Purpurogallin is an

aglycone An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone ...

natural product. It is an orange-red solid that is soluble in polar organic solvents but not in water. Its

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycoside ...

(ether-linked to sugar), called dryophantin, is found in nutgalls and oak barks. Purpurogallin can be prepared by oxidation of

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 ...

with

sodium periodate Sodium periodate is an inorganic salt, composed of a sodium cation and the periodate anion. It may also be regarded as the sodium salt of periodic acid. Like many periodates, it can exist in two different forms: sodium ''meta''periodate (formula‍ ...

Medicinal aspects

Purpurogallin is bioactive It can inhibit 2-hydroxy and 4-hydroxyestradiol methylation by

catechol-O-methyltransferase Catechol-''O''-methyltransferase (COMT; ) is one of several enzymes that degrade catecholamines (neurotransmitters such as dopamine, epinephrine, and norepinephrine), catecholestrogens, and various drugs and substances having a catechol struct ...

. It potently and specifically inhibits TLR1/

TLR2 Toll-like receptor 2 also known as TLR2 is a protein that in humans is encoded by the ''TLR2'' gene. TLR2 has also been designated as CD282 (cluster of differentiation 282). TLR2 is one of the toll-like receptors and plays a role in the immune sys ...

activation pathway.

References

Polyphenols Tropolones Tetrols Azulenes Pyrogallols {{phenol-stub