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Acarbose

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Identification
Molecular formula
C25H43NO18
CAS number
56180-94-0
IUPAC name
(2S,3S,4S,5R,6R)-6-[(2S,3R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-2-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
State
State

At room temperature, acarbose is typically in a solid state.

Melting point (Celsius)
166.00
Melting point (Kelvin)
439.15
Boiling point (Celsius)
252.00
Boiling point (Kelvin)
525.15
General information
Molecular weight
645.61g/mol
Molar mass
645.6090g/mol
Density
1.2800g/cm3
Appearence

Acarbose is a white to off-white powder.

Comment on solubility

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

This complex organic compound features multiple hydroxyl (-OH) groups and carboxylic acid functionalities, suggesting an interesting profile for solubility in various solvents.

Factors Influencing Solubility:

  • Polarity: The presence of numerous hydroxyl groups and a carboxylic acid moiety increases the compound's polarity, enhancing its solubility in polar solvents such as water.
  • Hydrogen Bonding: This compound can engage in extensive hydrogen bonding with solvent molecules, which typically improves solubility.
  • Steric Hindrance: The stereochemistry suggested by the extensive chiral centers may affect how well the compound interacts with solvent molecules.

In general, compounds with multiple hydroxyl and carboxyl groups are often soluble in aqueous solutions, as they can easily form interactions with water molecules. However, the specific configuration and overall three-dimensional structure of this compound could lead to variations in solubility. Thus, it may be soluble in:

  • Water: Likely due to its polar characteristics.
  • Alcohols: Such as ethanol or methanol, which can support solubilization due to similar polar attributes.
  • Aqueous Buffer Solutions: Particularly useful for maintaining overall stability during experimental procedures.

Further experimental investigation would be required to confirm the exact solubility parameters in various solvents, but the indications from its structural characteristics suggest it could favor solubility in polar environments.

Interesting facts

Exploring the Complex World of (2S,3S,4S,5R,6R)-6-[(2S,3R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-2-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

This compound belongs to the family of complex carbohydrates and is understood to possess significant biological activity due to its intricate structure. Here are some interesting aspects to consider:

  • Natural Occurrence: This compound can be found in various natural sources, particularly within certain plants and microbial metabolites. It has gained attention for its potential health benefits.
  • Biochemical Significance: Known for its role in biochemical pathways, this structure is essential in carbohydrate metabolism and can act as a signaling molecule in different biological processes.
  • Pharmacological Potential: Due to its multi-hydroxy functional groups, this compound has been explored for its potential applications in medicine, including antibacterial and anticancer properties.
  • Synthesis Challenges: The synthesis of such a complex molecule requires sophisticated organic chemistry techniques and can offer significant challenges due to its stereochemistry.

As a scientist or chemistry student, one can appreciate the elegance and complexity of this compound, along with its potential implications in health and illness management. As aptly noted in the field of medicinal chemistry, "The more complex a natural product is, the more potential it has for unique biological activity." This serves as a reminder of why such structures deserve thorough exploration and understanding.

In studying this compound, chemists not only expand their knowledge of carbohydrate chemistry but also their skills in synthetic techniques. The meticulous nature of its synthesis reflects the beautiful intersection of nature and science, captivating both students and seasoned researchers alike.

Synonyms
Hyaluronan
(2S,3S,4S,5R,6R)-6-[(2S,3R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid
Hyaluronic acid from Cockscomb
DTXSID90925319
DB08818
EN300-33419387
125935-84-4
Hexopyranuronosyl-(1->3)-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl-(1->4)hexopyranuronosyl-(1->3)-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranose