2-Hydroxy-2-phenylacetic acid

The product from Step 2 (220 mg) was mixed with (2R)-2-((lR)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid (256 mg) dissolved in 8 ml chloroform, 1-hydroxybenzotriazole (203 mg) and l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (201 mg) added, and the mixture stirred 3 hours at ambient temperature. Thereafter, the mixture was diluted with EtOAc, washed with 1 M NaOH, brine, dried, and concentrated. The material was purified by chromatography on silica gel using hexane/EtOAc, 2 1, and 314 mg product isolated. 

Synonyms a-Hydroxybenzeneacetic acid 2-Hydroxy-2-phenylacetic acid... 

Hareland WA, RL Crawford, PJ Chapman, S Dagley (1975) Metabolic function and properties of 4-hydroxy-phenylacetic acid 1-hydrolase from Pseudomonas acidovorans. J Bacteriol 121 272-285. 

Robinson et al. [263] have studied both at the laboratory and semi-technical scale the electrochemical generation of chromous ion (Cr(II)) for the reduction of sodium hydroxymandelate (SHM) to 4-hydroxy phenylacetic acid (HPA), a Tenormin intermediate, as a potential replacement for the existing Zn(Hg) reduction process. 

Davis BA, Yu PH, Carlson K, O Sullivan K, Boulton AA. 1982. Plasma levels of phenylacetic acid, m- and p-hydroxy-phenylacetic acid, and platelet monoamine oxidase activity in schizophrenic and other patients. Psychiatry Res 6 97. de la Torre R, Ortuno J, Pascual JA, Gonzalez, S, BaUesta J.1998. Quantitative determination of tricyclic... 

FIGURE 11.2 Separation of hydroxy-phenylacetic acids by displacement on a CIS reversed phase column (dimensions 4.6 X 250 mm). Carrier 0.1 M phosphate displacer 0.87 M aqueous -butanol. Flow rate 0.05 mL/ min temperature 25°C. (Reprinted with permission from Elsevier from Horvath, C. et al., J. Chromatogr., 218, 365, 1981. Copyright.)... 

Dopamine metabolism was covered in the discussion of general catecholamine biochemistry. Dopamine is stored in synaptic vesicles, and this storage can be manipulated. Although the reuptake of released DA is the major deactivating mechanism, MAO and COMT act enzymatically on DA in the same way as on NE. However, following the degradative pathway of NE, DA will finally be metabolized to homovanillic acid (3-methoxy-4-hydroxy-phenylacetic acid), since it lacks the P-hydroxyl group. 

Subject Phenylacetic Acid Mandelic Acid o-Hydroxy- phenylacetic Acid Phenyllactic Acid Phenyl- pyruvic Acid p-Hydroxy- phenylacetic Acid... 

Fig. 26. Increased fluorescent yield (arbitrary scale) per Tb3+ ion at 545 nm as produced by decreasing the volume of solubilizate in each micelle. V = volume of mixture (1 1 by volume) of 0.5M TbCl3 and 0.5M HPA (= hydroxy-phenylacetic acid) solutions which has been solubilized in 1 ml of 2 10 2mol dm-3 AOT in isooctane. [J. Colloid Interface Sci. 56, 168 (1976))...

Use of Iron from Fe3+EDDHA (Iron-ethylenediamine di(o-hydroxy-phenylacetic acid)). Iron-inefficient T3238fer tomato developed iron deficiency because it could not absorb iron from FeEDDHA (7). In contrast, the iron-efficient T3238FER tomato used iron from FeEDDHA because it could reduce Fe3+ to Fe2+. Chaney et al. (34) showed that for... 

In the hydrolysate of toxic components in the venom of bird-catching spiders (suborder Orthognatha, family Aviculariidae, subfamilies Grammostolinae and Theraphosinae), di-aminopropane, spermine, 4-hydroxyphenylpyruvic acid, 4-hydroxybenzoic acid, 4-hydroxy-phenylacetic acid, and 4-hydroxyphenyllactic acid have been identified. Separation and structure elucidation of the individual components of the original extract were not performed (35.36). 

In the metabolism study (29, 30, 31) the following seven metabolites, 6-(1-hydroxyethyl)-3-(Ijl-tetrazol-5-yl)-chromone (1 ), 6-acetyl-3-(lH-tetrazol-5-yl)chromone (I7)j 6-(2-hydroxyethyl)-3-(lH-tetrazol-5-yl)chromone (l ), (l,2-dihydroxyethyl)-3-( Ifl-tet razo 1 -5-y 1) chromone (1 ), glucuronide (20) (the structural elucidation is described below), 5 ethylsalicylic acid ( ) and 3-carboxy-4-hydroxy-phenylacetic acid ( ), were identified in the urine of rats, guinea pigs, rabbits, dogs and monkeys. These seven compounds were synthesized and used as reference compounds to unequivocally establish the structures of the urinary metabolites, and to allow evaluation of their antiallergic activity (32). The synthetic routes are shown below (Figure 4). 

