Piceol

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28032;
ChemSpider	7189;
ECHA InfoCard	100.002.548
PubChem CID	7469;
UNII	G1L3HT4CMH ;
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

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 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.

References

[1]

[2]

[3]

[4]

[5]

[6]

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Piceol

Contents

Uses

Metabolism

See also

References

Names
Chemical structure of piceol
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