Paraben esters have antimicrobial activity against molds and yeasts and are used in beer, soft drinks, and olives. 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. Jakob Søltoft-Jensen, Flemming Hansen, in Emerging Technologies for Food Processing, 2005. 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. In contrast, the Chinese laws keep BA addition at 200 mg kg− 1 as far as carbonated drinks are concerned. Benzoic acid (E210 or INS210, Table 2), a colorless aromatic carboxylic acid (Fig. 1 – 11 of 11 Results Glass Bottle; 30g. Alfa Aesar™ Methyl 3-hydroxy-4 … Figure 9.1. The process is catalyzed by cobalt or manganese naphthenates. Recently, benzoic acid has been prepared from toluene by employing TiO 2 nanotubes electrode. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. N-formylanthranilic acid. PubChem CID. However, the pH of common margarine is only a little lower than that needed to ensure the efficacy of benzoic acid. … Appreciable amounts have been found in most berries (around 0. Structures of benzoic acid and sodium benzoate. The total dose of benzoic acid is excreted within 10–14 hr and 75–80% is excreted within 6 hr. [36] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. [36] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters. Such products have a long history of use as topical antiseptics and inhalant decongestants. Benzoic acid and its salts are used as a food preservatives, represented by the E numbers E210, E211, E212, and E213. It is clear that benzoic acid and its derivatives are, hence, most often used as preservatives in acid food products. This acid can be dissolved in water at less than 3 g per liter. 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. Pesticide properties for Benzoic acid, including approvals, environmental fate, eco-toxicity and human health issues Benzoic acid is an organic acid first used in foods almost 100 years ago. Benzoic acid’s salt (sodium benzoate) is commonly used as a pH adjustor and preservative in food, preventing the growth of microbes to keep … The resulting benzoic acid is subsequently degraded in the usual manner. FEMA Number 2131 . Benzoic acid has a colourless appearance in its solid state, which is of a crystalline nature. This compound is gathered from the castor sacs of the North American beaver. EC Number: 200-618-2. Typically, benzene is rapidly converted to hippuric acid in the body and excreted in the urine. 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). It has a role as a human xenobiotic metabolite. BENZENECARBOXYLIC ACID, BENZENEFORMIC ACID, BENZENEMETHANOIC ACID, BENZOIC ACID, BENZOIC ACID,, CARBOXYBENZENE, DRACYCLIC ACID, PHENYLCARBOXYLIC ACID, and PHENYLFORMIC ACID Benzoic acid preservative prevents or delays nutritional losses due to microbiological, enzymatic, or chemical changes of foods … the salt in solution is converted to the acid … Benzoic acid is an extensively used food preservative. [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. Benzoic acid, aluminum salt. [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]. 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). Lethal dose for cats can be as low as 300 mg/kg body weight. 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. The mechanism starts with the absorption of benzoic acid into the cell. (2018). Foods in which benzoic acid may be used and maximum levels for its application are controlled by local food laws. Benzoic acid reacts with hydrogenating reagents to afford hexahydrobenzoic acid. Laboratory Chemical Safety Summary (LCSS) Datasheet. It is one of the benzoates, which also includes sodium benzoate and potassium benzoate. Shop a large selection of Benzoic Acid products and learn more about Benzoic Acid (Crystalline/Primary Standard), Fisher Chemical. Benzoate also specifically inhibits amino acid uptake and certain enzymes within the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase and lipase. At a temperature of 130 o C, the density of this compound reduces to 1.075 grams per cubic centimetre. 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). It is also one of the chemical compounds found in castoreum. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. 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). Benzoic acid is a colorless crystal solid that can reduce the energy of the surface in a reaction. 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). Levels of up to 24 mg/L have been reported in fermented cow's milk. The lower aliphatic esters of benzoic acid are first hydrolyzed by esterase, which abounds in the intestinal wall and liver. 68387. Benzoic acid levels in milk were also found to very sharply increase during fermentation, presumably due to the activity of lactic acid bacteria, Pseudomonas and/or Escherichia coli. 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. Coupling of silica gel thin-film microextraction (TFME) was done to find out SERS (Surface Enhanced Raman Scattering) and the authors made use of the fast identification of BA in carbonated drinks. Justus von Liebig and Friedrich Wöhler determined the composition of benzoic acid. 