Matt S. Melvin, Karen C. Avery, Jason W. Flora, Karl A. Wagner. Altria Client Services LLC l Regulatory Sciences 12Oct2016 Final 1
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1 Determination of 2,3-Butanedione, 2,3-Pentanedione, and Acetoin in Electronic Cigarette Formulations and Aerosols by Gas Chromatography-Mass Spectrometry Matt S. Melvin, Karen C. Avery, Jason W. Flora, Karl A. Wagner 1
2 Introduction Found in many foods and beverages, natural and processed 1 Compounds Generally Recognized as Safe (GRAS TM ) for ingestion (FEMA # s 2370, 2841, 2008) 2 Used as flavor additives to impart buttery or creamy notes 3 1) NIOSH (National Institute for Occupational Safety and Health) Draft Criteria for a recommended standard. Occupational Exposure to Diacetyl and 2,3-Pentanedione. Available: 2) Flavor and Extract Manufacturers Association, 2012 Respiratory Health and Safety in the Flavor Manufacturing Workplace Update. Available: 3) OSHA Occupational Exposure to Flavoring Substances: Health Effects and Hazard Control. SHIB Available: 2
3 Occupational Exposure Diacetyl inhalation exposure linked to the adverse respiratory condition, bronchiolitis obliterans 4 Acetyl propionyl inhalation exposure has caused bronchial and bronchiolar fibrosis in rats OSHA Worker Alert: Diacetyl substitutes that have not been proven to be safe include diacetyl trimer, 2,3-hexanedione, 2,3-heptanedione,and 2,3- pentanedione. 6 4) Kreiss K, et al Clinical bronchiolitis obliterans in workers at a microwave-popcorn plant. New Engl J Med 347(5): ) Morgan DL, et al. Bronchial and bronchiolar fibrosis in rats exposed to 2,3-pentanedione vapors: implications for bronchiolitis obliterans in humans. Toxicol Pathol ); 6) OSHA, OSHA Worker Alert: Diacetyl and Substitutes., DTSEM 11/2010, Available: 3
4 Relevance to Electronic Cigarettes Diacetyl and acetyl propionyl recommended for analysis by U.S. FDA in the 2016 Draft Guidance for Industry on ENDS products 10 FEMA cautioned manufacturers on the use of flavorings in e-cigarettes 9 GRAS TM status does not indicate safety for use in an inhalation product All three compounds identified in commercial electronic cigarette formulations (e-liquids) and aerosols 7,8 7) Allen JG, et al. Flavoring chemicals in e-cigarettes: diacetyl, 2,3-pentanedione, and acetoin in a sample of 51 products, including fruit-, candy-, and cocktailflavored e-cigarettes. Environ Health Perspect, 2015, 124: ) Farsalinos, et al. Evaluation of Electronic Cigarette Liquids and Aerosol for the Presence of Selected Inhalation Toxins. Nicotine & Tobacco Research, 2015, ) FEMA, 10) Draft Guidance for Industry, Premarket Tobacco Product Applications for Electronic Nicotine Delivery Systems, May
5 Methods of Analysis Overview Derivatization with 2,4- dinitrophenyl hydrazine (DNPH) Derivatization with O- (pentafluorobenzyl)hydroxylamine (PFBHA) Advantage that can be analyzed with other carbonyl s of interest Derivatization increases complexity of analysis 11) OSHA. OSHA Method 1012, Washington, DC:OSHA Available: 12) Guan, X. et al. An Optimized Method for the Measurement of Acetaldehyde by High-Performance Liquid Chromatography Alcohol Clin Exp Res, Vol 36, No 3, 2012: pp ) Uchiyama S. et al. Determination of acrolein and other carbonyls in cigarette smoke using coupled silica cartridges impregnated with hydroquinone and 2,4-dinitrophenylhydrazine J. Chromatogr. A 1217 (2010)
6 Direct Analysis Methods OSHA Method 1013 for diacetyl and acetoin in air samples 14 Huang, et al., (2015) reported method for diacetyl in e-liquids 15 Serve as starting point for method expansion Focus: Addition of other two analytes Include aerosol matrix Evaluate matched internal standard Decrease amount of base constituents introduced into instrument 14) OSHA. OSHA Method 1013, Washington, DC:OSHA Available: 15) Huang, C.B., Flora, J.A., Wagner, K.A. (2015). Determination of Diacetyl in E-vapor Products using Gas Chromatography and Mass Spectrometry, 2015 Tobacco Science Research Conference, Naples, Fl. 6
