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Wikipedia

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
  • 99-93-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28032
ChemSpider
  • 7189
ECHA InfoCard 100.002.548
  • 7469
UNII
  • G1L3HT4CMH Y
  • DTXSID0029133
  • 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
  • CC(=O)C1=CC=C(C=C1)O
Properties
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).

Uses edit

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 edit

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 edit

References edit

  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.

piceol, phenolic, compound, found, needles, mycorrhizal, roots, norway, spruces, picea, abies, picein, glucoside, piceol, chemical, structure, piceolnamespreferred, iupac, name, hydroxyphenyl, ethan, oneother, names, hydroxyphenyl, ethanone4, hydroxyacetopheno. 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 piceolNamesPreferred IUPAC name 1 4 Hydroxyphenyl ethan 1 oneOther names 1 4 Hydroxyphenyl ethanone4 Hydroxyacetophenone4 Hydroxyacetophenonep HydroxyacetophenoneIdentifiersCAS Number 99 93 4 Y3D model JSmol Interactive imageChEBI CHEBI 28032ChemSpider 7189ECHA InfoCard 100 002 548PubChem CID 7469UNII G1L3HT4CMH YCompTox Dashboard EPA DTXSID0029133InChI InChI 1S C8H8O2 c1 6 9 7 2 4 8 10 5 3 7 h2 5 10H 1H3Key TXFPEBPIARQUIG UHFFFAOYSA NInChI 1S C8H8O2 c1 6 9 7 2 4 8 10 5 3 7 h2 5 10H 1H3Key TXFPEBPIARQUIG UHFFFAOYSA NSMILES CC O C1 CC C C C1 OPropertiesChemical formula C 8H 8O 2Molar mass 136 150 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Uses 2 Metabolism 3 See also 4 ReferencesUses editPiceol 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 editDiprenylated 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 editParoxypropione where the acetyl group is replaced by a propionyl group ApocyninReferences edit Lokke 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 Munzenberger Babette Heilemann Jurgen 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 Lokke 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 U S Patent 4 524 217 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 Sigstad Elizabeth Catalan Cesar A N Diaz Jesus G Herz Werner 1993 Diprenylated derivatives of p hydroxyacetophenone from Ophryosporus macrodon Phytochemistry 33 165 169 doi 10 1016 0031 9422 93 85415 N Retrieved from https en wikipedia org w index php title Piceol amp oldid 1179521607, wikipedia, wiki, book, books, library,

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