Piceol

Short description: Phenolic compound found in Norway spruces

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

PubChem CID

* 7469

UNII |

* G1L3HT4CMH Y

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

Tracking categories (test):

* SizeSet

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]

## Contents

* 1 Uses
* 2 Metabolism
* 3 See also
* 4 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 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

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

## 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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*[CID]: Compound ID