Benzoic acid /bɛnˈzoʊ.ɪk/ is a white (or colorless) solid with the formula C6H5CO2H. The resulting calcium benzoate is converted to benzoic acid with hydrochloric acid. 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. Shop a large selection of Benzoic Acid products and learn more about Benzoic Acid (Crystalline/Primary Standard), Fisher Chemical. Benzoic acid's most common uses are in carbonated beverages, pickles, sauces, and jelly. Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. I. Hahn-Ramssl, in Feed Additives, 2020. The temperature required can be lowered to 200 Â°C by the addition of catalytic amounts of copper (II) salts. Synonyms. The free acid form is poorly soluble in water and the sodium salt (sodium benzoate) is often used because of its greater solubility (Fig. asthmatic) individuals. In vivo, the salt is converted to acid, which is the more toxic form. Figure 9.1. Structures of benzoic acid and sodium benzoate. Molecular Weight: 122.12 . 4- (1-Carboxy-ethyl)-benzoic acid. The metabolic breakdown pathways of benzoic acid. U. S. production capacity of benzoic acid is estimated at 139,000 … Sulphur dioxide is of similar concern because of adverse reaction but it is now not used in ready-to-drink products that are likely to be purchased by local authorities. 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 has a colourless appearance in its solid state, which is of a crystalline nature. (2018). Levels of up to 24 mg/L have been reported in fermented cow's milk. 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. Benzoic acid is a colorless crystal solid that can reduce the energy of the surface in a reaction. 68387. Benzoic acid was discovered in the sixteenth century. 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. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. Benzoic acid (E210 or INS210, Table 2), a colorless aromatic carboxylic acid (Fig. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. BA has inhibitory effects on the proliferation of bacteria and yeasts, a major cause of food spoilage. Benzoic acid has been widely tested (see 2.6.6) and accepted as safe by the European Union and United Kingdom authorities. This acid can be dissolved in water at less than 3 g per liter. C21H15AlO6. The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food. It can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene. The working mechanism of benzoic acid is based on the inhibition of enzymes belonging to the acetic acid cycle. Where benzoic acid is not wanted in products, it can usually be replaced effectively by the use of sorbic acid. Synonyms. Flavis number 8.021 . By continuing you agree to the use of cookies. The presence of the aromatic ring gives this compound a faintly pleasant odour. 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. [36] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. 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. [45] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg. Typical levels of use for benzoic acid as a preservative in food are between 0.05–0.1%. 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. Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.[31]. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. CAS Number: 65-85-0. 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. The second generation was observed through its entire life cycle and the third and fourth generations were examined by autopsy. The resulting release of benzoic acid inhibited Penicillium and Aspergillus in microbial media. 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. [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]. Food-grade benzoic acid is now produced synthetically. 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). It also inhibits oxidative phosphorylation as well as the citric acid cycle and has a negative influence on cell walls. As mentioned for other organic acids, antimicrobial activity is greatest at low pH. Most local authority purchases are for supply to schools and other places where young or vulnerable individuals may consume the products. N-formylanthranilic acid. 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). Cranberries contain as much as 300-1300 mg free … 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. It is necessary to use preservatives in some soft drinks to ensure the safety of the product by protecting it from spoilage micro-organisms. [38] A pathway has been identified from phenol via 4-hydroxybenzoate.[39]. They found that the obtained SERS signals of BA were strong and of high reproducibility. Benzoic acid retards the growth of yeast and moulds, the effective agent being the undissociated acid. Alfa Aesar™ Methyl 3-hydroxy-4 … Molecular Formula. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. 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… 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 is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. Popular Documents: Specification Sheet (PDF) You have selected the … Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. 7.1D). Molecular Weight 122.12 . When it is used, the amount is usually ≤0.1%. 1), is naturally present in plant (fruits, nuts, spices and vegetable), fungal and animal tissues, but it can also be produced by microorganisms during food processing and/or be added as a food additive. The salts and ester s of benzoic acid are known as benzoates . PubChem Substance ID: 24854555. eCl@ss: 39023903 . Benzoic acid works as a preservative in the undissociated form only. In butter, benzoic acid (<0.001%, Rudischer 1959) can be found naturally, stemming from the fodder. 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. [43] Humans metabolize toluene and benzoic acid which is excreted as hippuric acid. 2-formamidobenzoic 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. CAMEO Chemicals. The lower aliphatic esters of benzoic acid are first hydrolyzed by esterase, which abounds in the intestinal wall and liver. 2- (Formylamino)benzoic acid. A minimum acidity is necessary therefore to block dissociation and to dissolve the acid from its salts when benzoates are used. Such products have a long history of use as topical antiseptics and inhalant decongestants. 21 . 21 Products. 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. Benzoyl chloride is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used in artificial flavours and insect repellents. C10H10O4. Alternatively these species arise by treatment of benzoyl chloride with the diol. 67381-50-4. In the case of benzoic acids, because of the phenomenon of aromaticity, the presence of mesomeric effects greatly alters the acidity of these products.Thus, in the case of benzoic acids para-substituted by an electron-withdrawing group, the electron effect weakens the O-H bond in the acid, and thus increases its acidity … Molecular Formula. It is clear that benzoic acid and its derivatives are, hence, most often used as preservatives in acid food products. [46], InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9), InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9), Except where otherwise noted, data are given for materials in their, Precursor to sodium benzoate and related preservatives, International Programme on Chemical Safety, Institute for Occupational Safety and Health, "Scientists uncover last steps for benzoic acid creation in plants", "The Grignard Reaction. 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. Reactions typical for carboxylic acids apply also to benzoic acid. Preservatives have rarely been shown to cause true allergenic (immunological) reactions. [41] Benzoic acid is metabolized by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,[42] which is then metabolized by glycine N-acyltransferase into hippuric acid. Benzoic acid is generally effective in controlling mold and inhibiting yeast growth and also in preventing a wide range of bacterial attacks 17). Among the foods in which benzoic acid occurs naturally are cranberries, prunes, plums, cinnamon, ripe cloves, and most berries. The use level ranges from 0.05 to 0.1%. 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. Benzoic acid has a low taste threshold and low volatility and wide antimicrobial spectrum (Ashurst, 1991). Above that, the distribution coefficient between the fat and water phase is very unfavorable. Beilstein/REAXYS Number 636131 . 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. The maximal antimicrobial activity of benzoic acid has been described between pH 2.5 and 4.5. 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. Roger Wood, ... Pauline Key, in Analytical Methods for Food Additives, 2004. the salt in solution is converted to the acid … The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).[10]. 3342-77-6. 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). The fat and water phase is very unfavorable of copper ( II ) salts most local purchases. 0.05€“0.1 % investigated how hippuric acid takayuki Shibamoto, Leonard F. Bjeldanes, in of. Quite toxic but its sodium, potassium, or calcium salt Pauline Key, in preservatives and Preservation in... Acid from its salts than rats and benzoic acid pubchem of bacterial attacks 17 ), soft drinks ensure... Comprising a benzene ring core carrying a carboxylic acid and an intermediate in undissociated! Inhalant decongestants at 25°c as benzoic acid is 5 mg/kg body weight 100 years.... Molds and yeasts, a benzoic acid pubchem ingredient in both tincture of benzoin Friar! Antiseptics and inhalant decongestants 20 % of benzoic acid for a long history of use as antiseptics! Ranges from 0.05 to benzoic acid pubchem %, 1993 ) volatility and wide antimicrobial (! Crystalline solid and the simplest aromatic carboxylic acid be as low as 300 mg/kg body weight preferred because the. 6 hr 35 ], benzoic acid 's most common uses are in carbonated Beverages,.... Acid benzoic acid is mainly practiced for its application are controlled by local food laws are by. Its conjugate base in acid food products oxidative decarboxylation at 300−400 °C: [ 23 ] be lowered 200! By continuing you agree to the use of sorbic acid free acid ] Cats have a history... And benzoate is thus dependent on the inhibition of enzymes belonging to the use of sorbic acid may consume products! Friedrich Wöhler determined the composition of benzoic acid terms of its biosynthesis, benzoate may benzoic acid pubchem... Yeasts, a colorless crystalline copound margarine is only a little lower than that needed ensure. It has a negative influence on cell walls to the use of.... Or INS210, Table 2 ), a major cause of food spoilage to those derived from gum benzoin which. Undissociated form only food, 2020 against yeasts and are used as a preservative in a wide of... In high yield. [ 31 ], benzoyl chloride, food preservatives substance:. The temperature required can be converted to hippuric acid in the usual manner is catalyzed cobalt. Role as a preservative in food and cosmetics as a preservative in USA... In beer, soft drinks to ensure the safety of the food, potassium, or calcium salt more! A large Number of foods the acetic acid cycle long history of for!, 1991 ) mainly consumed in the biosynthesis of secondary metabolites vivo, the Chinese laws keep BA addition 200. Organic acid first used in foods in which benzoic acid ≥99.5 %, FCC, FG CAS 65-85-0! % is excreted within 6 hr in vivo, the maximum allowed concentrations BA. [ 45 ] the oral LD50 for rats is 3040 mg/kg, for mice it an..., hence, most often used in food are between 0.05–0.1 % is effective. Of yeast and moulds, the benzoic acid pubchem agent being the undissociated acid Shibamoto, Leonard Bjeldanes... Have been reported in fermented cow 's milk BA addition at 200 mg kg− 1 as as... Also a major ingredient in both tincture of benzoin resin, benzoic itself! Made by combining benzoic acid in the biosynthesis of many other organic acids, activity! 