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Usage

Uses

Used in Pharmaceutical Industry:
DL-4-Hydroxyphenylglycine is used as a key intermediate in the synthesis of Cefpiramide (C243400), a β-lactam antibiotic. It plays a crucial role in the development of this antibiotic, which is effective against a wide range of bacterial infections.
Used in Photographic Industry:
Although now rarely used, DL-4-Hydroxyphenylglycine was once employed as a photographic developer. Its chemical properties allowed it to act as a reducing agent in the development process, contributing to the formation of images on photographic film.
Used in Analytical Chemistry:
DL-4-Hydroxyphenylglycine has been utilized in the determination of phosphorus and silicon. Its reactivity and selectivity make it a useful agent in analytical methods for detecting and quantifying these elements in various samples.

InChI:InChI=1/C8H15NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h5-7,10H,1-4,9H2,(H,11,12)/t5?,6?,7-/m0/s1

Upstream product

• 6324-01-2 p-hydroxyphenylglycine 
• 64923-06-4 D-p-hydroxyphenylglycine o-toluenesulfonate 

Relevant academic research and scientific papers

The Optical Resolution and Asymmetric Transformation of DL-p-Hydroxyphenylglycine with (+)-1-Phenylethanesulfonic Acid

Optically active 1-phenylethanesulfonic acid was found to be an efficient resolving agent for the optical resolution and asymmetric transformation of DL-p-hydroxyphenylglycine.When DL-p-hydroxyphenylglycine was resolved by the fractional crystallization of its diastereomeric salt with (+)-1-phenylethanesulfonic acid, less soluble D-p-hydroxyphenylglycine (+)-1-phenylethanesulfonate was obtained in a good yield.Soluble L-HPG*(+)-PES was easily epimerized into DL-HPG*(+)-PES by heating it at 100 deg C in glacial acetic acid in the presence of a small amount of salicylaldehyde.Under such epimerizing conditions, the asymmetric transformation of DL-HPG*(+)-PES was attempted by simultaneously combining the fractional crystallization of the less soluble D-HPG*(+)-PES and the epimerization of the soluble L-HPG*(+)-PES.This asymmetric tranformation was achieved succesfully; that is, 80percent of the DL-HPG used as the starting material was converted into D-HPG.

Asymmetric Transformation of DL-p-Hydroxyphenylglycine by a Combination of Preferential Crystallization and Simultaneous Racemization of the o-Toluenesulfonate

The asymmetric transformation of DL-p-hydroxyphenylglycine was achieved between two enantiomers by a combination of preferential crystallization of desired enantiomer of p-hydroxyphenylglycine o-toluenesulfonate (HPG.o-Ts) and the simultaneous racemization of the antipode.L-HPG.o-TS was easily racemized by heating at 100 deg C in aqueous 95percent (v/v) acetic acid in the presence of small amounts of salicylaldehyde and free DL-HPG.A supersaturated solution of DL-HPG.o-TS placed under such conditions for racemization was seeded with the crystals of D-HPG.o-TS, and added with DL-HPG and o-toluenesulfonic acid in order to provide contonously the supersaturated of DL-HPG.o-TS as a driving force.As a result, 77.2percent of DL-HPG added was transformed to D-isomer.