Preparation of beta-caryophyllene oxidation products and their determination in ambient aerosol samples.
Oxidation of beta-caryophyllene with ozone followed by reduction was carried out in dichloromethane. Reaction led to the formation of beta-caryophyllene aldehyde (11%, purity 90.8%) and beta-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. beta-Nocaryophyllone aldehyde was positively identified and quantified in ambient aerosol samples for the first time. The amount of quantified beta-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 beta-caryophyllene participate in biogenic aerosol formation over boreal forest during late spring.
Parshintsev
Jevgeni
J
Laboratory of Analytical Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55, 00014, Helsinki, Finland.
Nurmi
Joonas
J
Kilpeläinen
Ilkka
I
Hartonen
Kari
K
Kulmala
Markku
M
Riekkola
Marja-Liisa
ML
D000336:Aerosols / Q000737:chemistry; D000393:Air Pollutants; D000447:Aldehydes / Q000737:chemistry; D002623:Chemistry Techniques, Analytical / Q000379:methods*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D008956:Models, Chemical; D010083:Oxidants, Photochemical; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010126:Ozone / Q000737:chemistry; D010316:Particle Size; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013729:Terpenes / Q000737:chemistry
D000336:Aerosols; D000393:Air Pollutants; D000447:Aldehydes; D010083:Oxidants, Photochemical; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013729:Terpenes; D010126:Ozone; C024714:caryophyllene; D010100:Oxygen