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: