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Abietic Acid

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Identification
Molecular formula
C20H28O2
CAS number
514-10-3
IUPAC name
[(2S,4R,5R,6R,14S,16R)-14-hydroxy-7,11-dimethyl-6-(2-oxopyran-4-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate
State
State

Abietic acid is a solid at room temperature. It is stable under normal conditions but can slowly oxidize in air, forming a sticky resin.

Melting point (Celsius)
173.00
Melting point (Kelvin)
446.15
Boiling point (Celsius)
171.00
Boiling point (Kelvin)
444.15
General information
Molecular weight
302.45g/mol
Molar mass
302.4510g/mol
Density
1.0380g/cm3
Appearence

Abietic acid appears as colorless or pale yellowish solid crystals. These crystals are typically transparent and may appear in the form of thin flakes or elongated needles. The acid is known to discolor upon exposure to air and light, forming a resinous compound.

Comment on solubility

Solubility Overview

The solubility of the compound (2S,4R,5R,6R,14S,16R)-14-hydroxy-7,11-dimethyl-6-(2-oxopyran-4-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl acetate is influenced by several factors due to its complex structure and functional groups.

S factors affecting solubility:

  • Polarity: The presence of hydroxyl groups contributes a degree of polarity, which may enhance solubility in polar solvents such as water.
  • Hydrogen bonding: The ability to form hydrogen bonds can significantly affect the compound's solubility in various solvents.
  • Molecular weight: A higher molecular weight may lead to lower solubility due to increased van der Waals forces compared to lighter compounds.

It’s essential to consider the following when discussing its solubility:

  1. The compound may be more soluble in organic solvents like ethanol and acetone.
  2. In aqueous environments, solubility could be limited, suggesting a need for specific formulations or co-solvents for effective dissolution.
  3. Empirical studies would provide further insights into its solubility characteristics and behavior in different solvent systems.

As the compound has a notable structural complexity, testing in specific conditions will likely yield the most accurate solubility data. Understanding these properties is crucial for potential applications in pharmaceuticals and materials science.

Interesting facts

Interesting Facts about the Compound

This fascinating compound, known as (2S,4R,5R,6R,14S,16R)-14-hydroxy-7,11-dimethyl-6-(2-oxopyran-4-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl acetate, showcases not only unique structural features but also significant potential in various fields of research.

1. Complex Structure

The structural complexity of this compound is noteworthy, as it comprises:

  • Pentacyclic Framework: The pentacyclic structure plays a crucial role in the compound's chemical behavior and interactions.
  • Multiple Stereocenters: The presence of multiple stereocenters gives rise to its chiral nature, impacting its biological activity.
  • Functional Groups: The presence of hydroxy and acetate functional groups enhances its reactivity and solubility in organic solvents.

2. Biological Significance

This compound belongs to a class of natural products that display various biological activities. Some key highlights include:

  • Antimicrobial Properties: Certain derivatives of compounds with similar structures have shown activity against various pathogens.
  • Anticancer Potential: Research suggests that compounds with complex frameworks may inhibit cancer cell growth.
  • Enzyme Inhibition: The stereochemistry could interact with biological enzymes, offering pathways for drug development.

3. Applications in Drug Design

The complexity and unique properties of this compound make it an interesting candidate for drug design:

  • Prodrug Development: The acetate group may facilitate metabolic conversion into more active forms.
  • Structure-Activity Relationship Studies: Researchers can modify specific functional groups to enhance effectiveness.
  • Synthetic Pathways: Its intricate structure poses challenges and opportunities for synthetic chemists working on new methodologies.

In conclusion, the exploration of this compound not only enriches the field of organic chemistry but also opens avenues for innovative bioactive materials. As we delve deeper into its properties and applications, the potential to impact human health and medicine continues to grow.

Synonyms
SCHEMBL642991
AKOS015896777