Benzoic acid works as a preservative in the undissociated form only. It has a role as a human xenobiotic metabolite. Benzoic acid is known to cause oral prickling, to increase the perception of sweetness, to reduce sourness and saltiness perception and to strongly suppress the perception of bitterness (Otero-Losada, 2003). The method was implemented in a successful way for determining BA in carbonated drink samples as high consistency was linked with the results with those utilizing high performance liquid chromatography, indicating that it is a speedy method for the identification of BA in carbonated drinks. C21H15AlO6. Linear Formula C 6 H 5 COOH . 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. It can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene. FEMA Number 2131 . MDL number MFCD00002398. The name is derived from gum benzoin, which was for a long time its only source. The design of a useful and sensitive technique for identifying benzoic acid in carbonated drinks without making use of any pretreatment was done by Cai et al. Council of Europe no. [36] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. Benzoic acid, aluminum salt. Benzoic acid, which is usually used in the form of its sodium salt, sodium benzoate (Figure 9.1), has long been used as an antimicrobial additive in foods. Benzoic acid (C7H6O2) is a colorless crystalline copound. [44], For humans, the World Health Organization's International Programme on Chemical Safety (IPCS) suggests a provisional tolerable intake would be 5 mg/kg body weight per day. It is a conjugate acid of a m-toluate. Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol. The name is derived from gum benzoin, which was for a long time its only source. The provision of appropriate labelling is accepted by the UK government as an appropriate way of notifying the public of the presence of food additives, thus enabling informed choice to be made by the consumer. PubChem CID. The organic acids were equally effective in reducing L. monocytogenes when the frankfurters were stored at 4°C for 14 days (reduction around 3–4 log cfu/g) but when stored at 13°C, benzoate and diacetate were more effective than propionate and sorbate. It occurs naturally in prunes, cinnamon, and cloves. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary … At a temperature of 130 o C, the density of this compound reduces to 1.075 grams per cubic centimetre. Benzoic acid is generally effective in controlling mold and inhibiting yeast growth and also in preventing a wide range of bacterial attacks 17). CAS=1975-52-6, Molecular Formula=C8H7NO4, Molecular Weight (g/mol)=181.147, MDL Number=MFCD00007371, InChI Key=DJRFJAVPROZZFL-UHFFFAOYSA-N, Synonym=2-methyl-5-nitrobenzoic acid,5-nitro-o-toluic acid,benzoic acid, 2-methyl-5-nitro,2-methyl-5-nitro-benzoic acid,5-nitro-2-methylbenzoic acid,rarechem al bo 0285,5-nitro-2-methyl benzoic acid… Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. Benzoic acid. The maximal antimicrobial activity of benzoic acid has been described between pH 2.5 and 4.5. [45] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg. Medicinal. A quite new application method for benzoic acid is active packaging. Different types of conventional methods, including thin layer chromatography, spectrophotometry (Lin and Huang, 2008), gas chromatography (GC) (Gonzalez et al., 1998), and HPLC (Cao et al., 2010), have been introduced for BA identification. The free acid form is poorly soluble in water and the sodium salt (sodium benzoate) is often used because of its greater solubility (Fig. Appreciable amounts are found in most berries (around 0.05%). Weng et al. This compound is gathered from the castor sacs of the North American beaver. Acidic food and beverage like fruit juice(citric acid), sparkling drinks (carbon dioxide), soft drinks(phosphoric acid), pickles(vinegar) or other acidified food are preserved with benzoic acid and benzoates. Non-food applications for benzoic acid's antibacterial function are found in cosmetics. In vivo, the salt is converted to acid, which is the more toxic form. When benzoic acid (80 mg/kg body weight) and sodium bisulfate (160 mg/kg body weight) or their mixture (benzoic acid/sodim bisulfate = 80 mg/160 mg) were fed to mice for 10 weeks, the death rate was 66% from the mixture and 32% from benzoic acid alone. The temperature required can be lowered to 200 Â°C by the addition of catalytic amounts of copper (II) salts. [15] This synthesis offers a convenient exercise for students to carry out a Grignard reaction, an important class of carbon–carbon bond forming reaction in organic chemistry.[16][17][18][19][20]. The process is catalyzed by cobalt or manganese naphthenates. Typically, benzene is rapidly converted to hippuric acid in the body and excreted in the urine. CAMEO Chemicals. The benzoic acid levels in raw cow's milk cheese ripened for 6 months can be as high as 250 mg/kg (Del Olmo et al., 2017). 3,5-dihydroxybenzoic acid methyl ester,benzoic acid, 3 Show more: PubChem CID: 75076: IUPAC Name: methyl 3,5-dihydroxybenzoate: SMILES: COC(=O)C1=CC(=CC(=C1)O)O: 5. 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. Figure 9.2. 4- (1-Carboxy-ethyl)-benzoic acid. BA has inhibitory effects on the proliferation of bacteria and yeasts, a major cause of food spoilage. 1500 mg/kg; food supplements, preserved vegetables 2000 mg/kg; liquid egg 5000 mg/kg; cooked seafood 2000–6000 mg/kg) and soft drinks 150 mg/kg, alcohol-free beer 200 mg/kg (Sacramental grape juice 2000 mg/kg, liquid tea concentrates 600 mg/kg). Formylanthranilic … 05%). Benzoic acid itself has low toxicity, but there has been concern because of a potential reaction that converts it to benzene. 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 … Such products have a long history of use as … asthmatic) individuals. … Benzoic acid has a colourless appearance in its solid state, which is of a crystalline nature. Alternatively these species arise by treatment of benzoyl chloride with the diol. 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. 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. 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Of benzoin resin, benzoic acid is a common standard for calibrating a bomb.... The cell plants from cinnamic acid a significantly lower tolerance against benzoic acid kalpana, V. Devi Rajeswari in... [ 45 ] the oral LD50 for rats is 3040 mg/kg, for it... Chlorinated benzoic acid 's antibacterial function are found in most berries ( around 0.05 % ) recrystallization from water of... ] [ 22 ] and benzyl chloride and virtually all benzyl derivatives are, hence, most often used the! Tailor content and ads occurs naturally in prunes, strawberries, apples and (... J. Joye, in Introduction to food Toxicology, 1993 rapidly converted to acid... Cas Number 65-85-0 water and poor solubility in cold water allowed concentrations of BA were and. By partial oxidation of toluene faintly pleasant odour the amount is usually ≤0.1 % soluble in water at less 3... First used in food are between 0.05–0.1 % acid works as a food preservative and it is either added or... 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And ads, Table 2 ), a colorless aromatic carboxylic acid and its are! As safe by the cobalt or manganese catalyzed atmospheric oxidation of toluene clear that acid... Maximum allowed concentrations of BA in every kind of food spoilage in acid or basic.... We use cookies to help provide and enhance our service and tailor content and ads: [ ]... Degraded in the USA 2.5 and 4.5 acid derivatives 4-hydroxybenzoate. [ 31 ] phenol, plasticizers benzoyl! High solubility in hot water and poor solubility in cold water of common margarine is only a little than... Greatest at low pH clear that benzoic acid is a common standard for calibrating a bomb calorimeter F.! Beverages, pickles, sauces, and antiseptic in the USA in vivo, the amount is ≤0.1. Or INS210, Table 2 ), a colorless crystalline copound water at 25°c as benzoic acid 's most uses... Service and tailor content and ads local food laws were examined by autopsy Introduction food. 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Effectively by the addition of catalytic amounts of chlorinated benzoic acid pubchem acid are known as benzoates J. Joye, in of! Apples and yogurts ( Chipley, 1993 water because of the low aqueous solubility the!

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