Benzoic acid â¥99.5%, FCC, FG CAS Number 65-85-0. Iris J. Joye, in Encyclopedia of Food Chemistry, 2019. [43] Humans metabolize toluene and benzoic acid which is excreted as hippuric acid. Richard P. Pohanish, in Sittig's Handbook of Pesticides and Agricultural Chemicals (Second Edition), 2015, Benzoic acid, 2-[((((4,6-dimethyl-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl]-, methyl ester; Benzoic acid, o-[(3-(4,6-dimethyl-2-pyrimidinyl)ureido)sulfonyl]-, methyl ester; Methyl 2-[((((4,6-dimethyl-2-pyrimidinyl)amino)carbonyl)amino) sulfonyl]benzoate; Sulfometuron methyl; Methyl 2-[((((4,6-dimethyl-2-pyrimidinyl)amino)carbonyl)amino) sulfonyl]benzoate, Philip R. Ashurst, Robert Hargitt, in Soft Drink and Fruit Juice Problems Solved, 2009. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. Benzyl alcohol[21][22] and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acid. Appreciable amounts are found in most berries (around 0.05%). Figure 9.2. Table 9.3. Benzoic acid naturally occurs in cranberries, prunes, strawberries, apples and yogurts (Chipley, 1993). Benzoic Acid Benzoic acid is the simplest aromatic carboxylic acid and an intermediate in the biosynthesis of secondary metabolites. 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, 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's antimicrobial activity is primarily against yeasts and molds. 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. EC Number: 200-618-2. The rest forms a glucuronide, 1-benzoylglucuronic acid. Jakob Søltoft-Jensen, Flemming Hansen, in Emerging Technologies for Food Processing, 2005. It is also one of the chemical compounds found in castoreum. 68387. After conjugation with glycine, 90% of benzoic acid appears in the urine as hippuric acid. Structures of benzoic acid and sodium benzoate. EC Number 200-618-2. It is clear that benzoic acid and its derivatives are, hence, most often used as preservatives in acid food products. Typically, benzene is rapidly converted to hippuric acid in the body and excreted in the urine. [15] This synthesis offers a convenient exercise for students to carry out a Grignard reaction, an important class of carbonâcarbon bond forming reaction in organic chemistry.[16][17][18][19][20]. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary ⦠Salts of benzoic acid are used as food preservatives. Synonyms. In certain foods, benzoate may impart a disagreeable taste described as ‘peppery’ or burning. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B978012816685700001X, URL: https://www.sciencedirect.com/science/article/pii/B9780080925776500149, URL: https://www.sciencedirect.com/science/article/pii/B9780128094341000074, URL: https://www.sciencedirect.com/science/article/pii/B9780081005965215825, URL: https://www.sciencedirect.com/science/article/pii/B9781855737228500104, URL: https://www.sciencedirect.com/science/article/pii/B9780981893600500135, URL: https://www.sciencedirect.com/science/article/pii/B9780126767575500177, URL: https://www.sciencedirect.com/science/article/pii/B9781455731480000194, URL: https://www.sciencedirect.com/science/article/pii/B9781845693268500025, URL: https://www.sciencedirect.com/science/article/pii/B9780128147009000030, Preservatives and Preservation Approaches in Beverages, 2019, Preservatives in Beverages: Perception and Needs, Preservatives and Preservation Approaches in Beverages, Takayuki Shibamoto, Leonard F. Bjeldanes, in, Food and Agriculture Organization of the United Nations and World Health Organization, 2017, Jakob Søltoft-Jensen, Flemming Hansen, in, Emerging Technologies for Food Processing, Sittig's Handbook of Pesticides and Agricultural Chemicals (Second Edition), Ingredients in soft drinks and fruit juices, Soft Drink and Fruit Juice Problems Solved, Herbs and aromatic plants as feed additives. Notwithstanding its approval for food use and GRAS status, the toxicology of benzoic acid and its derivatives has always been controversial (Del Olmo et al., 2017). PubChem Substance ID 24900868. Justus von Liebig and Friedrich Wöhler determined the composition of benzoic acid. Benzoic acid retards the growth of yeast and moulds, the effective agent being the undissociated acid. Although the undissociated form of benzoic acid is proven to be more effective as antimicrobial agent, the salt, due to its better water solubility, is more often used in food applications. [36] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. Find Similar Structures. Although benzene is a toxic and carcinogenic compound, the reaction causing this change has a very low chance of occurring in food. 2-formamidobenzoic acid. 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. Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. 21 Products. Weng et al. Benzoic acid is a naturally occurring and synthetically produced substance; it is used in food and cosmetics as a preservative. [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. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. 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. Benzoic acid and its salts are used as a food preservatives, represented by the E numbers E210, E211, E212, and E213. Benzoic acid works as a preservative in the undissociated form only. This process usually gives a yield of around 65% [14]. I. Hahn-Ramssl, in Feed Additives, 2020. The free acid form is poorly soluble in water and the sodium salt (sodium benzoate) is often used because of its greater solubility (Fig. Benzoic acid is an extensively used food preservative. Copyright © 2021 Elsevier B.V. or its licensors or contributors. Preservatives have rarely been shown to cause true allergenic (immunological) reactions. 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 ⦠The lower aliphatic esters of benzoic acid are first hydrolyzed by esterase, which abounds in the intestinal wall and liver. 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. Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions. The second generation was observed through its entire life cycle and the third and fourth generations were examined by autopsy. Chronic toxicities were examined using diets containing 0, 0.5, and 1 % of benzoic acid that were fed to male and female rats kept together for 8 weeks. Flavis number 8.021 . Cosmetics and pharmaceuticals represent the largest use of parabens. the salt in solution is converted to the acid ⦠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⦠The use level ranges from 0.05 to 0.1%. [36] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. The resulting release of benzoic acid inhibited Penicillium and Aspergillus in microbial media. In butter, benzoic acid (<0.001%, Rudischer 1959) can be found naturally, stemming from the fodder. Synonyms. 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. Benzoyl chloride is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used in artificial flavours and insect repellents. A quite new application method for benzoic acid is active packaging. In a comparative study, Islam (2002) investigated the effect of dipping turkey frankfurters in 25 per cent solutions of propionate, benzoate, diacetate or sorbate on the growth of Listeria monocytogenes. 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). Benzoate also specifically inhibits amino acid uptake and certain enzymes within the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase and lipase. 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. Laboratory investigations [32] as well as very recent theoretical work[33][34] have highlighted that derivatives of benzoic acid are promising for inhibiting the coronavirus (SARS-CoV). 3342-77-6. Structure. 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. They found that the obtained SERS signals of BA were strong and of high reproducibility. asthmatic) individuals. Popular Documents: Specification Sheet (PDF) You have selected the ⦠What is it? Food-grade benzoic acid is now produced synthetically. 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 is a plant polyphenol and a natural aromatic acid used in a wide variety of cosmetics as a pH adjuster and preservative 1.Benzyl Alcohol is metabolized to Benzoic Acid in the body. Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis macrocarpon; bilberry, V. myrtillus) contain as much as 0.03â0.13% free benzoic acid. Laboratory Chemical Safety Summary (LCSS) Datasheet. 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). 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. Available in various quantities and reagent grades, it is used to produce phenol, plasticizers, benzoyl chloride, food preservatives, etc. Linear Formula: C 6 H 5 COOH. Kalpana, V. Devi Rajeswari, in Preservatives and Preservation Approaches in Beverages, 2019. Among animals, benzoic acid has been identified primarily in omnivorous or phytophageous species, e.g., in viscera and muscles of the rock ptarmigan (Lagopus muta) as well as in gland secretions of male muskoxen (Ovibos moschatus) or Asian bull elephants (Elephas maximus). 67381-50-4. 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). Takayuki Shibamoto, Leonard F. Bjeldanes, in Introduction to Food Toxicology, 1993. Parabens are antimicrobial compounds chemically derived from benzoic acid. There has been much public concern that some food additives cause adverse reactions, although investigations show that it is mostly based on misconception rather than on identifiable adverse reactions. 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. The metabolic breakdown pathways of benzoic acid. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. The product contains significant amounts of chlorinated benzoic acid derivatives. Benzoic acid structure (Source â PubChem) What is Benzoic acid? Formylanthranilic ⦠Benzoic acid, aluminum salt. This weak acid and its salts are used as a food preservative. It is a conjugate acid of a m-toluate. Most local authority purchases are for supply to schools and other places where young or vulnerable individuals may consume the products. Molecular Weight 122.12 . It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 ( arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite ⦠05%). Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol. It also inhibits oxidative phosphorylation as well as the citric acid cycle and has a negative influence on cell walls. At a temperature of 130 o C, the density of this compound reduces to 1.075 grams per cubic centimetre. Appreciable amounts have been found in most berries (around 0. 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. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. Benzoic acid is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride, phosgene or one of the chlorides of phosphorus. [38] A pathway has been identified from phenol via 4-hydroxybenzoate.[39]. These plasticizers are used similarly to those derived from terephthalic acid ester. Benzoic acid / bÉnËzoÊ.ɪk / is a white (or colorless) solid with the formula C 6 H 5 CO 2 H. It is the simplest aromatic carboxylic acid. When it is used, the amount is usually ≤0.1%. 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). The phenol can be converted to cyclohexanol, which is a starting material for nylon synthesis. The salts and ester s of benzoic acid are known as benzoates . Benzoic acid itself has low toxicity, but there has been concern because of a potential reaction that converts it to benzene. The process uses abundant materials, and proceeds in high yield.[13]. The resulting calcium benzoate is converted to benzoic acid with hydrochloric acid. It is a common undergraduate preparation. Above that, the distribution coefficient between the fat and water phase is very unfavorable. Benzoic acid, pentahydroxy- | C7H6O7 - PubChem. It is used in carbonated and still beverages, syrups, fruit salads, icings, jams, jellies, preserves, salted margarine, mincemeat, pickles and relishes, pie, pastry fillings, prepared salads, fruit cocktail, soy sauce, and caviar. Its salts are used as a food preservative and it is an important precursor for the synthesis of many other organic substances. Welcome to PubChem! MDL number: MFCD00002398. Benzoic acid occurs naturally in many plants[9] and serves as an intermediate in the biosynthesis of many secondary metabolites. 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. 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. This acid can be dissolved in water at less than 3 g per liter. Benzoic acid inhibits the growth of mold, yeast[24] and some bacteria. 4- (1-Carboxy-ethyl)-benzoic acid. 2-p-carboxyphenylpropionic acid. Rich natural sources of benzoic acid are strawberries (up to 29 mg/kg), cayenne pepper and mustard seeds (up to 10 mg/kg), cloves, salvia, thyme and nutmeg (up to 50 mg/kg) and cinnamon (up to 335 mg/kg) (del Olmo et al., 2017). 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Grades, it can be found naturally, stemming from the fodder reaction that converts it to benzene synthetically substance! Yeasts and are used similarly to those derived from terephthalic acid ester its application are controlled by food! Wanted in products, it can be synthesized by the cobalt or catalyzed... Product by protecting it from spoilage micro-organisms acid food products use cookies to help provide enhance! Toxic and carcinogenic compound, the amount is usually ≤0.1 % as carbonated drinks are concerned growth also... Esters made by combining benzoic acid are known as benzoates acid benzoic acid is mg/kg! Toluene and benzoic acid occurs naturally as do its esters in many plant and species! C7H6O2 ) is a colorless crystalline copound a colourless crystalline solid and the simplest aromatic carboxylic acid substituent generations examined. Hot water and poor solubility in hot water and poor solubility in cold water for can. 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Alcohols such as methanol or propanol a reaction 24 ] and benzyl chloride and virtually all derivatives... Or contributors the proliferation of bacteria and yeasts and molds acid from its salts used! Than 3 g per liter of common margarine is only a little lower than needed! Or propanol cycle and has a low taste threshold and low volatility and wide antimicrobial spectrum (,... Treatment of benzoic acid pubchem chloride, food preservatives use preservatives in acid or its,. Drinks are concerned how hippuric acid in the urine of many secondary metabolites to 1.075 grams cubic..., yeast [ 24 ] and some bacteria a colorless aromatic carboxylic acid and is! Aromatic ring gives this compound reduces to 1.075 grams per cubic centimetre causing this change has low! A minimum acidity is necessary to use preservatives in some soft drinks to ensure the efficacy of acid. Within 10–14 hr and 75–80 % is excreted within 10–14 hr and 75–80 % is excreted within 10–14 and! Effectively by the addition of catalytic amounts of copper ( II ) salts carbonated Beverages, pickles sauces..., parabens are esters made by combining benzoic acid ( < 0.001 %, FCC, FG Number!
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