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Linagliptin

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Identification
Molecular formula
C25H28N8O2
CAS number
668270-12-0
IUPAC name
2-(1-carboxy-2-hydroxy-propyl)-4-[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid
State
State

At room temperature, Linagliptin is in a solid state, specifically, as a crystalline powder.

Melting point (Celsius)
202.00
Melting point (Kelvin)
475.00
Boiling point (Celsius)
682.30
Boiling point (Kelvin)
955.45
General information
Molecular weight
474.52g/mol
Molar mass
474.5210g/mol
Density
1.2396g/cm3
Appearence

Linagliptin is typically a white to yellowish crystalline powder. It is practically insoluble in water, slightly soluble in methanol, and soluble in dimethyl sulfoxide (DMSO).

Comment on solubility

Solubility of 2-(1-carboxy-2-hydroxy-propyl)-4-[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid

The solubility of the compound 2-(1-carboxy-2-hydroxy-propyl)-4-[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid (C25H28N8O2) can be influenced by several factors that include molecular structure, polarity, and environmental conditions.

This compound contains:

  • Multiple hydrophilic functional groups such as carboxylic and hydroxyl groups, which can enhance its solubility in polar solvents.
  • A relatively large and complex molecular structure that may hinder dissolution in non-polar solvents.
  • Pyrrolidine moieties which generally have good solvation properties.

In general, compounds that have a combination of hydrophilic and hydrophobic characteristics exhibit solubility properties that can vary widely:

  • High solubility in water due to the presence of polar groups.
  • Reduced solubility in organic solvents because of the steric hindrance from bulky groups.

As a rule of thumb, "like dissolves like"; thus, the solubility of this compound would be favorable in polar solvents such as water or alcohol, while limit in non-polar solvents. The actual solubility may require experimental determination to ascertain precise behavior under specific conditions.

Interesting facts

Interesting Facts about 2-(1-Carboxy-2-hydroxy-propyl)-4-[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid

This compound is notable in the realm of medicinal chemistry due to its complex structure and potential applications. Here are some key highlights:

  • Diverse Functional Groups: The presence of multiple functional groups, such as carboxylic acids, dimethylcarbamoyl groups, and hydroxy moieties, makes this compound particularly versatile for various reactivity and binding properties.
  • Pyrrole Core: The pyrrole ring contributes significantly to the biological activity of the compound. Derivatives of pyrrole are known for their role in many pharmacologically active substances.
  • Designer Drug Potential: The combination of a pyrrolidine and a sulfanyl group within its structure indicates a potential for designing novel drugs that could have specific interactions within biological systems.
  • Research Avenues: This compound has potential implications in research areas such as drug delivery systems and targeted therapies, especially due to its structural complexity that may allow for tailored interactions with biomolecules.
  • Synthesis Challenges: The intricate synthesis pathway required to produce this compound can provide insights into advanced organic synthesis techniques, including the strategic use of protecting groups and reaction conditions.

In summary, 2-(1-carboxy-2-hydroxy-propyl)-4-[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid represents a fascinating template in the search for new therapeutic agents, suggesting the importance of such multi-functional structures in modern chemistry.

Synonyms
2-(1-carboxy-2-hydroxypropyl)-4-{[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-3-methyl-3,4-dihydro-2h-pyrrole-5-carboxylic acid
DTXSID30924745
2-(1-Carboxy-2-hydroxypropyl)-4-[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid