Benzoic acid's antimicrobial activity is primarily against yeasts and molds. The pK of benzoic acid is rather low (pK 4.20), so its main antimicrobial effect, due to the undissociated acid, will be for high acid foods such as ciders, soft drinks and dressings.  Benzoic acid is metabolized by butyrate-CoA ligase into an intermediate product, benzoyl-CoA, which is then metabolized by glycine N-acyltransferase into hippuric acid. Synonyms. BENZENECARBOXYLIC ACID, BENZENEFORMIC ACID, BENZENEMETHANOIC ACID, BENZOIC ACID, BENZOIC ACID,, CARBOXYBENZENE, DRACYCLIC ACID, PHENYLCARBOXYLIC ACID, and PHENYLFORMIC ACID Benzoic acid is used as a preservative in a wide variety of foods. Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. Preparation of Benzoic Acid", "Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent", "Experiment 3: Preparation of Benzoic Acid", "Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol", "Mechanism of action of benzoic acid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH", 10.1002/(SICI)1099-1565(199703)8:2<63::AID-PCA337>3.0.CO;2-Y, GSFA Online Food Additive Group Details: Benzoates (2006), EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners (Consleg-versions do not contain the latest changes in a law), BfR article Indications of the possible formation of benzene from benzoic acid in foods, "Covid-19 Drug Design via Quantum Mechanical Principles Leads to a New Corona-SARS Anti- Viral Candidate 2-Phosphono-Benzoic-Acid", "Molecular Docking Study on Several Benzoic Acid Derivatives against SARS-CoV-2", Experiment 2: Using Bomb Calorimetry to Determine the Resonance Energy of Benzene, "Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE", "Cryptanaerobacter phenolicus gen. nov., sp. Benzoic acid is most commonly found in industrial settings to manufacture a wide variety of products such as perfumes, dyes, topical medications and insect repellents. Benzoic acid is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride, phosgene or one of the chlorides of phosphorus. Benzoic acid is not allowed in all countries. Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The dissociation constant is 6.46 × 10−5 (Bosund 1960 and 1962), which means that the pH that is reached applying lactic acid is already sufficient.  Humans metabolize toluene and benzoic acid which is excreted as hippuric acid. Among the food additives reported to cause adverse reactions are benzoic acid and its derivatives (E210–213), which may trigger asthma characterised by breathing difficulties, shortness of breath, wheezing and coughing in sensitive (i.e. However, these methods are time-consuming with complicated pretreatments and require expensive instruments (Pylypiw and Grether, 2000). Paraben esters have antimicrobial activity against molds and yeasts and are used in beer, soft drinks, and olives. Copyright © 2021 Elsevier B.V. or its licensors or contributors. 21 Products. These plasticizers are used similarly to those derived from terephthalic acid ester. Benzoic acid has a low taste threshold and low volatility and wide antimicrobial spectrum (Ashurst, 1991). Benzoic acid Revision Date 23-Jan-2015 Evaporation Rate Not applicable Flammability (solid,gas) No information available Flammability or explosive limits Upper No data available Lower No data available Vapor Pressure 1.3 hPa @ 96 °C Vapor Density Not applicable Relative Density No information available Solubility â¦ Pesticide properties for Benzoic acid, including approvals, environmental fate, eco-toxicity and human health issues PubChem Substance ID: 24854555. [email protected]
ÑÐ²Ð°ÑÑÐºÐ¸, Creative Commons Attribution-ShareAlike License, This page was last edited on 21 December 2020, at 11:14. It occurs naturally in prunes, cinnamon, and cloves. Levels of up to 24 mg/L have been reported in fermented cow's milk. Formylanthranilic â¦ A quite new application method for benzoic acid is active packaging. Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. The maximal antimicrobial activity of benzoic acid has been described between pH 2.5 and 4.5. Benzoic acid's most common uses are in carbonated beverages, pickles, sauces, and jelly. Benzoic acid inhibits the growth of mold, yeast and some bacteria. For this reason, benzoic acid for human consumption was obtained by dry distillation of gum benzoin. It can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene. Benzoic acid was discovered in the sixteenth century. Benzoic acid (0.1%–0.2%) supplementation to broilers suppressed the growth in broiler chickens, the dry matter of the digesta increased in the crop and caeca, and decreased lactic acid bacteria and coliform bacteria (Jozefiak et al., 2010). The metabolic breakdown pathways of benzoic acid. Where benzoic acid is not wanted in products, it can usually be replaced effectively by the use of sorbic acid. Lethal dose for cats can be as low as 300 mg/kg body weight. Benzoic acid in the acid form is quite toxic but its sodium salt is mucii less toxic (Table 9.3). According to the US Food and Drug Administration, the restriction of BA addition in general types of food is kept as 1000 mg kg− 1. Iris J. Joye, in Encyclopedia of Food Chemistry, 2019. Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300â400 Â°C:. C8H7NO3. , In terms of its biosynthesis, benzoate is produced in plants from cinnamic acid. They found that the obtained SERS signals of BA were strong and of high reproducibility. The major food groups contributing to dietary intake of benzoic acid are a wide variety of foods permitted at the following levels; various foods 200–1000 mg/kg (prepared salads, confectionery, etc. Foods in which benzoic acid may be used and maximum levels for its application are controlled by local food laws. The authorisation and conditions of use of preservatives are governed in the European Union by Directive 95/2/EC of the European Parliament and Council of 20 February 1995 on Food Additives other than Colours and Sweeteners. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. Kalpana, V. Devi Rajeswari, in Preservatives and Preservation Approaches in Beverages, 2019. 4- (1-Carboxy-ethyl)-benzoic acid.  Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. It has a role as a human xenobiotic metabolite. , Concern has been expressed that benzoic acid and its salts may react with ascorbic acid (vitamin C) in some soft drinks, forming small quantities of carcinogenic benzene.. Such products have a long history of use as topical antiseptics and inhalant decongestants. EC Number: 200-618-2. FEMA Number 2131 . Benzoic acid (BA) is a commonly used antimicrobial preservative in food and beverages, especially in carbonated beverages, as it presents its strongest antibacterial activity at pH 2.5â4.0. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. Next to its natural occurrence in food, benzoic acid and its derivatives are also commonly supplemented as antibacterial and –fungal preservatives or flavoring agents (Del Olmo et al., 2017). CAMEO Chemicals. Reactions of benzoic acid can occur at either the aromatic ring or at the carboxyl group: Electrophilic aromatic substitution reaction will take place mainly in 3-position due to the electron-withdrawing carboxylic group; i.e. Benzoate also specifically inhibits amino acid uptake and certain enzymes within the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase and lipase. Information on maximum allowed limits of benzoic acid and its salt as food additives can be found in the Codex Alimentarius (Food and Agriculture Organization of the United Nations and World Health Organization, 2017). Any refusal to purchase products containing this preservative is therefore a matter of a condition of a commercial contract rather than because benzoic acid is in any way not permitted for use in soft drinks. The acceptable daily intake (ADI) for benzoic acid is 5 mg/kg body weight. 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