N-acetyl neuraminic acid
(-)-5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid
 
Notes:
an n-acyl derivative of neuraminic acid. n-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (from dorland, 28th ed, p1518) Isol. from eggs, milk and colostrum by acid or enzymic hydrol. of the constit. sialoproteins and oligosaccharides. Most abundant source is the nest cementing glycoprotein of the Chinese swiftlet used in birdsnest soup N-acetylneuraminic acid (NeuAc) or sialic acid is an acetyl derivative of the amino sugar neuraminic acid. It occurs in many glycoproteins, glycolipids, and polysaccharides in both mammals and bacteria. The most abundant sialic acid, NeuAc, is synthesized in vivo from N-acetylated D-mannosamine (ManNAc) or D-glucosamine (GlcNAc). NeuAc and its activated form, CMP-NeuAc, are biosynthesized in five consecutive reactions: UDP-N-acetylglucosamine (UDP-GlcNAc) N-acetylmannosamine (ManNAc) ManNAc 6-phosphate NeuAc 9-phosphate NeuAc CMP-NeuAc. CMP-NeuAc is transported into the Golgi apparatus and, with the aid of specific sialyltransferases, added onto nonreducing positions on oligosaccharide chains of glycoproteins and glycolipids. NeuAc is widely distributed throughout human tissues and found in several fluids, including serum, cerebrospinal fluid, saliva, urine, amniotic fluid, and breast milk. It is found in high levels in the brain, adrenal glands, and the heart. Serum and urine levels of the free acid are elevated in individuals suffering from renal failure. Serum and saliva Neu5Ac levels are also elevated in alcoholics. A disorder known as Salla disease or infantile NeuAc storage disease is also characterized by high serum and urine levels of this compound. The negative charge of is responsible for the slippery feel of saliva and mucins coating the body's organs. This particular sialic acid is known to act as a "decoy" for invading pathogens. NeuAc is also becoming known as an agent necessary for mediating ganglioside distribution and structures in the brain. Sialic acid (SA) is an N-acetylated derivative of neuraminic acid that is an abundant terminal monosaccharide of glycoconjugates. Normal human serum SA is largely bound to glycoproteins or glycolipids (Total sialic acid, TSA, 1.5-2.5 mmol/L), with small amounts of free SA (1-3 umol/L). Negatively charged SA units stabilize glycoprotein conformation in cell surface receptors to increase cell rigidity. This enables signal recognition and adhesion to ligands, antibodies, enzymes and microbes. SA residues are antigenic determinant residues in carbohydrate chains of glycolipids and glycoproteins, chemical messengers in tissue and body fluids, and may regulate glomeruli basement membrane permeability. Sialic acids are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host sialic acid is to regulate innate immunity. Sialic acid is the moiety most actively recycled for metabolic purposes in the salvage pathways in glycosphingolipid metabolism. Sialic acid is indispensable for the neuritogenic activities of gangliosides constituents which are unique in that a sialic acid directly binds to the glucose of the cerebroside, they are mutually connected in tandem, and some are located in the internal parts of the sugar chain. Sialylation (sialic acid linked to galactose, N-acetylgalactosamine, or linked to another sialic acid) represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. (PMID: 11425186, 11287396, 12770781, 16624269, 12510390, 15007099)
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(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid (Click)
CAS Number: 131-48-6Picture of molecule
Other: 11032-36-3
ECHA EINECS - REACH Pre-Reg: 205-023-1
FDA UNII: GZP2782OP0
Nikkaji Web: J10.009I
Beilstein Number: 1716283
MDL: MFCD00006620
XlogP3-AA: -3.50 (est)
Molecular Weight: 309.27223000
Formula: C11 H19 N O9
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin and hair conditioning
 
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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)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
skin protecting agents
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Carbosynth
For experimental / research use only.
N-Acetylneuraminic Acid
Jiangyin Healthway
N-Aceylneuraminic Acid
New functional food ingredients
Santa Cruz Biotechnology
For experimental / research use only.
N-Acetylneuraminic Acid ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
N-Acetylneuraminic acid from Escherichia coli, ≥98%
TCI AMERICA
For experimental / research use only.
N-Acetylneuraminic Acid Hydrate >98.0%(T)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: cosmetic ingredient for skin and hair conditioning
Recommendation for N-acetyl neuraminic acid usage levels up to:
 not for fragrance use.
 
Recommendation for N-acetyl neuraminic acid flavor usage levels up to:
 not for flavor use.
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EPA Substance Registry Services (TSCA): 131-48-6
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Laboratory Chemical Safety Summary : 8565
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Chemidplus: 0000131486
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References:
 (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 8565
Pubchem (sid): 134973567
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KEGG (GenomeNet): C19910
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FooDB: FDB001209
Export Tariff Code: 2932.99.9090
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
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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-acetylneuraminic acid
 neuraminic acid, N-acetyl-
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Articles:
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.
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