Profile of Benzoic Acid/Sodium Benzoate

Nov 1, 2011 | Contact Author | By: Michael J. Fevola, PhD, Johnson & Johnson
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Title: Profile of Benzoic Acid/Sodium Benzoate
benzoic acidx sodium benzoatex preservativesx organic acidsx
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Keywords: benzoic acid | sodium benzoate | preservatives | organic acids

Abstract: Benzoic acid (BA) is a leading choice due to its long and successful history of use preserving foods, drugs and cosmetics. Affirmed as GRAS (Generally Recognized As Safe) by the US Food & Drug Administration (FDA), BA and its sodium salt, sodium benzoate (NaB), are perhaps the most globally acceptable preservatives that have managed to avoid the controversy associated with many of the industry’s tried-and-true preservatives.

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M Fevola, Profile of Benzoic Acid/Sodium Benzoate, Cosm & Toil 126(11) 776 (2011)

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Driven by market demands for products that eschew well-established yet controversial preservatives, such as parabens and formaldehyde donors, and faced with a dwindling number of economical alternatives for safe and effective preservation, formulators are increasingly turning to organic acids to protect products from microbial contamination.1 Among these organic acids, benzoic acid (BA) is a leading choice due to its long and successful history of use preserving foods, drugs and cosmetics.2 Affirmed as GRAS (Generally Recognized As Safe) by the US Food & Drug Administration (FDA), BA and its sodium salt, sodium benzoate (NaB), are perhaps the most globally acceptable preservatives that have managed to avoid the controversy associated with many of the industry’s tried-and-true preservatives.3–5

Chemistry and Manufacture

BA, shown in Figure 1, is the simplest aromatic organic acid, comprising a phenyl ring substituted with a single carboxylic acid group. Its molecular formula is C7H6O2 corresponding to a molecular weight of 122.12 g/mol.6, 7 The compound occurs naturally at levels ranging from 10–1000 ppm in a wide variety of fruits and berries, beer, wine, coffee, black tea and cultured dairy products, such as cheese and yogurt.2 The highest concentrations of naturally occurring BA are found in gum benzoin, a resinous material isolated from trees of the genus Styrax, which may contain up to 20% BA.7 Although BA isolated from natural sources is commercially available,8 it can cost over an order of magnitude more than synthetic BA, making it impractical (and most likely unsustainable) for most commercial applications.

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Figure 1. Chemical structures of benzoic acid (BA) and sodium benzoate (NaB)

Figure 1. Chemical structures of benzoic acid (BA) and sodium benzoate (NaB)

BA, shown in Figure 1, is the simplest aromatic organic acid, comprising a phenyl ring substituted with a single carboxylic acid group.

Figure 2. Reaction conditions for synthesis of BA via air oxidation of toluene

Figure 2. Reaction conditions for synthesis of BA via air oxidation of toluene

Figure 2 depicts typical reaction conditions employed in BA production.

Figure 3. Percentage of BA in the acid form as a function of solution pH

Figure 3. Percentage of BA in the acid form as a function of solution pH

Figure 3 shows the percentage of BA in its acid form as a function of solution pH, demonstrating the sharp decline in BA activity with increasing pH, especially in the region of the pKa (4.19).

Biography: Michael J. Fevola, PhD, Johnson & Johnson

Michael J. Fevola, PhD, is a manager in the New Technologies group at Johnson & Johnson Consumer and Personal Products Worldwide in Skillman, NJ, where he leads R&D in polymer and surface chemistry. Fevola has authored 12 peer-reviewed articles and book chapters, is an inventor on six US patents, and is a member of the Personal Care Product Council’s International Nomenclature Committee and the Society of Cosmetic Chemists.

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