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Spiramycin

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Identification
Molecular formula
C43H74N2O14
CAS number
8025-81-8
IUPAC name
[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,16R)-4-acetoxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2,4-dimethyl-tetrahydropyran-3-yl] 3-methylbutanoate
State
State

Spiramycin is typically in a solid state at room temperature, appearing as a powder.

Melting point (Celsius)
110.00
Melting point (Kelvin)
383.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
843.05g/mol
Molar mass
843.0450g/mol
Density
1.1800g/cm3
Appearence

Spiramycin is a white or slightly yellow-white powder. It is practically insoluble in water but is soluble in ethanol, methanol, and acetone. It has a characteristic odor.

Comment on solubility

Solubility of [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[[4R,5S,6S,7R,9R,10R,16R)-4-acetoxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2,4-dimethyl-tetrahydropyran-3-yl] 3-methylbutanoate

The solubility of this complex compound can be influenced by various factors, considering its intricate structure and the functional groups present. Here are some key points to note:

  • Polarity: The presence of multiple hydroxyl groups and oxygen-containing moieties generally increases polarity, which can enhance solubility in polar solvents like water.
  • Hydrophobic regions: The hydrophobic sections due to large hydrocarbon chains may reduce overall solubility in water, leading to variable solubility in organic solvents.
  • Interactions: Hydrogen bonding with polar solvents can significantly affect solubility. The ability of the compound to form such interactions may allow for enhanced solubility in alcohols or other polar solvents.
  • Temperature effects: As with many organic compounds, an increase in temperature typically results in greater solubility for solids by providing more kinetic energy to overcome molecular interactions.

Understanding these factors is crucial when studying the solubility profile of this compound. As a general rule, solubility is not just about the presence of polar groups, but also how they interact with each other and the surrounding solvent environment.

In summary, while the presence of polar functional groups suggests potential solubility in polar solvents, the overall solubility is contingent upon balancing these interactions against the hydrophobic characteristics intrinsic to its structure.

Interesting facts

Interesting Facts about the Compound

This compound is a fascinating example of complex organic synthesis and showcases the intricate nature of natural product chemistry. It is a derivative of various natural compounds, specifically formed through multi-step synthesis that highlights both structural diversity and stereochemical complexity. Here are some intriguing details:

  • Natural Origin: Many similar compounds are derived from natural sources, often exhibiting biological activities that lend themselves to medicinal applications.
  • Stereochemistry: The detailed stereochemical configuration indicates that this compound has several chiral centers, which is vital in determining its biological function and activity.
  • Functional Groups: It includes a range of functional groups such as acetoxy, methoxy, and hydroxy, each contributing to its potential reactivity and interaction with biological targets.
  • Bioactivity: Compounds of this type are often investigated for therapeutic potential, including anti-inflammatory, antibacterial, and anticancer properties, making them exciting subjects for drug discovery.
  • Complexity of Synthesis: The synthesis of such compounds often requires sophisticated methodologies, including protection and deprotection strategies, as well as careful manipulation of reaction conditions to preserve sensitive functional groups.

Interestingly, the study of this compound could shed light on the broader category of glycosides and their pathways. As noted by researchers, "the complexity of molecular structures often correlates with their potential as lead compounds in pharmacology." Understanding and synthesizing such compounds not only deepen our knowledge of organic chemistry but also facilitate advancements in materials science and drug development.

As a chemistry student or researcher, delving into the nuances of this compound can provide ample opportunities for exploration, whether through synthesis, analysis, or therapeutic application. Exciting discoveries could lie in the synthesis pathways or in elucidating the mechanisms of action relevant to this compound.

Synonyms
NS00073682