Jack C. Cappozzo Separation Science Webinar March 12, 2013
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1 Jack C. Cappozzo Separation Science Webinar March 12, 2013
2 Research/Analytical Purpose Adulteration (economical/food safety) Authenticity (economical/quality) Quality Sensory Analytical Instrumentation
3 Adulteration Nineteen Arrested Over Alleged Olive Oil Fraud (Spain, Olive Oil Times) Spanish Police Say Palm, Avocado, Sunflower Was Passed Off as Olive Oil (Spain, Olive Oil Times) Two Plead Guilty in Olive Oil Fraud Scheme, Sentenced to Two Years in Jail (Spain, 2011, Olive Oil Times) Toxic Oil Syndrome (TOS), Spain 1981
4 Adulteration Quality Health Nutritional Loss Illness Economics
5 Economics At 10% adulteration (soybean oil), the producer saves about $0.20/Kg commodity pricing Metric Ton of Olive Metric Ton.$200 3 M Metric Tons in Spain 10% = 300,000 Metric $60 million (in Savings) Retail 10% oil (100 Kg) savings $ ,000
6 Analytical Tests Needed for EVOO/OO 23 tests (reduce that to about 20 tests) $$$$$$$$
7 Olive Oil (Extra Virgin) (Standards of Identity) Sterol composition and content Fatty acid composition Saturated fatty acid content in position 2 of the triglyceride Unsaponifiable material Wax content Erythrodiol and uvaol ECN 42 content UV Light Absorbency Moisture and Volatiles Metal Traces Hydrocarbons: stigmastadiene, stigmasta-3, 5 diene, and campesta-3, 5 diene Trans fatty acid isomer Total aliphatic alcohols DNA characterization Color Aspect Free Acidity Peroxide Value Insoluble Impurities Flash Point
8 Olive Oil (Standards of Identity) Sensory Halogenated Solvents Additives Heavy Metals & Pesticide Residues
9 Olive Oil (IFSH Focus) Technology for Olive Oil Authenticity & Adulteration Rapid Technology for Olive Oil Quality (Sensory) Collaborators Agilent Alpha Mos AOCS LC-MS/MS and QTOF GC-MS ICP-MS Electronic Nose (FID) Statistical Analysis Software Goal Rapid Techniques to relate to sensory quality (Rapid) Technology to confirm Authenticity and Adulteration
10 Technology LC-Q-TOF Electronic Nose/GC-MS PCA Statistical Mapping
11 Mass Spectroscopy LC-MS-TOF (Q- TOF) LC-MS/MS
12 LC-QTOF Sample Prep and Chromatographic Parameters Method: 5 ml oil diluted with 5 ml hexane extracted twice with 10 ml methanol, evaporated and reconstituted in 50% methanol in water. (Polar Fraction) Chromatographic separation achieved on a Poroshell 120 EC-C µm column kept at 45 o C Gas temp was 325 o C with a flow of 10 L/min Nebulizer was 45 psig Analysis was conducted in positive ionization mode Injection volume 5 µl The mobile phase was a gradient of 0.1% acetic acid in water and acetonitrile starting at 5% ACN and increasing to 100% ACN over 25 min with a post time of 3 min.
13 Italian Olive Oil/Soybean Oil
14 Overlay
15 Oil Analysis Using QTOF Technology Chromatograms Produced Using MFE (Molecular Feature Extraction) and Contain Several Thousands of Compounds Olive Oil from Palestine Soybean Oil
16 Mass Profiler Professional MPP software allows multivariance statistical analysis of MS data Data can be filtered based on set parameters and organized into entity lists.
17 Mass, Retention Time
18 PCA Italian Olive Oil
19 Olive Oil Varieties
20 PCA Analysis of Olive Oils and Olive Oils Combined with Vegetable Oils
21 Venn Diagram of Olive Oils and Olive Oils Overlap with Soybean Specific entity lists can be displayed in many different ways. An example is A Venn diagram representing similarities and differences among various groups of samples.
