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Spiramycin

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Identification
Molecular formula
C43H74N2O14
CAS number
8025-81-8
IUPAC name
[(3R,5S,6S,7R,8S,9R,12R,13S,14R,15R)-6-[(2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyl-tetrahydropyran-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetoxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
State
State
Spiramycin is typically a solid at room temperature. It is used in veterinary settings as well as in human medicine.
Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
580.00
Boiling point (Kelvin)
853.15
General information
Molecular weight
843.04g/mol
Molar mass
843.0420g/mol
Density
1.2800g/cm3
Appearence

Spiramycin appears as a white to off-white crystalline powder. It may have an odor characteristic of macrolide antibiotics. The compound is typically used in a pure form or as the base or salt for pharmaceutical preparations.

Comment on solubility

Solubility of the Compound

The solubility of the compound [(3R,5S,6S,7R,8S,9R,12R,13S,14R,15R)-6-[(2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyl-tetrahydropyran-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetoxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate can be quite complex due to its large and intricate molecular structure.

This compound features multiple polar functional groups and alkyl chains, which can influence its solubility in different solvents. Here are some critical considerations:

  • Polarity: The presence of acetoxy and dimethylamino groups increases the polarity of the molecule, which may enhance solubility in polar solvents like water or alcohols.
  • Hydrophobic Regions: The vast hexamethyl and dioxaspiro portions of the structure could create hydrophobic regions that decrease solubility in aqueous mediums while favoring solubility in organic solvents like ethers or chloroform.
  • Hydrogen Bonding: Potential for intramolecular and intermolecular hydrogen bonding may complicate solubility, sometimes leading to lower solubility in solvents that typically dissolve related compounds.

In summary, while the intricate design of this compound may suggest nuanced solubility properties, it is vital to conduct empirical tests to determine the precise solubility characteristics in various solvents. As a general guiding principle, the balance between polar and non-polar characteristics greatly dictates solubility behavior.

Interesting facts

Exploring the Unique Properties of a Complex Compound

The compound (3R,5S,6S,7R,8S,9R,12R,13S,14R,15R)-6-[(2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyl-tetrahydropyran-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetoxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl acetate is an intriguing example of a highly functionalized organic molecule. Here are some interesting facts about this compound:

  • Chirality: This compound contains multiple stereocenters, making it chiral. This property significantly impacts its biological activity and interaction with enzymes and receptors in living organisms.
  • Complex Structure: The presence of various functional groups, including acetoxy and dimethylamino groups, enhances the compound's potential as a therapeutic agent. Such structural complexity often leads to unique pharmacological properties.
  • Applications: Compounds with similar frameworks are frequently explored for their potential as pharmaceuticals, particularly in the fields of cancer treatment and antimicrobial activity.
  • Synthetic Challenges: The synthesis of such complex molecules can be a challenge in organic chemistry, often requiring advanced techniques like multi-step synthesis and stereoselective reactions.
  • Potential Research Areas: Scientists continue to study this compound for its implications in drug design, particularly in enhancing efficacy while reducing side effects through targeted delivery mechanisms.

As defined by the intricate arrangement of its atoms, this compound exemplifies the beauty and complexity of organic chemistry. In the words of a famous chemist, *"The beauty of chemistry lies in the complexity of its structure."* As research progresses, the exploration of such compounds will undoubtedly lead to exciting discoveries in both chemistry and the pharmaceutical sciences.

Synonyms
Oleandocetin
[(3R,5S,6S,7R,8S,9R,12R,13S,14R,15R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
[(3S,5S,6S,7R,8S,9R,12R,13S,14S,15R)-6-[(2S,3R,4S,6R)-3-Acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
TAO
Prestwick_594
CHEMBL1200719
GTPL10209
FT57702
[(3~{R},5~{S},6~{S},7~{R},8~{S},9~{R},12~{R},13~{S},14~{R},15~{R})-6-[(2~{S},3~{R},4~{S},6~{R})-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2~{R},4~{S},5~{S},6~{S})-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
[(3R,5S,6S,7R,8S,9R,12R,13S,14R,15R)-6-[(2S,3R,4S,6R)-3-acetoxy-4-(dimethylamino)-6-methyl-tetrahydropyran-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetoxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-2,11-dioxaspiro[2.13]hexadecan-14-yl] acetate