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
- Molecular Weight:
- 309.27
- MOL File:
- 131-48-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/6/26 9:37:22
| Melting point | 184-186 °C |
|---|---|
| Boiling point | 449.56°C (rough estimate) |
| alpha | -32 º (c=2,water) |
| Density | 1.3580 (rough estimate) |
| refractive index | -32 ° (C=1, H2O) |
| storage temp. | -20°C |
| solubility | 50 g/L (20°C) |
| form | synthetic, crystalline |
| pka | 2.41±0.54(Predicted) |
| color | White to Off-White |
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H319 | |||||||||
| Precautionary statements | P264-P280-P305+P351+P338-P337+P313 | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
N-Acetylneuraminic acid price More Price(23)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A2388 | N-Acetylneuraminic acid from Escherichia coli, ≥98% | 131-48-6 | 10MG | ₹6603.25 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A2388 | N-Acetylneuraminic acid from Escherichia coli, ≥98% | 131-48-6 | 25MG | ₹12946.7 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A2388 | N-Acetylneuraminic acid from Escherichia coli, ≥98% | 131-48-6 | 100MG | ₹34152.88 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A2388 | N-Acetylneuraminic acid from Escherichia coli, ≥98% | 131-48-6 | 250MG | ₹56160.1 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A2388 | N-Acetylneuraminic acid from Escherichia coli, ≥98% | 131-48-6 | 1G | ₹116119.78 | 2022-06-14 | Buy |
N-Acetylneuraminic acid Chemical Properties,Uses,Production
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.
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.
N-Acetylneuraminic acid Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| HRV Global Life Sciences | +91-9820219686 +91-9820219686 | Telangana, India | 379 | 58 | Inquiry |
| Rivashaa Agrotech Biopharma Pvt. Ltd. | +91-26463395 +91-7926462688 | Gujarat, India | 1615 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| Otto Chemie Pvt. Ltd. | +91 9820041841 | Mumbai, India | 5873 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Sisco Research Laboratories Pvt. Ltd. | +91-22-4268 5800 | Mumbai, India | 4317 | 58 | Inquiry |
| Central Drug House(P) Ltd. | 91-11-49404040 | New Delhi, India | 6160 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
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