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PubMed2002

A novel organic intercalation system with layered polymer crystals as the host compounds derived from 1,3-diene carboxylic acids.

A new type of organic intercalation system using poly(muconic acid) and poly(sorbic acid) crystals as the host compounds is described. The layered polymer crystals as the host are derived from benzyl-, dodecyl-, or naphthylmethylammonium salts of (Z,Z)-muconic or (E,E)-sorbic acids by topochemical polymerization. The subsequent solid-state hydrolysis of the resulting ammonium polymer crystals provides the corresponding carboxylic acid polymer crystals. When alkylamines are reacted with poly(muconic acid) or poly(sorbic acid) crystals dispersed in methanol at room temperature for a few hours, the intercalation proceeds to give layered ammonium polymer crystals via solid-state reactions, in which the polymers maintain a layered structure throughout. The interplanar spacing value of the polymer crystals changes according to the size of the guest molecules; that is, it exactly depends on the carbon number of the alkylamines used for each reaction of poly(muconic acid) or poly(sorbic acid) crystals. The stacking structure of alkyl chains with a tilt in the intercalated alkylammonium layers exists irrespective of the chemical and crystal structures of the host polymers. The intercalation of higher alkylamines into poly(muconic acid) crystals proceeds fast and quantitatively, while the conversion is dependent on the reaction conditions such as the structure and amount of the amine and the reaction time during the intercalation with poly(sorbic acid) crystals, due to the difference in the repeating layered structures of these polymer crystals. Some functional amines are also used as the guest molecules for this organic intercalation system.

Journal Article↗
PubMed1986

Synergistic effects of weak-acid preservatives and pH on the growth of Zygosaccharomyces bailii.

In completely randomised factorial experiments, individual and synergistic effects of pH, benzoic acid and sorbic acid on the growth rate of the yeast Zygosaccharomyces bailii were determined, and expressed in polynomial equations. Synergism between benzoic and sorbic acid was pH dependent. A distinct effect of the anionic form of benzoic acid on doubling time was demonstrated by experiments in which concentrations of benzoic acid and benzoate were varied. The resultant polynomial equation showed that both species act synergistically.

Benzoates↗
PubMed1985

Comparative effects of antifungal compounds on the nutritional value of diets containing moldy corn for broiler chicks.

Propionic acid (.3%), sorbic acid (.3%), and Agrosil (.6%) were equally effective in preventing the decrease in fat in diets containing moldy corn (the fat content of which was restored by soybean oil) during 25 days of storage and in completely maintaining the nutritional value of the diets as evaluated by chick performance. Lower levels of either sorbic acid (.05%) or Agrosil (.1 and .3%) were not effective. None of the fungistats were able to prevent the decrease in dietary fat after storage periods longer than 50 days, but this decrease was consistently and significantly (P less than .05) slower in the propionic acid-supplemented diet.

Animal Feed↗
PubMed1963

Sorbic Hydroxamic Acid, an Antifungal Agent Effective over a Wide pH Range.

Sorbic hydroxamic acid was prepared from sorbic acid by esterification and treatment with hydroxylamine (mp 133 to 135 C, pK(a) 8.8). Its ultraviolet spectrum in acid solution had a single absorption maximum at 262 mmu; in alkaline solution the maximal absorption shifted to 255 mmu and significant absorption appeared at 280 to 300 mmu. At concentrations of 0.1% (w/v), sorbic hydroxamic acid prevented the growth of Aspergillus niger, Penicillium notatum, Botrytis cinerea, Cladosporium herbarum, and a Rhizopus species in grape juice over the pH range 3.6 to 9.2, although sorbic acid was not effective at pH 5.7 and above.

Journal Article↗
PubMed2004

Dietary self-selection for organic acids by the piglet.

Two feeding trials using 48 weaned crossbred piglets each were carried out to determine the effect of acidifying diets with potassium diformate (K-diformate), formic or sorbic acid on dietary preferences in piglets. In Exp. 1 two reference groups were fed either an unacidified diet or a diet containing 2.4% of K-diformate with no choice for selection. Furthermore, piglets in choice group 1 and 2 had the choice between an unacidified diet and a diet supplemented with 1.2 and 2.4% K-diformate, respectively. In Exp. 2, animals of three reference groups received exclusively an unacidified diet or diets supplemented with 1.2% formic acid or 1.2% sorbic acid, respectively. The animals of the choice groups had the choice between an unacidified diet and diets with 1.2% formic acid or 1.2% sorbic acid, respectively. In Exp. 1 average daily feed intake, daily gain and feed conversion ratio were 751 g, 458 g and 1.64 kg/kg, respectively, with no significant differences between treatments. In both choice feeding groups animals chose the diets on offer at random (each around 50%). In Exp. 2 growth and feed intake were not affected by the treatment, but feed conversion ratio was enhanced due to the 1.2% formic acid supplementation. Animals of both organic acid choice groups showed a significant preference for the unacidified diets in each experimental week. The formic acid and sorbic acid diets represented on average only 13.5% and 23.5% of the total feed intake. The present results demonstrate that the inclusion of 1.2% sorbic or formic acid or 2.4% of K-diformate in piglet diets has no negative impact on feed intake, but in a situation of choice feeding, piglets will refuse diets acidified with 1.2% formic or sorbic acid, presumably because of negative taste cues. Acidifying the diets with varying amounts of a K-diformate had no effect on dietary preferences of piglets.

Animal Feed↗
PubMed1980

Formation of mutagens by sorbic acid-nitrite reaction: effects of reaction conditions on biological activities.

Conditions of the reaction between sorbic acid and sodium nitrite generating mutagenic principles were examined. In the rec-assay and the Ames reversion assay, the maximal mutagenic activity was obtained in a pH range of 3.5-4.2. Mutagenic and growth-inhibitor activities of five C-nitro and C-nitroso compounds were studied. The product Y, 2-methyl-1,4-dinitropyrrole, was the strongest mutagen among them.

Drug Interactions↗
PubMed2002

Effect of antifungal agents on biological fitness of Lygus hesperus (Heteroptera: Miridae).

Artificial diets have become important components of rearing systems for insects that are used for research purposes and in commercial production. Because the rearing conditions for insects also provide ideal settings for mold growth, antifungal additives are often used to reduce diet contamination. However, the antifungal agents must not only be effective in mold suppression, they must also be safe to the target insects of the rearing programs. The toxicity of five commonly used antifungal agents (benzoic acid, formalin, methyl paraben, propionic acid, and sorbic acid) was tested using diet bioassays on Lygus hesperus Knight, and the effect on biological fitness was measured. Biological fitness was defined as total number of survivors, mean biomass (dry weight) accumulated per cage over the total treatment period, egg production, time to adult emergence, and time to start of egg laying. Methyl paraben and formalin were found to have significant negative effects on these measurements of biological fitness. Challenge tests to determine the ability of the antifungal agents to suppress mold growth when inoculated into the diet medium are currently in progress.

Animals↗
PubMed1985

[Chemical preservation of food].

Preservation of foodstuffs has always been a necessity for a number of reasons: the durability of food is limited, numerous foodstuffs are only available during a short harvesting season, the transport routes of food or raw materials from the production site to the consumers are continuously increasing in length and the consumers in modern society characterized by division of labor and changed shopping habits increasingly insist on buying durable products. Beyond this, there are medical-hygienic efforts aimed at inhibiting the growth of micro-organisms in food. The hazard to health which many bacteria carry, has been long known. Recently, a number of fungi have been shown to form toxins during their growth on foodstuffs. There are two methods of food preservation: the physical and the chemical. The greater proportion of foodstuffs is rendered durable by physical procedures: drying, cooling, deep-freezing and heating. But chemical preservation also plays a prominent role. The use of preservatives is often combined with physical methods. The application of preservatives has a long history, such as the use of common salt, smoke or sulfur dioxide. Some of these agents, such as benzoic acid, are achievements of the last century. Others, such as propionic acid and sorbic acid, result from research during the last few decades. The preservatives now in use have been thoroughly tested for their toxicological properties. Their use in the food industry is subject to stringent legal regulations. The consumer can be certain of not running any risk by partaking foods which contain preservatives.

Benzoates↗
PubMed1991

Metabolism of 1,4-dinitro-2-methylpyrrole, a mutagen formed by a sorbic acid-nitrite reaction, by intestinal bacteria.

1,4-Dinitro-2-methylpyrrole (DNMP), a mutagenic product formed by the interaction of two common food additives, sorbic acid and sodium nitrite, was transformed to 1-nitro-2-methyl-4-aminopyrrole (NMAP) by human fecal mixtures and various intestinal bacterial strains. Under anaerobic conditions the cell suspensions of Actinomyces, Bacteroides, Clostridium, Eubacterium, Fusobacterium, and Peptostreptococcus spp. demonstrated the nitroreduction activity. Under aerobic conditions, only Actinomyces and Bacteroides spp. showed activity, and this was at a decreased level. In cell suspensions of Bacteroides thetaiotaomicron VPI 5482, NAD(P)H and glucose accelerated the reduction rate, whereas dicoumarol and heat significantly inhibited the rate, and flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) did not affect the rate. With cell-free preparations of the same strain, reduction required NAD(P)H as a cofactor in a dose-dependent fashion and was inactivated by air and heat.

Bacteria, Anaerobic↗
PubMed1996

Comparison of the inhibitory action on Saccharomyces cerevisiae of weak-acid preservatives, uncouplers, and medium-chain fatty acids.

