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Mebendazole

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Identification
Molecular formula
C16H13N3O3
CAS number
31431-39-7
IUPAC name
5-(methylamino)-2-[[3,5,9-trimethyl-2-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
State
State

At room temperature, mebendazole is a solid. It is typically encountered in its powdered form when used in pharmaceuticals, particularly for its role as an anthelmintic or anti-worming treatment.

Melting point (Celsius)
288.00
Melting point (Kelvin)
561.00
Boiling point (Celsius)
645.00
Boiling point (Kelvin)
918.00
General information
Molecular weight
295.19g/mol
Molar mass
295.1900g/mol
Density
1.3200g/cm3
Appearence

Mebendazole appears as a white to slightly yellow powder in its pure form. It is practically insoluble in water and slightly soluble in methanol and ethanol, which are characteristics that affect its formulation as an oral medication.

Comment on solubility

Solubility of 5-(methylamino)-2-[[3,5,9-trimethyl-2-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid

The solubility of the compound C16H13N3O3 can be influenced by various factors due to its complex structure. Understanding its solubility is essential for predicting its behavior in different environments. Here are some important considerations:

  • Polarity: The presence of functional groups such as carboxylic acid contributes to its polarity, which typically enhances the compound's solubility in polar solvents like water.
  • Hydrogen bonding: The ability of the compound to form hydrogen bonds can significantly increase its solubility in water and other polar protic solvents.
  • Solvent-effects: The solubility may vary widely depending on the choice of solvent. For example, organic solvents may dissolve the compound differently compared to aqueous solutions.
  • Temperature: Increasing temperature generally improves solubility for many solids; thus, solubility may increase with temperature changes.

In summary, while we may anticipate a degree of solubility based on the compound's structure, the exact solubility parameters can only be defined with empirical data. Experimentation is crucial for a precise assessment, as the interactions between the solute and solvent will dictate the overall solubility.

Interesting facts

Interesting Facts about 5-(methylamino)-2-[[3,5,9-trimethyl-2-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid

This complex organic compound demonstrates the fascinating intricacies of chemical architecture that can emerge when various functional groups combine. Here are some intriguing highlights:

  • Structural Diversity: The compound exhibits a unique structure characterized by the presence of multiple functional groups, including a benzoxazole and a dioxaspiro moiety. Such structural diversity is essential for influencing the compound's reactivity and biological interactions.
  • Biological Applications: Compounds like this one, especially those with intricate structures, often serve as potential leads in pharmaceutical research. They explore activities that could result in significant therapeutic effects, possibly acting as antioxidants or targeting specific pathways related to diseases.
  • Mechanistic Insight: The inclusion of the methylamino group plays a crucial role in enhancing solubility in various organic solvents, which is vital for drug formulation. As a scientist, understanding the mechanistic attributes of such groups can lead to improved efficacy in drug delivery systems.
  • Inspiration from Nature: The presence of the pyrrole ring hints at inspiration from natural products known for their myriad biological activities. This shows how chemistry can draw from the complexity of the natural world to create synthetic compounds with desired properties.
  • Research Implications: The exploration of such compounds involves extensive techniques, including spectroscopic methods and computational chemistry, to predict how they behave in various conditions. This contributes not only to academic knowledge but also to practical advancements in materials science and medicinal chemistry.

In summary, the study of 5-(methylamino)-2-[[3,5,9-trimethyl-2-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid exemplifies the blend of creativity and scientific rigor that defines modern chemistry. The intricate interplay between its structural elements not only garners academic curiosity but also reflects the vast potential of chemical compounds to impact human health and technology.

Synonyms
DL-Calcimycin
52665-69-7
1212378-76-1
SCHEMBL258989
DTXSID80860649
5-(methylamino)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-((S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methyl)benzo[d]oxazole-4-carboxylic acid
NCGC00015265-02
A829191
5-(Methylamino)-2-({3,9,11-trimethyl-8-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid