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PubMed2005

On the generation and outcome of 3-(N-phenylamino)propane-1,2-diol derivatives in deodorized model oils related to toxic oil syndrome.

Toxic Oil Syndrome (TOS) was a massive food-born intoxication that occurred in Spain in 1981 and affected more than 20,000 people. TOS was attributed to the ingestion of rapeseed oil that had been adulterated with aniline, illegally refined, and delivered for human consumption. Two chemical species derived from aniline have been identified in oil batches: fatty acid anilides, qualified as biomarkers of the adulterated oil, and fatty acid esters of 3-(N-phenylamino)propane-1,2-diol (PAP), considered toxic oil biomarkers. These esters were generated by chemical processes during oil refining, specifically in the deodorization step, which involves treatment of the oil at high temperatures under vacuum to remove volatile contaminants. Since PAP derivatives are strongly associated with TOS, their formation and putative interconversion in a toxic oil model has been studied. The main results obtained are (i) only triglycerides and aniline are required to produce PAP esters, thus eliminating the possibility that unknown activators present in the deodorization tank were required for toxification of the oil; (ii) PAP and PAP mono- and diesters are chemically interrelated, as are anilides and PAP esters to an even higher degree. In addition to the reaction of aniline with triglycerides, anilides can be also formed via attack of PAP esters by aniline. However, the most important source of anilides during deodorization seems to be the thermal decomposition of PAP esters. Overall, these results suggest that the generation and outcome of PAP derivatives during deodorization is a complex scenario whereby PAP esters are not only generated from different reactions but decompose to produce anilides, among other compounds. In addition to providing a rapeseed oil model that reproduces the composition of case oils with respect to anilides and PAP derivatives, the results presented herein further support the hypothesis imputing PAP diesters or their metabolites for the intoxication episode.

Anilides↗
PubMed2002

Deodorizing effects of tea catechins on amines and ammonia.

Deodorizing effects of tea catechins on amines were examined under alkaline conditions to eliminate the neutralization reaction. They showed deodorizing activity on ethylamine, but none on dimethylamine or trimethylamine. Deodorizing activity on ethylamine was found to be in the order of (-)-epigallocatechin gallate > gallic acid > (-)-epigallocatechin (EGC) > (-)-epicatechin gallate > ethyl gallate >> (+)-catechin = (-)-epicatechin. Further, reaction products of EGC with methylamine, ethylamine, and ammonia were detected by HPLC, indicating that a deodorizing reaction other than neutralization occurs. From structural analysis of the reaction product with the methylamine isolated as a peracetylated derivative, the product was presumed to be methylamine substituted EGC, in which the hydroxyl group of EGC at the 4' position is replaced by the methylamino group. The same replacement reaction took place in the case of ethylamine and ammonia.

Amines↗
PubMed2004

[Microbiological and physicochemical evaluation of pasteurized beverages fortified with orange deodorized residues extracts].

Microbiological and physicochemical parameters of pasteurized beverages conditioned with aqueous extracts from orange deodorized residues were evaluated. The fruits used were selected according to following criterion: homogenous maturity, without physical damage and absence of apparent chlorophyll. Orange peels were dried and transformed to flour. The juice was evaluated by means of these parameters: pH 3.90, degrees Brix 10, titrable acidity 0.33 g of citric acid/100 mL and total carotenoids 0.0078 mg/mL. Volatil compounds of the flour that may to cause bitterness were separated by means of two methods of deodorization: distillation in current of vapor and in autoclave to 121 degrees C; then, the flour was extracted with water (relation 1:50 p/v). Pasteurized citric beverages (orange juice) were elaborated adding the deodorized extracts. pH, degrees Brix, titrable acidity and total carotenoids showed no significant differences (P>0.05). Microbiological results were according to pasteurized products. Sensorial analysis by untrained panel showed no signiificant differences. In conclusion, the deodorant processes were effectives and permitted the inclusion of aquasoluble compounds as flavonoids with antioxidant activity.

Beverages↗
PubMed1993

Radiopacity of household deodorizers, air fresheners, and moth repellents.

Household deodorizers and moth repellents are common agents implicated in many childhood poisonings. Their ingredients usually include either paradichlorobenzene or naphthalene compressed into a solid ball or another shape, sometimes with added essential oils and fragrances. Because medically naphthalene is a more important toxin than paradichlorobenzene, with hematologic and nervous system effects, clinicians often seek to discern which product has been ingested. We discovered fortuitously that a mothball swallowed by a retarded adult was radiopaque, and so designed an in vitro experiment to study the radiopacity of a variety of household deodorizers and products. Of 10 products screened for radiopacity by two radiologists, those containing paradichlorobenzene were consistently strongly radiopaque; those containing naphthalene were radiolucent. A third alternative ingredient which is used in some toilet bowl deodorizers, cetrimonium bromide, was also radiopaque. Radiopacity of paradichlorobenzene or cetrimonium bromide-containing products did not dissipate with time. We speculate that the halogen within the chemical structure of these compounds accounts for their radiopacity. We conclude that paradichlorobenzene-containing commercial products can be distinguished clinically from those containing naphthalene by the performance of an abdominal radiograph.

Administration, Oral↗
PubMed2006

Using minced horseradish roots and peroxides for the deodorization of swine manure: a pilot scale study.

Enzymes that have proven to be capable of removing toxic compounds from water and soil may also be useful in the deodorization of animal manures. Considering that pork production in the US is a $40-billion industry with over half a million workers, odor control to protect air quality in the neighboring communities must be considered an essential part of managing livestock facilities. This pilot scale (20-120 L) study tested the use of minced horseradish (Armoracia rusticana L.) roots (1:10 roots to swine slurry ratio), with calcium peroxide (CaO(2) at 34 mM) or hydrogen peroxide (H(2)O(2) at 68 mM), to deodorize swine slurry taken from a 40,000-gallon storage pit at the Pennsylvania State University's Swine Center. Horseradish is known to contain large amounts of peroxidase, an enzyme that, in the presence of peroxides, can polymerize phenolic odorants and thus reduce the malodor. Twelve compounds commonly associated with malodor (seven volatile fatty acids or VFAs, three phenolic compounds and two indolic compounds) were used as odor indicators. Their concentration in swine slurry before and after treatment was determined by gas chromatography (GC) to assess the deodorization effect. The pilot scale testing demonstrated a complete removal of phenolic odorants (with a detection limit of 0.5 mg L(-1)) from the swine slurry, which was consistent with our previous laboratory experiments using 30-mL swine slurry samples. Horseradish could be recycled (reused) five times while retaining significant reduction in the concentration of phenolic odorants. In view of these findings, inexpensive plant materials, such as horseradish, represent a promising tool for eliminating phenolic odorants from swine slurry.

Animals↗
PubMed2006

Isolation and structural analysis of the cyclic fatty acid monomers formed from eicosapentaenoic and docosahexaenoic acids during fish oil deodorization.

Long-chain polyunsaturated fatty acids (LC-PUFAs) present in fish oils are thermolabile molecules. Among the degradation reactions encountered, thermal cyclization occurs during refining or other heat treatments. Numerous studies have been carried out in the past to quantify and determine the structures of cyclic fatty acid monomers (CFAMs) formed from oleic, linoleic and linolenic acids in heated vegetable oils. Recently, much attention have been given to LC-PUFAs due to their potential health benefits. However, data on quantification of CFAMs formed from these fatty acids, such as eicosapentaenoic acid (EPA, cis-5, cis-8, cis-11, cis-14, cis-17 20:5) and docosahexaenoic acid (DHA, cis-4, cis-7, cis-10, cis-13, cis-16, cis-19 22:6), the two main LC-PUFAs in fish oils, are scarce. In the present study, structural analyses of CFAMs formed from EPA and DHA during the deodorization of fish oil are presented. Fish oil sample was deodorized at 250 degrees C for 3 h under a pressure of 1.5 mbar in a laboratory deodorizer. The CFAMs formed during heat treatment of fish oil were isolated by a combination of saponification, esterification, urea fractionations and column chromatography. Structural analyses of C20- and C22-CFAMs were achieved by gas-chromatography electronic-ionization mass-spectrometry (GC-EI-MS) of their 4,4-dimethyloxazoline (DMOX) derivatives. We identified seven out of 13 possible structures of hydrogenated CFAMs formed from EPA, and nine out of 16 possible structures of CFAM formed from DHA. Major CFAMs from both EPA and DHA were cyclohexyl isomers. All possible cyclohexyl isomers were found but only nine out of 18 of the cyclopentyl isomers were present in concentration sufficient for identification. Chemical mechanisms involved in the formation of polyunsaturated LC-PUFAs have been investigated. The results have shown that general principle involved in the cyclization of LC-PUFAs is same as that for the thermal cyclization of oleic, linoleic and alpha-linolenic acids.

Chromatography, High Pressure Liquid↗
PubMed2002

A fatal case of n-butane poisoning after inhaling anti-perspiration aerosol deodorant.

We report a case of sudden death due to n-butane poisoning after the inhalation of anti-perspiration aerosol deodorant. The deceased was a 15-year-old boy who was found unresponsive on the road, and was pronounced dead after 1.25h. A spray can of anti-perspiration deodorant and vinyl bags were found in a thicket near the scene. An autopsy revealed pulmonary edema, cerebral edema and congestion of the organs. Using qualitative gas chromatography/mass spectrometry, the existence of n-butane was ascertained. The concentration of n-butane (in microl/ml or microl/g) was estimated to be 15.3 in the blood, 13.3 in the brain, 26.6 in the liver, 7.5 in the lung, and 13.6 in the kidney. These n-butane levels in the blood and in the tissues were higher than those of previous reports of death associated with n-butane inhalation. We concluded that the cause of death was n-butane poisoning and presumed that n-butane in the can of anti-perspiration aerosol deodorant induced fatal cardiac arrhythmia.

Journal Article↗
PubMed2000

Characteristics of hydrogen sulfide removal in a carrier-packed biological deodorization system.

The relationship between the characteristics of carriers in a carrier-packed biological deodorization (CPBD) reactor and the efficiency of H(2)S removal was studied. From the result of a deodorization experiment using three different carriers (each of which obtained a high level of H(2)S removal), the best carrier was cylindrical and the surface and inside of the carrier had macro pores (about 1mm in diameter). The carrier also had large porosity and surface area. Each of these characteristics, with the exception of the large surface area, corresponded to the characteristics that resulted in a high discharge efficiency of sulfuric acid. A deodorization experiment using two carriers that differed only in size showed that K(G)a was a very important operating parameter of the apparatus. Therefore, the size of the carrier should be as small as possible within certain technical limitations.

Journal Article↗
PubMed2004

Two kinds of ammonia-oxidizing bacteria isolated from biologically deodorizing plants in cold district.

Two kinds of ammonia-oxidizing bacteria isolated from biologically deodorizing plants in cold districts in Japan were identified as Nitrosomonas sp. IWT202 and Nitrosomonas sp. IWT514. The optimum pHs for growth were 8.0 (IWT202) and 7.5 (IWT514). Although rockwool samples for isolation were collected from the same plants, the optimum temperature for growth of strain IWT202 (37 degrees C) differed from that of strain IWT514 (30 degrees C). The bacteria had a higher (IWT202, 37 degrees C) and lower (IWT514, 20 degrees C) growth temperature than is usually the case. Both strains were shown to differ completely in regard to the effect of the ammonium sulfate concentration in the medium for a 20 degrees C culture and 30 degrees C culture. The inoculation of these bacteria provides the possibility of recovering ammonia-oxidizing activity, when the ammonia-oxidizing activity is lowered in biological deodorizing plants in cold districts. It seems that these strains are suitable for application to deodorization.

Journal Article↗
PubMed1999

Characteristics of a high-concentration-ammonium sulfate-requiring ammonia-oxidizing bacterium isolated from deodorization plants of chicken farms.

A high-concentration-ammonium sulfate-requiring, ammonia-oxidizing bacterium, strain K1, was newly isolated from packed tower biological deodorization plants of chicken farms. The cells of strain K1 are rods (0.1-1.0 x 1.0-2.0 microm), gram negative, obligately aerobic, and nonmotile. Colonies (1-2 mm in diameter) on a plate culture are reddish, circular, and smooth. Intracytoplasmic membranes characteristic of nitrifying bacteria are present. The G+C content of the total DNA is 48.5 mol%. The similarity of 16S rRNA (%) to N. europaea ATCC 25978T (type strain) is 93.77%. This bacterium has a higher optimal growth temperature (35 degrees C) than is usually the case and tolerance up to 40 degrees C. The optimum concentration of ammonium sulfate in the medium is 303 mM, which should make it applicable for use in deodorization plants for enhancing the efficiency of deodorization. Phosphoglycerate kinase (PGK) and triosephosphate isomerase (TIM) were found to possess high specific activities (5700 and 4 x 10(5) U/mg, respectively) compared to the activities of these enzymes in strain ATCC 25978T (300 and 14 U/mg).

Journal Article↗
PubMed2002

Deodorization of soybean proteins by enzymatic and physicochemical treatments.

