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Synonym name: Benzoic acid
Catalogue No.: SBP00049
Cas No.: 65-85-0
Formula: C7H6O2
Mol Weight: 122.123
Physical Description: Cryst.
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams. Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
NMR of Benzoic acid
HPLC of Benzoic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
37.3000
1.8651
-.9696
1.5308
3.4049
14.8871
Low
87.2524
1.0549
Yes
No
No
No
Yes
No
0.0
Yes
Yes
Yes
Yes
Benzoic acid (CAS No.: 65-85-0), as a simple natural aromatic carboxylic acid, is widely found in various plants, especially abundant in berries, fruits, and certain resins. Its structural feature is the attachment of a carboxylic acid group to the benzene ring, giving it unique chemical and biological properties. Benzoic acid is not only commonly used as a preservative in various consumer products such as food, beverages, and cosmetics, but is also widely used for its excellent antibacterial and antifungal activities, and has also shown various potential biological activities in pharmacological research. In recent years, with the deepening development of natural product pharmacology, the molecular mechanisms of benzoic acid, its target lineage, and druggability evaluation have gradually become research hotspots, promoting its potential applications in the pharmaceutical field.
This paper will systematically review the chemical structure and physicochemical properties of benzoic acid, its plant origin and extraction methods, detail its pharmacological activity and mechanism of action, evaluate its druggability parameters and pharmacokinetic characteristics, and finally look ahead to its clinical application prospects, aiming to provide a comprehensive scientific basis for basic research and clinical development of benzoic acid.
Benzoic acid has a molecular formula of C_7H_6O_2 and a molecular weight of 122.1230. Its structural core consists of a benzene ring (aromatic nucleus) connected to a carboxylic acid (–COOH) substituent, chemically named benzoic acid. The LogP value of benzoic acid is 1.8651, indicating moderate lipid solubility and sufficient solubility in both aqueous and lipid phases. Its topological polar surface area (TPSA) is 37.3 Ų, indicating moderate molecular polarity and favorable binding to multiple biological targets.
The water solubility is 1.5308 (usually mg/mL or g/L, with specific references to be confirmed), indicating that benzoic acid has a certain solubility in water, facilitating its distribution and transport within living organisms. Benzoic acid has low blood-brain barrier permeability, limiting its distribution in the central nervous system, which is beneficial for its safety and side effect control. The hERG channel inhibition test was negative, indicating that benzoic acid is less likely to induce arrhythmias and has a relatively high safety profile. The Ames mutagenic test result was 0.0, indicating no obvious genotoxicity.
Benzoic acid has good chemical stability, is easy to synthesize and modify, and its carboxyl acid groups can be structurally diversified through chemical reactions such as esterification and amidation, expanding its biological activity and range of applications.
Benzoic acid is widely found in various plants, especially berries (such as cranberries and blueberries), spice plants (such as cinnamon and clove), certain resins, and flowers. The biosynthesis of benzoic acid in plants mainly occurs through the phenylalanine metabolic pathway, produced by intermediates such as styracrylic acid and phenylpyruvate.
Traditional benzoic acid extraction methods mainly include solvent extraction, distillation, and crystallization separation. Common solvents include ethanol, methanol, water, and ethyl acetate. In recent years, with the development of green chemistry and efficient separation technologies, new technologies such as supercritical CO_2 extraction, microwave-assisted extraction, and ultrasonic-assisted extraction have been applied to the efficient extraction of benzoic acid, improving extraction rates and purity.
After extraction, benzoic acid is typically purified by recrystallization, column chromatography, or high-performance liquid chromatography (HPLC) to ensure quality standards for pharmacological research and industrial applications.
The pharmacological activity of benzoic acid is mainly reflected in its antibacterial, antifungal, preservative, and enzyme inhibitory effects. As a natural preservative, benzoic acid and its salts (sodium benzoate, potassium benzoate) are widely used in food and cosmetics to inhibit the growth of various bacteria and fungi, extending product shelf life.
