N-Acetylneuraminic acid
- CAS No.
- 131-48-6
- Chemical Name:
- N-Acetylneuraminic acid
- Synonyms
- SIALIC ACID;NEU5AC;NAN;NANA;Acetylneuraminic acid;NeuAc;LACTAMINIC ACID;(-)-N-ACETYLNEURAMINIC ACID;(2S,4S,5R,6R)-5-AcetaMido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid;N-AcetyIneuraminic acid
- CBNumber:
- CB6713403
- Molecular Formula:
- C11H19NO9
- Molecular Weight:
- 309.27
- MDL Number:
- MFCD00006620
- MOL File:
- 131-48-6.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| biological source | synthetic |
| 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. |
| Major Application | food and beverages |
| Cosmetics Ingredients Functions |
SKIN CONDITIONING SKIN PROTECTING |
| 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 |
| InChIKey | SQVRNKJHWKZAKO-PFQGKNLYSA-N |
| SMILES | 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 |
| LogP | -1.897 (est) |
| CAS DataBase Reference | 131-48-6(CAS DataBase Reference) |
| NCI Dictionary of Cancer Terms | sialic acid |
| FDA UNII | GZP2782OP0 |
| ATC code | M09AX05 |
| EPA Substance Registry System | Neuraminic acid, N-acetyl- (131-48-6) |
| UNSPSC Code | 85151701 |
| NACRES | NA.79 |
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 | TSCA listed | |||||||||
| HS Code | 29329970 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Eye Irrit. 2 | |||||||||
| NFPA 704 |
|
N-Acetylneuraminic acid price More Price(113)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 19023 | N-Acetylneuraminic acid analytical standard | 131-48-6 | 10mg | $156 | 2026-04-30 | Buy |
| Sigma-Aldrich | 1612619 | N-Acetylneuraminic acid United States Pharmacopeia (USP) Reference Standard | 131-48-6 | 200mg | $500 | 2026-04-30 | Buy |
| Sigma-Aldrich | 110138 | N-AcetylneuraminicAcid,Synthetic-CAS131-48-6-Calbiochem Acomponentofmucoproteins,mucopolysaccharides,andmucolipids. | 131-48-6 | 1g | $222 | 2026-04-30 | Buy |
| TCI Chemical | A0639 | N-Acetylneuraminic Acid Hydrate >98.0%(T) | 131-48-6 | 1g | $56 | 2026-04-30 | Buy |
| TCI Chemical | A0639 | N-Acetylneuraminic Acid Hydrate >98.0%(T) | 131-48-6 | 5g | $161 | 2026-04-30 | Buy |
N-Acetylneuraminic acid Chemical Properties, Uses, 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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Zhejiang Zhengshuo Biological Technology Co., Ltd | 13665754639 | wulicheng2@126.com | China | 21 | 58 |
| Shandong Mingfeng Pharmaceutical and Technology Co. Ltd | 053155551677 15315114555 | 1345456643@qq.com | China | 298 | 58 |
| Ning Bo hongxiang bio-chem Co.,Ltd. | 574-66003444 13071918355 | hongyubiochem@aliyun.com | China | 9 | 60 |
| Nanjing UltraPure Biotech Co., Ltd. | 025-82263158 13851993283 | 2842979086@qq.com | China | 243 | 58 |
| Xi`an Tian Guangyuan Biotech Co., Ltd. | 17791861264 | 3752088972@qq.com | China | 170 | 58 |
| Hangzhou Linran Biotechnology Co. LTD | 0571-18067987-92 18067987892;13738142397 | 2543558860@qq.com | China | 137 | 58 |
| Zhengbainian (Shanghai) International Trade Co., Ltd. | 13381511189 | 3849936813@qq.com | China | 457 | 58 |
| Shandong Yuhe Pharmaceutical Technology Co., LTD | 15263077727 | 1436425847@qq.com | China | 296 | 58 |
| Shaanxi xintianyu Biotechnology Co., Ltd. | 029-32565555 18710500080 | 1064976462@qq.com | China | 413 | 58 |
| Lihe Biotechnology (Shandong) Co., Ltd | 13176691201 15588824841 | lhswsd@126.com | China | 32 | 58 |
Related articles
- N-Acetylneuraminic Acid: A Comprehensive Overview for Chemistry Professionals
- N-Acetylneuraminic acid (Neu5Ac), commonly known as sialic acid, is a pivotal molecule in biochemistry and glycobiology.
- Oct 29,2024
- Physiological Function and Preparation of N-Acetylneuraminic acid
- N-acetylneuraminic acid is a component of oligosaccharide chains of mucins, glycoproteins, and glycolipids that play an essent....
- Jul 15,2022
View Latest Price from N-Acetylneuraminic acid manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
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2026-09-14 | N-Acetylneuraminic acid
131-48-6
|
0.99 | RongNa Biotechnology Co.,Ltd | ||||
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2026-09-14 | N-acetylneuraminic acid
131-48-6
|
1kg | 0.99 | 20tons | HANGZHOU INVERTIN BIOPHARMA CO., LTD. | ||
 |
2026-09-14 | N-Acetylneuraminic acid
131-48-6
|
$300.00-500.00 | 1kg | 99% | 5000 | HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD |
-
- N-Acetylneuraminic acid
131-48-6
- 0.99
- RongNa Biotechnology Co.,Ltd
-
- N-acetylneuraminic acid
131-48-6
- 0.99
- HANGZHOU INVERTIN BIOPHARMA CO., LTD.
-
- N-Acetylneuraminic acid
131-48-6
- $300.00-500.00
- 99%
- HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
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