ChemicalBook > CAS DataBase List > N-Acetylneuraminic acid

N-Acetylneuraminic acid

Product Name
N-Acetylneuraminic acid
CAS No.
131-48-6
Chemical Name
N-Acetylneuraminic acid
Synonyms
SIALIC ACID;NAN;NEU5AC;NANA;NeuAc;(-)-N-ACETYLNEURAMINIC ACID;LACTAMINIC ACID;Acetylneuraminic acid;(4S,5R,6R,7S,8R)-5-Acetamido-4,6,7,8,9-pentahydroxy-2-oxononanoic acid;O-SIALIC ACID
CBNumber
CB6713403
Molecular Formula
C11H19NO9
Formula Weight
309.27
MOL File
131-48-6.mol
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N-Acetylneuraminic acid Property

Melting point:
184-186 °C
alpha 
-32 º (c=2,water)
Boiling point:
449.56°C (rough estimate)
Density 
1.3580 (rough estimate)
refractive index 
-32 ° (C=1, H2O)
storage temp. 
-20°C
solubility 
50 g/L (20°C)
pka
2.41±0.54(Predicted)
form 
synthetic, crystalline
color 
White to Off-White
optical activity
-32
Water Solubility 
50 g/L (20 ºC)
Sensitive 
Air Sensitive
Merck 
14,8484
BRN 
1716283
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
SQVRNKJHWKZAKO-PFQGKNLYSA-N
LogP
-1.897 (est)
CAS DataBase Reference
131-48-6(CAS DataBase Reference)
EPA Substance Registry System
Neuraminic acid, N-acetyl- (131-48-6)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
F 
3-10-23
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29329970
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
19023
Product name
N-Acetylneuraminic acid
Purity
analytical standard
Packaging
10mg
Price
$141
Updated
2024/03/01
Sigma-Aldrich
Product number
1612619
Product name
N-Acetylneuraminic acid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$497
Updated
2024/03/01
Sigma-Aldrich
Product number
110138
Product name
N-AcetylneuraminicAcid,Synthetic-CAS131-48-6-Calbiochem
Purity
Acomponentofmucoproteins,mucopolysaccharides,andmucolipids.
Packaging
1g
Price
$199
Updated
2024/03/01
TCI Chemical
Product number
A0639
Product name
N-Acetylneuraminic Acid Hydrate
Purity
>98.0%(T)
Packaging
1g
Price
$56
Updated
2024/03/01
TCI Chemical
Product number
A0639
Product name
N-Acetylneuraminic Acid Hydrate
Purity
>98.0%(T)
Packaging
5g
Price
$161
Updated
2024/03/01
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N-Acetylneuraminic acid Chemical Properties,Usage,Production

Description

N-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.

Physical properties

The numbering of the sialic acid structure begins at the carboxylate carbon and continues around the chain. The configuration which places the carboxylate in the axial position is the alpha-anomer.
The alpha-anomer is the form that is found when sialic acid is bound to glycans, however, in solution it is mainly (over 90 %) in the beta-anomeric form. A bacterial enzyme with sialic acid mutarotase activity, NanM, has been discovered which is able to rapidly equilibrate solutions of sialic acid to the resting equilibrium position of around 90 % beta 10 % alpha.

Uses

N-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.

Definition

ChEBI: N-Acetylneuraminic acid is n-Acetylneuraminic acid with beta configuration at the anomeric centre. It has a role as an epitope. It is functionally related to a beta-neuraminic acid. It is a conjugate acid of a N-acetyl-beta-neuraminate.

Biosynthesis

In bacterial systems, sialic acids are biosynthesized by an aldolase enzyme. The enzyme uses a mannose derivative as a substrate, inserting three carbons from pyruvate into the resulting sialic acid structure. These enzymes can be used for chemoenzymatic synthesis of sialic acid derivatives.

Biological Functions

Sialic acid-rich glycoproteins (sialoglycoproteins) bind selectin in humans and other organisms. Metastatic cancer cells often express a high density of sialic acid-rich glycoproteins. This overexpression of sialic acid on surfaces creates a negative charge on cell membranes. This creates repulsion between cells (cell opposition) and helps these late-stage cancer cells enter the blood stream.
Sialic acid also plays an important role in human influenza infections.
Many bacteria also use sialic acid in their biology, although this is usually limited to bacteria that live in association with higher animals (deuterostomes). Many of these incorporate sialic acid into cell surface features like their lipopolysaccharide and capsule, which helps them evade the innate immune response of the host.[6] Other bacteria simply use sialic acid as a good nutrient source, as it contains both carbon and nitrogen and can be converted to fructose-6- phosphate, which can then enter central metabolism.
Sialic acid-rich oligo saccharides on the glyco conjugates ( glyco lipids, glyco proteins, proteoglycans) found on surface membranes help keep water at the surface of cells . The sialic acid - rich regions contribute to creating a negative charge on the cells' surfaces. Since water is a polar molecule with partial positive charges on both hydrogen atoms, it is attracted to cell surfaces and membranes. This also contributes to cellular fluid uptake.
Sialic acid can "hide" mannose antigens on the surface of host cells or bacteria from mannose - binding lectin . This prevents activation of complement.
Sialic acid in the form of poly sialic acid is an unusual posttranslational modification that occurs on the neural cell adhesion molecules (NCAMs). In the synapse, the strong negative charge of the polysialic acid prevents NCAM cross-linking of cells.

