Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces (''

Picea abies ''Picea abies'', the Norway spruce or European spruce, is a species of spruce native to Northern, Central and Eastern Europe. It has branchlets that typically hang downwards, and the largest cones of any spruce, 9–17 cm long. It is very close ...

''). Picein is the glucoside of piceol.

Uses

Piceol is used in the synthesis of several pharmaceutical drugs including

octopamine Octopamine (molecular formula C8H11NO2; also known as OA, and also norsynephrine, ''para''-octopamine and others) is an organic chemical closely related to norepinephrine, and synthesized biologically by a homologous pathway. Octopamine is ofte ...

sotalol Sotalol, sold under the brand name Betapace among others, is a medication used to treat and prevent abnormal heart rhythms. It is only recommended in those with significant abnormal heart rhythms due to potentially serious side effects. Evidence ...

bamethan Bamethan is a vasodilator Vasodilation is the widening of blood vessels. It results from relaxation of smooth muscle cells within the vessel walls, in particular in the large veins, large arteries, and smaller arterioles. The process is th ...

, and

dyclonine Dyclonine (Dyclocaine) is an oral anaesthetic that is the active ingredient of Sucrets, an over-the-counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray. It is a local anesthetic, used topically as the hydr ...

. Piceol can be used to make acetaminophen by

oxime In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted ...

formation with hydroxylamine and subsequent

Beckmann rearrangement The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successfully performed on haloimines and nitrone ...

in acid. Anticonvulsants are also possible by

Mannich reaction In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl () functional group by formaldehyde () and a primary or secondary amine () or ammonia (). ...

Metabolism

Diprenylated derivatives of piceol can be isolated from '' Ophryosporus macrodon''. 4-Hydroxyacetophenone monooxygenase is an enzyme that transforms piceol into O-acetyl

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...

. This enzyme is found in '' Pseudomonas fluorescens''.

References

{{Reflist Aromatic ketones Phenols

Uses

Metabolism

See also

References