2,5-Dihydroxybenzaldehyde
[CAS# 1194-98-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic aldehyde (containing acetal, hemiacetal)
• Name: 2,5-Dihydroxybenzaldehyde
• Synonyms: Gentisaldehyde
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• CAS Registry Number: 1194-98-5
• EC Number: 214-789-6
• SMILES: C1=CC(=C(C=C1O)C=O)O

Properties

• Melting point: 98-102 °C
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

2,5-Dihydroxybenzaldehyde is a compound of great interest in both academic research and industrial applications, having been first synthesized and characterized in the early 20th century. Discovered through organic synthesis, 2,5-Dihydroxybenzaldehyde is derived from a benzene ring structure with hydroxyl groups located at the 2 and 5 positions relative to the aldehyde functional group (-CHO). This arrangement imparts unique chemical reactivity and properties. The presence of hydroxyl groups on the aromatic ring makes 2,5-Dihydroxybenzaldehyde a strong candidate for a variety of chemical reactions. Its aldehyde functionality allows for easy modification and functionalization, enabling the synthesis of derivatives with tailored properties. The compound exhibits moderate solubility in polar solvents, enhancing its utility in solution applications.

In organic synthesis, 2,5-Dihydroxybenzaldehyde is a versatile building block for the preparation of complex molecules and pharmaceutical intermediates. It is capable of selective chemical transformations, such as oxidation and reduction reactions, enabling the synthesis of bioactive compounds and natural product analogs. Researchers have exploited its structure to introduce specific functional groups.

Besides academic research, 2,5-dihydroxybenzaldehyde has practical applications in various industrial fields. It is a precursor for the production of specialty chemicals, including dyes, pigments, and polymer additives. Its incorporation into polymer matrices enhances material properties, such as thermal stability and mechanical strength, making it invaluable in polymer science and engineering.

In the biomedical field, 2,5-dihydroxybenzaldehyde exhibits promising pharmacological activities. Studies have highlighted its antioxidant properties, which play a vital role in alleviating oxidative stress and inflammation-related diseases. Ongoing research explores its potential as a therapeutic agent for neurodegenerative diseases and cancer, underscoring its importance in modern medicine.

References

1982. Phenolic aldehydes and aldoximes as indicators for direct titration of ferric ions with diethylenetriaminepentaacetic acid (DTPA). Microchimica Acta.
DOI: 10.1007/bf01206934

2018. Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure-Activity Relationship Models. Medicinal Chemistry Research.
DOI: 10.1007/s00044-018-2245-2

2024. Investigation of the efficacy on tyrosinase enzyme of 5-substituted-1H-tetrazole derivatives synthesized with Pd-containing nanoparticle. Journal of Chemical Sciences.
DOI: 10.1007/s12039-024-02254-w