{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T21:36:18Z","timestamp":1790717778308,"version":"4.1.0"},"reference-count":58,"publisher":"American Chemical Society (ACS)","issue":"28","license":[{"start":{"date-parts":[[2020,7,8]],"date-time":"2020-07-08T00:00:00Z","timestamp":1594166400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/na","name":"Altria Client Services LLC","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,7,21]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Exposure to diacetyl (DA) has been linked to the respiratory condition bronchiolitis obliterans. Previous research has demonstrated that DA and other \u03b1-dicarbonyl compounds can be detected in both the e-liquids and aerosols of e-vapor products (EVPs). While some EVP manufacturers may add these compounds as flavor ingredients, the primary objective of this work was to determine the potential for the formation of \u03b1-dicarbonyl compounds during the generation of aerosols from EVPs where no DA or other \u03b1-dicarbonyl compounds are added to the e-liquid. A novel ultraperformance liquid chromatography-mass spectrometry-based analytical method for the determination of DA, acetyl propionyl, glyoxal, and methylglyoxal was developed and validated. Next, eight commercially available cig-a-like-type EVPs were evaluated for \u03b1-dicarbonyl formation. Increased levels of \u03b1-dicarbonyls were observed in the aerosols of all evaluated EVPs compared to their respective e-liquids. Mechanistic studies were conducted using a model microwave reaction system to identify key reaction precursors for DA generated from propylene glycol (PG) and carbon-13-labeled glycerin (GLY). These studies, along with the corresponding retrosynthetic analysis, resulted in the proposed formation pathway where hydroxyacetone is generated from PG and\/or GLY. Hydroxyacetone then participates in an aldol condensation with formaldehyde where formaldehyde can also be generated from PG and\/or GLY; the resultant product then dehydrates to form DA. This proposed pathway was further investigated through in situ synthetic organic experiments within the model microwave reaction system. This work establishes that DA is formed in the aerosol generation process of the EVPs tested though at levels below toxicological concern.<\/jats:p>","DOI":"10.1021\/acsomega.0c02018","type":"journal-article","created":{"date-parts":[[2020,7,8]],"date-time":"2020-07-08T16:21:42Z","timestamp":1594225302000},"page":"17565-17575","source":"Crossref","is-referenced-by-count":14,"title":["Formation of Diacetyl and Other \u03b1-Dicarbonyl\nCompounds during the Generation of E-Vapor Product Aerosols"],"prefix":"10.1021","volume":"5","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3608-503X","authenticated-orcid":true,"given":"Matt S.","family":"Melvin","sequence":"first","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karen C.","family":"Avery","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Regina M.","family":"Ballentine","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jason W.","family":"Flora","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"William","family":"Gardner","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Georgios D.","family":"Karles","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yezdi B.","family":"Pithawalla","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donna C.","family":"Smith","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kimberly D.","family":"Ehman","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karl A.","family":"Wagner","sequence":"additional","affiliation":[{"name":"Altria Client Services LLC , , 601 East Jackson Street , , ,","place":["Richmond, Virginia, United States, 23219"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,7,8]]},"reference":[{"key":"2026090210085833800_cit1","unstructured":"Family Smoking Prevention and Tobacco Control Act.\n          \n          Public Law 111-31\n(H.R.1256), 2009. https:\/\/www.congress.gov\/111\/plaws\/publ31\/PLAW-111publ31.pdf (accessed 09\/05\/2019)."},{"key":"2026090210085833800_cit2","unstructured":"U.S. Food and Drug Administration (FDA).