Environmentally Friendly o-Cresol-Furfural-Formaldehyde Resin as an Alternative to Traditional Phenol-Formaldehyde Resins for Paint Industry.

This paper describes studies on the preparation of an o-cresol-furfural-formaldehyde resin in the presence of an alkaline catalyst and its modification with n-butanol or 2-ethylhexanol. The novelty of this research is to obtain a furfural-based resin of the resole type and its etherification. Such resins are not described in the literature and also are not available on the market. The obtained resin based on furfural, which can be obtained from agricultural waste, had a low minimum content of free o-cresol < 1 wt.%, furfural < 0.1 wt.%, and formaldehyde < 0.1 wt.%. The resin structure was characterized by mass spectrometry (ESI-MS), FT-IR, and NMR spectroscopy, which showed the presence of hydroxymethylene groups in the resin before modification and alkyl groups derived from n-butanol and 2-ethylhexanol after modification. The etherified resins had a lower viscosity and were more flexible (DSC) than the resin before modification and they can be used as an environmentally friendly, safe, and sustainable alternative to traditional phenol-formaldehyde resins in the paint industry. They demonstrate the ability to create a protective coating with good adherence to metal substrates and an excellent balance of flexibility and hardness.

Impacts of o-cresol spill on composition and function of river sediment and soil microbial communities.

o-Cresol is a toxic substance with strong irritating and corrosive effects on skin and mucous membranes. To date, information on the effects of o-cresol on microbial communities in the natural environment is very limited. In the present study, 16S rRNA sequencing and metagenomic technique were carried out to elucidate the effects of the o-cresol spill on microbial communities in river sediments and nearby soils. o-Cresol spill induced the increase in the relative abundance of phyla Planctomycetes and Gemmatimonadetes, suggesting their resilience to o-cresol-induced stress. Uncultured Gemmatimonadetes genera and the MND1 genus exhibited enrichment, while the Pseudomonas genus dominated across all samples, indicating their potential pivotal roles in adapting to the o-cresol spill. Moreover, o-cresol spill impaired the metabolic functions of microbes but triggered their defense mechanisms. Under o-cresol pressure, microbial functions related to carbon fixation were upregulated and functions associated with sulfur metabolism were downregulated. In addition, the o-cresol spill led to an increase in functional genes related to the conversion of o-cresol to 3-methylcatechol. Several genes involved in the degradation of aromatic compounds were also identified, potentially contributing to the biodegradation of o-cresol. This study provides fresh insights into the repercussions of an abrupt o-cresol spill on microbial communities in natural environments, shedding light on their adaptability, defense mechanisms, and biodegradation potential.

Effects of o-cresol on the growth and biochemical compositions in marine microalgae.

To assess the toxic effects of o-cresol on marine organisms, Skeletonema costatum and Phaeodactylum tricornutum were chosen as test subjects to investigate its impact on growth and biochemical compositions. The results indicated that the 96-h EC50 values for o-cresol in S. costatum and P. tricornutum were 7.99 mg/L and 13.28 mg/L, respectively, demonstrating a moderate and slight toxicity level. Conversely, the maximum no-effect concentration (NOEC) for o-cresol in S. costatum and P. tricornutum were 2.43 mg/L and 0.43 mg/L, respectively, classifying their chronic toxicity grades as negligible and low toxic. Following a 96-h exposure period, the content of photosynthetic pigments in S. costatum did not significantly differ from the control group (P > 0.05). Conversely, the levels of total protein, total lipid, and carbohydrate in microalgae were significantly induced (P < 0.05) as the concentration of o-cresol increased. Higher concentrations of o-cresol generally stimulated the synthesis of biochemical compositions in algae cells, which serves as an active defense mechanism in response to pollution stress. To comprehensively evaluate the potential risk of o-cresol to marine ecosystems, it is crucial to strengthen its toxicity studies on marine fish and crustaceans in the future.

Mixture Toxicity of Three Unconventional Gas Fracking Chemicals, Barium, O-Cresol, and Sodium Chloride, to the Freshwater Shrimp Paratya australiensis.

The 96-h acute toxicity of barium (Ba2+ ), o-cresol, and sodium chloride (NaCl) to Paratya australiensis was assessed in single, binary, and ternary combinations in addition to three biochemical assays: glutathione S-transferase, acetylcholinesterase, and sodium-potassium adenosine triphosphatase. The 96-h lethal concentrations that expressed 50% mortality (LC50) in the single-toxicant exposures were Ba2+ = 23.4 mg/L, o-cresol = 12.2 mg/L, and NaCl = 4198 mg/L. Mortality from o-cresol exposure occurred between 11 and 22 mg/L, whereas Ba2+ was more gradual across 10-105 mg/L, and most of the NaCl mortality occurred between 2050 and 4100 mg/L. Toxic units were used to assess the binary and ternary interactions of the toxicants. A more than additive effect was observed for most combinations in the binary chemical exposures, with the ternary combinations yielding highly synergistic interactions. Greater synergism was observed with the 96-h LC50 of o-cresol in combination with the three concentrations of NaCl (1025, 2050, and 3075 mg/L) compared with Ba2+ , with toxic units of 0.38, 0.48, and 0.10 (o-cresol) and 0.71, 0.67, and 0.50 (Ba2+ ). No notable enzyme activity trends were observed in the enzyme biomarker responses from both individual and mixture exposures. Although acute single-species toxicity tests tend to underestimate the effects of Ba2+ , o-cresol, and NaCl on populations, communities, and ecosystems in seminatural (e.g., mesocosms) and natural systems, there are currently no published acute toxicity data available for P. australiensis and the three toxicants used in the present study. The present study shows that chemicals with different toxicity mechanisms can potentially lead to more synergistic responses. Environ Toxicol Chem 2023;42:481-494. © 2022 The Authors. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC.

Perna canaliculus as an Ecological Material in the Removal of o-Cresol Pollutants from Soil.

Soil contamination with cresol is a problem of the 21st century and poses a threat to soil microorganisms, humans, animals, and plants. The lack of precise data on the potential toxicity of o-cresol in soil microbiome and biochemical activity, as well as the search for effective remediation methods, inspired the aim of this study. Soil is subjected to four levels of contamination with o-cresol: 0, 0.1, 1, 10, and 50 mg o-cresol kg-1 dry matter (DM) of soil and the following are determined: the count of eight groups of microorganisms, colony development index (CD) and ecophysiological diversity index (EP) for organotrophic bacteria, actinobacteria and fungi, and the bacterial genetic diversity. Moreover, the responses of seven soil enzymes are investigated. Perna canaliculus is a recognized biosorbent of organic pollutants. Therefore, microbial biostimulation with Perna canaliculus shells is used to eliminate the negative effect of the phenolic compound on the soil microbiome. Fungi appears to be the microorganisms most sensitive to o-cresol, while Pseudomonas sp. is the least sensitive. In o-cresol-contaminated soils, the microbiome is represented mainly by the bacteria of the Proteobacteria and Firmicutes phyla. Acid phosphatase, alkaline phosphatase and urease can be regarded as sensitive indicators of soil disturbance. Perna canaliculus shells prove to be an effective biostimulator of soil under pressure with o-cresol.

Determination of three cresol isomers in sewage sludge by solid-liquid extraction with low temperature purification and gas chromatography-mass spectrometry.

Cresols are chemical contaminants derivative from phenol which can be found in sewage sludge. However, little attention has been given to monitoring these compounds in environmental matrices in the literature. Thus, the objective of this study was to develop a simple method based on solid-liquid extraction with low temperature purification for determining three cresol isomers in sludge. The quantification of these compounds was performed by gas chromatography coupled to mass spectrometry with a previous derivatization step. After a detailed study, the cresol recovery was higher than 91%, with relative standard deviation lower than 12% and a limit of quantification of 20 µg kg-1. Linearity was achieved between 10 and 90 µg L-1 (R2 > 0.98) with the standard solutions prepared in matrix extracts due to the trouble caused by the matrix effect. The proposed method was applied with success for monitoring cresols in sewage sludge samples coming from six different wastewater treatment plants. All samples showed contamination by cresols, mainly p-cresol with values between 32.3 and 516.9 µg kg-1. The majority of the analyzed samples showed a total sum of the isomers higher than the maximum residue limit established by Brazilian legislation (160 µg kg-1).

Catalytic degradation of O-cresol using H2 O2 onto Algerian Clay-Na.

Clay material is used as a catalyst to degrade an organic pollutant. This study focused on the O-cresol oxidative degradation in aqueous solution by adding H2 O2 and Mont-Na. The catalytic tests showed a high catalytic activity of Mont-Na, which made it possible to achieve more than 84.6% conversion after 90 min of reaction time at 55°C in 23.2 mM H2 O2 . The pH value was found to be negatively correlated with the degradation rate of O-cresol. UV-Vis spectrophotometry revealed that the increase of degradation rate at low pH is related to the formation of 2-methylbenzoquinone as intermediate product. In addition, the content of iron in Mont-Na decreased after the catalytic test, bringing further evidence about the O-cresol catalytic oxidation. The mineralization of O-cresol is also confirmed by the different methods of characterization of Mont-Na after the catalytic oxidation test. The effect of the O-cresol oxidation catalyzed by natural clay is significant. PRACTITIONER POINTS: Algerian Montmorillonite-Na is used as a catalyst to degrade an organic pollutant: O-cresol. It shows a great potential for catalyst properties in the presence of the oxidizing reagent H2 O2 . It proved to be an effective means for the degradation of O-cresol contained in wastewaters.

Biochemical and microbiological activity of soil contaminated with o-cresol and biostimulated with Perna canaliculus mussel meal.

The choice of the study subject was a consequence of the growing interest in volatile organic compounds which are strongly dispersed in the environment. The knowledge of o-cresol's capability for being broken down by bacteria should be supplemented by studies aimed at determining the biochemical and microbiological activity of soils. o-Cresol was applied at the following rates: 0, 0.1, 1, 10, and 50 mg of o-cresol kg-1 d.m. of soil to determine its effect on the biological properties of soil. The activity of dehydrogenases, catalase, urease, acid phosphatase, alkaline phosphatase, arylsulfatase, and ß-glucosidase, the eight groups of microorganism counts, was determined in soil samples after 45 days and the barley yield was determined. Preventive biostimulation with Perna canaliculus mussel meal, illustrated by means of the index of fertility (IF), was conducted in order to eliminate the adverse effect of o-cresol. The soil and crop resistance index (RS) was used to illustrate the response of barley, and R:S-the rhizosphere effect index was used to determine the effect of the crop on the enzymatic activity of soil. o-Cresol had a beneficial effect on the biological activity of soil at an acceptable rate of 0.1 and 1 mg kg-1 d.m. of soil, and it became its inhibitor after being applied at 10 and 50 mg kg-1 d.m. of soil, which also brought about a decrease in the resistance of spring barley. Dehydrogenases are the most sensitive, and catalase is the least sensitive, to the pressure of o-cresol in soil. Mussel meal can be recommended as a biostimulator of soil fertility. It also eliminated the negative effect of o-cresol on its biological activity.

Liquid-liquid extraction of phenolic compounds from water using ionic liquids: Literature review and new experimental data using [C2mim]FSI.

In this work, the capability of the ionic liquid, 1-ethyl-3-methylimidazolium bis(fluorosulfonyl)imide, [C2mim]FSI, to extract o-cresol, 2-chlorophenol, resorcinol and phenol from water, reaching the legal limit of 1 mg L-1 was analyzed. The extraction process was carried out for each one of these phenolic compounds varying the initial concentration in water from 3 mg L-1 to 1000 mg L-1, and for aqueous mixtures of the four phenolic compounds in the same concentration range. Because of the scarcity of physical properties of the [C2mim]FSI, density, speed of sound, dynamic viscosity and refractive index were measured from 293.15 to 343.15 K at atmospheric pressure. From the experimental data, the thermal expansion coefficient and the isentropic compressibility for the pure ionic liquid were calculated. Even though [C2mim]FSI is hydrophobic, it can solve small quantities of water that can hinder the recovery of the ionic liquid, consequently the solubility of water in the ionic liquid was determined at several temperatures and atmospheric pressure. In addition to experimental data, a literature review on the use of ionic liquids to extract phenolic compounds from water was performed.

Toluene abuse markers in marginalized populations.

Toluene abuse is one of the most common addictions among marginalized Roma. The aim of the study was the comparison of urinary toluene metabolite levels in marginalized population of Eastern Slovakia as compared to the majority population, and to verify the validity of the answers, given in the questionnaires, regarding toluene abuse. The study was carried out as part of the HEPA-META project aiming to map the prevalence of health problems in marginalized Roma. The majority of people living outside the area of the segregated Roma communities comprised the control group. The total number of study participants was 770. Statistically significant differences in the levels of hippuric acid and o-cresol were found between Roma and the majority population. Variations in urinary hippuric acid levels in addition to toluene abuse can be caused also by dietary factors, medical treatment as well as alcohol consumption, which is frequent (not only) in marginalized communities.

Unexpected solvent effects on the UV/Vis absorption spectra of o-cresol in toluene and benzene: in contrast with non-aromatic solvents.

Cresol is a prototype molecule in understanding intermolecular interactions in material and biological systems, because it offers different binding sites with various solvents and protonation states under different pH values. It is found that the UV/Vis absorption spectra of o-cresol in aromatic solvents (benzene, toluene) are characterized by a sharp peak, unlike the broad double-peaks in 11 non-aromatic solvents. Both molecular dynamics simulations and electronic structure calculations revealed the formation of intermolecular π-complexation between o-cresol and aromatic solvents. The thermal movements of solvent and solute molecules render the conformations of o-cresol changing between trans and cis isomers. The π-interaction makes the cis configuration a dominant isomer, hence leading to the single keen-edged UV/Vis absorption peak at approximately 283 nm. The free conformation changes between trans and cis in aqueous solution rationalize the broader absorption peaks in the range of 260-280 nm. The pH dependence of the UV/Vis absorption spectra in aqueous solutions is also rationalized by different protonation states of o-cresol. The explicit solvent model with long-ranged interactions is vital to describe the effects of π-complexation and electrostatic interaction on the UV/Vis absorption spectra of o-cresol in toluene and alkaline aqueous (pH > 10.3) solutions, respectively.

Enabling the valorization of guaiacol-based lignin: Integrated chemical and biochemical production of cis,cis-muconic acid using metabolically engineered Amycolatopsis sp ATCC 39116.

Lignin is nature's second most abundant polymer and displays a largely unexploited renewable resource for value-added bio-production. None of the lignin-based fermentation processes so far managed to use guaiacol (2-methoxy phenol), the predominant aromatic monomer in depolymerized lignin. In this work, we describe metabolic engineering of Amycolatopsis sp. ATCC 39116 to produce cis,cis-muconic acid (MA), a precursor of recognized industrial value for commercial plastics, from guaiacol. The microbe utilized a very broad spectrum of lignin-based aromatics, such as catechol, guaiacol, phenol, toluene, p-coumarate, and benzoate, tolerated them in elevated amounts and even preferred them over sugars. As a next step, we developed a novel approach for genomic engineering of this challenging, GC-rich actinomycete. The successful introduction of conjugation and blue-white screening, using ß-glucuronidase, enabled tailored genomic modifications within ten days. Successive deletion of two putative muconate cycloisomerases from the genome provided the mutant Amycolatopsis sp. ATCC 39116 MA-2, which accumulated 3.1gL-1 MA from guaiacol within 24h, achieving a yield of 96%. The mutant was found also capable to produce MA from a guaiacol-rich true lignin hydrolysate, obtained from pine through hydrothermal conversion. This provides an important proof-of-concept to successfully coupling chemical and biochemical process steps into a value chain from the lignin polymer to an industrial chemical. In addition, Amycolatopsis sp. ATCC 39116 MA-2 was able to produce 2-methyl MA from o-cresol (2-methyl phenol), which opens possibilities towards polymers with novel architecture and properties.

Diazepam influences urinary bioindicator of occupational toluene exposure.

In the present study, we investigated the influence of diazepam (DZP) on the excretion of TOL by examining their urinary metabolites, hippuric acid (HA) and ortho-cresol (o-C). Male Wistar rats were exposed to TOL (20ppm) in a nose-only exposure chamber (6h/day, 5days/week for 6 weeks) with simultaneous administration of DZP (10mg/kg/day). Urinary o-C levels were determined by GC-MS, while HA, creatinine (CR), DZP and its metabolite, nordiazepam, were analysed by HPLC-DAD. The results of a Mann-Whitney U test showed that DZP influenced the urinary excretion of o-C (p<0.05). This pioneering study revealed that there was an interaction between DZP and TOL, probably by the inhibition of the CYP isoforms (CYP2B6, CYP2C8, CYP2E1, and CYP1A2) involved in the oxidative metabolism of the solvent. This is relevant information to be considered in the biomonitoring of occupational toluene exposure.

Cigarette smoking behaviour and blood metabolomics.

