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PubMed1964

MECHANISMS IN THE INHIBITION OF MICROORGANISMS BY SORBIC ACID.

York, George K. (University of California, Davis), and Reese H. Vaughn. Mechanisms in the inhibition of microorganisms by sorbic acid. J. Bacteriol. 88:411-417. 1964.-Oxidative assimilation of glucose, acetate, succinate, and fumarate by washed cells of Escherichia coli, Pseudomonas aeruginosa, and Saccharomyces cerevisiae was inhibited by concentrations of sorbic acid ranging from 15 to 105 mg per 100 ml. At higher concentrations, the oxidation of these substrates was inhibited. Oxidative phosphorylation by submicroscopic particles of E. coli was reduced by about 30% by 37 mg per 100 ml of sorbic acid. The sulfhydryl enzymes fumarase, aspartase, and succinic dehydrogenase were inhibited by sorbic acid. The loss of activity of sorbic acid after reacting with cysteine suggested that a thiol addition occurred, which is believed to be the mechanism of action against sulfhydryl enzymes or cofactors.

Acetates↗

PubMed1991

Determination of sorbic acid in margarine and butter by high-performance liquid chromatography with fluorescence detection.

A procedure is reported for the separation and determination of sorbic acid, as a derivative of 4-bromoethyl-6,7-dimethoxycoumarin, by reversed-phase high-performance liquid chromatography with fluorescence detection using enanthic acid as an internal standard. Sorbic acid, separated from samples of commercial margarine and butter by steam distillation, was evaluated using the proposed procedure and by UV absorption and visible spectrophotometric methods (AOAC). The preparation of the calibration graph and the determination of sorbic acid with the visible spectrophotometric method was improved. The sorbic acid content determined using UV and visible spectrophotometric methods was higher than that obtained with the reversed-phase performance liquid chromatographic method owing to the presence of interfering substances in the samples. The range of recovery and the precision of the proposed method and the reference methods are also reported.

Animals↗

PubMed2004

New method for the determination of benzoic and sorbic acids in commercial orange juices based on second-order spectrophotometric data generated by a pH gradient flow injection technique.

Two widely employed antimicrobials, benzoic and sorbic acids, were simultaneously determined in commercial orange juices employing a combination of a flow injection system with pH gradient generation, diode array spectrophotometric detection, and chemometric processing of the recorded second-order data. Parallel factor analysis and multivariate curve resolution-alternating least-squares were used for obtaining the spectral profiles of sample components and concentration profiles as a function of pH, including provisions for managing rank-deficient data sets. An appropriately designed calibration with a nine-sample set of binary mixtures of standards, coupled to the use of the second-order advantage offered by the applied chemometric techniques, allowed quantitation of the analytes in synthetic test samples and also in commercial orange juices, even in the presence of unmodeled interferents (with relative prediction errors of 8.7% for benzoic acid and 2.5% for sorbic acid). No prior separation or sample pretreatment steps were required. The comparison of results concerning commercial samples with a laborious reference technique yielded satisfactory statistical indicators (recoveries were 99.0% for benzoic acid and 101.4% for sorbic acid).

Benzoic Acid↗

PubMed1991

Anaerobic degradation of sorbic acid by sulfate-reducing and fermenting bacteria: pentanone-2 and isopentanone-2 as byproducts.

Strictly anaerobic bacteria were enriched and isolated from freshwater sediment sources in the presence and absence of sulfate with sorbic acid as sole source of carbon and energy. Strain WoSo1, a Gram-negative vibrioid sulfate-reducing bacterium which was assigned to the species Desulfoarculus (formerly Desulfovibrio) baarsii oxidized sorbic acid completely to CO2 with concomitant stoichiometric reduction of sulfate to sulfide. This strain also oxidized a wide variety of fatty acids and other organic compounds. A Gram-negative rod-shaped fermenting bacterium, strain AmSo1, fermented sorbic acid stoichiometrically to about equal amounts of acetate and butyrate. At concentrations higher than 10 mM, sorbic acid fermentation led to the production of pentanone-2 and isopentanone-2 (3-methyl-2-butanone) as byproducts. Strain AmSo1 fermented also crotonate and 3-hydroxybutyrate to acetate and butyrate, and hexoses to acetate, ethanol, hydrogen, and formate. The guanine-plus-cytosine content of the DNA was 41.8 +/- 1.0 mol%. Sorbic acid at concentrations higher than 5 mM inhibited growth of this strain while strain WoSo1 tolerated sorbic acid up to 10 mM concentration.

Bacteria, Anaerobic↗

PubMed1984

Stimulation of aflatoxin B1 and T-2 toxin production by sorbic acid.

