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N-Acetylneuraminic acid

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Identification
Molecular formula
C11H19NO9
CAS number
131-48-6
IUPAC name
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
State
State

At room temperature, N-Acetylneuraminic acid is typically found in the solid state. It forms part of the outer coating of many cells and is biologically significant. Sialic acid is an important constituent of glycoproteins and glycolipids in prokaryotic and eukaryotic cells.

Melting point (Celsius)
185.00
Melting point (Kelvin)
458.15
Boiling point (Celsius)
748.00
Boiling point (Kelvin)
1 021.15
General information
Molecular weight
309.27g/mol
Molar mass
309.2730g/mol
Density
1.7001g/cm3
Appearence

N-Acetylneuraminic acid, commonly known as sialic acid, appears as a white, crystalline powder. It is highly hygroscopic and soluble in water. This compound is notable for its structural complexity and significance in biological systems.

Comment on solubility

Solubility of (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

The solubility characteristics of the complex compound C11H19NO9 are influenced by its unique structural features and functional groups. Here are some important points to consider regarding its solubility:

  • Hydrophilicity: The presence of multiple hydroxyl groups (-OH) and a sulfooxy group contributes significantly to its hydrophilic nature, enhancing its solubility in water.
  • Amide functionality: The acetamido group provides potential interactions via hydrogen bonding, which can further increase solubility in polar solvents.
  • Acidic nature: The carboxylic acid group can ionize under physiological conditions, making the compound more soluble in aqueous environments at certain pH levels.
  • Conformation: The stereochemistry of the compound may also impact how it interacts with solvents, influencing solubility profiles.

In summary, this compound is likely to exhibit good solubility in water, particularly due to its polar functional groups and the ability to form hydrogen bonds. It’s essential to consider conditions such as pH and temperature, which can alter the solubility behavior of such compounds.

Interesting facts

Interesting Facts about (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

This complex organic compound is a fascinating subject of study due to its structural intricacies and potential biological significance. Here are some engaging aspects that highlight the importance of this compound in the field of chemistry:

  • Stereochemistry: The compound features multiple stereocenters, indicating a rich stereochemistry that contributes to its unique three-dimensional shape. Understanding the configuration of each chiral center is crucial as it plays a vital role in the compound's biological activity.
  • Biological Relevance: Compounds with similar structures often exhibit significant biological activity, particularly in medicinal chemistry. Some researchers are investigating the potential roles of such compounds in drug development and disease treatment.
  • Functional Groups: This compound contains various functional groups, including amide, hydroxyl, and carboxylic acid groups, which are known for their ability to form strong hydrogen bonds. This capacity can enhance the solubility and reactivity in biological systems.
  • Synthetic Challenges: The synthesis of such complex organic molecules presents several challenges for chemists, especially regarding stereocontrol and yield. Mastery of synthetic techniques is necessary to produce this compound efficiently.
  • Potential Applications: The potential applications of this compound extend to various fields, including pharmaceuticals, agriculture, and biotechnology. Understanding its properties could lead to innovations in these areas.

In conclusion, this compound is a prime example of how intricate organic chemistry can lead to significant discoveries and applications. Its unique structure and potential biological applications continue to inspire scientists to explore its capabilities.

Synonyms
Chondroitin sulfate
9007-28-7
39455-18-0
Chondroitin 4-sulfate
Chondroitine sulfate
Sodium chondroitin sulfate
Chondroitin 4-sulfate sodium salt
chondroitin sulfate C
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
25322-46-7
Condrosulf
Chondroitinsulfate C
Chondroitin sulfate A sodium salt
Chondroitin 4 and 6 sulfate
Chondron
Structum
Gepan
Uropol S
Chondroitin, 6-(hydrogen sulfate)
EINECS 246-844-5
Chondroitin sulfate sodium salt from shark cartilage
UNII-7LWQ6472SP
7LWQ6472SP
SCHEMBL4577901
CHEMBL5266347
DTXSID601017238
(2S,3S,4S,5R,6R)-6-[[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxy-4-oxanyl]oxy]-3,4,5-trihydroxy-2-oxanecarboxylic acid
MSK11005
Chondroitin sulfate A sodium salt - Average MW 10,000 - 30,000
Chondroitin sulfate A sodium salt - Average MW 20,000 - 30,000
AKOS015896487
ND 3482
YC15288
YC31416
NCGC00390235-01
YC165869
YC178504
Chondroitin, hydrogen sulfate, sodium salt
NS00014054
D85172
Chondroitin sulfate A sodium salt - 90%, from Bovine Cartilage
Chondroitin sulfate A sodium salt - Average MW 10,000 - 50,000
Alternating Copoly b-glucuronic acid-(1?3)-N-acetyl-b-galactosamine-4-sulfate-(1?4)
Alternating Copoly beta-glucuronic acid-(1?3)-N-acetyl-beta-galactosamine-4-sulfate-(1?4)
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid