Analytical challenges in the chemical assessment of food and related consumer products
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1 Analytical challenges in the chemical assessment of food and related consumer products Chris Wright, Justin Frosina, Jasper van Heemst & Louise Bishop British American Tobacco Group Research & Development Southampton UK
2 Outline Chemical testing requirements Suites of substances Established approaches Testing for compliance vs testing for safety Unknown substances and TTC Targeted and non-targeted screening approaches Advances and potential constraints
3 Chemical testing requirements Foodstuffs (excluding nutritional analysis) - Natural toxicants, e.g. mycotoxins - Environmental contaminants, e.g. trace metals, dioxins, PAHs - Process contaminants, e.g. 3-MCPD, acrylamide - Regulated residues, e.g. pesticides, veterinary medicines - Food contact residues, e.g. benzophenone, ESBO Cosmetics - Residues in ingredients, e.g. PAHs in carbon black - Constituent evaluation, e.g. allergens - Process contaminants, e.g. N-nitrosamines in hair dyes Other FMCGs - Compliance monitoring, e.g. Bisphenol A in feeding bottles - Due diligence, e.g. stability of ingredients
4 Testing processes - Food Risk-based approach - food or ingredient type, region of origin - relevant residue classes / suites Screening approaches - in vitro assays, semi-quantitative methods Confirmatory analytical methods - quantitative, selective, accurate, rugged Certification traceable to accredited test Quality control (internal & external) - proficient, comparable, robust data
5 Tobacco and regulatory requirements Combustible products tar, nicotine Smokeless products nicotine, ph WHO Framework Convention on Tobacco Control Wide range of measures to reduce the demand for tobacco To be implemented in legislation by signatories to the treaty Family Smoking Prevention and Tobacco Control Act, 2009 FDA authority to regulate the content, marketing and sale of tobacco products Harmful and Potentially Harmful Constituents of tobacco and tobacco smoke
6 Aflatoxin B1 Anabasine Acetamide Revised TPSAC HPHC list April 2012ent (Schedule 2) Cobalt Coumarin Ammonia Toluene Styrene Quinoline Phenol m+p - Cresol 1 - aminonaphthalene 4- aminobiphenyl Crotonaldehyde Catechol Hydrogen cyanide (NAB) Acrylamide A-α-C (2-amino-9H-pyrido[2,3-b]indole) Benzo(b)furan Benzo[c]phenanthrene Chlorinated dioxins/furans Chrysene N-nitrosodimethylamine (NDMA) Cyclopenta[c,d]pyrene N-Nitrosomorpholine (NMOR) Dibenzo[a,h]anthracene Dibenzo[a,e]pyrene Dibenzo[a,h]pyrene Dibenzo[a,i]pyrene Dibenzo[a,l]pyrene 2,6-Dimethylaniline Ethyl Carbamate (urethane) Ethylbenzene Ethylene oxide Furan (Pyridine) (NFDPM) N-nitrososarcosine (NSAR) (NAT) Nornicotine (Hydroquinone) Cadmium Selenium Acetaldehyde Acrolein Formaldehyde 1,3 Butadiene NNK Nicotine Benzene CO Nickel Glu-P-1 (2-Amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole) Glu-P-2 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole) Vinyl Chloride (3 aminobiphenyl) Benzo[a]pyrene o-anisidine Acetone 2- aminonaphthalene NNN Acrylonitrile Chromium Mercury Trp-P-1 Vinyl Acetate Benz[a]anthracene Methyl ethyl ketone Lead Benz[j]aceanthrylene (Butyraldehyde) (NO/Nox) Benzo[b]fluoroanthene Propionaldehyde Arsenic o-cresol Isoprene Benzo[k]fluoroanthene (Resorcinol) Beryllium IQ (2-Amino-3-methylimidazo[4,5-f]quinoline) Caffeic acid Hydrazine Indeno[1,2,3-cd]pyrene MeA- α-c (2-Amino-3- methyl)-9h-pyrido[2,3- b]indole) 5-Methylchrysene Naphthalene FCTC Trp-P Nitrobenzene 2-Nitropropane N-Nitrosodiethanolamine (NDELA) Nitromethane N-Nitrosomethylethylamine