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Preparation of β-caryophyllene oxidation products and their determination in ambient aerosol samples

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Abstract

Oxidation of β-caryophyllene with ozone followed by reduction was carried out in dichloromethane. Reaction led to the formation of β-caryophyllene aldehyde (11%, purity 90.8%) and β-nocaryophyllone aldehyde (79%, purity 99%). Compounds were purified and separated by liquid–liquid extraction and flash chromatography. Identifications were achieved by electron-impact and electrospray ionization mass spectrometry, and precise structures were confirmed by one and two-dimensional nuclear magnetic resonance spectroscopy. The prepared compounds were used in the analysis of ambient aerosol samples collected during spring 2003 at Hyytiälä, Finland. β-Nocaryophyllone aldehyde was positively identified and quantified in ambient aerosol samples for the first time. The amount of quantified β-nocaryophyllone aldehyde of aerosol origin was 17.4 ± 1.0 ng m−3 of sampled air. Comparison with previous findings led to the conclusion that oxidation products of β-caryophyllene participate in biogenic aerosol formation over boreal forest during late spring.

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Acknowledgements

Helsinki University Environmental Research Centre (HERC) provided funding for this research. We would like to thank Professor Tuulia Hyötyläinen for discussions, Valteri Mäkelä for running the NMR, and Dr Raimo Timonen for the loan of the ozone generator.

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Authors and Affiliations

  1. Laboratory of Analytical Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55, 00014, Helsinki, Finland

    Jevgeni Parshintsev, Joonas Nurmi, Kari Hartonen & Marja-Liisa Riekkola

  2. Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55, 00014, Helsinki, Finland

    Ilkka Kilpeläinen

  3. Division of Atmospheric Sciences, Department of Physical Sciences, University of Helsinki, P.O. Box 64, 00014, Helsinki, Finland

    Markku Kulmala

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  1. Jevgeni Parshintsev
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  2. Joonas Nurmi
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  3. Ilkka Kilpeläinen
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  4. Kari Hartonen
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  5. Markku Kulmala
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  6. Marja-Liisa Riekkola
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Correspondence to Marja-Liisa Riekkola.

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Parshintsev, J., Nurmi, J., Kilpeläinen, I. et al. Preparation of β-caryophyllene oxidation products and their determination in ambient aerosol samples. Anal Bioanal Chem 390, 913–919 (2008). https://doi.org/10.1007/s00216-007-1755-4

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  • DOI: https://doi.org/10.1007/s00216-007-1755-4

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