BACKGROUND: Identifying circulating metabolites related to cigarette smoking may provide insight into the biological mechanisms of smoking-related diseases and the nature of addiction. However, previous studies are limited, generally small, and have largely targeted a priori metabolites. METHODS: We examined associations between cigarette smoking and metabolites using an untargeted metabolomics approach in 892 men and women from four studies including participants from Italy, USA, China and Finland. We examined associations between individual log-transformed metabolites and two key smoking phenotypes (current smoking status and cigarettes per day [cig/day]) using linear regression. Fixed-effect meta-analysis was used to combine results across studies. Strict Bonferroni thresholds were used as our significance criteria. We further examined associated metabolites with other metrics of smoking behaviuor (current versus former, former versus never, smoking duration and years since quitting) in the US study. RESULTS: We identified a total of 25 metabolites associated with smoking behaviours; 24 were associated with current smoking status and eight with cig/day. In addition to three well-established nicotine metabolites (cotinine, hydroxycotinine, cotinine N-oxide), we found an additional 12 xenobiotic metabolites involved in benzoatic (e.g. 3-ethylphenylsulphate) or xanthine metabolism (e.g. 1-methylurate), three amino acids (o-cresol sulphate, serotonin, indolepropionate), two lipids (scyllo-inositol, pregnenolone sulphate), four vitamins or cofactors [e.g. bilirubin (Z,Z)], and one carbohydrate (oxalate). CONCLUSIONS: We identified associations between cigarette smoking and a diverse range of metabolites. Our findings, with further validation in future studies, have implications regarding aetiology and study design of smoking-related diseases.

Capabilities and limitations of dispersive liquid-liquid microextraction with solidification of floating organic drop for the extraction of organic pollutants from water samples.

Dispersive liquid-liquid microextraction with solidification of floating organic drop (DLLME-SFO) is one of the most interesting sample preparation techniques developed in recent years. Although several applications have been reported, the potentiality and limitations of this simple and rapid extraction technique have not been made sufficiently explicit. In this work, the extraction efficiency of DLLME-SFO for pollutants from different chemical families was determined. Studied compounds include: 10 polycyclic aromatic hydrocarbons, 5 pesticides (chlorophenoxy herbicides and DDT), 8 phenols and 6 sulfonamides, thus, covering a large range of polarity and hydrophobicity (LogKow 0-7, overall). After optimization of extraction conditions using 1-dodecanol as extractant, the procedure was applied for extraction of each family from 10-mL spiked water samples, only adjusting sample pH as required. Absolute recoveries for pollutants with LogKow 3-7 were >70% and recovery values within this group (18 compounds) were independent of structure or hydrophobicity; the precision of recovery was very acceptable (RSD<12%) and linear behavior was observed in the studied concentration range (r(2)>0.995). Extraction recoveries for pollutants with LogKow 1.46-2.8 were in the range 13-62%, directly depending on individual LogKow values; however, good linearity (r(2)>0.993) and precision (RSD<6.5%) were also demonstrated for these polar solutes, despite recovery level. DLLME-SFO with 1-dodecanol completely failed for extraction of compounds with LogKow≤1 (sulfa drugs), other more polar extraction solvents (ionic liquids) should be explored for highly hydrophilic pollutants.

Contact sensitizing potential of pyrogallol and 5-amino-o-cresol in female BALB/c mice.

Hair dye components such as pyrogallol and cresol have been shown previously to promote allergic reactions such as rashes, dermal inflammation, irritation and dermatitis. The objective of this study was to determine the contact sensitization potential of pyrogallol (PYR) and 5-amino-o-cresol (AOC) when applied dermally to female BALB/c mice. Measurement of the contact hypersensitivity response was initially accomplished using the local lymph node assay. For PYR, significant increases in the proliferation of lymph node cells were observed at concentrations of 0.5% (w/v) and higher. For AOC, borderline increases, albeit significant, in auricular lymph node cell proliferation were observed at 5% and 10%. Results from the irritancy assay suggested that PYR, but not AOC, was an irritant. To further delineate whether PYR was primarily an irritant or a contact sensitizer, the mouse ear swelling test (MEST) was conducted. A significant increase in mouse ear thickness was observed at 72h following challenge with 0.5% PYR in mice that had been sensitized with 5% PYR. In contrast, no effects were observed in the MEST in mice sensitized and challenged with the highest achievable concentration of AOC (10%). Additional studies examining lymph node subpopulations and CD86 (B7.2) expression by B cells further support the indication that PYR was a sensitizer in BALB/c mice. The results demonstrate that PYR is both a sensitizer and an irritant in female BALB/c mice. However, the contact sensitization potential of AOC is minimal in this strain of mouse.

Aerobic biodegradation of a mixture of monosubstituted phenols in a sequencing batch reactor.

A sequencing batch reactor (SBR) was inoculated with p-nitrophenol-degrading activated sludge to biodegrade a mixture of monosubstituted phenols: p-nitrophenol (PNP), PNP and o-cresol; and PNP, o-cresol and o-chlorophenol. Settling times were progressively decreased to promote biomass granulation. PNP was completely biodegraded. The PNP and o-cresol mixture was also biodegraded although some transitory accumulation of intermediates occurred (mainly hydroquinone and catechol). o-Chlorophenol was not biodegraded and resulted in inhibition of o-cresol and PNP biodegradation and complete failure of the SBR within a few days. The biomass had very good settling properties when a settling time of 1 min was applied: sludge volume index (SVI5) below 50 mL g(-1), SVI5/SVI30 ratio of 1 and average particle size of 200 µm.

Immobilized acclimated biomass-powdered activated carbon for the bioregeneration of granular activated carbon loaded with phenol and o-cresol.

The objectives of the study are to use immobilized acclimated biomass and immobilized biomass-powdered activated carbon (PAC) as a novel approach in the bioregeneration of granular activated carbon (GAC) loaded with phenol and o-cresol, respectively, and to compare the efficiency and rate of the bioregeneration of the phenolic compound-loaded GAC using immobilized and suspended biomasses under varying GAC dosages. Bioregeneration of GAC loaded with phenol and o-cresol, respectively, was conducted in batch system using the sequential adsorption and biodegradation approach. The results showed that the bioregeneration efficiency of GAC loaded with phenol or o-cresol was basically the same irrespective of whether the immobilized or suspended biomass was used. Nonetheless, the duration for bioregeneration was longer under immobilized biomass. The beneficial effect of immobilized PAC-biomass for bioregeneration is the enhancement of the removal rate of the phenolic compounds via adsorption and the shortening of the bioregeneration duration.

Biodegradation kinetics of o-cresol by Pseudomonas putida DSM 548 (pJP4) and o-cresol removal in a batch-recirculation bioreactor system

The biodegradation kinetics of o-cresol was examined by acclimatized P. putida DSM 548 (pJP4) in batch experiments at varying initial o-cresol concentrations (from 50 to 500 mg/L). The kinetic parameters of o-cresol aerobic biodegradation were estimated by using the Haldane substrate inhibition equation. The biodegradation kinetics of o-cresol was investigated. In batch culture reactors, the Maximum specific growth rate (μmax), Monod constant (Ks) and the inhibition constant (Ki) were established as 0.519 h-1, 223.84 mg/L and 130.883 mg/L, respectively. o-cresol biodegradation in a batch-recirculation bioreactor system by immobilized P. putida was also studied. The recycled packed bed reactor system, which was composed of Ca-alginate beads and pumice on which cells immobilized, has been performed to determine possible stability for further developments.

A Study on Urinary Excretion of o-Cresol and Hippuric Acid of Workers Daily Exposed to Toluene on Each Day of the Week / 항공우주의학회지

BACKGROUND: The purpose of this study is to find out the relationship between the airborne toluene concentrations and the daily urinary metabolites such as hippuric acid and o-cresol for a sequential 5 days and to provide the appropriate sampling time for a special physical examination in the workers exposed to toluene. METHODS: The volunteers of 36 workers in the shoe making company were selected to measure the concentrations of airborne toluene exposure and to sample the daily urines in pre and end-shift for sequential 5 days form Monday to Friday and to get self-administered questionnaire including the items such as job records, disease records, smoking, alcohol drinking, eating some foods containing benzoic acid before work. RESULTS: The geometric means of toluene concentrations showed 46.40 ppm as the lowest value on Monday and 62.31 ppm as the highest one on Thursday. But there is no significant difference between both of those. The concentrations of hippuric acid and o-cresol in urine sampled on end-shift were higher than that of the others and showed statistically significant differences on each day. The metabolites of toluene were not related with taking alcohol and some foods containing benzoic acid as a result of logistic regression. CONCLUSION: From the above results, it is suggested that the hippuric acid and o-cresol in urine be very useful for biological monitoring in the workers exposed to toluene. Moreover, the daily hippuric acid and o-cresol concentrations in urine are also important for toluene exposure assessment and the further study has to be conducted to find out the tendency of biological exposure indices for continuous toluene exposure.