Aspergillus flavus grown on yeast extract-sucrose medium produced higher amounts of aflatoxin B1 in the presence of 0.025% sorbic acid than without this chemical with a maximum at 17 days of incubation. Addition of 0.05 to 0.0125% sorbic acid stimulated T-2 toxin production of Fusarium acuminatum cultures grown on maize meal. The highest amounts of the mycotoxin were detected in 14-day-old cultures containing 0.025% sorbic acid. It is assumed that certain amounts of sorbic acid near the minimal inhibitory concentration reduce the activity of the tricarboxylic acid cycle; this may lead to an accumulation of acetyl coenzyme A, which is an essential intermediate in the biosynthesis of aflatoxin B1 and T-2 toxin.

Aflatoxin B1↗

PubMed1988

Effect of some syrup constituents on the solubility of sorbic acid.

The effects of sucrose, glucose, sorbitol, and saccharin on the aqueous solubility of sorbic acid at 20 and 37 degrees C were determined. Sucrose, glucose, and sorbitol decreased the solubility of sorbic acid with increasing concentrations at both temperatures. Increasing the concentrations of these sweetening agents resulted in decreases in the dielectric constants. Calculation of the free energy and enthalpy changes indicated that the dissolution process for sorbic acid became progressively unfavorable with increasing sugar concentration.

Chemistry, Pharmaceutical↗

PubMed2000

Sorbic acid resistance: the inoculum effect.

Zygosaccharomyces is a genus associated with the more extreme spoilage yeasts. Zygosaccharomyces spoilage yeasts are osmotolerant, fructophiles (preferring fructose), highly-fermentative and extremely preservative-resistant. Zygosaccharomyces bailii can grow in the presence of commonly-used food preservatives, benzoic, acetic or sorbic acids, at concentrations far higher than are legally permitted or organolepically acceptable in foods. An inoculum effect has been described for many micro-organisms and antimicrobial agents. The minimum inhibitory concentration (MIC) increases with the size of the inoculum; large inocula at high cell density therefore require considerably higher concentrations of inhibitors to prevent growth than do dilute cell suspensions. A substantial inoculum effect was found using sorbic acid against the spoilage yeast Zygosaccharomyces bailii NCYC 1766. The inoculum effect was not caused by yeasts metabolizing or adsorbing sorbic acid, thereby lowering the effective concentration; was not due to absence of cell-cell signals in dilute cell suspensions; and was not an artefact, generated by insufficient time for small inocula to grow. The inoculum effect appeared to be caused by diversity in the populations of yeast cells, with higher probability of sorbic acid-resistant cells being present in large inocula. It was found that individual cells of Zygosaccharomyces bailii populations, grown as single cells in microtitre plate wells, were very diverse, varying enormously in resistance to sorbic acid. 26S ribosomal DNA sequencing did not detect differences between the small fraction of resistant 'super cells' and the average population. Re-inoculation of the 'super cells' after overnight growth on YEPD showed a normal distribution of resistance to sorbic acid, similar to that of the original population. The resistance phenotype was therefore not heritable and not caused by a genetically distinct subpopulation. It was concluded that resistance of the spoilage yeast Zygosaccharomyces bailii to sorbic acid was due to the presence of small numbers of phenotypically resistant cells in the population.

Base Sequence↗

PubMed2002

Estimates of the mean per capita daily intake of benzoic and sorbic acids in Brazil.

The daily intakes of benzoates and sorbates from selected food categories were estimated in Brazil in 1999. The Budget method was used as a first screening procedure for the estimation of the safety aspects of the maximum permitted levels of benzoates and sorbates established by the Brazilian food legislation. This screening indicated that benzoates should be further investigated. In a second step, the daily intakes of these preservatives were assessed by combining measured levels of these additives with national food consumption data derived from a household economic survey and a packaged good market survey. Benzoate and sorbate levels in soft drinks, fruit juices, margarine, yoghurt and cheese were determined by HPLC with a photodiode array detector (detection at 228 nm for benzoic acid, 260 nm for sorbic acid). The estimated intakes of benzoates and sorbates for the average consumer were below the ADIs, ranging from 0.3 to 0.9 and 0.2 to 0.3 mg kg(-1) body weight, respectively. Soft drinks were identified as the main source of benzoates representing >80% of the estimated intake.

Benzoates↗

PubMed1984

Depletion of the reduced glutathione level in the liver and production of the mutagens in the intestine in the mice inducing hepatoma by feeding on a high level dose of sorbic acid.

