Dehydroabietic acid (DHA) is a naturally occurring

abietane Abietane is an organic compound with the formula C20H36. It is a tricyclic, saturated hydrocarbon with an elaborate stereochemistry. It is a colorless solid. It is of little biochemical interest except as a reference structure of the abietanes. ...

-type

diterpenoid Diterpenes are a class of terpenes composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primar ...

resin acid Resin acid refers to any of several related carboxylic acids found in tree resins. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids occur in nature as tacky, yellowish gum ...

found predominantly in coniferous trees. It is a major component of rosin and is utilized in various industrial applications due to its chemical properties.

Chemical structure and properties

Dehydroabietic acid has the molecular formula C₂₀H₂₈O₂ and a molecular weight of 300.44 g/mol. It appears as a white to off-white solid with a melting point of 150–153 °C and a boiling point of approximately 390 °C. The compound is practically insoluble in water but soluble in organic solvents such as ethanol and acetone.

Biological activity

It exhibits a range of biological activities, including: * Anti-inflammatory: Acts as a dual activator of peroxisome proliferator-activated receptors alpha and gamma (PPAR α/γ), contributing to its anti-inflammatory effects. * Antimicrobial: Demonstrates antibacterial properties against multidrug-resistant strains. * Anticancer: Certain derivatives have shown cytotoxic activity against various cancer cell lines, indicating potential as anticancer agents.

Applications and safety

Due to its bioactivity, dehydroabietic acid is used in: * Pharmaceutical research: As a lead compound for developing anti-inflammatory and anticancer drugs. * Industrial applications: In the synthesis of varnishes, adhesives, and as a component in the production of paper and other materials. Dehydroabietic acid should be handled with care. It is harmful if swallowed and can cause skin and eye irritation. Appropriate personal protective equipment should be used when handling the compound.

References

{{DEFAULTSORT:Dehydroabietic acid Diterpenes Resins Carboxylic acids Isopropyl compounds