LLE Hexane 60% aqueous MeOH MeOH/H O (1 1 v/v) Tyrosol, 2.3-dihydroxyphenylethanol, oleuropein glycoside, hydroxytyrosol, dihydrocaffeic acid, cinnamic acid, 4-hydroxy-phenylacetic acid, gentisic acid, taxifolin, syringic acid, ferulic acid, luteolin, o-coumaric acid, p-coumaric acid, quercetin, vanillic acid, 4-hydroxy-benzoic acid, caffeic acid, 3,4-dihydroxyphenylacetic acid, gallic acid, and protocatechuic acid UV-vis (200 nm) ESI-MSD CZE-DAD HPLC... 

Pigment from Lycoperdon gemmatum, Batsch. Brown needles. Sol. EtOH. Spar. sol. H.O. Insol. Et20. HgOa -+ HCl —homogentisic anhydride. KOH fusion —> p-hydroxy-phenylacetic acid. 

Interference by Endogenous p-Hydroxy-phenylacetic Acid with Estimation of N-Acetyl-p-aminophenol in Urine by Gas Chromatography... 

Palomo, J., G. Fernandez-Lorente, C. Mateo, M. Puentes, R. Femandez-Lafuente, and J. M. Guisan. 2002a. Modulation of the Enantioselectivity of Candida antarctica B Lipase Via Conformational Engineering. Kinetic Resolution of ( )-a-Hydroxy-Phenylacetic Acid Derivatives. Tetrahedron Asymmetry 13 (12) 1337-1345. 

Synonyms a-Hydroxybenzeneacetic acid -hydroxy-oetoluic acid a -hydroxy phenylacetic acid phenylhydroxyacetic acid phenylglycolic acid amylgdalic acid amygdalinic acid paramandelic acid Trade names Camdelate, Uromaline... 

Acetoxy-2,6-di-t rf-butyl-4-methyl-2,5-cyclohexadienone in dimethylformamide added under Ng to a stirred soln. of K-rer/-butoxide in dimethylformamide, and allowed to stand 1 hr. at room temp. 6-methyl-2,4-di-t r/-butyl-3-hydroxy-phenylacetic acid. Y 83%. F. e. s. A. Nishinaga et al.. Synthesis 1976, 553. 

Preparation by reaction of m-hydroxy-phenylacetic acid with resorcinol in the presence of boron trifluoride etherate under argon on a water bath for 1 h (93%) [5208]. 

Figure 5. Hydroxylation of L-tyrosine to L-3,4-dihy-droxyphenylalanine (A) and conversion of 4-hydroxy-phenylacetic acid to 3,4-dihydroxyphenylacetic acid by Klebsiella oxytoca (B) (64).

Alkylation of the monobenzyl ether of hydroquinone 34 with mesylate 35, gives ether 36. Hydrogenolytic removal of the benzyl group gives phenol 37. This affords cicloprolol (38) when subjected to the standard alkylation scheme 17]. In much the same vein, alkylation of g-hydroxy-phenylethanol 39, obtainable from the corresponding phenylacetic acid, with epichlorohydrin... 

Lithium enolates of carboxylic acids such as phenylacetic acid or of amides such as N-methyl-N-phenylvaleric acid amide 1974 are oxidized by BTSP 1949 to a-hydroxy acids, which are isolated after esterification, e.g., to 1973, or to a-hydroxyamides such as 1975 [155] (Scheme 12.43) (cf. also the formation of 3-hydroxybutyrolactam 1962). 

The taxonomic application of the ability of enteric organisms to grow with 4-hydroxy-phenylacetate (Cooper and Skinner 1980) and 3-hydroxyphenylpropionic acid (Burlingame and Chapman 1983) has been established. In addition, it has been demonstrated that the enzyme that carries out the hydroxylation has a wide substrate range extending to 4-meth-ylphenol, and even to 4-chlorophenol (Prieto and Garcis 1994). 

Biological. Reported degradation products by the microorganism Alcaligenes BM-2 for a mixture of polychlorinated biphenyls include monohydroxychlorobiphenyl, 2-hydroxy-6-oxo-chlorophenylhexa-2,4-dieonic acid, chlorobenzoic acid, chlorobenzoylpropionic acid, chloro-phenylacetic acid, and 3-chlorophenyl-2-chloropropenic acid (Yagi and Sudo, 1980). 

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