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Oroxin A

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Identification
Molecular formula
C20H22O6
CAS number
83226-60-0
IUPAC name
3-[(1S,5R,6S,13S,15S)-13,15,18-trihydroxy-5-methyl-19-oxapentacyclo[8.7.2.01,13.02,10.05,9]nonadecan-6-yl]-2H-furan-5-one
State
State

This compound is a solid at room temperature with a crystalline appearance. The solid nature is attributed to its complex structure and molecular interactions.

Melting point (Celsius)
210.00
Melting point (Kelvin)
483.00
Boiling point (Celsius)
383.30
Boiling point (Kelvin)
656.50
General information
Molecular weight
346.42g/mol
Molar mass
346.4160g/mol
Density
1.3201g/cm3
Appearence

This compound appears as a white or slightly off-white crystalline solid. Its structure is quite complex, encompassing multiple rings and hydroxyl groups.

Comment on solubility

Solubility of 3-[(1S,5R,6S,13S,15S)-13,15,18-trihydroxy-5-methyl-19-oxapentacyclo[8.7.2.01,13.02,10.05,9]nonadecan-6-yl]-2H-furan-5-one

The solubility of this complex compound is influenced by several structural features:

  • Hydroxyl Groups: The presence of multiple hydroxyl groups (–OH) typically enhances solubility in polar solvents, such as water. In this case, the trihydroxy nature of the molecule may contribute to its ability to hydrogen bond with water molecules.
  • Furan Moiety: The furan ring system can interact with both polar and non-polar solvents, potentially allowing for significant solubility in organic solvents as well.
  • Overall Structure: Despite possessing polar functional groups, the large hydrophobic pentacyclic structure may reduce solubility in highly polar solvents. This leads to an interesting balance in solubility characteristics.

In summary, the solubility of this compound can be seen as a balance between polar and non-polar interactions. It likely exhibits significant solubility in polar solvents, while the complex hydrophobic regions may limit its solubility in non-polar solvents. As always, experimental verification is necessary to understand its solubility behavior fully.

Interesting facts

Interesting Facts about 3-[(1S,5R,6S,13S,15S)-13,15,18-trihydroxy-5-methyl-19-oxapentacyclo[8.7.2.01,13.02,10.05,9]nonadecan-6-yl]-2H-furan-5-one

This compound is a fascinating example of complex organic chemistry, belonging to the category of furan derivatives, which are known for their unique ring structures and significant biological activities. Here are some intriguing aspects:

  • Structural Complexity: The molecular structure exhibits a pentacyclic configuration, which is rare and makes the compound highly interesting for structural chemists. Its intricate stereochemistry is characterized by multiple chiral centers leading to diverse possible stereoisomers.
  • Biological Significance: Compounds with such intricate cyclic structures are often found in nature, particularly in plant secondary metabolites. They can exhibit a range of biological activities, including anti-inflammatory, antibacterial, and antitumor properties.
  • Application Potential: Due to its unique structure, this compound may serve as a lead in drug development. Researchers often explore similar compounds to investigate their potential in medicinal chemistry, especially in targeting complex biological pathways.
  • Synthetic Challenges: The synthesis of such complex organic molecules poses significant challenges. The multiple steps required in the synthetic pathway often involve intricate reaction conditions, potentially leading to a significant amount of research dedicated to optimizing these methods.

In summary, 3-[(1S,5R,6S,13S,15S)-13,15,18-trihydroxy-5-methyl-19-oxapentacyclo[8.7.2.01,13.02,10.05,9]nonadecan-6-yl]-2H-furan-5-one is not just a chemical compound but also a testament to the beauty and complexity of organic chemistry. Its potential applications in pharmaceutical research could lead to new breakthroughs in health and medicine.


Synonyms
DTXSID10949390
3,5,19-Trihydroxy-8,19-epoxycard-20(22)-enolide