Acetoin is a precursor to diacetyl in e-cigarette liquids

Food Chem Toxicol. 2019 Nov:133:110727. doi: 10.1016/j.fct.2019.110727. Epub 2019 Aug 1.

Abstract

Use of the e-liquid flavourings diacetyl and acetyl propionyl has raised concerns that they might cause respiratory diseases amongst vapers. Product surveys show that these compounds, plus a less toxic alternative, acetoin, are widely used in e-liquids. We have investigated the chemistry of acetoin, acetyl propionyl and diacetyl in e-liquids. They are reactive, with concentrations falling substantially over time. Acetyl propionyl is the most reactive, diacetyl less so, and acetoin significantly more stable. Their reactivity is pH-enhanced when nicotine is present in the e-liquid. Of major concern, we found that acetoin generates diacetyl in e-liquids. We found diacetyl formation in all acetoin-containing e-liquids, but it is not an acetoin-contaminant. Diacetyl concentrations were proportional to acetoin content, grew over time, and formation was accelerated by nicotine. E-liquids stored for up to 18 months contained significant diacetyl, and reduced acetoin levels, showing that acetoin is a long-term diacetyl source. Other reaction pathways operate, and we advance mechanisms to explain this area of e-liquid chemistry. Acetoin use in e-liquids is an inevitable source of diacetyl exposure for e-cigarette users. Acetoin, acetyl propionyl and diacetyl are avoidable hazards for vapers, and we recommend e-liquid manufacturers move away from their use in e-liquid formulations.

Keywords: Acetoin; Acetylpropionyl; Diacetyl; E-Liquids; E-cigarettes.

MeSH terms

  • Acetoin / analysis
  • Acetoin / chemistry*
  • Diacetyl / analysis
  • Diacetyl / chemical synthesis*
  • Drug Stability
  • Electronic Nicotine Delivery Systems*
  • Flavoring Agents / analysis
  • Flavoring Agents / chemistry*
  • Glycerol / chemistry
  • Hydrogen-Ion Concentration
  • Nicotine / chemistry
  • Oxidation-Reduction
  • Pentanones / analysis
  • Propylene Glycol / chemistry

Substances

  • Flavoring Agents
  • Pentanones
  • Propylene Glycol
  • Nicotine
  • Acetoin
  • Diacetyl
  • 2,3-pentanedione
  • Glycerol