Isopimaric acid

Isopimaric Acid

Chemical structure of isopimaric acid

Isopimaric acid is a naturally occurring diterpene resin acid found in the oleoresin of various conifer species. It is a member of the pimarane family of diterpenes and is known for its role in the defense mechanisms of trees against herbivores and pathogens.

Chemical Structure

Isopimaric acid has the molecular formula C₂₀H₃₀O₂. It is characterized by a bicyclic structure with a carboxylic acid functional group. The structure of isopimaric acid is similar to other resin acids such as abietic acid and pimaric acid, but it differs in the configuration of its carbon skeleton.

Biosynthesis

Isopimaric acid is synthesized in conifers through the mevalonate pathway, which is a key metabolic pathway that produces isoprenoids. The biosynthesis involves the cyclization of geranylgeranyl pyrophosphate (GGPP) to form the pimarane skeleton, followed by oxidation and rearrangement to yield isopimaric acid.

Biological Role

In conifers, isopimaric acid is a component of the oleoresin, a sticky substance that exudes from the bark and wood when the tree is injured. This resin acts as a physical barrier and contains compounds that are toxic or deterrent to insects and pathogens. Isopimaric acid contributes to the antimicrobial and insect-repellent properties of the resin.

Applications

Isopimaric acid and its derivatives have been studied for their potential applications in various fields. They have shown promise as antimicrobial agents, anti-inflammatory agents, and in the synthesis of biodegradable polymers.

Related Compounds

Isopimaric acid is closely related to other resin acids such as abietic acid, pimaric acid, and sandaracopimaric acid. These compounds share similar biosynthetic pathways and structural features, but differ in their specific chemical configurations and biological activities.

Related Pages

• Diterpene
• Resin acid
• Conifer
• Oleoresin