4-Hydroxyphenylacetic acid
[CAS# 156-38-7]

Identification

• Classification: Natural product >> Natural phenols
• Name: 4-Hydroxyphenylacetic acid
• Synonyms: p-Hydroxyphenylacetic acid
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• CAS Registry Number: 156-38-7
• EC Number: 205-851-3
• SMILES: C1=CC(=CC=C1CC(=O)O)O

Properties

• Melting point: 147-152 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Hydroxyphenylacetic acid, an aromatic organic compound, was first identified in the early 20th century and has since gained recognition for its diverse applications in both research and industry. It is a derivative of phenylacetic acid, distinguished by the presence of a hydroxyl group at the para position relative to the carboxyl group on the aromatic ring.

One of the primary applications of 4-Hydroxyphenylacetic acid is in the field of pharmacology and medicine. It is an important metabolite of the neurotransmitter dopamine, playing a role in the biochemical pathways involved in neurotransmitter regulation. Its presence in biological systems is used as a marker for various neurological and psychiatric conditions, including Parkinson's disease and depression. As a result, it is employed in research to understand and monitor changes in neurotransmitter metabolism and to evaluate the effects of therapeutic interventions.

In addition to its role in medical research, 4-Hydroxyphenylacetic acid is utilized in the synthesis of various chemical compounds. It serves as an intermediate in the production of pharmaceuticals, agrochemicals, and other fine chemicals. Its chemical reactivity allows it to participate in a range of reactions, facilitating the creation of substances with specific properties and functionalities. This makes it a valuable component in the development of new materials and products in the chemical industry.

Furthermore, 4-Hydroxyphenylacetic acid finds applications in the field of analytical chemistry. It is used as a standard in chromatographic techniques, such as high-performance liquid chromatography (HPLC), to quantify and analyze phenolic compounds in various samples. Its stability and well-defined properties make it a reliable reference compound for ensuring accurate and reproducible analytical results.

Despite its utility, the use of 4-Hydroxyphenylacetic acid must be managed with consideration of its potential impacts. Research continues to explore its safety profile and environmental effects to ensure that it is used responsibly in both research and industrial applications.

References

1979. A gas chromatographic-mass spectrometric assay for nine hydroxyphenolic acids in uremic serum. Clinica chimica acta; international journal of clinical chemistry.
URL: https://pubmed.ncbi.nlm.nih.gov/487594

2024. Physiochemical and Therapeutic Properties of Stingless Bee Miracle Liquid. Honey in Food Science and Physiology.
DOI: https://doi.org/10.1007/978-981-97-3565-5_9

2009. Bioconversion of tyrosol into hydroxytyrosol and 3,4-dihydroxyphenylacetic acid under hypersaline conditions by the newHalomonassp. strain HTB24. FEMS Microbiology Letters.
URL: https://pubmed.ncbi.nlm.nih.gov/17937662