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). This process usually gives a yield of around 65% [14]. In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter. BA has inhibitory effects on the proliferation of bacteria and yeasts, a major cause of food spoilage. Such products have a long history of use as … As mentioned for other organic acids, antimicrobial activity is greatest at low pH. Degradation pathways for benzoic acid have also been studied in detail and the results have supported harmlessness of this substance. It is a conjugate acid of a m-toluate. 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. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. [38] A pathway has been identified from phenol via 4-hydroxybenzoate.[39]. Benzoic acid occurs naturally in many plants[9] and serves as an intermediate in the biosynthesis of many secondary metabolites. [37], In terms of its biosynthesis, benzoate is produced in plants from cinnamic acid. Individual local authorities may have their own specific reasons for not wishing to purchase drinks containing benzoic acid. The working mechanism of benzoic acid is based on the inhibition of enzymes belonging to the acetic acid cycle. If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%. 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. The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst. 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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. A quite new application method for benzoic acid is active packaging. Typical levels of use for benzoic acid as a preservative in food are between 0.05–0.1%. Where benzoic acid is not wanted in products, it can usually be replaced effectively by the use of sorbic acid. Council of Europe no. MDL number MFCD00002398. 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 a preservative that occurs naturally in some foods such as cranberries, prunes, and cinnamon. Benzoic acid is not allowed in all countries. MDL number: MFCD00002398. Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. Benzoic acid ≥99.5%, FCC, FG CAS Number 65-85-0. Benzoic acid is generally effective in controlling mold and inhibiting yeast growth and also in preventing a wide range of bacterial attacks 17). Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary … The crystal structure is monoclinic. 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. 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. It is excreted as hippuric acid. Cosmetics and pharmaceuticals represent the largest use of parabens. Benzoic acid was originally found as a by-product of the distillation of … sodium benzoate is 180 times as soluble in water at 25°c as benzoic acid. Benzoic acid is a naturally occurring and synthetically produced substance; it is used in food and cosmetics as a preservative. Benzoic acid has been widely tested (see 2.6.6) and accepted as safe by the European Union and United Kingdom authorities. Most local authority purchases are for supply to schools and other places where young or vulnerable individuals may consume the products. Benzoic acid naturally occurs in cranberries, prunes, strawberries, apples and yogurts (Chipley, 1993). 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). 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. M-toluic acid is a methylbenzoic acid carrying a methyl substituent at position 3. No changes in normal patterns of growth, reproduction, or lactation during life were recorded and no morphological abnormalities were observed from the autopsies. 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. [29][30] As the principal component of gum benzoin, benzoic acid is also a major ingredient in both tincture of benzoin and Friar's balsam. This amount, however, is not sufficient for preservation. 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). [25] 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. [36], In Taipei, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had benzoic acid. 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. The metabolic breakdown pathways of benzoic acid are shown in Figure 9.2. [43] Humans metabolize toluene and benzoic acid which is excreted as hippuric 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). The name is derived from gum benzoin, which was for a long time its only source. 3342-77-6. BA has inhibitory effects on the proliferation of bacteria and yeasts, a major cause of food spoilage. Benzoic acid. The effect results from greater permeability of the unionized form into microorganisms. The maximal antimicrobial activity of benzoic acid has been described between pH 2.5 and 4.5. It also inhibits oxidative phosphorylation as well as the citric acid cycle and has a negative influence on cell walls. Benzoic acid retards the growth of yeast and moulds, the effective agent being the undissociated acid. 2-formamidobenzoic acid. 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. We use cookies to help provide and enhance our service and tailor content and ads. 2- (Formylamino)benzoic acid. Chemical Safety. 7.1D). 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. [35], Benzoic acid occurs naturally as do its esters in many plant and animal species. They found that the obtained SERS signals of BA were strong and of high reproducibility. The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food. In butter, benzoic acid (<0.001%, Rudischer 1959) can be found naturally, stemming from the fodder. Roger Wood, ... Pauline Key, in Analytical Methods for Food Additives, 2004. The second generation was observed through its entire life cycle and the third and fourth generations were examined by autopsy. Weng et al. Benzoic acid's most common uses are in carbonated beverages, pickles, sauces, and jelly. 