Benzoic acid exhibits inhibitory effects on both Gram-positive and Gram-negative bacteria, especially showing strong inhibitory effects against common pathogens such as Staphylococcus aureus, Escherichia coli, and Salmonella. Its antibacterial mechanism mainly involves damaging the integrity of cell membranes, lowering intracellular pH, and inhibiting cellular metabolic activities.
Benzoic acid has an inhibitory effect on various fungi (such as yeast and mold) and is commonly used to prevent mold in food and cosmetics. Its mechanism involves interfering with the synthesis and function of fungal cell membranes, inhibiting key enzyme activities.
Benzoic acid has been reported to have inhibitory activity on EC 1.13.11.33 (arachidonic acid 15-lipoxygenase) and EC 3.1.1.3 (triglycerol lipase). By inhibiting lipase, benzoic acid may influence lipid metabolism, regulating energy metabolism and has anti-inflammatory potential. Inhibiting arachidonic acid 15-lipoxygenase may reduce the production of inflammatory mediators and exert anti-inflammatory effects.
Additionally, benzoic acid, as a human heterogenetic metabolite and a metabolite of plants and algae, participates in various metabolic pathways, demonstrating its diverse functions within living organisms.
The biological activity of benzoic acid depends on its interactions with various molecular targets, especially in the field of antimicrobial activity. Relevant targets include:
Benzoic acid achieves broad-spectrum antibacterial and antifungal effects through multi-target synergistic action. Additionally, its inhibitory effects on lipase and lipoxygenase suggest its potential value in regulating inflammatory responses and metabolic diseases.
The druggability parameters of benzoic acid indicate its promising potential for drug development. The molecular weight of 122.1230 complies with the Lipinski rule, and the LogP of 1.8651 is moderate, indicating good membrane permeability and bioavailability. TPSA of 37.3 Ų is lower than 140 Ų, indicating good cell membrane penetration capability.
Moderate water solubility, which is beneficial for the preparation of oral preparations and absorption in the body. The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects. hERG channel inhibition negative, reducing the risk of cardiotoxicity. The Ames test is non-mutagenic and has relatively high safety.
Pharmacokinetics, benzoic acid is mainly metabolized in the liver by producing metabolites such as benzoyl-CoA, which are then excreted in urine. Its half-life is moderate, making it suitable for everyday use. It is widely distributed in the body, but its penetration into the central nervous system is limited.
The metabolic stability and safety of benzoic acid make it suitable for use as pharmaceutical excipients, preservatives, and potential therapeutic molecules.
Benzoic acid, as a long-standing natural preservative, has been widely used in the food industry and cosmetics sectors. With deeper understanding of its pharmacological activity and molecular mechanisms, the clinical application prospects of benzoic acid have gradually expanded.
Benzoic acid's inhibitory effects on various pathogenic bacteria and fungi provide a theoretical basis for anti-infective drug development. In the future, structural optimization and compatibility can be used to improve its antibacterial spectrum and efficacy, enabling the development of new antimicrobials or adjunctive therapies.
By inhibiting lipoxygenase and lipase, benzoic acid demonstrates potential anti-inflammatory and lipid metabolism regulation. Its application in chronic inflammation, metabolic syndrome, and related diseases warrants further study.
Benzoic acid's excellent safety and druggability make it suitable as an excipient in drug delivery systems or in combination with other drugs to enhance efficacy and reduce resistance.
Although benzoic acid possesses diverse biological activities, its clinical application still faces challenges such as dose limitations, insufficient targeting, and rapid metabolism in vivo. Future research should focus on:
Benzoic acid, as a naturally occurring and structurally simple aromatic carboxylic acid, holds significant value in food preservation and pharmaceuticals due to its broad antibacterial, antifungal, and enzyme-inhibiting activities. Its favorable druggability parameters and safety laid the foundation for its clinical development. In the future, through multidisciplinary research and optimizing molecular structure and application strategies, benzoic acid is expected to become a strong candidate for novel anti-infective, anti-inflammatory, and metabolic disease treatments. Systematic and in-depth pharmacological mechanism analysis and clinical research will drive the transformation of benzoic acid from traditional preservatives to modern medicines, expanding its application prospects in the field of natural product pharmacology.
Shenshuai
Wenjing
Hedandan
