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Penicillin G

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Identification
Molecular formula
C16H18N2O4
CAS number
61-33-6
IUPAC name
methyl (1R,9S,10R,13S,20S)-9-hydroxy-12-methyl-11-oxa-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-tetraene-10-carboxylate
State
State

At room temperature, penicillin G exists as a solid in the form of a white crystalline powder. It is typically stored in its solid state and is reconstituted as required for medical use.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.15
Boiling point (Celsius)
350.00
Boiling point (Kelvin)
623.15
General information
Molecular weight
334.39g/mol
Molar mass
334.3900g/mol
Density
1.2500g/cm3
Appearence

Methyl (1R,9S,10R,13S,20S)-9-hydroxy-12-methyl-11-oxa-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-tetraene-10-carboxylate, known as Penicillin G, appears as a white crystalline powder. It is typically odorless and has a bitter taste.

Comment on solubility

Solubility of Methyl (1R,9S,10R,13S,20S)-9-hydroxy-12-methyl-11-oxa-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-tetraene-10-carboxylate

The solubility characteristics of methyl (1R,9S,10R,13S,20S)-9-hydroxy-12-methyl-11-oxa-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-tetraene-10-carboxylate (C16H18N2O4) are influenced by several factors, making it an intriguing compound to study:

  • Polarity: The presence of hydroxyl (-OH) and carboxylate (-COO-) functional groups indicates that this compound may have a degree of polarity that could enhance its solubility in polar solvents, such as water.
  • Hydrogen bonding: The ability to form hydrogen bonds due to the hydroxyl group may facilitate interactions with water molecules, potentially increasing solubility in aqueous environments.
  • Alkyl chains: The presence of hydrocarbon portions could affect its overall solubility in organic solvents, making it more soluble in non-polar solvents, such as hexane or ether, compared to polar solvents.
  • Conformational structure: The complex cyclic structure could introduce steric factors that may hinder solubility; thus, the molecular geometry plays a significant role in how the compound interacts with solvents.

In conclusion, while the specific solubility data of methyl (1R,9S,10R,13S,20S)-9-hydroxy-12-methyl-11-oxa-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-tetraene-10-carboxylate in various solvents has yet to be extensively documented, it is reasonable to anticipate moderate solubility in polar solvents owing to its functional groups, coupled with possible solubility in non-polar solvents due to its hydrocarbon regions.

Interesting facts

Interesting Facts about Methyl (1R,9S,10R,13S,20S)-9-Hydroxy-12-Methyl-11-Oxa-8,17-Diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-Tetraene-10-Carboxylate

This unique compound is noteworthy due to its complex molecular structure and potential biological activities. Here are some key aspects that make it a subject of interest in chemical research:

  • Skeletal Diversity: The compound features an intricate arrangement of rings and bonds, indicative of its classification as a *diazahexacyclic* compound, which plays a significant role in its reactivity and interaction with biological systems.
  • Functional Group Variety: The presence of a hydroxyl group (-OH) and a carboxylate group (-COO-) highlights its multifunctionality, suggesting potential applications in medicinal chemistry. These groups can contribute to hydrogen bonding and solubility in biological environments.
  • Chirality and Stereochemistry: With multiple stereogenic centers, this compound exhibits chirality, which can lead to enantiomeric forms with different biochemical activities. As the saying goes in chemistry, “*the structure dictates function*,” and the precise arrangement of atoms can influence its therapeutic efficacy.
  • Potential Pharmacological Properties: Compounds with similar structural features have been studied for their roles as *antimicrobial*, *anticancer*, and *anti-inflammatory agents*. This places the methyl ester derivative in a promising category for future drug development.
  • Synthesis Challenges: The synthesis of such complex molecules poses challenges that require advanced synthetic techniques, showcasing the ingenuity of organic chemists. These methods often require multiple steps and careful control of reaction conditions to achieve the desired stereochemistry.

In summary, methyl (1R,9S,10R,13S,20S)-9-hydroxy-12-methyl-11-oxa-8,17-diazahexacyclo[11.6.1.110,13.01,9.02,7.017,20]henicosa-2,4,6,14-tetraene-10-carboxylate represents a fascinating intersection of structural complexity, functional potential, and synthetic challenge, marking it as a compound worthy of further exploration in the realm of chemical sciences.