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Environ Sci Technol

Title:		"Monoterpene and Sesquiterpene alpha-Hydroxy Organosulfates: Synthesis, MS/MS Characteristics, and Ambient Presence"
Author(s):		Wang Y; Ma Y; Li X; Kuang BY; Huang C; Tong R; Yu JZ;
Address:		"State Environmental Protection Key Laboratory of the Formation and Prevention of Urban Air Pollution Complex , Shanghai Academy of Environmental Sciences , Shanghai 200233 , China. Institute of Environmental Pollution and Health, School of Environmental and Chemical Engineering , Shanghai University , Shanghai 200444 , China"
Journal Title:		Environ Sci Technol
Year:		2019
Volume:		20191017
Issue:		21
Page Number:		12278 - 12290
DOI:		10.1021/acs.est.9b04703
ISSN/ISBN:		1520-5851 (Electronic) 0013-936X (Linking)
Abstract:		"Organosulfates (OSs) derived from biogenic volatile organic compounds are important compounds signifying interactions between anthropogenic sulfur pollution and natural emission. In this work, we substantially expand the OS standard library through the chemical synthesis of 26 alpha-hydroxy OS standards from eight monoterpenes (i.e., alpha- and beta-pinene, limonene, sabinene, Delta(3)-carene, terpinolene, and alpha- and gamma-terpinene) and two sesquiterpenes (i.e., alpha-humulene and beta-caryophyllene). The sulfation of unsymmetrically substituted 1,2-diol intermediates produced a regioisomeric mixture of two OSs. The major regioisomeric OSs were isolated and purified for full NMR characterization, while the minor regioisomers could only be determined by liquid chromatograph-mass spectrometer (MS). The tandem mass spectra of the molecular ion formed through electrospray ionization confirmed the formation of abundant bisulfate ion fragments (m/z 97) and certain minor ion fragments characteristic of the carbon backbone. A knowledge of the MS/MS spectra and chromatographic retention times for authentic standards allows us to identify alpha-hydroxy OSs derived from six monoterpenes and beta-caryophyllene in ambient samples. Notably, among two possible regioisomers of alpha-hydroxy OSs, we only detected the isomers with the sulfate group at the less substituted carbon position derived from alpha-pinene, limonene, sabinene, Delta(3)-carene, and terpinolene in the ambient samples. This observation sheds light on the atmospheric OS formation mechanisms"
Keywords:		Aerosols Monoterpenes *Sesquiterpenes Sulfates *Tandem Mass Spectrometry;
Notes:		"MedlineWang, Yuchen Ma, Yingge Li, Xiaojing Kuang, Bin Yu Huang, Cheng Tong, Rongbiao Yu, Jian Zhen eng 2019/10/05 Environ Sci Technol. 2019 Nov 5; 53(21):12278-12290. doi: 10.1021/acs.est.9b04703. Epub 2019 Oct 17"