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Erythromycin

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Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
(3S,5S,10S,13R,14S,17R)-3-[[(3aR,6R)-2,4-dimethyl-2-phenyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
State
State

At room temperature, erythromycin is typically in a solid state, appearing as a crystalline powder. It is stable under recommended storage conditions.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.00
Boiling point (Celsius)
806.00
Boiling point (Kelvin)
1 079.00
General information
Molecular weight
733.94g/mol
Molar mass
733.9370g/mol
Density
1.2473g/cm3
Appearence

Erythromycin is typically found as a white to off-white, odorless or practically odorless crystalline powder. It is known for its bitter taste and can appear as white crystals when in its purest form. Erythromycin is often available as a solid for medicinal use.

Comment on solubility

Solubility Overview

The compound with the name (3S,5S,10S,13R,14S,17R)-3-[[[3aR,6R)-2,4-dimethyl-2-phenyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde presents a complex structure influenced by its stereochemistry and functional groups, which has important implications for its solubility.

Key Points on Solubility

  • Steric Hindrance: The large multi-bridged structure may create steric hindrances, typically limiting solubility in polar solvents.
  • Functional Groups: The presence of multiple hydroxyl (-OH) groups generally enhances hydrogen bonding with water, possibly improving solubility in polar solvents.
  • Potential for Lipophilicity: The extensive hydrocarbon chains and any aromatic components imply that the compound may also have significant lipophilic characteristics.
  • Overall Solubility: Due to the conflicting influences of its hydrophilic and lipophilic features, solubility may vary substantially across different solvents, showing moderate solubility in some organic solvents while potentially being less soluble in water.

In conclusion, the solubility of this compound is influenced by a delicate balance of its structural elements. As such, further empirical studies would be necessary to determine precise solubility characteristics in various solvents.

Interesting facts

Interesting Facts about (3S,5S,10S,13R,14S,17R)-3-[[(3aR,6R)-2,4-dimethyl-2-phenyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

This complex organic compound, often referred to by its more manageable classification, showcases the incredible diversity and intricacy available in the study of organic chemistry. Here are some fascinating points about this compound:

  • Stereochemistry: The compound features several chiral centers, which contributes to its potential stereoisomers. The spatial arrangement of the atoms can significantly influence the compound's interactions and reactions, making its stereochemistry crucial for its applications.
  • Natural Products: Many compounds similar to this one are derived from natural sources. In fact, chemical structures like these often serve as templates for the synthesis of biologically active natural products or pharmaceuticals.
  • Functional Groups: The compound contains both hydroxyl and aldehyde functional groups, which are essential for reactivity. These groups can participate in various chemical reactions, including oxidation and substitution, adding to the compound's versatility in synthesis.
  • Applications: Given its complex structure, this compound may exhibit a range of biological activities. It could be investigated for use in drug development, potentially in treating diseases or conditions due to its unique molecular features.
  • Challenges in Synthesis: Synthesizing such a large and intricate molecule presents numerous challenges. Short reactions paths, the need for protecting groups, and handling multiple reaction conditions are all part of the excitement in pursuing the total synthesis of this compound.

Quote from a chemist: “Every complex structure tells a story of chemistry, revealing not just how it is formed, but also how it interacts with the world around it.” This compound is an excellent example of how intricate chemical designs can lead to a myriad of potential applications and discoveries in the field of chemistry.

Synonyms
Acetophenonhelveticosid
Acetophenonehelveticoside
Acetophenonhelveticosid [German]
28719-24-6
5-beta-Card-20(22)-enolide, 3-beta-((2,6-dideoxy-3,4-O-(alpha-methylbenzylidene)-beta-D-ribo-hexopyranosyl)oxy)-5,14-dihydroxy-19-oxo-
RefChem:316983
DTXSID10951377
3-{[2,6-Dideoxy-3,4-O-(1-phenylethylidene)hexopyranosyl]oxy}-5,14-dihydroxy-19-oxocard-20(22)-enolide