\n          \n          Deeming tobacco products to be subject\nto the Federal Food, Drug,\nand Cosmetic Act, as amended by the Family Smoking Prevention and\nTobacco Control Act; restrictions on the sale and distribution of\ntobacco products and required warning statements for tobacco products;\nfinal rule. Federal Register 81, 28974-29106, 2016. https:\/\/www.gpo.gov\/fdsys\/pkg\/FR-2016-05-10\/pdf\/2016-10685.pdf (accessed 09\/05\/2019)."},{"key":"2026090210085833800_cit3","unstructured":"U.S. Food and Drug Administration (FDA).\n          \n          Guidance for Industry. Premarket tobacco\nproduct applications for\nelectronic nicotine delivery systems. 2019. https:\/\/www.fda.gov\/media\/127853\/download (accessed 09\/05\/2019)."},{"key":"2026090210085833800_cit4","doi-asserted-by":"publisher","first-page":"168","DOI":"10.1093\/ntr\/ntu176","article-title":"Evaluation of electronic\ncigarette liquids and aerosol for the presence of selected inhalation\ntoxins","volume":"17","author":"Farsalinos","year":"2015","journal-title":"Nicotine Tob. Res."},{"key":"2026090210085833800_cit5","doi-asserted-by":"publisher","first-page":"9644","DOI":"10.1021\/acs.est.6b01741","article-title":"Emissions from electronic cigarettes:\nkey parameters affecting the release of harmful chemicals","volume":"50","author":"Sleiman","year":"2016","journal-title":"Environ. Sci. Technol."},{"key":"2026090210085833800_cit6","unstructured":"U.S. Department of Health and Human Services, Centers for Disease Control and Prevention.\n          \n          Electronic cigarettes\n-- What\u2019s the bottom line?, 2019. https:\/\/www.cdc.gov\/tobacco\/basic_information\/e-cigarettes\/pdfs\/Electronic-Cigarettes-Infographic-508.pdf (accessed 09\/05\/2019)."},{"key":"2026090210085833800_cit7","doi-asserted-by":"publisher","first-page":"634","DOI":"10.1111\/1541-4337.12150","article-title":"Diacetyl in foods:\na review of safety and sensory characteristics","volume":"14","author":"Clark","year":"2015","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"2026090210085833800_cit8","doi-asserted-by":"publisher","first-page":"6919","DOI":"10.1007\/s00253-013-4955-1","article-title":"Influence of valine and other amino acids on total\ndiacetyl and 2,3-pentanedione levels during fermentation of brewer\u2019s\nwort","volume":"97","author":"Krogerus","year":"2013","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"2026090210085833800_cit9","doi-asserted-by":"publisher","first-page":"3280","DOI":"10.1021\/jf9902292","article-title":"Origin of 2,3-pentanedione\nand 2,3-butanedione in d-glucose\/l-alanine\nMaillard model systems","volume":"47","author":"Yaylayan","year":"1999","journal-title":"J. Agric. Food Chem."},{"key":"2026090210085833800_cit10","doi-asserted-by":"publisher","first-page":"162","DOI":"10.1097\/ACI.0b013e3280298235","article-title":"Flavoring-related\nbronchiolitis obliterans","volume":"7","author":"Kreiss","year":"2007","journal-title":"Curr. Opin. Allergy\nClin. Immunol."},{"key":"2026090210085833800_cit11","unstructured":"Flavor and Extract Manufacturers Association (FEMA).\n          \n          Respiratory health and safety in the flavor manufacturing\nworkplace, 2012. https:\/\/tobacco.ucsf.edu\/sites\/tobacco.ucsf.edu\/files\/u9\/ResH%26S%202012%20FINAL.pdf (accessed 09\/05\/2019)."},{"key":"2026090210085833800_cit12","doi-asserted-by":"publisher","first-page":"509","DOI":"10.1055\/s-0032-1325161","article-title":"Obliterative (constrictive) bronchiolitis","volume":"33","author":"Lynch","year":"2012","journal-title":"Semin. Respir. Crit. Care Med."},{"key":"2026090210085833800_cit13","doi-asserted-by":"publisher","first-page":"330","DOI":"10.1056\/NEJMoa020300","article-title":"Clinical bronchiolitis obliterans in workers at a microwave-popcorn\nplant","volume":"347","author":"Kreiss","year":"2002","journal-title":"N. Engl. J. 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Pharmacol."},{"key":"2026090210085833800_cit17","doi-asserted-by":"publisher","first-page":"829","DOI":"10.1016\/j.ajpath.2012.05.021","article-title":"Respiratory and olfactory\ncytotoxicity of inhaled 2,3-pentanedione in Sprague-Dawley rats","volume":"181","author":"Hubbs","year":"2012","journal-title":"Am. J. Pathol."