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Book Antimicrobials in Food

Book Antimicrobials in Food

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Published by: dobt on Feb 27, 2012
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The variability of the levels of benzoic acid in samples of commercial food products may indicate
a preferential binding of this compound by certain food constituents. For example, Ganzfried and
McFeeters (1976) developed a model system to evaluate binding of benzoic acid by lipids and
proteins. Both bound benzoic acid to approximately the same extent. An equation was obtained to
estimate the ratio of bound to unbound acid in food products based on their lipid and protein
content. Heintze (1978) reported that benzoic acid accumulated in the lipid phase of herring salad,
although stability was not adversely affected with time. Sodium benzoate has been shown to inhibit
the growth of some of the microorganisms used for analyzing the vitamin content of foods (Voigt
et al., 1979).

Models were tested in several food systems to determine the inhibition of 18 strains of
L. monocytogenes by benzoic acid and other compounds (Ramos-Nino et al., 1996). In foods with
high protein or lipid content, antilisterial activity was much lower than predicted, making the models
unacceptable under these conditions.

FIGURE 2.6Proposed pathway for the anaerobic microbial metabolism of benzoic acid. Note: This sequence
of reactions is compiled from several studies. Solid arrows indicate intermediates detected in benzoate-grown
cultures. Dashed arrows indicate proposed intermediates. Source: Adapted from Koch et al. (1993); Harwood
and Gibson (1997).

Benzoic Acid

O

OH CoA-SH

O

O

O

S-CoA

O

S-CoA

S-CoA

O

S-CoA 2H

OH

O

OH

S-CoA −2H

O

S-CoA 2H

H

2O

H

2O

O

S-CoA H

2O

2H

Benzoyl-CoA

Cyclohex-1, 4-diene
carboxyl-CoA

Cyclohex-1, 5-diene
carboxyl-CoA

Cyclohex-1-ene
carboxyl-CoA

2-Hydroxycyclohexane
carboxyl-CoA

6-Hydroxycyclohex-1-ene
carboxyl-CoA

O S-CoA

COOH

O

HO

S-CoA

COOH

Pimelyl-CoA

3-Hydroxypimelyl-CoA

Acetyl-CoA + CO

2

2-Ketocyclohexane
carboxyl-CoA

Sodium Benzoate and Benzoic Acid

29

In the early 1990s it was discovered that the combination of ascorbic acid and sodium or
potassium benzoate in beverages could, under certain conditions, generate detectable levels of
benzene. In one case (a fruit juice–mineral water combination), benzene levels higher than the
permissible levels for mineral waters prompted a recall in one state. Subsequent studies indicated
that soft drinks containing both ascorbic acid and sodium benzoate could produce very low levels
of detectable benzene. Gardner and Lawrence (1993) demonstrated that low levels of detectable
benzene could be produced in aqueous solutions of sodium benzoate and ascorbic acid in the
presence of the transition metal catalysts iron (III) or copper (II). Although the detectable yield
was extremely low (<1 ppb), the authors recommended that the combination of ascorbic acid and
sodium benzoate in foods and beverages be evaluated more carefully. Similar results were reported
by McNeal et al. (1993) when they analyzed several foods and fruit-flavored soft drinks for benzene.

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