Mutagenicity was detected using Salmonella typhimurium TA98 in the acidic components of the intestinal contents of mice, in which a high incidence of hepatoma had been reported due to feeding on a diet containing 15% sorbic acid (Ishizawa et al., 1980). Furthermore, the glutathione level in the liver of the 15% sorbic acid group was decreased to 40% of the amount found in controls after a 3-month feeding period, and this low level was maintained for long periods (12 months) until the end of the experiments. There was also a close correlation between the extent of depletion of the hepato-glutathione level and the concentration of sorbic acid added to the diet. Consequently, the hepatoma which developed in mice fed a 15% sorbic acid diet was considered to be induced both by the depletion of the hepato-glutathione level over the long periods, and by the gradual production of various mutagens in the intestine which were absorbed and transferred to liver to be metabolically activated.

Animals↗

PubMed2006

Food preservatives sodium sulfite and sorbic acid suppress mitogen-stimulated peripheral blood mononuclear cells.

Antioxidant preservatives prolong the quality of food and ensure the nutritional adequacy, palatability and safety of many processed foods and beverages. Effects of sodium sulfite (E221) and sorbic acid (E200) were investigated in human peripheral blood mononuclear cells (PBMC) which were purified from blood of healthy donors. Cells were stimulated with the mitogen phytohaemagglutinin in vitro, which induces proliferation of T-cells and the production of Th1-type cytokines like interferon-gamma. The latter triggers enzyme indoleamine (2,3)-dioxygenase, which degrades tryptophan, and GTP cyclohydrolase I, which leads to increased neopterin production, in monocyte-derived macrophages. Sodium sulfite and sorbic acid suppressed both these biochemical changes in a dose-dependent way (P<0.01 at 1 mM sodium sulfite and 50 mM sorbic acid). Data demonstrate a suppressive influence of sodium sulfite and sorbic acid on the activated Th1-type immune response.

Cell Proliferation↗

PubMedDate not supplied

14C-sorbic acid distribution in the aqueous and non-aqueous extracts of cooked millet dough (fura).

Millet flour was used to prepare the West African food, fura, preserved with sorbic acid. The lipid and protein fractions which appeared to bind sorbic acid or its degradation products were identified with the help of 14C-sorbic acid. Fractionation of the lipids and proteins from fura showed the 14C to be associated with the petroleum spirit crude fat extract (28 +/- 5%), the water-soluble (6.2 +/- 0.7%), the ethanol-soluble (4.5 +/- 0.7%), the salt-soluble (3.5 +/- 0.6%) and the acetic acid-soluble components (0.9 +/- 0.3%). Dialysis of the ethanol-, salt- and acetic acid-soluble fractions suggested that 14C activity tended to be associated with the low molecular weight components of these fractions.

Acetates↗

PubMed1985

Effects of sorbic acid feed fungistat on the intestinal microflora of floor-reared broiler chickens.

The intestinal microflora of a group of broilers fed a diet containing .04% sorbic acid from Days 1 through 49 of their lives was compared with broilers given a diet without the fungistat. Four broilers from each group were killed at 7, 21, 35, and 49 days, and intestinal sections of the duodenum, the lower small intestine, and both ceca were removed aseptically. Samples of the contents of the intestinal sections were analyzed microbiologically. Groups of microorganisms analyzed included total aerobes, total anaerobes, coliforms, streptococci, lactobacilli, clostridia, Bacteroides, Bifidobacterium, yeasts, and molds. Generally, there was a large variation in viable counts of microorganisms for birds of the same treatment. Of the nine groups of microorganisms analyzed the highest counts obtained (greater than 10(6)/g) were for total aerobes, total anaerobes, lactobacilli, and Bifidobacterium. Coliforms, streptococci, and clostridia showed intermediate counts (greater than 10(3)/g), while yeasts and molds and Bacteroides showed the lowest counts (greater than 10(2)/g). Total microbial numbers, in most cases and irrespective of sorbic acid treatment, were highest in the ceca, lower in the small intestine, and still lower in the duodenum. There were no major trends of microbial population changes observed in a given treatment, intestinal location, or group of organisms with age and time on feed. Inclusion of sorbic acid in the feed did not influence total aerobes, total anaerobes, lactobacilli, streptococci, Bifidobacterium, and clostridia. However, broilers on sorbic acid-containing feed had, at 49 days of age, lower coliform counts in the duodenum, lower yeast and mold counts in the ceca, and higher Bacteroides counts in the ceca.

Animal Feed↗

PubMed1984

Effects of sorbic acid and its salts on chromosome aberrations, sister chromatid exchanges and gene mutations in cultured Chinese hamster cells.

