Mesquitol is a

flavan-3-ol Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of comp ...

, a type of flavonoid. ''

Prosopis juliflora ''Prosopis juliflora'' ( es, bayahonda blanca, Cuji Venezuela, Trupillo Colombia, Aippia Wayuunaiki and long-thorn kiawe in Hawaii) is a shrub or small tree in the family Fabaceae, a kind of mesquite. It is native to Mexico, South America and th ...

'', an invasive

New World The term ''New World'' is often used to mean the majority of Earth's Western Hemisphere, specifically the Americas."America." ''The Oxford Companion to the English Language'' (). McArthur, Tom, ed., 1992. New York: Oxford University Press, p. ...

mesquite Mesquite is a common name for several plants in the genus '' Prosopis'', which contains over 40 species of small leguminous trees. They are native to dry areas in the Americas. They have extremely long roots to seek water from very far under gr ...

now found in Kenya, has unusually high levels of (-)-mesquitol in its heartwood. Mesquitol, with its

pyrogallol Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols. Production and reac ...

-type A-ring, is more susceptible to quinone formation at this ring, leading to aryl–aryl bond formation at carbon 5. The structural moieties constitute the proteracacinidin class of

proanthocyanidin Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More compl ...

s. Mesquitol-(5→8)-catechin atropisomers can be isolated from ''

Prosopis glandulosa ''Prosopis glandulosa'', commonly known as honey mesquite, is a species of small to medium-sized, thorny shrub or tree in the legume family (Fabaceae). Distribution The plant is primarily native to the Southwestern United States and Northern M ...

''.Synthesis of condensed tannins. Part 17. Oligomeric (2R,3S)-3,3′,4′,7,8-pentahydroxyflavans: atropisomerism and conformation of biphenyl and m-terphenyl analogues from Prosopis glandulosa(‘mesquite’). Esmé Young, Edward V. Brandt, Desmond A. Young, Daneel Ferreira and David G. Roux, J. Chem. Soc., Perkin Trans. 1, 1986, pages 1737-1749,

References

Flavanols Catechols {{aromatic-stub