O-Hydroxyphenylacetic acid

Brachiaria mutica, dried leaves Vanillic, p-hydroxybenzoic, o-hydroxyphenylacetic acids 74... 

Oxidative degradation of substituted pyruvic acids is accomplished by treating an aqueous solution of the sodium salt with 30% hydrogen peroxide (Superoxol) at 0-15°. Good descriptions have been published for the preparations of o-hydroxyphenylacetic acid (34%), 3,4-dim.ethoxy-phenylacetic acid (60%), m-chlorophenylacetic acid (57%), and o-nitro-phenylacetic acid. ... 

The pathway leading to o-tyrosine is of little quantitative significance in normal individuals however, it becomes important in phenylketonuria, and we shall see later that this disease is characterized by a considerable increase in the elimination of o-hydroxyphenylacetic acid. This acid may be formed from o-tyrosine through a pathway suggested by Armstrong et al. (AlO), which is summarized in Fig. 10. 

The main 2-hydroxyphenyl derivative is o-hydroxyphenylacetic acid, which is the predominant phenolic acid in the urine of phenylketonuric... 

Acetaldehyde Formaldehyde o-Hydroxyphenylacetic acid 6- Hydroxy coumarin 7- Hydroxycoumarin T same retention 8- Hydroxycoumarin J times for the column used propane phase... 

Polyethylene glycol, dextran, polyvinylpyrrolidone EDTA, tris(hydroxymethyl)aminomethane (TRIS), diethylenetriaminepentaacetic acid, inositol, hexaphosphate, ethylenediaminebis (O-hydroxyphenylacetic acid), desferal... 

Several synthetic chelating agents are being used in agriculture for the correction of deficiencies of one or more of the four metallic elements mentioned above. These include ethylenediaminetraacetic acid (EDTA), ethylenediamine di(o-hydroxyphenylacetic acid) (EDDHA), diethylenetriaminepentaacetic acid (DTPA), hydroxyethylethylene-diaminetriacetic acid (HEDTA), and nitrilotriacetic acid (NTA). (Wallace, 1960, 1963a, b, 1965 Haertl, 1963 Brown, 1969). 

Agrobactin has already been shown to serve as a siderophore in A. tumefaciens, in which organism it has the capacity to reverse inhibition of growth invoked by the presence of ethylenediamine-hydroxyphenylacetic acid) (EDDA). While Tait ( 5 ) referred to his "Compound III" as a "siderochrome", the previous name for siderophore, he did not demonstrate that the substance possessed this activity in denitrificans. 

In an infant with a serum phenylalanine concentration greater than 4 mg dl, the following have been recommended administration of 100 mg of ascorbic add 24 h prior to obtaining a repeat blood specimen, measurement of phenylalanine and tyrosine in blood, and evaluation of urine for the presence of phenylalanine, O-hydroxyphenylacetic acid, and phenylpyruvic acid, as well as tyrosine and tyrosine derivatives (p-hydroxyphenyllactic acid and p-hydroxyphenylpyruvic add) by chromatography and spot tests. Most infants will be found to have a transient defect that demands a new testing. 

Coumarin is degraded in the animal body by hydroxylation (Figure 3.3) [48,49, 56, 57, 59—61] in the rabbit, all six of the possible hydroxycoumarins are formed [49, 57, 62] although the major products are 3- (8) and 7-hydroxy-coumarins (9). The hydroxylation is followed by the opening of the a-pyrone ring via o-hydroxyphenylpyruvic (10) to yield finally o-hydroxyphenyllactic (11) and o-hydroxyphenylacetic acids (12). 

The enzymatic formation of o-hydroxyphenylacetic acid in mammalian liver has been confirmed [49, 56—58]. The suggested pathway consists of the transamination of phenylalanine (23) to phenylpyruvic acid (26), followed by the... 

Hydroxycoumarin is converted almost quantitatively in man to 3-glu-curonosidocoumarin (m.p. 207°, [aju —72.05°). There is no evidence that the pyrone ring is opened (106). 3-Hydroxycoumarin is the enol form of the lactone of o-hydroxyphenylpyruvic acid but, when fed to rabbits, it behaved in sharp contrast to the acid, which was oxidized largely to o-hydroxyphenylacetic acid. 

HOOC CH2)2N CH2CH2N(CH2C00H) CH2CH2N(CH2C00H)2 ethylenediamine di(o-hydroxyphenylacetic acid) 1.94 pH 2 70W4... 

Taniguchi, K. and Armstrong, M.D. (1963), The enzymatic formation of o-hydroxyphenylacetic acid./. Biol. Chem., 238,4091. 

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