[36] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. It is excreted as hippuric acid. Benzoic acid works as a preservative in the undissociated form only. Above that, the distribution coefficient between the fat and water phase is very unfavorable. The name is derived from gum benzoin, which was for a long time its only source. The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst. A quite new application method for benzoic acid is active packaging. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Benzoic acid is used as a preservative in a wide variety of foods. It is the simplest aromatic carboxylic acid. Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. [38] A pathway has been identified from phenol via 4-hydroxybenzoate.[39]. Benzoic acid itself has low toxicity, but there has been concern because of a potential reaction that converts it to benzene. 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. 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). 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. 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. This acid can be dissolved in water at less than 3 g per liter. Benzoic acid was discovered in the sixteenth century. Benzoic acid has a low taste threshold and low volatility and wide antimicrobial spectrum (Ashurst, 1991). 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. This compound is gathered from the castor sacs of the North American beaver. In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter. Copyright © 2021 Elsevier B.V. or its licensors or contributors. MDL number: MFCD00002398. Typical levels of use for benzoic acid as a preservative in food are between 0.05–0.1%. 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. Structure. 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. The rest forms a glucuronide, 1-benzoylglucuronic acid. I. Hahn-Ramssl, in Feed Additives, 2020. Benzoic acid's antimicrobial activity is primarily against yeasts and molds. 2-formamidobenzoic acid. CAMEO Chemicals. In butter, benzoic acid (<0.001%, Rudischer 1959) can be found naturally, stemming from the fodder. the salt in solution is converted to the acid … (1997) treated ionomer films with alkali. The working mechanism of benzoic acid is based on the inhibition of enzymes belonging to the acetic acid cycle. Benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. Table 9.3. Benzoate also specifically inhibits amino acid uptake and certain enzymes within the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase and lipase. It is the simplest aromatic carboxylic acid. Jakob Søltoft-Jensen, Flemming Hansen, in Emerging Technologies for Food Processing, 2005. It also inhibits oxidative phosphorylation as well as the citric acid cycle and has a negative influence on cell walls. Benzoic acid, pentahydroxy- | C7H6O7 - PubChem. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. Benzoic acid in the acid form is quite toxic but its sodium salt is mucii less toxic (Table 9.3). C10H10O4. Available in various quantities and reagent grades, it is used to produce phenol, plasticizers, benzoyl chloride, food preservatives, etc. Benzoic acid is an organic acid first used in foods almost 100 years ago. Molecular Formula. 68387. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. 4-Carboxy-alpha-methylbenzeneacetic acid. Benzoic acid’s salt (sodium benzoate) is commonly used as a pH adjustor and preservative in food, preventing the growth of microbes to keep … However, as for sorbic and propionic acid, benzoic acid has a certain antimicrobial activity in the dissociated form (Chipley, 1993). Appreciable amounts are found in most berries (around 0.05%). Benzoic acid preservative prevents or delays nutritional losses due to microbiological, enzymatic, or chemical changes of foods … The acceptable daily intake (ADI) for benzoic acid is 5 mg/kg body weight. Figure 9.2. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. 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. It is also one of the chemical compounds found in castoreum. sodium benzoate is 180 times as soluble in water at 25°c as benzoic acid. The process uses abundant materials, and proceeds in high yield.[13]. [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 sodium salt is preferred because of the low aqueous solubility of the free acid. 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 occurs naturally in prunes, cinnamon, and cloves. Molecular Formula. PubChem CID. The avoidance of organic solvents for the recrystallization makes this experiment particularly safe. The crystal structure is monoclinic. Beilstein/REAXYS Number 636131 . Benzoic acid is an organic aromatic monocarboxylic acid. PubChem Substance ID: 24854555. eCl@ss: 39023903 . [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. However, when using benzoic acid as food additive, care needs to be taken that the food product's taste is not altered in such way that it becomes unacceptable. It is one of the benzoates, which also includes sodium benzoate and potassium benzoate. Molecular Weight 122.12 . 