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6 P-Cymene Formation by Oxidation of Cyclohexadiene Monoterpenes – a Pitfall in Air Sampling of Terpenes

6 P-Cymene Formation by Oxidation of Cyclohexadiene Monoterpenes – a Pitfall in Air Sampling of... i18 Poster presentations inherent explosion safety. EN 838 advises their use for per- Poster presentations sonal sampling at up to 4 m/s, but with a minimum of 0.1 m/s. Considerable underestimations were found in a set of passive Abstract citation ID: wxac087.046 sampler results compared to pumped samplers for BTEX. A lit- erature review of laboratory and field studies was performed 6 P-Cymene Formation by Oxidation of to investigate theoretical explanations for the discrepancies Cyclohexadiene Monoterpenes – a Pitfall found. Based on results published in journals an underestima- in Air Sampling of Terpenes tion of concentration by passive samplers is not uncommon, although usually the difference is within an acceptable range. Jürgen Fauss, Claudia Reinmuth, Matthias Weigl German Temperature and relative humidity have known, quantifiable Social Accident Insurance Institution for the Foodstuffs effects, which are fairly small. High wind speed theoretically and Catering Industry (BGN), D-68165 Mannheim, causes increased, not decreased, uptake due to smaller diffu- Germany sion distances. This effect was confirmed experimentally, both It has been known for a long time that certain terpenes are sen- in wind tunnels and in field studies, according to literature. sitive to oxidation. Especially in the presence of small amounts, Real-time monitoring in company operations shows that per- as is the case in the environment or indoors, changes occur due sonal exposure in outdoor scenarios often fluctuates strongly to UV light or ozone exposition. Various oxidized products with short peaks over periods of seconds rather than minutes. have also been detected when sampling low terpene concen- Theoretically this may influence uptake by diffusion samplers trations using Tenax tubes and subsequent thermal desorp- depending on their design and some researchers do report that tion. Here we show that carrying out common air sampling passive samplers work less well under such conditions. Further of monoterpenes in the lower ppm range on charcoal tubes, research into passive sampler performance in fast fluctuating the atmospheric oxygen is sufficient to oxidize the most sen - conditions as found in the field appears necessary. sitive terpenes to a considerable extent, forming almost exclu- sively p-cymene. As expected, the extent of aromatization was strongest in the terpenes with a double unsaturated ring system such as α- or γ-terpinene or α-phellandrene while p-menthene Abstract citation ID: wxac087.048 or limonene were not affected. We studied the influence of 14 The Development and sampling time, temperature, humidity and storage time of Characterisation of Novel Monoclonal the coated tubes. Simultaneously conducted experiments with thermal desorption in the ppb range showed a significantly re - Antibodies (Mabs) for 1-Hydroxypyrene duced p-cymene formation compared to the activated charcoal Glucuronide (1-OHPyrG) Determination results. Our findings were confirmed by air samples of terpenes and Polycyclic Aromatic Hydrocarbon taken during the grinding of nutmegs. The concentrations of (PAH) Biomonitoring p-cymene determined were significantly higher than the terpene 1 2 2 3 pattern of nutmeg oil would have suggested. Thus, the detec- Lathan  Ball , Claire  Baker , Harry  Carter , Kate  Jones 1 2 tion of p-cymene during air sampling may be an artifact caused Chemitrace, Kendal, United Kingdom, Bioventix PLC, by the presence of cyclohexadiene monoterpenes. This is par- Farnham, United Kingdom, Health and Safety Executive, ticularly important because p-cymene is often used as an in- Buxton, United Kingdom ternal standard in terpene analysis thus preventing its artifact Objective:PAHs are produced during the incomplete burning formation from being noticed. of organic materials. PAH sources include vehicle exhaust, to- bacco smoke and waste incineration. Cancer is a significant endpoint of PAH exposure. Pyrene is a common component Abstract citation ID: wxac087.047 of PAH exposures and metabolism of pyrene leads to the ex- cretion of 1-OHPyrG in urine. Measurement of 1-OHPyrG has 12 A Review of Factors Influencing been used to assess occupational and environmental exposure Passive Sampler Performance in Outdoor to PAHs. The production of Mabs to 1-OHPyrG will allow the Workplaces with a Focus on Benzene development of novel PAH biomonitoring tests, facilitating the introduction of routine screening and safeguarding human 1 2 1 Ilse  Tuinman , Jan  Urbanus Shell, The Hague, health. Netherlands. Shell, Brussels, Belgium Methods:1-Pyrenebutyric acid was coupled to a carrier protein Passive or diffusion samplers have become standard tools and a sheep Mab raised to 1-OHPyrG. A second Mab which for exposure and compliance testing despite their limited ac- binds the Mab-1-OHPyrG immune complex was also produced curacy of 25-30%. Passive samplers have several advantages and a novel urinary non-competitive ELISA developed. Careful over active/pumped samplers, notably ease of use, low cost and formulation of assay buffers has overcome the heterogeneous http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Annals of Work Exposures and Health Oxford University Press