This study was initiated to establish whether inhibition of growth of yeasts by medium-chain fatty acids resembled that caused by weak-acid preservatives or uncouplers. Unlike sorbic acid and 2,4-dinitrophenol, decanoic acid caused rapid cell death at its inhibitory concentration. This suggested a mode of action by medium-chain fatty acids, distinct from both weak-acid preservatives and uncouplers. Sorbic acid and 2,4-dinitrophenol both increased lag and doubling times, reduced cell yields and inhibitory concentrations of both were highly pH sensitive. The possibility is discussed as to whether weak-acid preservatives and uncouplers share common modes of inhibition.

2,4-Dinitrophenol↗
PubMed2006

Lipid microencapsulation allows slow release of organic acids and natural identical flavors along the swine intestine.

The purpose of the present work was to investigate the in vivo concentrations of sorbic acid and vanillin as markers of the fate of organic acids (OA) and natural identical flavors (NIF) from a microencapsulated mixture and from the same mixture non-microencapsulated, and the possible consequences on the intestinal microbial fermentation. Fifteen weaned pigs were selected from 3 dietary groups and were slaughtered at 29.5 +/- 0.27 kg of BW. Diets were (1) control; (2) control supplemented with a blend of OA and NIF microencapsulated with hydrogenated vegetable lipids (protected blend, PB); and (3) control supplemented with the same blend of OA and NIF mixed with the same protective matrix in powdered form but without the active ingredient coating (non-protected blend, NPB). Stomach, cranial jejunum, caudal jejunum, ileum, cecum, and colon were sampled to determine the concentrations of sorbic acid and vanillin contained in the blend and used as tracers. Sorbic acid and vanillin were not detectable in pigs fed the control, and their concentrations were not different in the stomach of PB and NPB treatments. Pigs fed PB showed a gradual decrease of the tracer concentrations along the intestinal tract, whereas pigs fed NPB showed a decline of tracer concentration in the cranial jejunum and onwards, compared with the stomach concentrations. Sorbic acid and vanillin concentrations along the intestinal tract were greater (P = 0.02) in pigs fed PB compared with pigs fed NPB. Pigs fed PB had lower (P = 0.03) coliforms in the caudal jejunum and the cecum than pigs fed the control or NPB. Pigs fed the control or PB had a greater (P = 0.03) lactic acid bacteria plate count in the cecum than pigs fed NPB, which showed a reduction (P = 0.02) of lactic acid concentrations and greater (P = 0.02) pH values in the caudal jejunum. The protective lipid matrix used for microencapsulation of the OA and NIF blend allowed slow-release of both active ingredients and prevented the immediate disappearance of such compounds upon exiting the stomach.

Ammonia↗
PubMed2001

Targeted gene deletion in Zygosaccharomyces bailii.

Yeasts of the genus Zygosaccharomyces are notable agents of large-scale food spoilage. Despite the economic importance of these organisms, little is known about the stress adaptations whereby they adapt to many of the more severe conditions of food preservation. In this study it was shown that genes of Z. bailii, a yeast notable for its high resistances to food preservatives and ethanol, can be isolated by complementation of the corresponding mutant strains of Saccharomyces cerevisiae. It was also discovered that the acquisition by S. cerevisiae of a single small Z. bailii gene (ZbYME2) was sufficient for the former yeast to acquire the ability to degrade two major food preservatives, benzoic acid and sorbic acid. Using DNA cassettes containing dominant selectable markers and methods originally developed for performing gene deletions in S. cerevisiae, the two copies of ZbYME2 in the Z. bailii genome were sequentially deleted. The resulting Zbyme2/Zbyme2 homozygous deletant strain had lost any ability to utilize benzoate as sole carbon source and was more sensitive to weak acid preservatives during growth on glucose. Thus, ZbYME2, probably the nuclear gene for a mitochondrial mono-oxygenase function, is essential for Z. bailii to degrade food preservatives. This ability to catabolize weak acid preservatives is a significant factor contributing to the preservative resistance of Z. bailii under aerobic conditions. This study is the first to demonstrate that it is possible to delete in Z. bailii genes that are suspected as being important for growth of this organism in preserved foods and beverages. With the construction of further mutant of Z. bailii strains, a clearer picture should emerge of how this yeast adapts to the conditions of food preservation. This information will, in turn, allow the design of new preservation strategies. GenBank Accession Nos: ZbURA3 (AF279259), ZbTIM9 (AF279260), ZbYME2 (AF279261), ZbTRP1 (AF279262), ZbHHT1(AF296170).

Acids↗
PubMed1995

Micellar electrokinetic capillary chromatographic determination of artificial sweeteners in low-Joule soft drinks and other foods.

