbriated Escherichia coli to epithelial cells by meconium and feces of breast-fed and formula-fed newborns: mucins are the major inhibitory component. PubMed: 13C NMR investigation of the anomeric specificity of CMP-N-acetylneuraminic acid synthetase from Escherichia coli. PubMed: Specificity of antibodies to O-acetyl-positive and O-acetyl-negative group C meningococcal polysaccharides in sera from vaccinees and carriers. PubMed: Occurrence and characteristics of agglutination of Vibrio cholerae by serum from the eastern oyster, Crassostrea virginica. PubMed: Protective action of SCH 12223 against experimentally induced gastric and intestinal lesions. PubMed: [Toxicologic evaluation of nitrates entering the body with plant products]. PubMed: Purification, properties, and genetic location of Escherichia coli cytidine 5'-monophosphate N-acetylneuraminic acid synthetase. PubMed: N-acetylneuraminic acid concentrations in human milk oligosaccharides and glycoproteins during lactation. PubMed: Differential Adhesion and Infection of Nematodes by the Endoparasitic Fungus Meria coniospora (Deuteromycetes). PubMed: Uptake, metabolism and excretion of orally and intravenously administered, 14C- and 3H-labeled N-acetylneuraminic acid mixture in the mouse and rat.