6 P-Cymene Formation by Oxidation of Cyclohexadiene Monoterpenes – a Pitfall in Air Sampling of Terpenes

Annals of Work Exposures and Health , Volume 67 (Supplement_1): 1 – May 10, 2023

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Publisher
Oxford University Press
Copyright
© The Author(s) 2023. Published by Oxford University Press on behalf of the British Occupational Hygiene Society.
ISSN
2398-7308
eISSN
2398-7316
DOI
10.1093/annweh/wxac087.046
Publisher site
See Article on Publisher Site

Abstract

i18 Poster presentations inherent explosion safety. EN 838 advises their use for per- Poster presentations sonal sampling at up to 4 m/s, but with a minimum of 0.1 m/s. Considerable underestimations were found in a set of passive Abstract citation ID: wxac087.046 sampler results compared to pumped samplers for BTEX. A lit- erature review of laboratory and field studies was performed 6 P-Cymene Formation by Oxidation of to investigate theoretical explanations for the discrepancies Cyclohexadiene Monoterpenes – a Pitfall found. Based on results published in journals an underestima- in Air Sampling of Terpenes tion of concentration by passive samplers is not uncommon, although usually the difference is within an acceptable range. Jürgen Fauss, Claudia Reinmuth, Matthias Weigl German Temperature and relative humidity have known, quantifiable Social Accident Insurance Institution for the Foodstuffs effects, which are fairly small. High wind speed theoretically and Catering Industry (BGN), D-68165 Mannheim, causes increased, not decreased, uptake due to smaller diffu- Germany sion distances. This effect was confirmed experimentally, both It has been known for a long time that certain terpenes are sen- in wind tunnels and in field studies, according to literature. sitive to oxidation. Especially in the presence of small amounts, Real-time monitoring in company operations shows that per- as is the case in the environment or indoors, changes occur due sonal exposure in outdoor scenarios often fluctuates strongly to UV light or ozone exposition. Various oxidized products with short peaks over periods of seconds rather than minutes. have also been detected when sampling low terpene concen- Theoretically this may influence uptake by diffusion samplers trations using Tenax tubes and subsequent thermal desorp- depending on their design and some researchers do report that tion. Here we show that carrying out common air sampling passive samplers work less well under such conditions. Further of monoterpenes in the lower ppm range on charcoal tubes, research into passive sampler performance in fast fluctuating the atmospheric oxygen is sufficient to oxidize the most sen - conditions as found in the field appears necessary. sitive terpenes to a considerable extent, forming almost exclu- sively p-cymene. As expected, the extent of aromatization was strongest in the terpenes with a double unsaturated ring system such as α- or γ-terpinene or α-phellandrene while p-menthene Abstract citation ID: wxac087.048 or limonene were not affected. We studied the influence of 14 The Development and sampling time, temperature, humidity and storage time of Characterisation of Novel Monoclonal the coated tubes. Simultaneously conducted experiments with thermal desorption in the ppb range showed a significantly re - Antibodies (Mabs) for 1-Hydroxypyrene duced p-cymene formation compared to the activated charcoal Glucuronide (1-OHPyrG) Determination results. Our findings were confirmed by air samples of terpenes and Polycyclic Aromatic Hydrocarbon taken during the grinding of nutmegs. The concentrations of (PAH) Biomonitoring p-cymene determined were significantly higher than the terpene 1 2 2 3 pattern of nutmeg oil would have suggested. Thus, the detec- Lathan  Ball , Claire  Baker , Harry  Carter , Kate  Jones 1 2 tion of p-cymene during air sampling may be an artifact caused Chemitrace, Kendal, United Kingdom, Bioventix PLC, by the presence of cyclohexadiene monoterpenes. This is par- Farnham, United Kingdom, Health and Safety Executive, ticularly important because p-cymene is often used as an in- Buxton, United Kingdom ternal standard in terpene analysis thus preventing its artifact Objective:PAHs are produced during the incomplete burning formation from being noticed. of organic materials. PAH sources include vehicle exhaust, to- bacco smoke and waste incineration. Cancer is a significant endpoint of PAH exposure. Pyrene is a common component Abstract citation ID: wxac087.047 of PAH exposures and metabolism of pyrene leads to the ex- cretion of 1-OHPyrG in urine. Measurement of 1-OHPyrG has 12 A Review of Factors Influencing been used to assess occupational and environmental exposure Passive Sampler Performance in Outdoor to PAHs. The production of Mabs to 1-OHPyrG will allow the Workplaces with a Focus on Benzene development of novel PAH biomonitoring tests, facilitating the introduction of routine screening and safeguarding human 1 2 1 Ilse  Tuinman , Jan  Urbanus Shell, The Hague, health. Netherlands. Shell, Brussels, Belgium Methods:1-Pyrenebutyric acid was coupled to a carrier protein Passive or diffusion samplers have become standard tools and a sheep Mab raised to 1-OHPyrG. A second Mab which for exposure and compliance testing despite their limited ac- binds the Mab-1-OHPyrG immune complex was also produced curacy of 25-30%. Passive samplers have several advantages and a novel urinary non-competitive ELISA developed. Careful over active/pumped samplers, notably ease of use, low cost and formulation of assay buffers has overcome the heterogeneous

Journal

Annals of Work Exposures and HealthOxford University Press

Published: May 10, 2023

There are no references for this article.