N-Nitrosopiperidine (NPIP) N-nitrosopyrrolidine (NPYR) PhIP (2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) Polonium-210 Propylene oxide Uranium-235 Uranium-238 HC o-toluidine FDA HPHCs in Cigarette Smoke Acetaldehyde Acrolein Acrylonitrile 4-Aminobiphenyl 1-Aminonaphthalene 2-Aminonaphthalene Ammonia Benzene Benzo(a)pyrene 1,3-Butadiene Carbon monoxide Crotonaldehyde Formaldehyde Isoprene Nicotine (total) NNK NNN Toluene HPHCs in Smokeless Tobacco Acetaldehyde Arsenic Benzo(a)pyrene Cadmium Crotonaldehyde Formaldehyde Nicotine (total & free) NNK NNN
7 Classes of constituents FDA TPSAC April 2012 Trace metals Arsenic Beryllium Cadmium Chromium Cobalt Lead Mercury Nickel Polonium-210 Selenium Uranium-235 Uranium-238 Alkenes / cyanoalkanes 1,3-Butadiene Isoprene Hydrogen cyanide Nitromethane Others Aflatoxin B1 Nitrobenzene 2-Nitropropane Carbon monoxide PCDD/Fs Aromatic amines 4-Aminobiphenyl 1-Aminonaphthalene 2-Aminonaphthalene o-anisidine 2,6-Dimethylaniline o-toluidine Aromatics Benzene Ethylbenzene Toluene Caffeic acid Catechol o-, m-, p-cresol) Phenol Carbonyls Acetaldehyde Acetone Acrolein Crotonaldehyde Formaldehyde Methyl ethyl ketone Propionaldehyde Heterocycles Quinoline Styrene Polycyclic Aromatics Benz[a]anthracene Benz[j]aceanthrylene Benzo[b]fluoranthene Benzo[k]fluoranthene Benzo[b]furan Benzo[a]pyrene Benzo[c]phenanthrene Chrysene Cyclopenta[c,d]pyrene Dibenz[a,h]anthracene Dibenzo[a,e]pyrene Dibenzo[a,h]pyrene Dibenzo[a,i]pyrene Dibenzo[a,l]pyrene Indeno[1,2,3-cd]pyrene 5-Methylchrysene Naphthalene Alkaloids Anabasine Nicotine Nornicotine Low MW volatiles Acetamide Acrylamide Acrylonitrile Ammonia Ethyl carbamate (urethane) Ethylene oxide Furan Hydrazine Propylene oxide Vinyl acetate Vinyl chloride N-nitrosamines 4-(Methylnitrosamino)-1-(3-pyridyl)- 1-butanone N-Nitrosodiethanolamine (NDELA) N-Nitrosodiethylamine N-Nitrosodimethylamine (NDMA) N-Nitrosomethylethylamine N-Nitrosomorpholine (NMOR) N-Nitrosonornicotine (NNN) N-Nitrosopiperidine (NPIP) N-Nitrosopyrrolidine (NPYR) N-Nitrososarcosine (NSAR) Heterocyclic aromatic amines A-α-C (2-Amino-9H-pyrido[2,3- b]indole) Glu-P-1 (2-Amino-6- methyldipyrido[1,2-a:3',2'-d]imidazole) Glu-P-2 (2-Aminodipyrido[1,2-a:3',2'- d]imidazole) CA IQ (2-Amino-3-methylimidazo[4,5- f]quinoline) MeA-α-C (2-Amino-3-methyl)-9Hpyrido[2,3-b]indole) PhIP (2-Amino-1-methyl-6- phenylimidazo[4,5-b]pyridine) Trp-P-1 (3-Amino-1,4-dimethyl-5Hpyrido[4,3-b]indole) Trp-P-2 (1-Methyl-3-amino-5Hpyrido[4,3-b]indole )
8 Established / reference methods European Commission performance requirements (Food) - Decision 2002/657/EC Performance based criteria for selectivity, ruggedness, precision Specifications for separation and unambiguous identification Other specific EC Regulations - Mycotoxins (401/2006); - Dioxins and PCBs (1883/2006); - Lead, Cadmium, Tin, 3-MCPD and Benzo(a)pyrene (333/2007) Extensive use of HPLC/MS and GC/MS technologies Compatible with stable isotope dilution technique Generally one method per class of substances Limited throughput; significant effort to generate the data Does not guarantee that all substances of possible concern have been identified and evaluated - Sudan 1, acrylamide, melamine in milk, nitrofurans,
9 The Threshold of Toxicological Concern
10 Assessing unknown substances
11 Screening for toxicants making the unknown known Table 2 Compounds Identified in the Vapour Phase Scan Chromatogram for Sample 1 Peak No. RT (min) Compound Area % of Total Chloromethane x? ,3-Butadiene +? Methyl-1-Propene Buten-3-yne + Methanethiol Acetaldehyde ? ? Pentene +? Methyl-1-Butene Isoprene Furan ,4-Pentadiene + Ethanol ,3-Cyclopentadiene Propenal Propanal Acetone ? + 2-Methyl-1-Pentene Acetonitrile Methylpropanal Methylfuran Buten-2-one ,3-Butanedione Butanone Benzene-d6 + Benzene ? + 3-Methylbutanal ,5-Dimethylfuran Butenal Pentanone Toluene Ethylbenzene p-xylene Limonene Table 3 Compounds Identified in the Vapour Phase Scan Chromatogram for Sample 2 Peak No. RT (min) Compound Area % of Total Chloromethane x? ,3-Butadiene +? Methyl-1-Propene Buten-3-yne + Methanethiol Acetaldehyde ? ? Pentene +? Methyl-1-Butene Isoprene Furan ,3-Cyclopentadiene Propenal Propanal Acetone ? + 2-Methyl-1-Pentene Acetonitrile Methylpropanal Methylfuran Buten-2-one ,3-Butanedione Butanone Benzene-d6 + Benzene ,5-Dimethylfuran Butenal ? Toluene Ethylbenzene p-xylene Limonene
12 GC x GC - ToF analysis, 3R4F particulate 2-dimensional GC using orthogonal phases; peak capacity = product of the 2 peak capacities First dimension peaks cryogenically attenuated before release into second dimension Unit mass resolution ToF with fast scanning; short second column gives narrow and intense peaks Peak deconvolution using nominal mass spectrum; scripting for missing members of homologous series
13 GC / HR-ToF screening for toxicants 1D-GC coupled to multi-reflectron ToF mass analyser, capable of acquiring m/z at a resolution of (200Hz) to deconvolute peaks and identify substances by accurate mass.
14 Accurate mass peak id
15 GC/HRToF AIC[zoom], PP, 3R4F & RAL1
16 GC/HRToF difference output Peak # Name Type Match Similarity Concentration Conc. Units R.T. (s) Full Width at Half Height Area Height Peak Quality 1 Tris(trifluoromethyl) b Match % Peak 2 Match % Hexyn-3-ol Match % Peak 4 Match % Peak 4 Match % Ethane Match % Peak 7 Match % ChlorotrifluoromethanMatch % Peak 9 Match % Hydroxypipecolic aci Match % Hydrogen sulfide Match % Peak 12 Match % Propene Match % Peak 14 Match % H-1,2-Oxazine, tetrah Match % Terephthalic acid, pentmatch % Hydrogen sulfide Out of Tolerance % Propene Out of Tolerance % H-1,2-Oxazine, tetrah Out of Tolerance % Butyric acid, 2-bromo-,Out of Tolerance % Propylamine Out of Tolerance % Chloromethane Out of Tolerance % Cyanic acid, 2-methylp Out of Tolerance % Palladium, bis[(1,2,3-ü Out of Tolerance % Peak 35 Out of Tolerance % Methanethiol Out of Tolerance % Hydrogen cyanide Out of Tolerance % AdamantanemethylaOut of Tolerance % ,3-Butadiene, 2-meth Out of Tolerance % Furan Out of Tolerance % ,3-Cyclopentadiene Out of Tolerance % Carbamic acid, 4-pyridiOut of Tolerance % à-d-mannopyranoside,out of Tolerance % Hexane, 3,4-bis(1,1-dimOut of Tolerance % Hexyn-3-ol:7 Out of Tolerance % Methyl isocyanide Out of Tolerance % Peak 162 Out of Tolerance % Furan, 2-methyl- Out of Tolerance % Cyclohexene, 4,5-dibroOut of Tolerance % Trifluoromethyl-3-oxOut of Tolerance % Hexen-4-ol, 1-chloro Out of Tolerance % Fumaronitrile Out of Tolerance % Mannose dibenzyl merout of Tolerance % Toluene Out of Tolerance % Ethyl 2-(benzylamino)-Out of Tolerance % Benzene, 1,3-dimethylOut of Tolerance % Dodecane Out of Tolerance %
17 Learnings and observations Improvements Significant reduction in data processing effort Lead time reduced by 60 80% Selectivity and sensitivity increased Currently used in comparison mode Building database for targeted analysis Challenges Data processing peak quality parameters High resolution spectral library construction & use Quantification how to internally standardise? Data mining databases for group comparison
18 BAT Group R&D Justin Frosina Louise Bishop & Jasper van Heemst Leco Alec Kettle Alan Griffiths Thank you ACD Peter Russell & colleagues
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