A rapid method for the determination of artificial sweeteners in low-Joule soft drinks and other foods by micellar electrokinetic capillary chromatography (MEKC) is described. Caffeine, benzoic acid and sorbic acid, which are often added to soft drinks, can also be determined with this procedure. The artificial sweeteners, aspartame, saccharin, acesulfame-K, alitame and dulcin, and the other food additives are well separated in less than 12 min using an uncoated fused-silica capillary column with a buffer consisting of 0.05 M sodium deoxycholate, 0.01 M potassium dihydrogenorthophosphate, 0.01 M sodium borate operating at 20 kV. Dehydroacetic acid was used as the internal standard for the determinations. The levels of artificial sweeteners, preservatives and caffeine were in good agreement with those determined by the high-performance liquid chromatographic (HPLC) procedure currently used in our Laboratory. The MEKC procedure has the same order of repeatability, is faster and less costly to operate than the HPLC method.

Beverages↗
PubMed1984

An animal model for nonimmunologic contact urticaria.

The suitability of the guinea pig for studies on nonimmunologic contact urticaria (NICU) was investigated. Groups of five, female Hartley guinea pigs were challenged by applying 50 microliters of various concentrations of human NICU agents, benzoic acid (BA), sorbic acid (SA), cinnamic acid (CA), cinnamaldehyde (CAL), methyl nicotinate (MN) and dimethyl sulfoxide (DMSO), in absolute ethyl alcohol to both sides of the earlobe. The thickness of the ear (0.85 +/- 0.11 mm, means +/- SD, 100 animals) was measured with a string micrometer before application and at 5- to 30-min intervals thereafter. Maximal increase in ear thickness was produced within 30 to 40 min by 20% BA (0.70 +/- 0.09 mm), 10% SA (0.30 +/- 0.05 mm), 15% CA (0.58 +/- 0.12 mm), 5.0% CAL (0.37 +/- 0.09 mm), 0.2% MN (0.80 +/- 0.03 mm), and 100% DMSO (0.74 +/- 0.11 mm). All responses were dose dependent. The histology of the maximal reactions showed dermal edema, and intra- and perivascular infiltrate of heterophils (neutrophils in man), eosinophils, and some lymphocytes. DMSO also caused vacuolization of the epidermal cells. CAL, MN, and DMSO, applied to different parts of the guinea pig body, produced only erythema most frequently on the upper back, but BA, SA, and CA did not cause any reactions. The guinea pig ear-swelling test provides a quantitative animal model to screen human NICU agents.

Animals↗
PubMed2002

Plasma membrane injury induced by nonyl gallate in Saccharomyces cerevisiae.

AIMS: The aim was to investigate the antifungal actions of nonyl gallate against Saccharomyces cerevisiae ATCC 7754. METHODS AND RESULTS: The maximum potency of both the growth inhibitory and the fungicidal effect against the yeast strain was found in nonyl gallate among n-alkyl gallates tested. Nonyl gallate induced ROS generation dose-dependently in growing cells. This ester rapidly killed yeast cells even when cell division was restricted by cycloheximide. This ester inhibited glucose-induced medium acidification and promoted the efflux of intracellular potassium ions in a nongrowing condition. Moreover, nonyl gallate induced a leakage of calcein from artificially prepared liposomes to a greater extent than dodecyl gallate did. CONCLUSIONS: These results suggested nonyl gallate injured plasma membrane of S. cerevisiae, resulting in its exhibition of fungicidal effect accompanying with a leakage of intracellular materials from the cells. SIGNIFICANCE AND IMPACT OF THE STUDY: Our study reveals new knowledge on the antifungal actions of nonyl gallate against S. cerevisiae. When nonyl gallate is applied as a food preservative, the level of its addition to foods may be reduced because of its potent antifungal activity compared with weak acids including sorbic acid and benzoic acid.

Acids↗
PubMed2004

Chemical interactions between additives in foodstuffs: a review.

This paper critically reviews the key literature on food additive-additive chemical interactions published over the last 30 years together with appropriate relevant information on food additive-food component interactions. Five main classes of food additive are included, reflecting the research effort to date: the sulfur (IV) species of preservatives, synthetic food colouring materials, nitrate and nitrite, ascorbic acid, and sorbic acid. Within each class, aspects of the chemistry (reactivity), functionality, stability, use and reactions with other specific food additives are reviewed. Where appropriate, the importance of interactions of food additives with other components of food (i.e. nutrients and non-nutrients) has been assessed and certain aspects of toxicology included. The practical outcome of this review is presented as a set of recommendations for future research in this area. The use of the data in this review is proposed as a training set to develop the framework into a diagnostic tool. This might be used ultimately for the development of a multilevel framework, operating systematically, to understand the important parameters that dictate the outcome of additive interactions.

Drug Interactions↗