Popular Documents: Specification Sheet (PDF) You have selected the … C8H7NO3. This amount, however, is not sufficient for preservation. If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%. It is also one of the chemical compounds found in castoreum. 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. 4- (1-carboxyethyl)benzoic acid. However, benzoic acid in combination with carvacrol and thymol improved growth performance of broilers and turkeys, shifted the balance of intestinal microbiota by increasing the number of benfecicial lactobacilli and enhanced functionality of intestinal cells (Giannenas et al., 2014a,b). I. Hahn-Ramssl, in Feed Additives, 2020. 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). Benzoic acid is used as a preservative in a wide variety of foods. Most local authority purchases are for supply to schools and other places where young or vulnerable individuals may consume the products. It is a common undergraduate preparation. It is one of the benzoates, which also includes sodium benzoate and potassium benzoate. Although the addition of BA can extend the shelf life of drinks and prevent nutritional losses, excessive intake of BA may cause diarrhea, abdominal pain, and other symptoms and even interfere with the intermediate metabolic processes of the body. Tiny pieces of silica gel substrate were placed in an uncomplicated device that is made at home for conducting the TFME process and then determination of the BA content was done with the help of SERS after dropping colloidal gold onto the substrate. Glass Bottle; 30g. In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter. 21 . A thin film of silver is created at room temperature on a clean copper substrate with simple soaking in blue silver nitrate solution with or without the presence of adequate concentrations of benzoic acid … Michael Zeece, in Introduction to the Chemistry of Food, 2020. Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol. Welcome to PubChem! The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst. This acid can be dissolved in water at less than 3 g per liter. Benzoic acid. As the principal component of benzoin resin, benzoic acid is also a major ingredient in both tincture of benzoin and Friar's balsam. Benzoic acid itself has low toxicity, but there has been concern because of a potential reaction that converts it to benzene. Although benzene is a toxic and carcinogenic compound, the reaction causing this change has a very low chance of occurring in food. 4- (1-Carboxy-ethyl)-benzoic acid. N-formylanthranilic acid. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. It is most suitable for foods with a pH lower than 4.5, but has also found use in margarine, fruit salads, sauerkraut, jams and jellies. It is the simplest aromatic carboxylic acid. The process is catalyzed by cobalt or manganese naphthenates. Benzoic acid, C 7 H 6 O 2 (or C 6 H 5 COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid.The name derived from gum benzoin, which was for a long time the only source for benzoic acid. These plasticizers are used similarly to those derived from terephthalic acid ester. The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).[10]. Such products have a long history of use as topical antiseptics and inhalant decongestants. Benzoic acid retards the growth of yeast and moulds, the effective agent being the undissociated acid. The maximal antimicrobial activity of benzoic acid has been described between pH 2.5 and 4.5. Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. 7.1D). 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. benzoic acid is meta directing.[40]. it is most often used in the form of sodium benzoate because of the low aqueous solubility of the free acid. Available in various quantities and reagent grades, it is used to produce phenol, plasticizers, benzoyl chloride, food preservatives, etc. Benzoic acid inhibits the growth of mold, yeast[24] and some bacteria. The resulting benzoic acid is subsequently degraded in the usual manner. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. PubChem Substance ID: 24854555. eCl@ss: 39023903 . [26][27], 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.[28]. The crystal structure is monoclinic. The effect results from greater permeability of the unionized form into microorganisms. Benzoic acid, pentahydroxy- | C7H6O7 - PubChem. Benzoic acid has a colourless appearance in its solid state, which is of a crystalline nature. Benzoic acid is an extensively used food preservative. Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions. 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. Flavis number 8.021 . 3342-77-6. Alfa Aesar™ Methyl 3-hydroxy-4 … Food-grade benzoic acid is now produced synthetically. Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 Â°C:[23]. Linear Formula: C 6 H 5 COOH. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. 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 2.5–4.0. Benzyl alcohol[21][22] and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acid. The salts and ester s of benzoic acid are known as benzoates . Synonyms. 67381-50-4. It is clear that benzoic acid and its derivatives are, hence, most often used as preservatives in acid food products. EC Number: 200-618-2. 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). Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. 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. 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). Benzoic acid, added as either its sodium or its potassium salt, is a preservative permitted in the United Kingdom by the Miscellaneous Additives in Food Regulations 1995. 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 … It is the simplest aromatic carboxylic acid. Paraben esters have antimicrobial activity against molds and yeasts and are used in beer, soft drinks, and olives. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. Cranberries contain as much as 300-1300 mg free … 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. 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). Laboratory Chemical Safety Summary (LCSS) Datasheet. 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 2.5–4.0. Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. Consequently, it was useful to develop a convenient and effective method to detect BA (Chen et al., 2010). Benzoic acid works as a preservative in the undissociated form only. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. 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. [36] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. The mechanism starts with the absorption of benzoic acid into the cell. The antimicrobial effect of benzoic acid has been assumed only to be expressed by the undissociated acid interfering with the permeability of the cell membrane and the proton-motive force (Eklund, 1989). Benzoic acid /bɛnˈzoʊ.ɪk/ is a white (or colorless) solid with the formula C6H5CO2H. 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 use level ranges from 0.05 to 0.1%. This process usually gives a yield of around 65% [14]. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Preservatives have rarely been shown to cause true allergenic (immunological) reactions. Degradation pathways for benzoic acid have also been studied in detail and the results have supported harmlessness of this substance. Typical levels of use for benzoic acid as a preservative in food are between 0.05–0.1%. PubChem Substance ID 24900868. The acceptable daily intake (ADI) for benzoic acid is 5 mg/kg body weight. The name is derived from gum benzoin, which was for a long time its only source. Individual local authorities may have their own specific reasons for not wishing to purchase drinks containing benzoic acid. 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. The rest forms a glucuronide, 1-benzoylglucuronic acid. In butter, benzoic acid (<0.001%, Rudischer 1959) can be found naturally, stemming from the fodder. Benzoic acid is a constituent of Whitfield's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot. Figure 9.1. The temperature required can be lowered to 200 Â°C by the addition of catalytic amounts of copper (II) salts. Among the foods in which benzoic acid occurs naturally are cranberries, prunes, plums, cinnamon, ripe cloves, and most berries. Studies of the subacute toxicity of benzoic acid in mice indicated that ingestion of benzoic acid or its sodium salt caused weight loss, diarrhea, irritation of internal membranes, internal bleeding, enlargement of liver and kidney, hypersensitivity, and paralysis followed by death. Beilstein/REAXYS Number 636131 . In certain foods, benzoate may impart a disagreeable taste described as ‘peppery’ or burning. The sodium salt is preferred because of the low aqueous solubility of the free acid. BA has inhibitory effects on the proliferation of bacteria and yeasts, a major cause of food spoilage. Molecular Weight 122.12 . Benzoate acts essentially as a mould and yeast inhibitor in high acid foods and the poor activity at pH values above 4.0 limits its use against bacteria. Benzoic acid is a constituent of Whitfield's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate", "Studies on the mechanism of the antifungal action of benzoate", "Nearly 30% dried, pickled foods fail safety inspections", SIDS Initial Assessment Report for Benzoic Acid, Organisation for Economic Co-operation and Development, 2008 United States salmonellosis outbreak, 2017–18 South African listeriosis outbreak, 2018 Australian rockmelon listeriosis outbreak, Spanish Agency for Food Safety and Nutrition, https://en.wikipedia.org/w/index.php?title=Benzoic_acid&oldid=995501466, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Srpskohrvatski / српскохрватски, Creative Commons Attribution-ShareAlike License, This page was last edited on 21 December 2020, at 11:14. 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