Piceol Explained

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces (Picea abies).^{[1] [2]} Picein is the glucoside of piceol.^[3]

Uses

Piceol is used in the synthesis of several pharmaceutical drugs including octopamine, sotalol, bamethan, and dyclonine.

Piceol can be used to make acetaminophen by condensation with hydroxylamine and subsequent Beckmann rearrangement in acid.

Anticonvulsants are also possible by Mannich reaction:^[4]

Metabolism

Diprenylated derivatives of piceol can be isolated from Ophryosporus macrodon.^[5]

4-Hydroxyacetophenone monooxygenase is an enzyme that transforms piceol into O-acetylhydroquinone. This enzyme is found in Pseudomonas fluorescens.

See also

• Paroxypropione, where the acetyl group is replaced by a propionyl group.
• Apocynin

Notes and References

1. 2364913. 1990. Løkke. H.. Picein and piceol concentrations in Norway spruce. Ecotoxicology and Environmental Safety. 19. 3. 301–9. 10.1016/0147-6513(90)90032-z.
2. 10.1007/BF00239996. 24197010. Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce. Planta. 182. 1. 142–8. 1990. Münzenberger. Babette. Heilemann. Jürgen. Strack. Dieter. Kottke. Ingrid. Oberwinkler. Franz.
3. 10.1016/0147-6513(90)90032-Z. Picein and piceol concentrations in Norway spruce. Ecotoxicology and Environmental Safety. 19. 3. 301–309. 1990. Løkke. Hans. 2364913.
4. Keshari. Amit K.. Tewari. Aseem. Verma. Shweta S.. Saraf. Shailendra K.. Novel Mannich-bases as Potential Anticonvulsants: Syntheses, Characterization and Biological Evaluation. Central Nervous System Agents in Medicinal Chemistry . 17. 3. 2017. 1871-5249. 10.2174/1871524917666170717113524.
5. 10.1016/0031-9422(93)85415-N. Diprenylated derivatives of p-hydroxyacetophenone from Ophryosporus macrodon. Phytochemistry. 33. 165–169. 1993. Sigstad. Elizabeth. Catalán. César A.N.. Diaz. Jesús G.. Herz. Werner.