7 Method Development Overview Column screen: Stabiliwax, DB-5ms, Rtx-624, DB-17 Matched internal standard evaluation: Attempted to switch internal standard to diacetyl-d6 however observed decreasing response over time in presence of matrix Alternative internal standard selection: 7
8 Representative Chromatography Column: Restek Rtx-624 column, 30 m X 0.25 mm; 1.4 mm Internal Standard: 2,3-Hexanedione (HDO) Mid-Level Standard Acetoin HDO DA AP 8
9 Instrumental Conditions Parameters Instrument and Detector Agilent A GC-MSD Restek Rtx-624, GC Colum 30 m x 0.25 mm x 1.4 µm 50 C hold 5 min Oven Temperatures ramp 10 C/min to 75 C ramp 65 C/min to 235 C, hold 3 min. Flow rate 1.0 ml/min. Inlet Temperature 230 C Split Ratio 20:1 m/z 43 & 86 for diacetyl m/z 57 & 100 for acetyl propionyl Selected Ion Monitoring (SIM) m/z 43 & 88 for acetoin m/z 43 & 71 for 2,3-hexanedione Interface Temperature 240 C Ion Source Temperature 230 C Quadrupole Temperature 150 C Running Time 10.1 minutes 9
10 Method Development Matrices Sample ID PG/Gly Ratio (%) Water (%) Nicotine (%) Analyte Fortification e-liquid 1 Low 50/ Low e-liquid 1 High 50/ High Sample ID Sample Type DA (µg/g) AP (µg/g) Acetoin (µg/g) e-liquid 1 Low e-liquid e-liquid 1 High e-liquid e-liquid 1 Low Aerosol e-liquid 1 High Aerosol Reference e-liquids were added to empty MarkTen XL cartridges for aerosol collections 10
11 Sample Preparation Weigh 300 mg of e-liquid into vial Add 2 ml of water and IS solution Add 10 ml of DCM Vortex for 20 min Analyze by GC-MS 11
12 Fortified E-liquid: Extracted into 10 ml of DCM Acetoin PG GLY HDO AP DA Large amounts of PG and GLY introduced into instrument 12
13 Fortified E-liquid: Extracted into 10 ml of DCM from 2 ml of Water Acetoin PG DA AP HDO Decreased PG and GLY amounts more amenable to routine, highthroughput analysis GLY 13
14 Aerosol Trapping Efficiency (55 ml Puff Volume, 5 sec Puff Duration, 30 sec Puff Interval, Square Wave) N=5 DA AP Acetoin Cambridge Filter Pad 23.8% 7.7% 57.5% Impinger #1 76.2% 92.3% 42.5% Impinger #2 ND ND ND Targeted aerosol yield of mg per 25 puff block Cambridge filter pad followed by 2 impingers containing 20 ml of dichloromethane at 0 ºC 14
15 Aerosol Preparation Transfer CFP and impinger solution to vial Add 2 ml of water and IS solution Vortex for 20 min Analyze by GC-MS 15
16 120% 100% Aerosol Transfer Efficiency e-liquid 1 Low e-liquid 1 High 80% 60% 40% 20% 0% DA AP Acetoin Analytes transferred with high efficiency from e-liquid to aerosol (>78%) 16
17 Validation Matrices: Sample ID PG/Gly Ratio (%) Water (%) Nicotine (%) Analyte Fortification e-liquid 1 50/ none e-liquid 2 50/ none e-liquid 3 50/ none e-liquid 4 100/ none e-liquid 5 0/ none Reference e-liquids were added to empty MarkTen XL cartridges Fortification levels same as those used for development. 17
18 Validation Summary Parameter Diacetyl Acetyl Propionyl Acetoin Linearity R 2 > > > Range (µg/ml) Recovery e-liquid (% ) Aerosol (% ) Precision e-liquid (n=5; %RSD) < 5 < 7 < 7 Aerosol (n=5; %RSD) < 10 < 8 < 9 LOQ e-liquid (µg/g) Aerosol* (µg/g) *Assume aerosol mass = 0.1 g 18
19 Acetyl Propionyl and Acetoin (µg/g) Diacetyl (µg /g) Commercial Refill E-liquid Acetyl Propionyl Acetoin
20 µg per gram of e-liquid µg per gram of aerosol Commercial Devices Acetyl Propionyl Diacetyl Acetoin Acetyl Propionyl Diacetyl Acetoin A B C D E F Brand A B C D E F Brand 20
21 Developed and validated a method for diacetyl, acetyl propionyl, and acetoin in e-liquids and e-cigarettes aerosols Required no derivatization chemistry Simple sample preparation Summary Target analytes transferred efficiently to the aerosol Analytes were present in commercial products 12 of the 13 commercial refill e-liquids tested contained measurable levels of at least one analyte 1 of the 6 commercially available e-cigarettes contained measurable levels of all the analytes NuMark MarkTen XL products contained no measurable levels of the analytes. 21
22 Backup 22
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