The ability of sorbic acid and its potassium and sodium salts to induce chromosome aberrations, sister chromatid exchanges (SCE) and gene mutations in cultured Chinese hamster V79 cells was examined. Sodium sorbate caused significant induction of chromosome aberrations and SCE, and also induced 6-thioguanine-resistant mutations in a dose-dependent manner. The clastogenic potency of sodium sorbate was found to be less than one hundredth of that of the potent clastogen N-methyl-N'-nitro-N-nitrosoguanidine. The induction of SCE by sodium sorbate was twice the control level, whereas that by methyl methanesulphonate, a potent inducer of SCE, was 14 times the control level. The mutagenic potency of sodium sorbate was less than one-tenth that of ethyl methanesulphonate, a potent inducer of mutation, when compared at an equitoxic level. Sorbic acid and its potassium salt induced chromosome aberrations, but only at the highest doses tested. These compounds also induced 1.2 times the control level of SCE, but neither compound induced 6-thioguanine-resistant mutations. The cytogenetic activity of sodium sorbate was concluded not to be due to the effect of osmotic pressure or an impurity. These results indicate that sodium sorbate is a genotoxic agent, although its potency seems to be weak, and that sorbic acid and potassium sorbate are less genotoxic than the sodium salt.

Animals↗

PubMed1979

[Determination of sorbic acid, its salts and salicylic acid in food products of animal origin].

A foreign method for quantitative assay of sorbic acid and natrium sorbate in food stuff of plant origin was applied by the authors for food stuffs of animal origin. The conservant of the food stuff was isolated by water vapour distillation. Sorbic acid and natrium sorbate assay was performed on part of the distillate colorimetrically at wave length lambda--532 nm. The method proved highly sensitive (2 gammas and 94% reproduction). It can be used in conservant assay of various fish assortments, canned food, roe and some types of cheese. A qualitative method for proving the presence of salicylic acid is proposed, using water vapour distillation of the biological material. Part of the distillate produced is treated directly by 1% ferriammonium sulfate water solution. A violet tint of the solution proves the presence of salicylic acid in the product studied.

Animals↗

PubMed1980

Thin layer chromatography reflectometric determination of benzoic and sorbic acids in fruit beverages.

A procedure is proposed for the quantitative determination of both benzoic and sorbic acids in fruit beverages. This method is carried out by direct ultraviolet spectrophotometric measurements in silica chromatoplates after development with chloroform-methanol-water (65 + 35 + 7) and makes use of an internal standard. Applied to samples spiked with benzoic and sorbic acids, this technique gives accurate and reliable results with good recoveries. The sensitivity (about 1 ppm) is particularly convenient for trace level determination.

Benzoates↗

PubMed2000

Effect of novel water-soluble polymeric forms of sorbic acid against Fusarium oxysporum f.sp. radicis-cucumerinum.

New controlled release water-soluble formulations of sorbic (2,4-hexadienoic) acid were prepared and their inhibitory activity on mycelium growth of Fusarium oxysporum f.sp. radicis-cucumerinum was evaluated. The new products are epoxidized polymers of polyvinylpyrrolidone (PVP) containing covalently bonded sorbic acid (polymeric esters of sorbic acid) and complexes of PVP with hydrogen bonded sorbic acid, characterized by controlled release of sorbic acid. It was shown that the polymeric complexes of sorbic acid with PVP were more effective fungicidal agents than sorbic acid polymeric esters. In all cases the activity of polymeric derivatives (esters and complexes) was increased by lowering the molecular weight of the polymeric carriers. Controlled release formulations of these polymeric derivatives are new promising products due to their low toxicity, wide range of efficient concentrations for application and ability to regulate lyophilicity. Our data contribute to the understanding of the action mechanism of various polymeric sorbic acid formulations and can result in products which are particularly suitable for food and feed protection applications.

Delayed-Action Preparations↗

PubMed2002

Simultaneous determination of trans-resveratrol and sorbic acid in wine by capillary zone electrophoresis.

A method for separation and determination of sorbic acid, a food and beverage preservative, and trans-resveratrol, a biomedically active substance, in wine by capillary zone electrophoresis is described. A solid-phase extraction step on C18-column prior to the electrophoretic separation providing lower detection limits was used for trans-resveratrol determination. For determination of sorbic acid direct analysis of wine (without a preconcentration step) was used. The method is rapid and sensitive and was applied to the analysis of wines from Alsace, France.

Electrophoresis, Capillary↗

PubMed1979

Gas-liquid chromatographic determination of sorbic acid and sodium benzoate in table sirup.

A gas-liquid chromatographic method is described for the simultaneous determination of sorbic acid and sodium benzoate in table sirup. The preservatives are extracted from acidified sirup with ethyl acetate and are analyzed on a gas chromatograph equipped with a flame ionization detector and a glass column (4 ft X 4 mm id) containing 9% SP-1200 and 2% H3PO4 on Chromosorb W (AW). Coefficients of variation for sorbic acid and sodium benzoate are 0.62 and 0.41%, respectively. Analysis time is less than 20 min, with recoveries exceeding 90%.

Benzoates↗