MUDr. Dana Maňasková

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4-hydroxyfenylacetát

Synonyma

  • 4-hydroxyphenylacetic acid
  • 4-OH-phenylacetic acid
  • PAA
  • PHPA
  • AKOS 236-100
  • RARECHEM AL BO 0188
  • 4-carboxymethylphenol
  • 4-hydroxybenzeneacetic acid
  • 4-Hydroxy-Benzeneacetate
  • Alfa-toluic acid
  • Alpha tolylic acid
  • Parahydroxy phenylacetic acid
  • C8H8O3

Výskyt

  • Olive oil [1]
  • Beer in bound form [1]
  • Bladder, Kidney, Epidermis, Prostate [2]

Vznik

  • 4-hydroxyacetophenone + NADPH + oxygen › 4-hydroxyphenylacetate + NADP+ + H2O [3]
  • Tyrosine degradation II :
    • 4-hydroxyphenylpyruvate + 2 H+ + oxygen › 4-hydroxyphenylacetate + CO2 + H2O [3]
  • Oxidation product of phenethylamine
    • Monoamine oxidázou [4]

Degradace

  • 4-hydroxyphenylacetate + H2O › benzene-1,4-diol + acetate [3]
  • 4-hydroxyphenylacetate + FADH2 + oxygen › 3,4-dihydroxyphenylacetate + FAD + H+ + H2O [3]

Význam

  • Oxidative deaminated metabolite of p-tyramine [2]
  • Dopamine metabolite: 3, 4-hydroxy-phenylacetic acid (DOPAC) [6]
  • Metabolite of tyrosine via enteric bacteria [2]
    • In urine decreased significantly after the use of the neomycin [2]

Vyšší koncentrace

  • Fenylketonurie [5]
  • Jaterní nedostatečnost [5]

Moč

  • Urinary chromatograms obtained for several children with neurological disorders manifest by seizures, infantile autism, and mental retardation showed elevated excretion of 4-hydroxyphenylacetic (a metabolite of tyramine) and 4-hydroxyhippuric acids. [6]

Využití

  • Used in the illicit production of phenylacetone (used in the manufacture of meth/amphetamine), it is subject to controls in the United States. [4]
  • Active auxin (a type of plant hormone) [4]
    • Predominantly in fruits [4]
  • Some perfumes
    • Honey-like odour in low concentrations [4]
  • In penicillin G production
  • Treat type II hyperammonemia
    • Reduce the amounts of ammonia in a patient's bloodstream
      • Forming phenylacetyl-CoA
      • Reacts with nitrogen-rich glutamine to form phenylacetylglutamine
      • Secreted [4]
Literatura:

[1] 4-Hydroxyphenylacetic acid - Wikipedia, the free encyclopedia [Internet]. [citován 11. červen 2013]. Dostupné od: en.wikipedia.org/wiki/4-Hydroxyphenylacetic_acid
[2] HMDB: Showing metabocard for p-Hydroxyphenylacetic acid (HMDB00020) [Internet]. [citován 11. červen 2013]. Dostupné od: www.hmdb.ca/metabolites/hmdb00020
[3] MetaCyc 4-hydroxyphenylacetate [Internet]. [citován 11. červen 2013]. Dostupné od: biocyc.org/META/NEW-IMAGE?type=COMPOUND&object=4-HYDROXYPHENYLACETATE
[4] Phenylacetic acid - Wikipedia, the free encyclopedia [Internet]. [citován 11. červen 2013]. Dostupné od: en.wikipedia.org/wiki/Phenylacetic_acid
[5] Inborn Metabolic Diseases: Diagnosis and Treatment - Georges Van den Berghe - Google Books [Internet]. [citován 11. červen 2013]. Dostupné od: books.google.cz/books?id=IVaGNJ3Htz8C&pg=PA93&lpg=PA93&dq=4-OH-phenylacetic+acid&source=bl&ots=_esObTqlc6&sig=aVNcxampx3XU88wrWzncHMfH_hQ&hl=en&sa=X&ei=3aa3UdieDMvLsgavhYCYDg&redir_esc=y#v=onepage&q=4-OH-phenylacetic%20acid&f=false
[6] Peripherally administered growth hormone increase... [Horm Behav. 2004] - PubMed - NCBI [Internet]. [citován 11. červen 2013]. Dostupné od: www.ncbi.nlm.nih.gov/pubmed/15465529








O úroveň výše

Poslední aktualizace: 12. 6. 2013 1:46:45
© Dana Maňasková, metabalance.cz
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