Piceol

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Piceol
Piceol.PNG
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.548
Properties
C8H8O2
Molar mass 136.15 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[edit]

  1. Mofoxime & Pifoxime.
  2. para-benzoxyacetophenone has known use in the synthesis of Soterenol, mesuprine, sotalol, and metalol.
  3. Octopamine
  4. Bamethan
  5. Dietifen
  6. Dyclonine
  7. Claisen–Schmidt condensation with 3,4,5-Trimethoxybenzaldehyde.[4]
  8. [63990-49-8][5]
  9. [132948-69-7][6]

Metabolism[edit]

Diprenylated derivatives of piceol can be isolated from Ophryosporus macrodon.[7]

4-Hydroxyacetophenone monooxygenase is an enzyme that transforms piceol into 4-hydroxyphenylacetic acid. This enzyme is found in Pseudomonas fluorescens.

See also[edit]

References[edit]

  1. ^ Løkke H. Picein and piceol concentrations in Norway spruce. Ecotoxicol Environ Saf. 1990 Jun;19(3):301-9.
  2. ^ Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce. Babette Münzenberger, Jürgen Heilemann, Dieter Strack, Ingrid Kottke and Franz Oberwinkler, Planta, Volume 182, Number 1, pages 142-148, doi:10.1007/BF00239996
  3. ^ Picein and piceol concentrations in Norway spruce. Hans Løkke, Ecotoxicology and Environmental Safety, Volume 19, Issue 3, June 1990, Pages 301–309, doi:10.1016/0147-6513(90)90032-Z
  4. ^ Bandgar, Babasaheb P.; Gawande, Shrikant S.; Bodade, Ragini G.; Totre, Jalinder V.; Khobragade, Chandrahas N. (2010). "Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents". Bioorganic & Medicinal Chemistry. 18 (3): 1364–1370. doi:10.1016/j.bmc.2009.11.066. ISSN 0968-0896. 
  5. ^ Glozman, O. M.; Orlova, E. K.; Agavelyan, E. S.; Ismailov, Sh. I.; Nerobkova, L. N.; et al. Pharmaceutical Chemistry Journal, 1987 , vol. 21, # 3 p. 197 - 200 Khimiko-Farmatsevticheskii Zhurnal, 1987 , vol. 21, # 3 p. 309 - 312.
  6. ^ Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, , vol. 30, # 2 p. 281 - 285.
  7. ^ Diprenylated derivatives of p-hydroxyacetophenone from Ophryosporus macrodon. Elizabeth Sigstad, César A.N. Catalán, Jesús G. Diaz and Werner Herz, Phytochemistry, Volume 33, Issue 1, 29 April 1993, Pages 165–169, doi:10.1016/0031-9422(93)85415-N