},{"key":"2026090210085833800_cit18","doi-asserted-by":"publisher","first-page":"448","DOI":"10.1177\/0192623311431946","article-title":"Bronchial and bronchiolar\nfibrosis in rats exposed\nto 2,3-pentanedione vapors: implications for bronchiolitis obliterans\nin humans","volume":"40","author":"Morgan","year":"2012","journal-title":"Toxicol. Pathol."},{"key":"2026090210085833800_cit19","doi-asserted-by":"publisher","first-page":"3439","DOI":"10.3390\/ijerph120403439","article-title":"Nicotine levels and presence of selected tobacco derived\ntoxins in tobacco flavoured electronic cigarette refill liquids","volume":"12","author":"Farsalinos","year":"2015","journal-title":"Int. J. Environ. Res. Public Health"},{"key":"2026090210085833800_cit20","doi-asserted-by":"publisher","first-page":"1352","DOI":"10.1111\/add.12942","article-title":"E-cigarettes generate high levels\nof aldehydes only in \u2018dry puff\u2019 conditions","volume":"110","author":"Farsalinos","year":"2015","journal-title":"Addiction"},{"key":"2026090210085833800_cit21","doi-asserted-by":"publisher","first-page":"142","DOI":"10.1093\/chromsci\/bmw157","article-title":"Method for the determination of carbonyl\ncompounds in e-cigarette aerosols","volume":"55","author":"Flora","year":"2017","journal-title":"J. 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Int."},{"key":"2026090210085833800_cit27","doi-asserted-by":"publisher","first-page":"392","DOI":"10.1056\/NEJMc1413069","article-title":"Hidden formaldehyde\nin e-cigarette aerosols","volume":"372","author":"Jensen","year":"2015","journal-title":"New Engl. J. Med."},{"key":"2026090210085833800_cit28","doi-asserted-by":"publisher","first-page":"1319","DOI":"10.1093\/ntr\/ntu078","article-title":"Carbonyl\ncompounds in electronic\ncigarette vapors: effects of nicotine solvent and battery output voltage","volume":"16","author":"Kosmider","year":"2014","journal-title":"Nicotine Tob. Res."},{"key":"2026090210085833800_cit29","doi-asserted-by":"publisher","first-page":"1662","DOI":"10.1021\/acs.chemrestox.6b00188","article-title":"Chemical composition\nof aerosol from\nan e-cigarette: a quantitative comparison with cigarette smoke","volume":"29","author":"Margham","year":"2016","journal-title":"Chem. Res. Toxicol."},{"key":"2026090210085833800_cit30","doi-asserted-by":"publisher","first-page":"453","DOI":"10.1093\/ntr\/ntv080","article-title":"\u201cDirect dripping\u201d: a high-temperature,\nhigh-formaldehyde emission electronic cigarette use method","volume":"18","author":"Talih","year":"2016","journal-title":"Nicotine Tob. Res."},{"key":"2026090210085833800_cit31","doi-asserted-by":"publisher","first-page":"1219","DOI":"10.2116\/analsci.29.1219","article-title":"Determination of carbonyl\ncompounds generated from the e-cigarette using coupled silica cartridges\nimpregnated with hydroquinone and 2,4-dinitrophenylhydrazine, followed\nby high-performance liquid chromatography","volume":"29","author":"Uchiyama","year":"2013","journal-title":"Anal.\nSci."},{"key":"2026090210085833800_cit32","doi-asserted-by":"publisher","first-page":"3090","DOI":"10.1021\/jf302959k","article-title":"Reactivity\nof thermally treated alpha-dicarbonyl\ncompounds","volume":"61","author":"Pfeifer","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"2026090210085833800_cit33","doi-asserted-by":"publisher","first-page":"197","DOI":"10.1016\/S0021-9673(00)88074-7","article-title":"Determination of \u03b1-dicarbonyl compounds in cigarette\nsmoke","volume":"217","author":"Moree-Testa","year":"1981","journal-title":"J. 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Chem."},{"key":"2026090210085833800_cit44","doi-asserted-by":"publisher","first-page":"297","DOI":"10.1016\/j.jaap.2007.03.007","article-title":"Carbohydrate\npyrolysis\nmechanisms from isotopic labeling part 1: The pyrolysis of glycerin:\ndiscovery of completing fragmentation mechanisms affording acetaldehyde\nand formaldehyde and the implications for carbohydrate pyrolysis","volume":"80","author":"Paine","year":"2007","journal-title":"J. Anal. Appl. Pyrolysis"},{"key":"2026090210085833800_cit45","unstructured":"National Institute for Occupational Safety and Health (NIOSH).\n          \n          Draft-criteria for a recommended standard occupational\nexposure to diacetyl and 2,3-pentanedione&gt;, 2011. http:\/\/www.cdc.gov\/niosh\/docket\/archive\/pdfs\/NIOSH-245\/0245-081211-draftdocument.pdf (accessed 09\/05\/2019)."},{"key":"2026090210085833800_cit46","unstructured":"World Health Organization.\n          \n          Concise International\nChemical Assessment Document 57. 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Pyrolysis"},{"key":"2026090210085833800_cit49","doi-asserted-by":"publisher","first-page":"19","DOI":"10.1351\/pac196714010019","article-title":"General\nmethods for the construction of complex molecules","volume":"14","author":"Corey","year":"1967","journal-title":"Pure Appl. Chem."},{"key":"2026090210085833800_cit50","doi-asserted-by":"publisher","DOI":"10.1038\/srep42549","article-title":"Solvent\nchemistry in the electronic\ncigarette reaction vessel","volume":"7","author":"Jensen","year":"2017","journal-title":"Sci. Rep."},{"key":"2026090210085833800_cit51","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/B978-0-08-097742-3.00211-1","volume-title":"Comprehensive Organic Synthesis II","author":"Harada","year":"2014","edition":"2"},{"key":"2026090210085833800_cit52","first-page":"1218","volume-title":"March\u2019s Advanced\nOrganic Chemistry: Reactions, Mechanisms and Structure","author":"Smith","year":"2001"},{"key":"2026090210085833800_cit53","first-page":"681","volume-title":"Organic Synthesis","author":"Smith","year":"2016"},{"key":"2026090210085833800_cit54","doi-asserted-by":"publisher","first-page":"420","DOI":"10.3109\/10408444.2014.882292","article-title":"Diacetyl\nand 2,3-Pentanedione exposures associated with cigarette smoking:\nimplications for risk assessment of food and flavoring workers","volume":"44","author":"Pierce","year":"2014","journal-title":"Crit. Rev. Toxicol."},{"key":"2026090210085833800_cit55","doi-asserted-by":"publisher","first-page":"53","DOI":"10.15585\/mmwr.mm6702a1","article-title":"Current\ncigarette smoking among adults\n\u2500 United States, 2016.","volume":"67","author":"Jamal","year":"2018","journal-title":"Morb. Mortal.\nWkly. Rep."},{"key":"2026090210085833800_cit56","doi-asserted-by":"publisher","first-page":"160","DOI":"10.1093\/ntr\/ntw160","article-title":"Exposure\nto nicotine and selected\ntoxicants in cigarette smokers who switched to electronic cigarettes:\na longitudinal within-subjects observational study","volume":"19","author":"Goniewicz","year":"2017","journal-title":"Nicotine Tob. Res."},{"key":"2026090210085833800_cit57","doi-asserted-by":"publisher","first-page":"733","DOI":"10.1289\/ehp.1510185","article-title":"Flavoring\nChemicals in E-Cigarettes: Diacetyl, 2,3-Pentanedione, and Acetoin\nin a Sample of 51 Products, Including Fruit-, Candy-, and Cocktail-Flavored\nE-Cigarettes","volume":"124","author":"Allen","year":"2016","journal-title":"Environ. Health Perspect."},{"key":"2026090210085833800_cit58","doi-asserted-by":"publisher","first-page":"145","DOI":"10.1515\/cttr-2017-0015","article-title":"The Determination of\nDiacetyl and\nAcetylpropionyl in Aerosols From Electronic Smoking Devices Using\nGas Chromatography Triple Quad Mass Spectrometry","volume":"27","author":"Moldoveanu","year":"2017","journal-title":"Beitr. Tabakforsch. Int."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.0c02018","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/5\/28\/17565\/67783576\/acsomega.0c02018.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/5\/28\/17565\/67783576\/acsomega.0c02018.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T14:09:06Z","timestamp":1788358146000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/5\/28\/17565\/583885\/Formation-of-Diacetyl-and-Other-Dicarbonyl"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,8]]},"references-count":58,"journal-issue":{"issue":"28","published-online":{"date-parts":[[2020,7,8]]},"published-print":{"date-parts":[[2020,7,21]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.0c02018","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,7,8]]}}}