To utilize soy protein isolate (SPI) more widely, a convenient and effective method for deodorizing it is required. This paper reports a new deodorizing method using various types of solid adsorbents made of polystyrene, polymethacrylate, and zeolite, as well as charcoal. Treatment of the SPI solution with them decreased the hexanal content in the solution, whereas the content of linoleic acid was not much decreased. A brominated polystyrene adsorbent (SEPABEADS SP207) and a zeolite adsorbent (HSZ-360HUD) removed hexanal most effectively, although 30-40% of the total hexanal remained. A model experiment showed that their hexanal adsorption capacity was much higher than the hexanal content in the SPI solution and that an excess amount of hexanal added to the SPI solution was mostly removed by them. These results suggest that hexanal in the SPI solution can be classified into two types. Hexanal of type I may be free or bound weakly on the surface of proteins and is removable by the adsorbents, whereas hexanal of type II may be bound tightly inside proteins and is unremovable by the adsorbents. Despite the considerable amount of hexanal remaining in the SPI solution even in the most successful cases, the SPI solution was well deodorized as shown by the sensory test. Accordingly, type I hexanal may be closely related to the soybean odor. Removal of hexanal by the adsorbents was not much improved by alpha-chymotryptic digestion of SPI. Type II hexanal might be in similar states even in the chymotryptic digests.

Adsorption↗
PubMed2005

Deodorization of swine manure using minced horseradish roots and peroxides.

Public concerns about offensive odors from livestock manures are on the rise and so is the pressure to develop practical ways to reduce the odors. The use of minced horseradish (Armoracia rusticanaL) roots (1:10 w/v plant tissue to swine slurry ratio), with calcium peroxide (CaO2 at 26 or 34 mM) or hydrogen peroxide (H2O2 at 34, 52, or 68 mM) for the deodorization of swine manure, was evaluated through a series of laboratory experiments. The principle underlying this deodorization method is the oxidation of odorants by the concerted action of horseradish peroxidase (present in the plant tissue) and peroxide that serves as an electron acceptor, followed by polymerization of phenolic odorants with a possible copolymerization or adsorption of other odorant compounds. The deodorization effect was assessed by a human panel and gas chromatography (GC). In the case of the GC method, 12 compounds commonly associated with malodor (7 volatile fatty acids or VFAs, 3 phenolic compounds, and 2 indolic compounds) were used as odor indicators. Malodor assessment of the treated slurry by a human panel indicated a 50% reduction in odor intensity. GC results showed 100% removal of all phenolic odorants without reoccurrence for at least 72 h. In view of these data, using plant materials as enzyme carriers and peroxides as electron acceptors emerges as an effective approach to phenolic odor control in animal manure.

Animals↗
PubMed2004

Contribution of phospholipid pyrrolization to the color reversion produced during deodorization of poorly degummed vegetable oils.

The Ehrlich reaction was optimized to determine the formation of pyrrolized phospholipids in edible oils in an attempt to understand the color reversion produced during the deodorization of poorly degummed edible oils. The procedure consisted of the treatment of the oil with p-(dimethylamino)benzaldehyde in tetrahydrofuran/2-propanol at a controlled acidity and temperature and the spectrophotometric determination of adducts produced. The extinction coefficient of Ehrlich adducts was calculated by using 1-[1-(2-hydroxyethyl)-1H-pyrrol-2-yl]propan-1-ol (1) as a standard and was 15 300 M(-)(1) cm(-)(1). The response was linear and reproducible within the range of 0.334-48.6 microM of compound 1. When the assay was applied to a soybean oil treated with 100-1000 ppm of phosphatidylethanolamine and submitted to deodorization, the formation of pyrrolized phospholipids was observed at the same time that the disappearance of the phospholipid and the oil darkening were produced. The main changes were observed during the first steps of the deodorization process, when the oil was heated between 80 and 160 degrees C. During the initial heating of the oil until achieving 200 degrees C, oil darkening, phosphatidylethanolamine disappearance, and pyrrolized phospholipid formation were correlated, therefore suggesting a contribution of phospholipid pyrrolization to the oil darkening produced.

Benzaldehydes↗
PubMed2005

Elimination of pesticides in olive oil by refining using bleaching and deodorization.

The effects of the processing steps on some pesticides during physical refining of olive oil were determined. Oil samples were spiked with four types of pesticides, i.e. endosulfan (alpha-endosulfan, beta-endosulfan and endosulfan sulphate), simazine, oxifluorfen and diflufenican, and subjected to physical refining (bleaching and deodorization). The removal of contaminants by bleaching earths was compared using five types of commercial earths. Deodorization assays under laboratory (10 kg) and discontinuous pilot plant (200 kg) conditions at different temperatures and treatment times were carried out. Bleaching seemed effective only for the elimination of simazine. For removal of the other pesticides tested, a physical refining treatment was required at 240 degrees C in the deodorizing stage for different periods (1 h for diflufenican, oxifluorfen and alpha-endosulfan, 2 h for beta-endosulfan and 3 h for endosulfan sulphate).