22 ID Browser for Identification of Compounds included in Entity Lists An entity list can be also identified based on available databases and libraries using the ID browser
23 Table of representative 38 compounds identified in EVOO. Over 200 compounds identified. Name Formula Mass RT 12-amino-octadecanoic acid C18 H37 N O Oxo-4E-hexenoic acid C6 H8 O Vanillin C8H8O ,4-bis(methylene)-Hexanedioic acid C8 H10 O ,3-Dihydroxy-3-methylvaleric acid C6 H12 O Oleamide C18 H35 N O ,2-dimethyl-4-pentenoic acid C7 H12 O (R)-3-methyl-2-oxo-Pentanoic acid C6 H10 O ,2-dimethyl-3-butenoic acid C6 H10 O Hydroxycinnamic acid C9 H8 O oxo-4-pentenoic acid C5 H6 O (5R)-5-Hydroxyhexanoic acid C6 H12 O (R)-3-methyl-2-oxo-Pentanoic acid C6 H10 O Octenedioic acid C8 H12 O (5R)-5-Hydroxyhexanoic acid C6 H12 O keto-n-caprylic acid C8 H14 O ,2-dimethyl-4-pentenoic acid C7 H12 O Isovalerylglucuronide C11 H18 O E,4E,6E,8E-Decatetraenedioic acid C10 H10 O amino-undecanoic acid C11 H23 N O ethyl-3E-hexenoic acid C8 H14 O amino-dodecanoic acid C12 H25 N O ,8-dihydroxy-octanoic acid C8 H16 O ,2-dimethyl-4-pentenoic acid C7 H12 O methyl-pentadecanoic acid C16 H32 O ,12,14-octadecatrienoic acid C18 H30 O ,4,5-Trimethoxycinnamic acid C12 H14 O oxo-5,8-decadienoic acid C10 H14 O ,6-dioxo-decanoic acid C10 H16 O S-amino-pentanoic acid C5 H11 N O oxo-7-octenoic acid C8 H12 O (+)-catechin C15 H14 O Tyrosol C8H10O (+)-pinoresinol C20H22O Syringic acid C9H10O Caffeic acid C9H8O Elenolic acid C11 H14 O p-coumaric acid C9H8O
24 Name Formula Mass RT 12-amino-octadecanoic acid C18 H37 N O Oxo-4E-hexenoic acid C6 H8 O Vanillin C8H8O ,4-bis(methylene)-Hexanedioic acid C8 H10 O ,3-Dihydroxy-3-methylvaleric acid C6 H12 O Oleamide C18 H35 N O ,2-dimethyl-4-pentenoic acid C7 H12 O (R)-3-methyl-2-oxo-Pentanoic acid C6 H10 O ,2-dimethyl-3-butenoic acid C6 H10 O Hydroxycinnamic acid C9 H8 O oxo-4-pentenoic acid C5 H6 O (5R)-5-Hydroxyhexanoic acid C6 H12 O (R)-3-methyl-2-oxo-Pentanoic acid C6 H10 O Octenedioic acid C8 H12 O (5R)-5-Hydroxyhexanoic acid C6 H12 O keto-n-caprylic acid C8 H14 O ,2-dimethyl-4-pentenoic acid C7 H12 O Isovalerylglucuronide C11 H18 O E,4E,6E,8E-Decatetraenedioic acid C10 H10 O amino-undecanoic acid C11 H23 N O ethyl-3E-hexenoic acid C8 H14 O amino-dodecanoic acid C12 H25 N O ,8-dihydroxy-octanoic acid C8 H16 O ,2-dimethyl-4-pentenoic acid C7 H12 O methyl-pentadecanoic acid C16 H32 O ,12,14-octadecatrienoic acid C18 H30 O ,4,5-Trimethoxycinnamic acid C12 H14 O oxo-5,8-decadienoic acid C10 H14 O ,6-dioxo-decanoic acid C10 H16 O S-amino-pentanoic acid C5 H11 N O oxo-7-octenoic acid C8 H12 O (+)-catechin C15 H14 O Tyrosol C8H10O (+)-pinoresinol C20H22O Syringic acid C9H10O Caffeic acid C9H8O Elenolic acid C11 H14 O p-coumaric acid C9H8O Blue=phenolic compounds Green=fatty acids
25 PCA
26 3-D PCA
27 PCA Analysis of Italian (P) Greek (G) Olive Oils and Soybean Oil(B). Cluster analysis based on five sensors with the highest discrimination power.
28 Palestinian Olive Oil Adulterated with 2%, 5% and 10% Soybean Oil
29 IFSH Direction Oxidation correlated to Analytical Methods PV, FFA, Sensory correlated to Analytical Methods Continue with Adulteration and Authenticity ICP-MS HS-GC-MS Statistical Analysis PCA Mass Profiler Professional
30 IFSH Institute for Food Safety & Health (IFSH) Bedford Park, IL National Center for Food Safety and Technology (NCFST) At the Illinois Institute of Technology (IIT) Chicago 50:50 IIT:FDA Collaborative Model of Industry:Academia:FDA Food Safety Chemistry, Process Engineering, Microbiology (molecular biology) Nutrition (biological/clinical) In existence for 23 years
31
32 Thank you Questions?
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