Minquartynoic acid is an unsaturated, conjugated, and hydroxylated fatty acid containing four

triple bond A triple bond in chemistry is a chemical bond between two atoms involving six Electron pair bond, bonding electrons instead of the usual two in a covalent bond, covalent single bond. Triple bonds are stronger than the equivalent covalent bond, sin ...

s and belonging to the class of polyyne and alkynoic acids. It was only discovered in 1989. The acid is

optically active Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circul ...

, 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 ''Coula edulis'' is a tree in the genus '' Coula'', native to tropical western Africa from Sierra Leone to Angola. Both the timber and nuts have a number of uses. Description It is an evergreen tree growing to a height of , and has a dense crow ...

'', all of the family ''

Olacaceae Olacaceae is a family of flowering plants in the order Santalales. They are woody plants, native throughout the tropical regions of the world. , the circumscription of the family varies; some sources maintain a broad family, others split it int ...

''.

Synthesis

Minquartynoic acid can be synthesized starting from

azelaic acid Azelaic acid (AzA), or nonanedioic acid, is an organic compound with the formula HOOC(CH2)7carboxylic acid, COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse ind ...

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 Tuberculosis (TB), also known colloquially as the "white death", or historically as consumption, is a contagious disease usually caused by ''Mycobacterium tuberculosis'' (MTB) bacteria. Tuberculosis generally affects the lungs, but it can al ...

; also, it has been applied topically to treat skin irritations and

muscle pain Myalgia or muscle pain is a painful sensation evolving from muscle tissue. It is a symptom of many diseases. The most common cause of acute myalgia is the overuse of a muscle or group of muscles; another likely cause is viral infection, espec ...

Uses

In ''in vitro'' studies, minquartynoic acid was antiviral against HIV and cytotoxic against ten different cancer cell lines, including leukemia cells. In other studies, it has shown activity against

malaria Malaria is a Mosquito-borne disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...

and

Leishmania ''Leishmania'' () is a genus of parasitic protozoans, single-celled eukaryotic organisms of the trypanosomatid group that are responsible for the disease leishmaniasis. The parasites are transmitted by sandflies of the genus '' Phlebotomus'' ...

References

{{Fatty acids Alkenoic acids Fatty acids Conjugated diynes