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Rifampicin

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Identification
Molecular formula
C43H58N4O12
CAS number
13292-46-1
IUPAC name
[(7R,8S)-11-amino-5-heptanoyl-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
State
State
Solid at room temperature, typically in the form of crystalline powder. This compound is stable under normal conditions but tends to absorb moisture, hence should be stored properly to maintain its efficacy.
Melting point (Celsius)
183.00
Melting point (Kelvin)
456.15
Boiling point (Celsius)
865.00
Boiling point (Kelvin)
1 138.15
General information
Molecular weight
822.94g/mol
Molar mass
822.9380g/mol
Density
1.3000g/cm3
Appearence

Rifampicin appears as a reddish-brown crystalline powder. It is known for its distinct coloration, which is typical of many rifamycin antibiotics. Under the microscope, the crystalline nature is quite evident, and it is also hygroscopic, tending to absorb moisture from the air.

Comment on solubility

Solubility of [(7R,8S)-11-amino-5-heptanoyl-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

The solubility of the compound [(7R,8S)-11-amino-5-heptanoyl-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate can be influenced by a variety of factors, particularly due to its complex structure. Understanding its solubility can provide insights into its potential applications and efficacy. Here are some key points related to its solubility:

  • Polarity: The presence of functional groups such as amino, methoxy, and carbamate indicates that the compound may exhibit polar characteristics, enhancing solubility in polar solvents like water.
  • Hydrophilicity vs. Hydrophobicity: The balance between hydrophilic (water-attracting) and hydrophobic (water-repelling) regions in the compound structure plays a crucial role in determining solubility. This specific compound's hydrophobic heptanoyl chain may limit its solubility in water.
  • Solvent Compatibility: Solubility can vary significantly depending on the solvent used. The compound may be more soluble in organic solvents (e.g., ethanol, methanol) compared to aqueous environments due to combined hydrophobic effects.
  • Temperature Influence: Solubility typically increases with temperature, thus considering the temperature during experimentation can yield differing solubility results.

In summary, while the solubility of [(7R,8S)-11-amino-5-heptanoyl-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate can be expected to have some degree of solubility in both polar and non-polar solvents, specific experimental validation is necessary to clarify its exact solubility profile. As always, factors such as temperature and the specific composition of solvent must be considered for accurate assessments.

Interesting facts

Interesting Facts about [(7R,8S)-11-amino-5-heptanoyl-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

This complex molecular structure represents a fascinating compound that blends various functional groups and characteristics found in both organic and medicinal chemistry. Among the intriguing aspects of this compound are:

  • Biological Significance: The presence of amino (–NH2) and carbamate (–OC(=O)N) functional groups suggests potential biological activity, perhaps as a pharmaceutical agent or a derivative with drug-like properties.
  • Structural Complexity: The tetracyclic nature and unique stereochemistry (noted by the 7R and 8S configurations) highlight the compound's sophisticated arrangement, which can lead to distinct reactivity and interactions in biological systems.
  • Mechanistic Insights: The dual keto groups (–C=O) in the molecular structure often play significant roles in biochemical pathways, possibly influencing enzyme affinity and catalytic action.
  • Research Potential: This compound could be a subject of extensive research, particularly in evaluating its synthesis, stability, and potential applications in drug development and organic synthesis.

As noted by many chemists, “The beauty of chemistry lies in its complexity.” Understanding compounds like this one can illuminate pathways for innovation in pharmaceutical chemistry, leading to new therapeutic drugs. With its multifaceted structure, this compound exemplifies the potential for novel chemical activities.

In summary, [(7R,8S)-11-amino-5-heptanoyl-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate not only represents a unique challenge for chemists but also offers myriad opportunities towards enhancing our understanding of the molecular intricacies that underline biological functions.

Synonyms
4049-07-4
Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-6-amino-1-heptanoyl-8-(hydroxymethyl)-8a-methoxy-5-methyl-, carbamate (ester)
DTXSID70960869
(6-Amino-1-heptanoyl-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl hydrogen carbonimidate