Piceol

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]

Piceol

Chemical structure of piceol
Names
Preferred IUPAC name 1-(4-Hydroxyphenyl)ethan-1-one
Other names 1-(4-Hydroxyphenyl)ethanone 4-Hydroxy acetophenone 4'-Hydroxy acetophenone p-Hydroxyacetophenone
Identifiers
CAS Number	99-93-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28032
ChemSpider	7189
ECHA InfoCard	100.002.548
PubChem CID	7469
UNII	G1L3HT4CMH^Y
CompTox Dashboard (EPA)	DTXSID0029133
InChI InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3 Key: TXFPEBPIARQUIG-UHFFFAOYSA-N InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3 Key: TXFPEBPIARQUIG-UHFFFAOYSA-N
SMILES CC(=O)C1=CC=C(C=C1)O
Properties
Chemical formula	C8H8O2
Molar mass	136.150 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 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 4-hydroxyphenylacetic acid. This enzyme is found in Pseudomonas fluorescens.

See also

• Paroxypropione

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.