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Description
TCI E1473 Ethyl Hippurate is the ethyl ester of hippuric acid — that is, glycine whose amino group has been acylated by a benzoyl group — and it is supplied by TCI within the peptide chemistry category. In the laboratory this compound serves as a highly classical protected amino acid derivative: the benzoyl group protects the nitrogen while the ester group protects the carboxyl, so the molecule can be manipulated at the alpha position without interference from either of its reactive termini. This dual protective role is what has made it both a teaching material and a research material that remains in continuous use today in peptide chemistry and amino acid synthesis.
The characteristic that makes this compound a preferred choice is the acidity of the alpha proton, which sits between the amide nitrogen and the ester group and is therefore easy enough to deprotonate to form an enolate that can be alkylated or condensed with aldehydes. From this point the classical route towards azlactones, also known as oxazolones, opens up, and from an azlactone a wide variety of unusual amino acids of high value in peptide research can be produced. In addition, the benzoylglycine framework is a widely recognised substrate for testing hydrolytic enzymes, because cleavage of either the ester bond or the amide bond can be monitored easily.
In Indonesian laboratories this reagent fits naturally into university and institutional settings where organic synthesis, peptide chemistry and enzymology are taught and practised. Because a single compound demonstrates both nitrogen protection and carboxyl protection in one structure, it is convenient for practical classes that introduce protecting group strategy, while the same material is used in research groups preparing non-standard amino acid building blocks or running hydrolase assays.
Laboratory Applications
Protecting group instruction — the benzoyl group on nitrogen and the ethyl ester on the carboxyl let students see both protection modes demonstrated within one accessible molecule.
Enolate alkylation at the alpha carbon — the acidic alpha proton between the amide and ester allows straightforward deprotonation and subsequent alkylation to extend the side chain.
Aldol-type condensation with aldehydes — the enolate derived from this ester condenses with aldehydes, giving access to substituted derivatives useful for further synthetic elaboration.
Azlactone and oxazolone preparation — the benzoylglycine framework opens the classical route to azlactones, which are versatile intermediates in amino acid and peptide chemistry.
Hydrolytic enzyme testing — the ester and amide bonds are both readily cleavable and easy to monitor, making this a recognised substrate for hydrolase activity studies.
Specifications
Brand: TCI (Tokyo Chemical Industry)
CAS number: 1499-53-2
Chemical name: Ethyl Hippurate, the ethyl ester of hippuric acid (N-benzoylglycine)
Category: Chemistry > Chemical Biology > Peptide Chemistry
Product code: E1473
Pack sizes: available in standard TCI research and laboratory packs — please confirm the size required at the time of enquiry
Handling and Storage
Store the container tightly closed in a cool, dry place away from direct sunlight, heat sources and moisture, since the ester group is susceptible to hydrolysis over time. Keep the material in its original supplier container or in a clean, well-sealed glass or chemically compatible bottle, clearly labelled with the product name and CAS number. Handle in a well-ventilated area or fume hood, and wear a laboratory coat, safety goggles and suitable gloves to avoid contact with skin and eyes. Use clean and dry spatulas when weighing to prevent contamination of the stock, close the container immediately after use, and refer to the manufacturer's safety data sheet before first handling and for disposal of residues.