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. Roger Wood, ... Pauline Key, in Analytical Methods for Food Additives, 2004. This weak acid and its salts are used as a food preservative. 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 was originally found as a by-product of the distillation of … The mechanism starts with the absorption of benzoic acid into the cell. 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. Weng et al. Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis macrocarpon; bilberry, V. myrtillus) contain as much as 0.03–0.13% free benzoic acid. Benzoic Acid is a preservative that occurs naturally in some foods such as cranberries, prunes, and cinnamon. Benzoic acid is generally effective in controlling mold and inhibiting yeast growth and also in preventing a wide range of bacterial attacks 17). 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 … Linear Formula C 6 H 5 COOH . [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. They found that the obtained SERS signals of BA were strong and of high reproducibility. CAS Number: 65-85-0. Rosmarinic acid-rich extracts of sage, thyme, and rosemary had no effect on feed conversion and feed intake but 14–21 day broilers grew faster (Hernandez et al., 2004). [37], In terms of its biosynthesis, benzoate is produced in plants from cinnamic acid. The process is catalyzed by cobalt or manganese naphthenates. Degradation pathways for benzoic acid have also been studied in detail and the results have supported harmlessness of this substance. Synonyms. MDL number MFCD00002398. The use level ranges from 0.05 to 0.1%. Benzoic acid (E210 or INS210, Table 2), a colorless aromatic carboxylic acid (Fig. Benzoic acid /bɛnˈzoʊ.ɪk/ is a white (or colorless) solid with the formula C6H5CO2H. Cosmetics and pharmaceuticals represent the largest use of parabens. A minimum acidity is necessary therefore to block dissociation and to dissolve the acid from its salts when benzoates are used. The resulting release of benzoic acid inhibited Penicillium and Aspergillus in microbial media. It is necessary to use preservatives in some soft drinks to ensure the safety of the product by protecting it from spoilage micro-organisms. Alfa Aesar™ Methyl 3-hydroxy-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 … The total dose of benzoic acid is excreted within 10–14 hr and 75–80% is excreted within 6 hr. 7.1D). 67381-50-4. For this reason, benzoic acid for human consumption was obtained by dry distillation of gum benzoin. Chemical Safety. asthmatic) individuals. Synonyms. 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. benzoic acid is meta directing.[40]. Alternatively these species arise by treatment of benzoyl chloride with the diol. The second generation was observed through its entire life cycle and the third and fourth generations were examined by autopsy. 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. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. As mentioned for other organic acids, antimicrobial activity is greatest at low pH. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. Council of Europe no. M-toluic acid is a methylbenzoic acid carrying a methyl substituent at position 3. It has a role as a human xenobiotic metabolite. Benzoic acid is a colorless crystal solid that can reduce the energy of the surface in a reaction. As the principal component of benzoin resin, benzoic acid is also a major ingredient in both tincture of benzoin and Friar's balsam. The metabolic breakdown pathways of benzoic acid are shown in Figure 9.2. Paraben esters have antimicrobial activity against molds and yeasts and are used in beer, soft drinks, and olives. BENZENECARBOXYLIC ACID, BENZENEFORMIC ACID, BENZENEMETHANOIC ACID, BENZOIC ACID, BENZOIC ACID,, CARBOXYBENZENE, DRACYCLIC ACID, PHENYLCARBOXYLIC ACID, and PHENYLFORMIC 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 occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary … Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.[31]. Among the foods in which benzoic acid occurs naturally are cranberries, prunes, plums, cinnamon, ripe cloves, and most berries. Levels of up to 24 mg/L have been reported in fermented cow's milk. Figure 9.1. N-formylanthranilic acid. Molecular Weight: 122.12 . Food-grade benzoic acid is now produced synthetically. Typical levels of use for benzoic acid as a preservative in food are between 0.05–0.1%. Benzoic acid's most common uses are in carbonated beverages, pickles, sauces, and jelly. The free acid form is poorly soluble in water and the sodium salt (sodium benzoate) is often used because of its greater solubility (Fig. 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. If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%. EC Number 200-618-2. 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