Fate of pyrazines in the flavored liquids of e-cigarettes

References

• Adams, T. B., Doull, J., Feron, V. J., Goodman, J. I., Marnett, L. J., Munro, I. C., Newberne, P. M., Portoghese, P. S., Smith, R. L., Waddell, W. J., and Wagner, B. M. (2002). The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients. Food Chem. Toxicol., 40(4):429–451. doi:10.1016/S0278-6915(01)00123-5.
   PubMed Web of Science ®Google Scholar
• Alpert, H. R., Agaku, I. T., and Connolly, G. N. (2016). A study of pyrazines in cigarettes and how additives might be used to enhance tobacco addiction. Tob. Control, 25:444–450. doi:10.1136/tobaccocontrol-2014-051943.
   PubMed Web of Science ®Google Scholar
• ASH. (2016). Use of electronic cigarettes (vapourisers) among adults in Great Britain. from http://www.ash.org.uk/files/documents/ASH_891.pdf.
   Google Scholar
• Bach, L. (2016). Electronic Cigarettes and Youth. Retrieved December 2016, from http://www.tobaccofreekids.org/research/factsheets/pdf/0382.pdf.
   Google Scholar
• Breland, A., Soule, E., Lopez, A., Ramôa, C., El-Hellani, A., and Eissenberg, T. (2016). Electronic cigarettes: what are they and what do they do? Ann. N. Y. Acad. Sci., 1394:5–30. doi:10.1111/nyas.12977.
   PubMed Web of Science ®Google Scholar
• Brown, J., West, R., Beard, E., Michie, S., Shahab, L., and McNeill, A. (2014). Prevalence and characteristics of e-cigarette users in Great Britain: Findings from a general population survey of smokers. Addict. Behav., 39(6):1120–1125. doi:10.1016/j.addbeh.2014.03.009.
   PubMed Web of Science ®Google Scholar
• Caldwell, B., Sumner, W., and Crane, J. (2012). A systematic review of Nicotine by Inhalation: Is there a role for the inhaled route? Nicotine Tob. Res., 14(10):1127–1139. doi:10.1093/ntr/nts009.
   PubMed Web of Science ®Google Scholar
• Chickos, J. S., and Acree, W. E. J. (2003). Enthalpies of vaporization of organic and organometallic compounds, 1880–2002. from http://nist.gov/data/PDFfiles/jpcrd628.pdf.
   Google Scholar
• Connolly, G. N., Wayne, G. D., Lymperis, D., and Doherty, M. C. (2000). How cigarette additives are used to mask environmental tobacco smoke. Tob. Control, 9(3):283–291. doi:10.1136/tc.9.3.283.
   PubMed Web of Science ®Google Scholar
• Dai, H., and Hao, J. (2016). Flavored electronic cigarette use and smoking among youth. Pediatrics, 138. doi:10.1542/peds.2016-2513.
   PubMed Web of Science ®Google Scholar
• Farsalinos, K., Gillman, I., Melvin, M., Paolantonio, A., Gardow, W., Humphries, K., Brown, S., Poulas, K., and Voudris, V. (2015). Nicotine levels and presence of selected tobacco-derived toxins in tobacco flavoured electronic cigarette refill liquids. Int. J. Environ. Res. Public Health, 12(4):3439. doi:10.3390/ijerph120403439.
   PubMed Web of Science ®Google Scholar
• Filippidis, F. T., Laverty, A. A., Gerovasili, V., and Vardavas, C. I. (2016). Two-year trends and predictors of e-cigarette use in 27 European Union member states. Tob. Control, 26:98–104. doi:10.1136/tobaccocontrol-2015-052771.
   PubMed Web of Science ®Google Scholar
• Geiss, O., Bianchi, I., and Barrero-Moreno, J. (2016). Correlation of volatile carbonyl yields emitted by e-cigarettes with the temperature of the heating coil and the perceived sensorial quality of the generated vapours. Int. J. Hyg. Environ. Health, 219(3):268–277. doi:10.1016/j.ijheh.2016.01.004.
   PubMed Web of Science ®Google Scholar
• Heinzler, M., and Eichner, K. (1992). The role of Amadori compounds during cocoa processing-formation of aroma compounds under roasting conditions. Z Lebensm Unters Forsch, 21:445–450.
   Google Scholar
• Herrington, J. S., and Myers, C. (2015). Electronic cigarette solutions and resultant aerosol profiles. J. Chromatogr. A, 1418:192–199. doi:10.1016/j.chroma.2015.09.034.
   PubMed Web of Science ®Google Scholar
• Huang, Y., and Barringer, S. A. (2011). Monitoring of cocoa volatiles produced during roasting by Selected Ion Flow Tube-Mass Spectrometry (SIFT-MS). J. Food Sci., 76(2):C279–C286. doi:10.1111/j.1750-3841.2010.01984.x.
   PubMed Web of Science ®Google Scholar
• Hutzler, C., Paschke, M., Kruschinski, S., Henkler, F., Hahn, J., and Luch, A. (2014). Chemical hazards present in liquids and vapors of electronic cigarettes. Arch. Toxicol., 88(7):1295–1308. doi:10.1007/s00204-014-1294-7.
