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by | Mar 16, 2018 | Hosta

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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.[citation needed]

Piceol can be used to make acetaminophen by oxime formation with hydroxylamine and subsequent Beckmann rearrangement in acid.[4]

Anticonvulsants are also possible by Mannich reaction:[5]

Metabolism

Diprenylated derivatives of piceol can be isolated from Ophryosporus macrodon.[6]

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

See also

References

  1. ^ Løkke, H. (1990). "Picein and piceol concentrations in Norway spruce". Ecotoxicology and Environmental Safety. 19 (3): 301–9. doi:10.1016/0147-6513(90)90032-z. PMID 2364913.
  2. ^ Münzenberger, Babette; Heilemann, Jürgen; Strack, Dieter; Kottke, Ingrid; Oberwinkler, Franz (1990). "Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce". Planta. 182 (1): 142–8. doi:10.1007/BF00239996. PMID 24197010.
  3. ^ Løkke, Hans (1990). "Picein and piceol concentrations in Norway spruce". Ecotoxicology and Environmental Safety. 19 (3): 301–309. doi:10.1016/0147-6513(90)90032-Z. PMID 2364913.
  4. ^ U.S. patent 4,524,217
  5. ^ Keshari, Amit K.; Tewari, Aseem; Verma, Shweta S.; Saraf, Shailendra K. (2017). "Novel Mannich-bases as Potential Anticonvulsants: Syntheses, Characterization and Biological Evaluation". Central Nervous System Agents in Medicinal Chemistry. 17 (3). doi:10.2174/1871524917666170717113524. ISSN 1871-5249.
  6. ^ Sigstad, Elizabeth; Catalán, César A.N.; Diaz, Jesús G.; Herz, Werner (1993). "Diprenylated derivatives of p-hydroxyacetophenone from Ophryosporus macrodon". Phytochemistry. 33: 165–169. doi:10.1016/0031-9422(93)85415-N.
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