Food Analysis↗
PubMed2004

Isolation and characterization of sulphur-oxidizing Thiomonas sp. and its potential application in biological deodorization.

AIMS: To isolate and characterize a sulphur-oxidizing bacterial strain from activated sludge and to evaluate its potential application in biological deodorization. METHODS AND RESULTS: A dominant sulphur-oxidizing bacterial strain, designated as strain SS, was isolated from an enrichment culture using thiosulphate as a sole energy source and CO2 as a sole carbon source. The cells of this organism were aerobic, rod-shaped, Gram-negative and motile. Strain SS could grow autotrophically, heterotrophically as well as mixotrophically. Autotrophic growth was observed at pH values ranging from 2.3 to 9.0. Phylogenetic analyses revealed that strain SS belonged to Group 1 of the genus Thiomonas, closely related to Thiomonas perometabolis and Thiomonas intermedia. The thiosulphate oxidation rates of strain SS at different pH values were evaluated in terms of oxygen uptake using a Micro-Oxymax respirometer. The results showed that the maximum oxidation rate of 5.65 mg l(-1) h(-1) occurred at 56 h of growth and pH 6.0. Continuous H2S removal study demonstrated that strain SS could remove more than 99% of H2S when the inlet concentration was below 58.6 ppm. Further increase of the inlet concentration to 118 ppm gave rise to a decline in the removal efficiency to ca 90%. CONCLUSIONS: The strong acidification of the culture medium during the later period could result in the deterioration of the growth activity and the metabolism activity of strain SS. In practical application, the problems caused by the end-product inhibition and the acidification can be alleviated by periodical replacement of culture medium with fresh medium. Given the physiological flexibility and the ability to remove H2S rapidly and efficiently, strain SS could be a good 'deodorizing' candidate. SIGNIFICANCE AND IMPACT OF THE STUDY: This is the first time that Thiomonas species has been reported for biological deodorization application.

Betaproteobacteria↗
PubMed1983

The effect of the guinea pig maximization protocol on the irritant response to deodorized kerosene - the excited skin syndrome.

Deodorized kerosene in a concentration of 50 g/100 g in pet. did not cause cutaneous inflammation in 10 control guinea pigs. The proportion of 19 guinea pigs exhibiting inflammation following exposure to deodorized kerosene in the guinea pig maximization test increased, but the increase was not significant. The response in a group of 40 animals, half exposed to tetraethyleneglycol diacrylate and half to nonylphenol polyethoxylate-6, increased (z = 3.505, p = 0,004). The inflammatory response was related to concentration in both groups of animals which exhibited inflammatory responses to deodorized kerosene. The relevance of this alteration and irritant response to the interpretation of predictive tests in animals for sensitization, routine patch testing and repeated insult contact dermatitis is discussed.

Animals↗
PubMed1990

[Effects of lamprey oil prepared under different deodorization conditions on serum lipids, reticuloendothelial system and antibody production in mice].

Fresh lamprey oil (F-La) is known to contain a large amount of eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids. When F-La was deodorized with steam at 280 degrees C and 1 mmHg for 1 h, the contents of EPA and DHA were reduced and unidentified peaks were detected by gas-liquid chromatography. In male ddY mice, one week feeding of the lamprey oil deodorized at 280 degrees C (H-La) remarkably decreased the serum triglyceride level and increased the liver weight 2.0-fold. H-La also lowered the corrected phagocytic index (alpha), which is an indicator of activities of reticuloendothelial system, but suppressed relatively little the antibody production against sheep red blood cells. It is suggested that H-La contains biologically active substances, which have potent hepatotoxic and serum triglyceride-reducing effects. This biologically active substances appear to be derived from long-chain polyunsaturated fatty acids under thermal deodorization conditions.

Animals↗
PubMedDate not supplied

[Development of microbiological technology of air deodoration in laboratory-industrial conditions using a pilot plant].

Laboratory tests were performed to select a complex of bacterial strains capable of effective deodoration of waste air produced by an animal formulated feed works under elevated temperature with the presence of numerous organic pollutants. The complex included species from the general Nocardia, Rhodococcus, and Comamonas. The biocatalyst was tested in a real industrial process with the use of a pilot plant for microbiological deodoration of waste air. The test lasted for over six months and confirmed the efficiency of the development method of deodoration.

Air Pollution↗