2-p-carboxyphenylpropionic acid. Acute Toxicity of Sodium Benzoate. Synonyms. Its salts are used as a food preservative and it is an important precursor for the synthesis of many other organic substances. 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. Molecular Formula. 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. 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. C10H10O4. benzoic acid is meta directing.[40]. Molecular Formula. Molecular Weight 122.12 . Benzoic acid, a white, crystalline organic compound belonging to the family of carboxylic acids, widely used as a food preservative and in the manufacture of various cosmetics, dyes, plastics, and insect repellents.. First described in the 16th century, benzoic acid exists in many plants; it makes up about 20 percent of gum … 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. Parabens are antimicrobial compounds chemically derived from benzoic acid. Among the foods in which benzoic acid occurs naturally are cranberries, prunes, plums, cinnamon, ripe cloves, and most berries. Benzyl alcohol[21][22] and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acid. 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. Find Similar Structures. 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). 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. Figure 9.2. 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. The temperature required can be lowered to 200 Â°C by the addition of catalytic amounts of copper (II) salts. [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. Thus, the maximum allowed concentrations of BA in every kind of food are restricted by legislation. Formylanthranilic … Benzoic Acid Benzoic acid is the simplest aromatic carboxylic acid and an intermediate in the biosynthesis of secondary metabolites. Cranberries contain as much as 300-1300 mg free … CAMEO Chemicals. Benzoic acid is used as a preservative in a wide variety of foods. A minimum acidity is necessary therefore to block dissociation and to dissolve the acid from its salts when benzoates are used. 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. [45] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg. Linear Formula C 6 H 5 COOH . The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).[10]. 21 Products. The metabolic breakdown pathways of benzoic acid. Benzoic acid / bɛnˈzoʊ.ɪk / is a white (or colorless) solid with the formula C 6 H 5 CO 2 H. It is the simplest aromatic carboxylic acid. Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol. Beilstein/REAXYS Number 636131 . Beilstein/REAXYS Number: 636131 . Benzoate plasticizers, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained by transesterification of methyl benzoate with the corresponding diol. Molecular Weight: 122.12 . The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. 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. U. S. production capacity of benzoic acid is estimated at 139,000 … Benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. 21 . Benzoic acid has a low taste threshold and low volatility and wide antimicrobial spectrum (Ashurst, 1991). [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 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. Linear Formula: C 6 H 5 COOH. 4- (1-Carboxy-ethyl)-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. Benzoic acid works as a preservative in the undissociated form only. However, as for sorbic and propionic acid, benzoic acid has a certain antimicrobial activity in the dissociated form (Chipley, 1993). However, these methods are time-consuming with complicated pretreatments and require expensive instruments (Pylypiw and Grether, 2000). I. Hahn-Ramssl, in Feed Additives, 2020. Molecular Formula. Benzoic acid's antimicrobial activity is primarily against yeasts and molds. [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. It can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene. The acceptable daily intake (ADI) for benzoic acid is 5 mg/kg body weight. 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 … 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 … Preservatives have rarely been shown to cause true allergenic (immunological) reactions. By continuing you agree to the use of cookies. Benzoic acid was discovered in the sixteenth century. Benzoic acid in the acid form is quite toxic but its sodium salt is mucii less toxic (Table 9.3). 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. C8H7NO3. The product contains significant amounts of chlorinated benzoic acid derivatives. Typical levels of use for benzoic acid as a preservative in food are between 0.05–0.1%. 4-Carboxy-alpha-methylbenzeneacetic acid. [11] These latter also investigated how hippuric acid is related to benzoic acid. Are known as benzoates /ˈbɛnzoʊ.eɪt/ taste threshold and low volatility and wide antimicrobial spectrum Ashurst! Chlorinated benzoic acid also includes sodium benzoate and potassium benzoate has inhibitory on! Therefore to block dissociation and to dissolve the acid form is quite toxic but its sodium salt, benzoate was. Cas Number 65-85-0 human xenobiotic metabolite preferred because of its biosynthesis, benzoate is to. 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