2,4-Dihydroxybenzoic acid
[CAS# 89-86-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 2,4-Dihydroxybenzoic acid
• Synonyms: 4-Hydroxysalicylic acid; beta-Resorcylic acid
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.12
• CAS Registry Number: 89-86-1
• EC Number: 201-946-9
• FEMA: 3798
• SMILES: C1=CC(=C(C=C1O)O)C(=O)O

Properties

• Melting point: 225-227 °C
• Water solubility: 8 g/L (20 °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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,4-Dihydroxybenzoic acid, commonly referred to as β-resorcylic acid, is a benzoic acid derivative with two hydroxyl groups located at the 2 and 4 positions on the benzene ring. This compound belongs to the family of hydroxybenzoic acids, which are commonly found in nature as plant metabolites. Its chemical structure allows for diverse reactivity, making it an essential intermediate in various synthetic applications.

The discovery of 2,4-dihydroxybenzoic acid dates back to early research in organic chemistry that focused on the exploration of naturally occurring compounds. It was primarily isolated from plants where it acts as a component of various secondary metabolites. Over time, its importance in the field of organic synthesis has increased due to its ability to serve as a precursor for numerous chemical reactions.

In terms of application, 2,4-dihydroxybenzoic acid is widely used in the pharmaceutical industry. It serves as a building block in the synthesis of bioactive molecules, especially in the creation of drugs with antimicrobial, anti-inflammatory, and anticancer properties. For example, it can be used in the production of resorcylic acid lactones, which possess antifungal and anticancer properties.

The cosmetic industry also benefits from 2,4-dihydroxybenzoic acid, utilizing its antioxidant properties. It helps protect skin cells from oxidative stress, thus preventing premature aging. Moreover, its presence in formulations can enhance the stability and efficacy of cosmetic products.

Beyond pharmaceuticals and cosmetics, 2,4-dihydroxybenzoic acid plays a role in the food industry as a preservative due to its antimicrobial properties. It is also explored for use in organic electronics and materials science, where its structural features allow for applications in the development of new materials with unique electronic properties.

References

2023. Design, Synthesis, and In Vitro and In Vivo Bioactivity Studies of Hydrazide-Hydrazones of 2,4-Dihydroxybenzoic Acid. International Journal of Molecular Sciences, 24(24).
DOI: 10.3390/ijms242417481

2023. 2,4‐Dihydroxybenzoic Acid, a Novel SA Derivative, Controls Plant Immunity via UGT95B17‐Mediated Glucosylation: A Case Study in Camellia Sinensis. Advanced science (Weinheim, Baden-Wurttemberg, Germany), 11(8).
DOI: 10.1002/advs.202307051

2024. Supramolecular assembly in 2-amino-5-bromo-3-methylpyridinium-2,4-dihydroxybenzoate monohydrate mediated by hydrogen bonding interactions: experimental and theoretical approach. Chemical Papers, 78(5).
DOI: 10.1007/s11696-023-03260-x