Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. sodium benzoate is 180 times as soluble in water at 25°c as benzoic 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. In butter, benzoic acid (<0.001%, Rudischer 1959) can be found naturally, stemming from the fodder. Benzoic acid naturally occurs in cranberries, prunes, strawberries, apples and yogurts (Chipley, 1993). PubChem Substance ID: 24854555. eCl@ss: 39023903 . Benzoic acid is a naturally occurring and synthetically produced substance; it is used in food and cosmetics as a preservative. This weak acid and its salts are used as a food preservative. It occurs naturally in prunes, cinnamon, and cloves. By continuing you agree to the use of cookies. [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. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. Beilstein/REAXYS Number 636131 . … 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 … 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. The name is derived from gum benzoin, which was for a long time its only source. 2-formamidobenzoic acid. Linear Formula: C 6 H 5 COOH. 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). 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 is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride, phosgene or one of the chlorides of phosphorus. Foods in which benzoic acid may be used and maximum levels for its application are controlled by local food laws. Benzoic acid /bɛnˈzoʊ.ɪk/ is a white (or colorless) solid with the formula C6H5CO2H. Structure. Benzoic acid has a low taste threshold and low volatility and wide antimicrobial spectrum (Ashurst, 1991). Copyright © 2021 Elsevier B.V. or its licensors or contributors. Benzoic acid is an organic aromatic monocarboxylic acid. 05%). The lower aliphatic esters of benzoic acid are first hydrolyzed by esterase, which abounds in the intestinal wall and liver. [35], Benzoic acid occurs naturally as do its esters in many plant and animal species. [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. Appreciable amounts have been found in most berries (around 0. The salts and ester s of benzoic acid are known as benzoates . Roger Wood, ... Pauline Key, in Analytical Methods for Food Additives, 2004. Reactions typical for carboxylic acids apply also to benzoic acid. Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.[31]. 7.1D). 21 . 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. Popular Documents: Specification Sheet (PDF) You have selected the … 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). Appreciable amounts are found in most berries (around 0.05%). Molecular Formula. Benzoic acid or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA. M-toluic acid is a methylbenzoic acid carrying a methyl substituent at position 3. This acid can be dissolved in water at less than 3 g per liter. Benzoic acid works as a preservative in the undissociated form only. As the principal component of benzoin resin, benzoic acid is also a major ingredient in both tincture of benzoin and Friar's balsam. U. S. production capacity of benzoic acid is estimated at 139,000 … Council of Europe no. Benzoic acid in the acid form is quite toxic but its sodium salt is mucii less toxic (Table 9.3). It also inhibits oxidative phosphorylation as well as the citric acid cycle and has a negative influence on cell walls. 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). The sodium salt is preferred because of the low aqueous solubility of the free acid. 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,, 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. Such products have a long history of use as … According to the US Food and Drug Administration, the restriction of BA addition in general types of food is kept as 1000 mg kg− 1. As mentioned for other organic acids, antimicrobial activity is greatest at low pH. Linear Formula C 6 H 5 COOH . However, these methods are time-consuming with complicated pretreatments and require expensive instruments (Pylypiw and Grether, 2000). Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. It can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene. [37], In terms of its biosynthesis, benzoate is produced in plants from cinnamic acid. A minimum acidity is necessary therefore to block dissociation and to dissolve the acid from its salts when benzoates are used. 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's most common uses are in carbonated beverages, pickles, sauces, and jelly. 4-Carboxy-alpha-methylbenzeneacetic 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. Benzoic acid was discovered in the sixteenth century. Figure 9.2. 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. Synonyms. The dissociation constant is 6.46 × 10−5 (Bosund 1960 and 1962), which means that the pH that is reached applying lactic acid is already sufficient. The maximal antimicrobial activity of benzoic acid has been described between pH 2.5 and 4.5. The product contains significant amounts of chlorinated benzoic acid derivatives. C21H15AlO6. 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. Benzoic acid is not allowed in all countries. Benzoic acid, aluminum salt. The process is catalyzed by cobalt or manganese naphthenates. Benzoic acid ≥99.5%, FCC, FG CAS Number 65-85-0. Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. [36], In Taipei, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had benzoic acid. Molecular Formula. Benzoic acid’s salt (sodium benzoate) is commonly used as a pH adjustor and preservative in food, preventing the growth of microbes to keep … 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. The total dose of benzoic acid is excreted within 10–14 hr and 75–80% is excreted within 6 hr. 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 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. [36] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. it is most often used in the form of sodium benzoate because of the low aqueous solubility of the free acid. Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol. The acceptable daily intake (ADI) for benzoic acid is 5 mg/kg body weight. Benzoic acid reacts with hydrogenating reagents to afford hexahydrobenzoic acid. Benzoic acid occurs naturally in many plants[9] and serves as an intermediate in the biosynthesis of many secondary metabolites. Benzoic acid preservative prevents or delays nutritional losses due to microbiological, enzymatic, or chemical changes of foods … 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. 2-p-carboxyphenylpropionic acid. Parabens are antimicrobial compounds chemically derived from benzoic acid. Benzoic acid is an extensively used food preservative. Molecular Weight 122.12 . (1997) treated ionomer films with alkali. FEMA Number 2131 . 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. 4- (1-Carboxy-ethyl)-benzoic 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. Benzoate also specifically inhibits amino acid uptake and certain enzymes within the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase and lipase. Jakob Søltoft-Jensen, Flemming Hansen, in Emerging Technologies for Food Processing, 2005. It is necessary to use preservatives in some soft drinks to ensure the safety of the product by protecting it from spoilage micro-organisms.