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.

in vitro

N-Acetylneuraminic acid (0 - 2 mg/mL, 2 days) has no effect on cell proliferation but significantly decreases the tyrosinase protein level, the number of melanosomes, and the p62 protein level and increases the CCT3, CCT5, and LC3-II protein levels and mRNA levels in B16 melanoma cells.
N-Acetylneuraminic acid (0 - 500 μM, 12 h) specifically binds to RhoA and Cdc42 and activates cardiomyocytes' Rho/ROCK-JNK/ERK signaling.

in vivo

N-Acetylneuraminic acid (0 - 20 mg/kg, i.p., twice a day for 6 weeks) triggers myocardial injury in healthy rats.

N-Acetylneuraminic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-Acetylneuraminic acid manufacturers

Sinoway Industrial co., ltd.
Product
N-Acetylneuraminic Acid / Sialic Acid 131-48-6
Price
US $0.00/KG
Min. Order
2KG
Purity
98% up
Supply Ability
20 tons
Release date
2021-07-07
Hebei Longbang Technology Co., Ltd
Product
N-Acetylneuraminic acid 131-48-6
Price
US $6.00/kg
Min. Order
1kg
Purity
More than 99%
Supply Ability
2000KG/Month
Release date
2024-05-23
Changsha Staherb Natural Ingredients Co., Ltd.
Product
Sialic acid 131-48-6
Price
US $0.00/G
Min. Order
1G
Purity
98% HPLC
Supply Ability
1000KG
Release date
2022-10-20

131-48-6, N-Acetylneuraminic acidRelated Search:

N-Acetyl-L-cysteine Acetylsalicylic acid Stearic acid Folic acid L(+)-Arginine Ethyl 2-(Chlorosulfonyl)acetate Citric acid Hyaluronic acid Neuraminidase Acetylcholine Acetaminophen N-OLEOYLSARCOSINE FMOC-ARG(BOC)2-OH Ascoric Acid 4,7,8,9-TETRA-O-ACETYL-N-ACETYLNEURAMINIC ACID METHYL ESTER N-Glycolylneuraminic acid N-Acetyl-β-neuraminic acid methyl ester monohydrate cytidine 5'-monophospho-N-acetylneuraminic acid, sodium,CMP-NAN, CMP-NANA, CMP-NeuAc, CMP-Sialic acid,CMP-b-D-Sialic Acid, DisodiumSalt

  • 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulosonicaci
  • LACTAMINIC ACID
  • 5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-2-NONU
  • 5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID
  • 5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-NONULOPYRANOSONIC ACID HYDRATE
  • 5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTONONULOSONIC ACID
  • 5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTONULOSONIC ACID
  • 5-ACETYLAMINO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID
  • ACETYLNEURAMINIC ACID, N-
  • N-Acethyl-NeuramiNic acid
  • N-ACETYLNEURAMINIC ACID, SYNTHETIC
  • N-ACETYLNEURAMINIC ACID FROM E. COLI
  • N-ACETYLNEURAMINIC ACID FROM ESCHERICHIA COLI
  • N-ACETYLNEURAMINIC ACID FROM SHEEP SUBMAXILLARY GLAND
  • (-)-N-ACETYLNEURAMINIC ACID, SYNTHETIC, CRYSTALLINE
  • NANA, Sialic Acid
  • N-Acetyl-Neuraminic?Acid?(Sialic?Acid)
  • Acetylneuraminic acid
  • 5-acetamido-3,5-dideoxy-d-glycero-d-galacto-nonulopyranosonic acid
  • 5-acetylamino-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
  • N-Acetyl-D-neuraminic acid 97%
  • AceneuramicAcid
  • N-Acetylneuraminic acidfree acid (Neu5Ac)
  • Galactononulosonic acid
  • N-Acetylneuraminic acid >99%
  • NANA, synthetic sialic acid
  • N-ACETYLNEURAMINIC ACID extrapure for biochemistry
  • N-Acetylneuraminic acid from Escherichia coli, Lactaminic acid, NANA, Sialic acid
  • Lactaminic acid, NAN, NANA, Sialic acid, 5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid
  • (2S,4S,5R,6R)-5-Acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
  • 5-N-Acetyl-D-neuraminic acid
  • D-glycero-D-galacto-Nonulosonic acid, 5-acetamido-3,5-dideoxy-
  • N-Acetylsialic acid
  • Sialomucin
  • 5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
  • NANA Hydrate
  • Neu5Ac Hydrate
  • N-Acetylneuraminic Acid 〔NANA, Sialic Acid〕
  • N-ACETYLNEURAMINIC ACID FROM ESCHERI
  • N-acetyl-beta-neuraminic acid
  • N- acetyl neuroammonia acid
  • sialic acid 131-48-6
  • NAN
  • N-Acetylneuraminicacid from bovine milk
  • 2-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-1H-isoindole-1,3(2H)-dione
  • 2-[4-[4-(2-Methoxyphenyl)piperazine-1-yl]butyl]-2H-isoindole-1,3-dione
  • 2-[4-[4-(2-Methoxyphenyl)piperazine-1-yl]butyl]isoindoline-1,3-dione
  • N-[4-[4-(2-Methoxyphenyl)piperazino]butyl]phthalimide
  • N-Acetylneuraminic acid,97%
  • N-Acetylneuraminic acid ,98%
  • N-Acetylneuraminic acid,5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Lactaminic acid, NAN, NANA, Sialic acid
  • N-Acetylneuraminic Acid (200 mg)
  • N-Acetylneuraminic a
  • N-Acetylneuraminic acid 98%
  • N-Acetyl NeuraMinic Acid/NANA/Neu5Ac/SA
  • Sialic Acid 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonic Acid
  • 5-AcetaMido-3,5-Dideoxy-D-Glycero-D-GalaCLo-Nonulopyranosonic Acid
  • (2S,4S,5R,6R)-5-AcetaMido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid