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Penicillic acid

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Identification
Molecular formula
C8H10O4
CAS number
90-65-3
IUPAC name
[(6S,7S,8R)-8-butyl-3-[(3-formamido-2-hydroxy-benzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate
State
State

At room temperature, penicillic acid exists in a solid state, typically as a crystalline powder. This makes it easy to handle and measure in laboratory settings. It should be stored properly to prevent degradation and contamination, especially by moisture and air.

Melting point (Celsius)
83.50
Melting point (Kelvin)
356.65
Boiling point (Celsius)
330.00
Boiling point (Kelvin)
603.15
General information
Molecular weight
172.15g/mol
Molar mass
172.1490g/mol
Density
1.3000g/cm3
Appearence

Penicillic acid appears as a colorless, crystalline solid. It is often found in its crystalline form but can also present as a white powder. The compound is known for its ability to form crystals when purified, and it is classified under mycotoxins commonly produced by certain species of Penicillium and Aspergillus fungi.

Comment on solubility

Solubility Characteristics

The compound (6S,7S,8R)-8-butyl-3-[(3-formamido-2-hydroxy-benzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate presents a unique and complex solubility profile. Given its intricate structure, several factors affect its solubility behavior:

  • Polarity: The presence of polar groups, such as the formamido and hydroxy functional groups, may enhance its solubility in polar solvents.
  • Hydrogen Bonding: The ability of the compound to participate in hydrogen bonding plays a crucial role in solubility, particularly in water and alcohol-based solvents.
  • Hydrophobic Interactions: The butyl and methyl groups introduce hydrophobic characteristics, which could limit solubility in aqueous environments but favor solubility in organic solvents.
  • Concentration Effects: At different concentrations, the compound may exhibit varying solubility due to changes in intermolecular interactions.

In practical applications, it can be anticipated that this compound may display:

  1. Higher Solubility: In organic solvents such as ethanol and dimethyl sulfoxide (DMSO).
  2. Moderate Solubility: In polar protic solvents like methanol and water.
  3. Limited Solubility: In non-polar solvents due to the aforementioned hydrophobic interactions.

Ultimately, understanding the solubility of this compound is essential for its potential applications in various fields, including pharmaceuticals and materials science. This knowledge allows for optimized formulations and effective utilization of the compound in diverse environments.

Interesting facts

Interesting Facts about [(6S,7S,8R)-8-butyl-3-[(3-formamido-2-hydroxy-benzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate

This compound represents an intriguing blend of structural complexity and potential biochemical applications. Notably, it plays a significant role in pharmaceutical research, particularly due to its intricate molecular structure that contributes to its biological activity. Here are some key points of interest:

  • Chiral Centers: The presence of chiral centers at the 6, 7, and 8 positions highlights the importance of stereochemistry in the compound’s function, affecting how it interacts with biological systems.
  • Functional Groups: With functionalities such as the formamido and hydroxyl groups, the compound is poised to exhibit remarkable reactivity, making it a candidate for various biochemical interactions.
  • Potential Applications: The compound could have applications in drug design, specifically in targeting certain pathways in diseases, thanks to its ability to mimic or inhibit biological molecules.
  • Natural Products Inspiration: Compounds similar to this one often draw inspiration from natural products, indicating that nature continues to be an excellent guide for synthetic chemistry.
  • Multi-Stage Synthesis: The synthesis likely involves multiple steps which could teach valuable lessons on reaction mechanisms and the importance of functional group manipulation in organic chemistry.

In essence, this compound exemplifies the rich interplay between structure and function in the world of organic compounds, providing fertile ground for study and application in the field of medicinal chemistry. As future research unfolds, the full potential of [(6S,7S,8R)-8-butyl-3-[(3-formamido-2-hydroxy-benzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate could very well lead to significant advances in therapeutics.

Synonyms
Blastomycin [NF]
EINECS 208-335-6
NSC 58239
UNII-7JMI3P2Y5R
7JMI3P2Y5R
Butanoic acid, 3-methyl-, 8-butyl-3-((3-(formylamino)-2-hydroxybenzoyl)amino)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester, (2R-(2R*,3S*,6S*,7R*,8R*))-
[(6S,7S,8R)-8-butyl-3-[(3-formamido-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate
Butanoic acid, 2(or 3)-methyl-, 3-((3-(formylamino)-2-hydroxybenzoyl)amino)-8-butyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester, (2R,3S,6S,7R,8R)-
Isovaleric acid, N-ester with N-(7-butyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-formamidosalicylamide, stereoisomer