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Brefeldin A

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Identification
Molecular formula
C16H24O4
CAS number
20350-15-6
IUPAC name
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
State
State

This compound is in a solid state at room temperature.

Melting point (Celsius)
200.00
Melting point (Kelvin)
473.15
Boiling point (Celsius)
296.85
Boiling point (Kelvin)
570.00
General information
Molecular weight
280.36g/mol
Molar mass
280.3070g/mol
Density
1.3045g/cm3
Appearence

Brefeldin A is a white crystalline solid. It is known for its distinct appearance when purified, often forming needle-like crystals.

Comment on solubility

Solubility Overview

The compound named (1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde presents a unique solubility profile owing to its complex structure. Understanding its solubility is crucial for various applications, especially in pharmaceuticals and material science.

Factors Influencing Solubility

The solubility of this compound is affected by several factors:

  • Polarity: The presence of multiple hydroxyl groups typically enhances solubility in polar solvents such as water.
  • Molecular Weight: With a high molecular weight due to its intricate structure, solubility can be reduced in certain media.
  • Hydrogen Bonding: The ability to form hydrogen bonds may increase solubility in alcohols and similar solvents.
  • Functional Groups: Functionalities like the aldehyde group and furan ring can contribute to its interaction with various solvents.

Solubility Insights

In summary:

  • The compound is likely soluble in polar solvents such as methanol and ethanol.
  • It may show limited solubility in nonpolar solvents like hexane or toluene due to its hydrophilic character.
  • The presence of multiple functional groups allows for a degree of selectivity in solvents, making it versatile but also complex in terms of solubility behavior.

Overall, while understanding the solubility of such a complex molecule can be daunting, when taken into consideration with its structural attributes, one can predict how it will interact within various environments.

Interesting facts

Interesting Facts about (1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde

This complex compound is a fascinating example of the rich diversity found in organic chemistry. Here are some engaging points that showcase its unique attributes:

  • Structural Complexity: The compound features a detailed bicyclic and tricyclic structure, which results in over **twelve rings**. This level of complexity makes it a great subject for studying stereo-specific reactions.
  • Functional Diversity: With three hydroxyl (–OH) groups and an aldehyde (–CHO) group, the compound demonstrates multiple functional groups, allowing for versatile chemical reactivity and potential applications in organic synthesis.
  • Biological Relevance: Compounds with a similar structure are often investigated for their biological activities. They might possess therapeutic properties, which can lead to potential drug development opportunities in pharmaceutical chemistry.
  • Isomeric Forms: The specified stereochemistry indicates a variety of isomers. Each isomer may display different physical and chemical properties, highlighting the importance of chirality in medicinal chemistry.
  • Connection to Natural Products: Many complex organic compounds like this one are inspired by or derived from natural sources. They may mimic or enhance the effects of biologically active natural products.

As noted by renowned chemist Linus Pauling, "The structure of a compound is a key to its function." This compound, with its intricate architecture, exemplifies this principle beautifully, paving the way for exciting discoveries in the realms of synthetic organic chemistry and medicinal applications.

Overall, the study of such elaborate compounds not only enriches our understanding of organic structures but also opens avenues for innovation in various scientific fields.

Synonyms
CALOTROPIN
Pecilocerin A
Pekilocerin A
1986-70-5
HSDB 3470
UNII-3XK21U1BZS
3XK21U1BZS
NSC 143925
CALOTROPIN [MI]
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
DTXSID10173613
NSC-143925
Card-20(22)-enolide, 14-hydroxy-19-oxo-3,2-((tetrahydro-3,4-dihydroxy-6-methyl-2H-pyran-2,3-diyl)bis(oxy))-, (2alpha(2S,4S,6R),3beta,5alpha)-
(2.ALPHA.,3.BETA.,5.ALPHA.)-14-HYDROXY-19-OXO-2,3-(((2S,3S,4S,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))CARD-20(22)-ENOLIDE
CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-2,3-(((2S,3S,4S,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))-, (2.ALPHA.,3.BETA.,5.ALPHA.)-
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo(12.11.0.03,12.05,10.015,23.018,22)pentacosane-14-carbaldehyde
(1S,3R,7R,9S,10S,14R,15S,18R,19R,22S)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo(12.11.0.03,12.05,10.015,23.018,22)pentacosane-14-carbaldehyde
(1S,3R,7R,9S,10S,14R,15S,18R,19R,22S)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
POKILOCERIN A
DTXCID4096104
(2ALPHA,3BETA,5ALPHA)-14-HYDROXY-19-OXO-2,3-(((2S,3S,4S,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))CARD-20(22)-ENOLIDE
CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-2,3-(((2S,3S,4S,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))-, (2ALPHA,3BETA,5ALPHA)-
CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-3,2-((TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-2,3-DIYL) BIS(OXY))-, (2ALPHA(2S,4S,6R),3BETA,5ALPHA)-
Card20(22)enolide, 14hydroxy19oxo3,2((tetrahydro3,4dihydroxy6methyl2Hpyran2,3diyl)bis(oxy)), (2alpha(2S,4S,6R),3beta,5alpha)
CHEBI:3329
SCHEMBL868547
CHEMBL495949
BDBM50277173
NS00094620
C08855
Q27106025