Minquartynoic acid
Minquartynoic acid is an unsaturated, conjugated, and hydroxylated fatty acid containing four triple bonds and belonging to the class of polyyne and alkynoic acids. It was only discovered in 1989. The acid is optically active, but there are conflicting data regarding the rotation of the natural S-isomer.
Discovery
The acid was initially isolated by R.J. Marles, N.R. Farnsworth and D.A. Neill in 1989 from the stem of the Amazonian tree Minquartia guianensis.Natural occurrence
The acid occurs only in small quantities in the bark or twigs of a few plant species, such as Minquartia guianensis, Ochanostachys amentacea, and Coula edulis, all of the family Olacaceae.Synthesis
Minquartynoic acid can be synthesized starting from azelaic acid monomethyl ester in a seven-step synthesis. Another synthesis of the compound has also been published.An infusion of the acid has been used by Ecuadorian indigenous people to treat intestinal parasitic infections, lung cancer, and tuberculosis; also, it has been applied topically to treat skin irritations and muscle pain.