Phenylglycollic acid

Mandelic acid with a 13 - 20 % enantiomeric excess of the (R)-isomer has been obtained from reduction of phenylglycolic acid in aqueous alcohol buffers containing strychnine in low concentration. The optical yield depends upon pH and is highest (20 - 24 %) at pH 0 or 9.2 and at low current density. In the pH range 2-4, the optical yield drops to 2-8% [42]. The higher result compares well with the maximum value of 20% excess R-isomer found from reduction of (-)-menthyl phenylglycolate in aqueous buffers where the (-)-menthyl ester is the only chiral reagent present [43 ]. 

Note that we have used the following notation for hydroxy acids in this section, -O-Gly for the glycolic acid residue -0CH2C(0)-, likewise -O-Ile is the isoleucic acid residue -OCH(CHMeEt)C(0)-, -O-Leu is the leucic acid residue -0CH(iBu)C(0)-, -O-Phe is the (3-phenyllactic acid residue -0CH(Bzl)C(0)-, and -O-Phg is the phenylglycolic acid residue -OCHPhC(O)-. 

Rule-based or systematic nomenclature (e.g., International Union of Pure and Applied Chemistry [IUPAC] or CAS nomenclature) is based on a set of linguistic rules that apply to its structure. For example, the IUPAC and CAS names for mandelic acid are 2-phenyl-2-hydroxyacetic acid and benzeneacetic acid, a-hydroxy-, respectively. The number of possible systematic names is practically endless. A small, but not nearly exhaustive, set of other systematic names includes phenylglycolic acid, phe-nylhydroxyacetic acid, ( )-a-hydroxybenzeneacetic acid, ( )-a-hydroxyphenylacetic acid, ( )-2-hydroxy-2-phenylethanoic acid, ( )-Mandelic acid, (RS)-Mandelic acid, DL-Amygdalicacid,DL-Hydroxy(phenyl)aceticacid,DL-mandelicacid,paramandelic acid, a-hydroxy- a-toluic acid, a-hydroxyphenylacetic acid, a-hydroxybenzeneacetic... 

Synonyms. Amygdalic Acid Phenylglycollic Acid Racemic Mandelic Acid. 

Palladium, hydride, 158 Para anc n, 151 Paraffine, 175 Paratoluidine, 175 Perchloric acid hydrates, 253 Perlite, 310 Phenanthiene, 289 Phenylammonium, phenolate of, 318 Phenylglycolic acid, 294 Phenol, 314, 318, 319 Phosphide of hvdro n, 398 Phosphonium, bromide of, 340 Phosphorus, 184, 284, 334, 396, 410 perchloride, 346 Picric acid. 105, 227 Pinonic acid, 292 Platinum, chlorides, 400 Potash, 393... 

Phenoxyacetic Acid, Phenoxyethanoic acid O-phenylglycolic acid phenyl ether glycolic acid Phenylium. C HgO, mol wt 152.14. C 63.15%, H 5.30%, O 31.55%. Prepd from phenol and monochloroacetic acid Giacosa, J. Prakl. Chem. [2] 19, 396 (1879) van Alphen, Rec. Trav. Chim. 46, 148 (1927). 

S)-Mandelic (1) and (/ )-mandelic acid (2) are the more familiar names for the chiral antipodes of a-hydroxybenzeneacetic acid, also known as phenylglycolic acid or amygdalic acid. As orthorhombic plates from water, pure mandelic acid melts at 119 °C and has a Ks = 43 X 10 " M. Mandelic acid is moderately soluble in water (1 g to 6.3 mL water) and very soluble in ether and isopropanol. Therapeutically, mandelic acid is most commonly used as a urinary antiseptic [1]. 

Synonyms cas 122-59-8 glycolic acid phenol ether phenoxyethanoic acid o-phenylglycolic acid ... 

Synonyms Amygdalic acid Amygdalinic acid Benzoglycolic acid Glycolic acid, phenyl- a-Hydroxyphenylacetic acid o-Hydroxy-a-toluic acid DL-Mandelic acid L-Mandelic acid Paramandelic acid Phenylglycolic acid... 

Phenylglycollic acid Phenylglyconic acid Phenylhydroxyacetic acid a-Phenylhydroxyacetic acid Racemic mandelic acid... 

Synonyms Glycolic acid phenyl ether Glycollic acid phenyl ether Phenoxyethanoic acid o-Phenylglycolic acid Phenylium Empirical CaHsOs Formula C6H5OCH2COOH Properties Off-wh. cryst. solid, sour odor, honeylike taste readily sol. in alcohol, ether, benzene, CS2, glac. acetic acid, oxygenated and aromatic soivs. si. sol. in water m.w. 152.14 m.p. 95 C b.p 285 C (some decomp.)... 

Hydro mandelic Acid (2 - Hydroxy -phenylglycollic acid, 2-tt-dihydroxyphenylacetic acid, 2-x-dihydroxy-x-tohtic acid)... 

Hydroiqrnumdelic Acid 3-Hydroxy phenylglycollic acid, Z-a-dihydroxypkenylacetic acid, Z-a-dihydroxy-a-tolme acid). 

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