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Brefeldin A

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Identification
Molecular formula
C16H24O4
CAS number
20350-15-6
IUPAC name
(3S,5S)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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, Brefeldin A is a solid. It is stable under standard laboratory conditions, but should be stored in a cool, dry place to maintain its integrity and efficacy in research applications.

Melting point (Celsius)
204.00
Melting point (Kelvin)
477.15
Boiling point (Celsius)
724.15
Boiling point (Kelvin)
997.30
General information
Molecular weight
280.36g/mol
Molar mass
280.3280g/mol
Density
1.2925g/cm3
Appearence

Brefeldin A appears as a white crystalline solid. It is known for its use in scientific research and can form colorless needles when purified.

Comment on solubility

Solubility of (3S,5S)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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

The solubility of (3S,5S)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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 can be influenced by several factors:

  • Polarity: The presence of multiple hydroxyl groups and a methoxy group in the structure suggests that this compound may exhibit reasonable solubility in polar solvents such as water or alcohols.
  • Hydrophobic Characteristics: Despite its potential for polar solubility, the larger hydrophobic cyclopenta[a]phenanthrene component may limit solubility in more polar environments.
  • Solvent Choice: It may show varying solubility profiles depending on the solvent used, indicating potential compatibility with organic solvents over aqueous solutions.

As with many complex organic compounds, solubility will ultimately depend on the balance between hydrophilic (water-attracting) and hydrophobic (water-repelling) properties. However, it is essential to conduct experimental solubility testing to draw definitive conclusions regarding the behavior of this compound in various media.

Interesting facts

Interesting Facts about (3S,5S)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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 molecule showcases the fascinating world of organic chemistry, especially in the field of natural product synthesis. Here are some captivating aspects of this compound:

  • Structural Complexity: The structure of this compound is representative of a class of molecules known as polycyclic organic compounds, which can instigate multidisciplinary studies, ranging from medicinal chemistry to materials science.
  • Potential Biological Activity: Due to its multiple hydroxyl (-OH) groups and methoxy groups, this compound may exhibit interesting bioactivity, making it a candidate for research in drug development.
  • Natural Sources: Compounds of this nature are often inspired by natural products derived from plants and fungi, reflecting the potential for discovery of new therapeutic agents through natural extraction and synthesis.
  • Stereochemistry: The stereochemical configurations at multiple chiral centers (as indicated by the 'S' and 'R' notations) add layers of complexity to the molecule’s reactivity and interaction with biological systems, highlighting the importance of chirality in pharmacology.
  • Synthetic Challenges: The synthesis of such intricate compounds requires advanced techniques such as asymmetric synthesis and protection-deprotection strategies, showcasing the ingenuity required in modern organic synthesis.

In conclusion, the study of (3S,5S)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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 offers a glimpse into the intricate relationships between molecular structure, biological function, and synthetic chemistry, making it an exciting topic for further exploration in scientific research.

Synonyms
(3S,5S,10S,13R,14S)-5,14-dihydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-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
(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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
(3S,5S)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-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