   PubMed Web of Science ®Google Scholar
• Ishiguro, S., and Sugawara, S. (1977). Comparisons of volatile N-Containing compounds in the smoke of lamina and midrib of flue-cured tobacco leaves. Agric. Biol. Chem., 41(2):377–382.
   Web of Science ®Google Scholar
• Leffingwell, J. C. (1976). Nitrogen components of leaf and their relationship to smoking quality and aroma. Recent Adv. Tob. Sci, 2(1–31). http://www.leffingwell.com/download/LEFF-TCRC-1976.pdf.
   Google Scholar
• Leffingwell J. C., Young H. J., and Bernasek E. (1972). Tobacco Flavoring for Smoking Products. R.J. Reynolds Tobacco Company, Winston-Salem. http://www.leffingwell.com/download/TobaccoFlavorBook.pdf.
   Google Scholar
• Lim, H.-H., and Shin, H.-S. (2017). Determination of volatile organic compounds including alcohols in refill fluids and cartridges of electronic cigarettes by headspace solid-phase micro extraction and gas chromatography–mass spectrometry. Anal. Bioanal. Chem., 409(5):1247–1256. doi:10.1007/s00216-016-0049-0.
   PubMed Web of Science ®Google Scholar
• Lu, X., Zhao, M., Kong, H., Cai, J., Wu, J., Wu, M., Hua, R., Liu, J., and Xu, G. (2004). Characterization of complex hydrocarbons in cigarette smoke condensate by gas chromatography–mass spectrometry and comprehensive two-dimensional gas chromatography–time-of-flight mass spectrometry. J. Chromatogr. A, 1043(2):265–273. doi:10.1016/j.chroma.2004.05.089.
   PubMed Web of Science ®Google Scholar
• Marcilla, A., Martínez, I., Berenguer, D., Gómez-Siurana, A., and Beltrán, M. I. (2012). Comparative study of the main characteristics and composition of the mainstream smoke of ten cigarette brands sold in Spain. Food Chem. Toxicol., 50(5):1317–1333. doi:10.1016/j.fct.2012.01.046.
   PubMed Web of Science ®Google Scholar
• Marco, E., and Grimalt, J. O. (2015). A rapid method for the chromatographic analysis of volatile organic compounds in exhaled breath of tobacco cigarette and electronic cigarette smokers. J. Chromatogr. A, 1410:51–59. doi:10.1016/j.chroma.2015.07.094.
   PubMed Web of Science ®Google Scholar
• McMillen, R. C., Gottlieb, M. A., Shaefer, R. M. W., Winickoff, J. P., and Klein, J. D. (2015). Trends in electronic cigarette use among U.S. Adults: Use is increasing in both smokers and nonsmokers. Nic. Tob. Res., 17(10):1195–1202. doi:10.1093/ntr/ntu213.
   PubMed Web of Science ®Google Scholar
• Melkonian, G., Eckelhoefer, H., Wu, M., Wang, Y., Tong, C., Riveles, K., and Talbot, P. (2003). Growth and angiogenesis Are inhibited in Vivo in developing tissues by Pyrazine and its derivatives. Toxicol. Sci., 75(2):393–401. doi:10.1093/toxsci/kfg123.
   PubMed Web of Science ®Google Scholar
• Pankow, J. F. (1994). An absorption model of gas/particle partitioning of organic compounds in the atmosphere. Atmos. Environ., 28(2):185–188. doi:10.1016/1352-2310(94)90093-0.
   Web of Science ®Google Scholar
• Pankow, J. F. (2001). A consideration of the role of gas/particle partitioning in the deposition of nicotine and other tobacco smoke compounds in the respiratory tract. Chem. Res. Toxicol., 14(11):1465–1481. doi:10.1021/tx0100901.
   PubMed Web of Science ®Google Scholar
• Pankow, J. F. (2017). Calculating compound dependent gas-droplet distributions in aerosols of propylene glycol and glycerol from electronic cigarettes. Journal of Aerosol Science, 107:9–13. doi:10.1016/j.jaerosci.2017.02.003.
   Web of Science ®Google Scholar
• Pellegrino, R. M., Tinghino, B., Mangiaracina, G., Marani, A., Vitali, M., Protano, C., Osborn, J. F., and Cattaruzza, M. S. (2012). Electronic cigarettes: An evaluation of exposure to chemicals and fine particulate matter (PM). Ann. Ig., 24:279–288.
   PubMedGoogle Scholar
• Peng, F., Sheng, L., Liu, B., Tong, H., and Liu, S. (2004). Comparison of different extraction methods: steam distillation, simultaneous distillation and extraction and headspace co-distillation, used for the analysis of the volatile components in aged flue-cured tobacco leaves. J. Chromatogr. A, 1040(1):1–17. doi:10.1016/j.chroma.2004.03.057.
   PubMed Web of Science ®Google Scholar
• Pickard, S., Becker, I., Merz, K.-H., and Richling, E. (2013). Determination of the alkylpyrazine composition of coffee using Stable Isotope Dilution–Gas Chromatography–Mass Spectrometry (SIDA-GC-MS). J. Agric. Food Chem., 61(26):6274–6281. doi:10.1021/jf401223w.
   PubMed Web of Science ®Google Scholar
• Purkis, S. W., Mueller, C., and Intorp, M. (2011). The fate of ingredients in and impact on cigarette smoke. Food Chem. Toxicol., 49(12):3238–3248. doi:10.1016/j.fct.2011.09.028.
   PubMed Web of Science ®Google Scholar
• Riveles, K., Roza, R., Arey, J., and Talbot, P. (2004). Pyrazine derivatives in cigarette smoke inhibit hamster oviductal functioning. Reprod. Biol. Endocrinol., 2(1):23. doi:10.1186/1477-7827-2-23.
   PubMedGoogle Scholar
• Sakoguchi, A., Ueoka, R., Kato, Y., and Arai, Y. (1995). Vapor pressures of alkylpyridines and alkylpyrazines. KAGAKU KOGAKU RONBUN, 21(1):219–223. doi:10.1252/kakoronbunshu.21.219.
   Web of Science ®Google Scholar
• Sala, C., Mestres, M., Martı́, M. P., Busto, O., and Guasch, J. (2002). Headspace solid-phase microextraction analysis of 3-alkyl-2-methoxypyrazines in wines. J. Chromatogr. A, 953(1–2):1–6. doi:10.1016/S0021-9673(02)00123-1.
   PubMed Web of Science ®Google Scholar
• Schmeltz, I., and Hoffmann, D. (1977). Nitrogen-containing compounds in tobacco and tobacco smoke. Chem. Rev., 77:295–311. doi:10.1021/cr60307a001.
   Web of Science ®Google Scholar
• Syamlal G., Jamal A., King B. A., and JM, M. (2016). Electronic cigarette use among working adults — United States, 2014. MMWR Morb Mortal Wkly Rep, 65:557–561. doi:10.15585/mmwr.mm6522a1.
   PubMed Web of Science ®Google Scholar
• Talbot, P. (2008). In vitro assessment of reproductive toxicity of tobacco smoke and its constituents. Birth Defects Research (Part C), 84(1):61–72. doi:10.1002/bdrc.20120.
   PubMedGoogle Scholar
• Talih, S., Balhas, Z., Eissenberg, T., Salman, R., Karaoghlanian, N., El Hellani, A., Baalbaki, R., Saliba, N., and Shihadeh, A. (2015). Effects of user puff topography, device voltage, and liquid nicotine concentration on electronic cigarette nicotine yield: Measurements and model predictions. Nicotine Tob. Res., 17(2):150–157. doi:10.1093/ntr/ntu174.
   PubMed Web of Science ®Google Scholar
• Talih, S., Balhas, Z., Salman, R., El-Hage, R., Karaoghlanian, N., El-Hellani, A., Baassiri, M., Jaroudi, E., Eissenberg, T., Saliba, N., and Shihadeh, A. (2017). Transport phenomena governing nicotine emissions from electronic cigarettes: Model formulation and experimental investigation. Aerosol Sci. Technol., 51(1):1–11. doi:10.1080/02786826.2016.1257853.
   PubMed Web of Science ®Google Scholar
• Tierney, P. A., Karpinski, C. D., Brown, J. E., Luo, W., and Pankow, J. F. (2016). Flavour chemicals in electronic cigarette fluids. Tob. Control, 25(e1):e10–e15. doi:10.1136/tobaccocontrol-2014-052175.
   PubMed Web of Science ®Google Scholar
• Treesuwan, W., Hirao, H., Morokuma, K., and Hannongbua, S. (2012). Characteristic vibration patterns of odor compounds from bread-baking volatiles upon protein binding: density functional and ONIOM study and principal component analysis. J. Mol. Model., 18(5):2227–2240. doi:10.1007/s00894-011-1227-9.
   PubMed Web of Science ®Google Scholar
• Weeks, W. W., Campos, M. P., and Moldoveanu, S. (1995). Pyrolysis of Cherry Red Tobacco and 1-Deoxy-1-[(S)-2-(3-pyridyl)-1-pyrrolidinyl]-.beta.-D-fructose (Pyranose and Furanose Isomers) Amadori Products of Cherry Red Tobacco. J. Agric. Food Chem., 43(8):2247–2253. doi:10.1021/jf00056a052.
   Web of Science ®Google Scholar
• Yang, J., Pan, Z., Takeoka, G., Mackey, B., Bingol, G., Brandl, M. T., Garcin, K., McHugh, T. H., and Wang, H. (2013). Shelf-life of infrared dry-roasted almonds. Food Chem., 138(1):671–678. doi:10.1016/j.foodchem.2012.09.142.
   PubMed Web of Science ®Google Scholar
• Zhu, S.-H., Sun, J. Y., Bonnevie, E., Cummins, S. E., Gamst, A., Yin, L., and Lee, M. (2014). Four hundred and sixty brands of e-cigarettes and counting: Implications for product regulation. Tob. Control, 23(suppl 3):iii3–iii9. doi:10.1136/tobaccocontrol-2014-051670.
   PubMed Web of Science ®Google Scholar