- Structure, Uses & Formula, What Is a Pharmacy Information System (PIS)? Therefore, benzoic acid is said to be an aromatic carboxylic acid. For physicochemical, thermodynamic, transport, spectra, and other property data & information, the followings are available from “Mol-Instincts”, a chemical database based on quantum mechanics: The SMILES string of benzoic acid is OC(=O)c1ccccc1, which can be can be imported by most molecule editors for conversion back into two-dimensional drawings or three-dimensional models of the benzoic acid. 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. Its structure contains a six-carbon ring with alternate single and double bonds and –COOH group attached to that ring which makes it as benzoic acid. The second substitution reaction (on the right) is slower because the first nitro group is deactivating. Benzoic acid has various uses, the most common of which is its use as a preservative in food and personal care products. It is clear that benzoic acid and its derivatives are, hence, most often used as preservatives in acid food products. For all syntheses, benzoic acid can be purified by recrystallization from water owing to its high solubility in hot and poor solubility in cold water. Benzoic acid is very useful in the food industry, personal care industry and in medicine as well. 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, Adele Papetti, Raffaella Colombo, in Evaluation Technologies for Food Quality, 2019. These plasticizers are used similarly to those derived from terephthalic acid ester. However, as for sorbic and propionic acid, benzoic acid has a certain antimicrobial activity in the dissociated form (Chipley, 1993). The structure of 2-(toluene-4-sulfonylamino)-benzoic acid (I) derived from X-ray diffraction of a single crystal was presented and verified by using FT-IR, NMR, and elemental analyses. Actually, as parabens are not dissociable, their activity is practically independent of pH. Did you know… We have over 220 college ), it forms benzoyl chloride that is an example of acyl or acid halides. For a better understanding of the chemical structure, an interactive 3D visualization of benzoic acid is provided here. The benzene molecule comprises an aromatic ring of six carbon atoms. 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/B9780081005965215825, 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/B9780128142172000147, URL: https://www.sciencedirect.com/science/article/pii/B9781455731480000200, URL: https://www.sciencedirect.com/science/article/pii/B9780124159235000253, URL: https://www.sciencedirect.com/science/article/pii/B9781455731480000145, URL: https://www.sciencedirect.com/science/article/pii/B9781455731480000030, 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), High-performance capillary electrophoresis for food quality evaluation, Food Process Engineering and Technology (Second Edition). Sorry!, This page is not available for now to bookmark. Since it contains an aromatic ring, benzoic acid, is called as an aromatic carboxylic acid, and due to that ring, this compound gets its pleasant odor. eval(ez_write_tag([[300,250],'newworldencyclopedia_org-large-mobile-banner-1','ezslot_3',167,'0','0']));eval(ez_write_tag([[300,250],'newworldencyclopedia_org-large-mobile-banner-1','ezslot_4',167,'0','1']));eval(ez_write_tag([[300,250],'newworldencyclopedia_org-large-mobile-banner-1','ezslot_5',167,'0','2'])); Like any other nitrile or amide, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions. For this reason, benzoic acid for human consumption was obtained by dry distillation of gum benzoin. Decarboxylation is the removal of carbon dioxide as sodium carbonate (Na2CO3) by treating the  sodium salt of benzoic acid (sodium benzoate) using soda lime (mixture of NaOH & CaO) to form benzene. Because of its anti-fungal properties, it's an ingredient in topical anti-fungal cream, ointments, and lotions that can help treat athlete's foot and ringworm. During the halogenation of benzoic acid, chlorine (Cl, ) reacts with benzoic acid in presence of a catalyst ferric chloride (FeCl, Decarboxylation is the removal of carbon dioxide as sodium carbonate (Na. ) What volume of acid is needed to neutralize the bicarbonate? 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. [9], For humans the WHO's International Programme on Chemical Safety (IPCS) suggests a provisional tolerable intake would be 5 mg/kg body weight per day. Since it contains an aromatic ring, benzoic acid, is called as an aromatic carboxylic acid, and due to that ring, this compound gets its pleasant odor. It consists of a carboxyl group attached to a benzene ring. Aspirin: Structure, Molecular Weight & Functional Group, Over 83,000 lessons in all major subjects, {{courseNav.course.mDynamicIntFields.lessonCount}}, Biological and Biomedical Reactions of benzoic acid can occur at either the aromatic ring or the carboxylic group: Electrophilic aromatic substitution reaction will take place mainly in 3-position to the electron-withdrawing carboxylic group. Salts of benzoic acid are used as food preservatives. Working Scholars® Bringing Tuition-Free College to the Community, Write the chemical formula for benzoic acid and recognize its components, Point out its common uses in preservatives, medicine and plastics. Borane DMS is selectively used to reduce carboxylic acid to alcohol. 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. 's' : ''}}. On the other hand, the conjugate acid of any base, A^-, is simply HA, that is the parent base plus a proton, H^+.

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