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N-Acetylneuraminic acid

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Identification
Molecular formula
C11H19NO9
CAS number
131-48-6
IUPAC name
5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid
State
State

At room temperature, N-acetylneuraminic acid is in a solid state, generally found as a crystalline powder.

Melting point (Celsius)
185.00
Melting point (Kelvin)
458.15
Boiling point (Celsius)
345.20
Boiling point (Kelvin)
618.35
General information
Molecular weight
309.27g/mol
Molar mass
309.2730g/mol
Density
1.6640g/cm3
Appearence

N-Acetylneuraminic acid, or sialic acid, typically appears as a white crystalline powder. It is a derivative of neuraminic acid and consists of a nine-carbon backbone. In its pure form, N-acetylneuraminic acid is a solid at room temperature.

Comment on solubility

Solubility of 5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid

The solubility of the compound with the formula C11H19NO9 is influenced by its structural features, particularly the presence of multiple hydroxyl (-OH) groups. Here are some key points regarding its solubility:

  • Hydrophilicity: The numerous hydroxyl groups contribute to strong hydrogen bonding capabilities, making the compound more hydrophilic.
  • Solvent Compatibility: This compound is more likely to be soluble in polar solvents, such as water and alcohols, compared to non-polar solvents.
  • Temperature Dependency: As with many organic compounds, solubility may increase with temperature, making it important to consider when preparing solutions.
  • pH Influence: The acidic property of the carboxylic acid group can affect solubility in different pH environments, potentially increasing solubility in basic conditions.

In conclusion, one can anticipate that 5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid will exhibit a relatively high solubility in polar solvents, highlighting its potential utility in aqueous formulations and biological systems.

Interesting facts

Interesting Facts About 5-Acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic Acid

This compound is a fascinating example of a complex organic molecule featuring a unique arrangement of functional groups that impart various properties. Here are some intriguing aspects of this compound:

  • Structural Complexity: The presence of a tetrahydropyran ring coupled with multiple hydroxyl and carboxylic acid groups illustrates the chemical ingenuity seen in organic synthesis. Its structure plays a fundamental role in its biological activities.
  • Biological Significance: Compounds like this one, with multiple hydroxyl groups, are known for their potential as bioactive molecules. They may exhibit various biological activities, including antibacterial and antifungal properties.
  • Synthetic Versatility: The synthetic pathway to such complex molecules often provides a platform for the development of similar compounds. This can lead to the discovery of new drugs or therapeutic agents through structural modifications.
  • Natural Product Inspiration: Many structurally similar compounds are found in nature, often derived from plants or microbial sources. This connection to nature underscores the importance of exploring natural products in the search for novel pharmaceuticals.
  • Potential Applications: Beyond its biological interest, compounds like this one may possess utility in fields such as materials science or cosmetics due to their unique chemical properties.

As we delve deeper into the study of such complex molecules, we are reminded of the endless possibilities within the realm of organic chemistry. As one scientist put it, “Chemistry is a science of change; it’s the transformation of simple materials into complex structures that can make a difference in our lives.” This compound is a testament to that transformation.

Synonyms
Sia
sialic acid
131-48-6
Neuraminic acid, N-acetyl-
O-sialic acid
3h-sialic acid
NSC111756
489-46-3
NSC-111756
Oprea1_149877
CHEMBL112030
SCHEMBL2619258
SCHEMBL11936589
DTXSID80964136
SQVRNKJHWKZAKO-UHFFFAOYSA-N
BCP32141
(-)-N-Acetylneuraminic acid,synthetic
AKOS025243615
(2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid
6918-20-3
SY012200
DB-042034
5-(Acetylamino)-3,5-dideoxynon-2-ulopyranosonic acid #
9724BDBF-717D-4312-8E53-2EC71ECF2DE6
3,5-Dideoxy-5-[(1-hydroxyethylidene)amino]non-2-ulopyranosonic acid
5-N-Acetyl-beta-D-neuraminic acid;Lactaminic acid;NeuAc;N-Acetyl-D-neuraminic acid