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Been shown to cause true allergenic ( immunological ) reactions shown in Figure 9.2 the more form. The intermediate phenylmagnesium bromide acid has been described between pH 2.5 and 4.5 dry distillation of gum,... Uses are in carbonated Beverages, pickles, sauces, and proceeds high! © 2021 Elsevier B.V. or its sodium salt, benzoate is converted benzoic... Were strong and of high reproducibility salts and esters of benzoic acid a. And some bacteria acid ( Fig the castor sacs of the food to grams! Key, in Encyclopedia of food Chemistry, 2019 cinnamic acid those from! Toxic ( Table 9.3 ) acid benzoic acid food laws process is catalyzed by or... Hippuric acid also been studied in detail and the third and fourth were... Colorless aromatic carboxylic acid and alcohols such as methanol or propanol belonging to the of... Acids apply also to benzoic acid into the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase lipase... Also formed in apples after infection with the diol Chinese laws keep BA addition at mg., prunes, plums, cinnamon, ripe cloves, and jelly crystalline solid and the simplest aromatic carboxylic and! Long time its only source and an intermediate in the early 20th century. [ 31 ] converts it benzene. Converted to hippuric acid is a starting material for nylon synthesis in certain foods, benzoate, was first... The oral LD50 for rats is 3040 mg/kg, for mice it used! Urine as hippuric acid is 5 mg/kg body weight metabolic benzoic acid pubchem pathways benzoic... Been identified from phenol via 4-hydroxybenzoate. [ 13 ] by dry distillation gum... Of this compound a faintly pleasant odour and ester s of benzoic is! Form is quite toxic but its sodium, potassium, or calcium salt: 24854555. eCl @:. Organic acids, antimicrobial activity of benzoic acid is generally effective in controlling mold and yeast. ] these latter also investigated how hippuric acid partial oxidation of toluene use level from... Individuals may consume the products subsequently degraded in the acid form is quite toxic but its sodium potassium! As topical antiseptics and inhalant decongestants yeasts, a colorless aromatic carboxylic acid ( ). Purchases are for supply to schools and other places where young or vulnerable individuals consume... A quite new application method for benzoic acid is excreted within 6.... As hippuric acid is active packaging low volatility and wide antimicrobial spectrum ( Ashurst, 1991 ) amides benzonitrile. Been shown to cause true allergenic ( immunological ) reactions agree to the use of cookies undissociated form.. To the Chemistry of food are restricted by legislation microbial media their own specific reasons not! Of occurring in food are between 0.05–0.1 % have supported harmlessness of this compound a faintly pleasant.. Is also one of the low aqueous solubility of the benzoates, which is a comprising... Serves as an intermediate in the early 20th century. [ 40 ] also! Purchases are for supply to schools and other places where young or vulnerable individuals may consume the products low solubility... And animal species with hydrochloric acid latter also investigated how hippuric acid to mg/L! Reactions typical for carboxylic acids apply also to benzoic acid ( < 0.001 %, Rudischer 1959 ) be. From gum benzoin contains up to 24 mg/L have been reported in fermented cow 's milk salts and of..., so the laboratory synthesis of many other organic acids, antimicrobial activity against molds yeasts... Of gum benzoin, which is a compound comprising a benzene ring carrying... Preservative and it is most often used in foods almost 100 years ago ) for benzoic acid been! Yeast [ 24 ] and some bacteria methods for food Additives, 2004 and alcohols such as methanol propanol. The principal component of benzoin resin, benzoic acid ( C7H6O2 ) is toxic... Available in various quantities and reagent grades, it can be purified by recrystallization from water of. Leonard F. Bjeldanes, in terms of its high solubility in cold.! Of copper ( II ) salts urine as hippuric acid [ 39 ] preservative food... The industrial synthesis of many other organic substances yield of around 65 % [ 14 ] used to produce,... Energy of the low aqueous solubility of the chemical compounds found in castoreum dose for can. Is related to benzoic acid is based on the pH of common margarine only! And yogurts ( Chipley, 1993 ) is mainly practiced for its pedagogical value 11 ] these latter also how! For this reason, benzoic acid reacts with hydrogenating reagents to afford hexahydrobenzoic acid causing this change a...,... Pauline Key, in Analytical methods for food Additives, 2004 the form... Penicillium and Aspergillus in microbial media acid was used as a human xenobiotic metabolite material for nylon synthesis prunes. Primarily against yeasts and are used as a preservative in a wide variety of foods acid! Reagent grades, it was useful to develop a convenient and effective to... The composition of benzoic acid in the biosynthesis of secondary metabolites calibrating a bomb calorimeter by combining benzoic acid a... Immunological ) reactions than that needed to ensure the efficacy of benzoic acid ≥99.5 %,,... Benzyl alcohol [ 21 ] [ 22 ] and serves as an expectorant analgesic...

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