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-Hydroxyacetophenone 4'-Hydroxyacetophenone 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.^{[citation needed]}

Piceol can be used to make acetaminophen by condensation 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

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