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Ethylation of the common benzyl group caused the fragmentation of that group to increase from m/z 137 to 165
Spectrum of dihydrocapsaicin derivative 10
Method II. Analysis of capsaicin in hot pepper fruits Prepare samples (Red Serrano and Caribbean Red) Identification and isolation of capsaicin Internal standard was added to the extracted capsaicin GC/MS Analysis using same parameters as the standard 11
Conclusions An ethylated capsaicin derivative can be used as an internal standard by GS/MS techniques to quantify the amount of capsaicin and dihydrocapsaicin in hot peppers. However, an optimal derivatization with 100 mg of capsaicin is needed to efficiently quantify capsaicin and dihydrocapsaicin in a variety of hot peppers. Once an appropriate amount of internal standard is constructed and free of errors, a calibration curve can be constructed. 16
Successes and Failures Operation and method procedures Capsaicin derivatization- Trial and Error Suitable reaction guidelines Advantages and disadvantages Alkylating reagents and targeted functional group Derivatization side reactions and contamination NaOH on capsaicin and derivatized product 17
Use of a different alkylating reagent such as DMF* for comparison Experiment with different evaporation/drying methods Use of derivatized internal standard on capsaicin products other than hot peppers 19 Future Studies *Boger, Dale. Thermal Atropisomerism of TeicoplaninAglycon Derivatives: Preparation of the P,P,P and M,P,P Atropisomer of the TeicoplaninAglycon via Selective Equilibration of the DE Ring System, J. Am. Chem. Soc. 2000, 122, 10047-10055
Acknowledgments Dr. David von Minden Dr. Steven Meier Dean of College of Mathematics and Science and Dr. Cheryl Frech Ryan Hays Amanda Bridges, Will Watkins and Monkey Business from Lawton, OK 20
21 Literature Resources 1. Govindarajan V.S. and Sathyanarayana M.N. Capsicum-Production, Technology, Chemistry, and Quality. Part V: Impact on Physiology. Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization sequences. Food Sci. and Nutr. 1991, 29, 435–474. 2. Bucholz, C. F. ChemischeUntersuchungDerTrockenenReifenSpanischenPfeffers [Chemical Investigation of Dry, Ripe Spanish Peppers]. AlmanachoderTaschenbuchfürScheidekünstler und Apotheker (Weimar) [Almanac or Pocket-Book for Analysts (Chemists) and Apothecaries. 1816, 37, 1–30. 3. Thresh, J. C. Isolation of Capsaicin. The Pharmaceutical Journal and Transactions. 1876. 3rd series, 6, 941–947. 4. Späth, E. and Darling, S.Synthese des Capsaicins. Chem. Ber. 1930, 63B, 737–743. 5. Kosuge, S., Inagaki, Y., and Okumura, H. Studies on the Pungent Principles of Red Pepper. Part VIII. On the Chemical Constitutions of the Pungent Principles. Nippon Nogei Kagaku Kaishi. J. Agric. Chem. Soc. 1964, 35, 923–927. 6.New Mexico State University—College of Agriculture and Home Economics Home Page. "Chile Information—Frequently Asked Questions. http://web.archive.org/web/20070504035555/http://spectre.nmsu.edu/dept/academic.html?i=1274&s=sub. (accessed Dec 1, 2010). 7. Razavi, R., Chan, Y., and Afifiyan, F.N. et al. TRPV1+ Sensory Neurons Control Beta Cell Stress and Islet Inflammation in Autoimmune Diabetes. Cell. 2006. 127, 6, 1123–1135. 8.Mori, A., Lehmann, S. and O’ Kelly J. et al. Capsaicin, A Component of Red Peppers, Inhibits the Growth of Androgen-Independent, p53 Mutant Prostate Cancer Cells. Cancer Research. (American Association for Cancer Research). 2006, 66, 6, 3, 222–3,229. 9. Which Treatment for Postherpetic Neuralgia? PLoS Medicine. 2005, 2, 7, e238. 10.Glinski, W., Glinska-Ferenz, M., and Pierozynska-Dubowska, M. Neurogenic Inflammation Induced by Capsaicin in Patients with Psoriasis. Actadermato-Venereologica (ActaDermVenereol). 1991, 71, 1, 51–54. 11. The Journal of the American Pharmacists Association. Note on Capsicums. 1912, 1, 453–454. 12. Cooper, T.H., Guzinski, J.A., and Fisher, C. Improved High-Performance Liquid Chromatography Method for the Determination of Major Capsaicinoids in Capsicum Oleoresins. J. Agric. Food Chem. 1991, 39, 2253–2256. 13. Li, H., Pordesimo, L.O., Igathinathane, C., and Vinyard. B. Physical Property Effects on Drying of Chile Peppers. International Journal of Food Properties. 2009. 12, 2, 316–330.
23 Literature Resources Antonious, G., & Jarret, R. (2006). Screening Capsicum Accessions for Capsaicinoids Content. Journal of Environmental Science & Health, Part B -- Pesticides, Food Contaminants, & Agricultural Wastes, 41(5), 717-729. Barbero, G., Liazid, A., Palma, M., & Barroso, C. (2008). Ultrasound-assisted extraction of capsaicinoids from peppers. Talanta, 75(5), 1332-1337 Li, H., Pordesimo, L., Igathinathane, C., & Vinyard, B. (2009). Physical Property Effects on Drying of Chile Peppers. International Journal of Food Properties, 12(2), 316-330. Li, F., Lin, Y., Wang, X., Geng, Y., & Wang, D. (2009). Preparative isolation and purification of capsaicinoids from Capsicum frutescens using high-speed counter-current chromatography. Separation & Purification Technology, 64(3), 304-308. Thompson, R., Phinney, K., Welch, M., & White V., E. (2005). Quantitative determination of capsaicinoids by liquid chromatography-electrospray mass spectrometry. Analytical & Bioanalytical Chemistry, 381(7), 1441-1451 Thompson, R., Pennino, M., Brenner, M., & Mehta, M. (2006). Isolation of individual capsaicinoids from a mixture and their characterization by 13C NMR spectrometry. Talanta, 70(2), 315-322. Von Minden, D. , & D’Amato, N. (1977) Simultaneous Determination of Cocaine and Benzoylecgonine in Urine by Gas-Liquid Chromatography. Analytical Chemistry, 49(13), 1974-1976.
24 What is Capsaicin? Definition: Capsaicin is a colorless pungent crystalline compound derived from the genus Capsicum. Capsaicin is the source of the “hotness” found in peppers such as chili, cayenne and jalapeno. Why is it a “hot” topic?
This chemical is a cancer fighter, a digestive aid and a powerful pain killer.
It is found in a high-dose dermal patch called Qutenza1 that is used to treat the pain of peripheral neuropathy (i.e. Shingles).
Capsaicin creams are primarily used to relieve pain and itching. Some conditions include back pain, fibromyalgia, psoriasis, and arthritis2.
The American Association for Cancer Research reports studies suggesting capsaicin is able to kill prostate cancer cells by causing them to undergo apoptosis3.
(2010). QUTENZA. Monthly Prescribing Reference, 26(6), A.16. Retrieved from Academic Search Complete database Welland, D. (2008). Spice Up Your Cuisine To Help Protect Against Heart Disease, Cancer, Diabetes. (Cover story). Environmental Nutrition, 31(10), 1-4. Retrieved from Academic Search Complete database. (2006). HOW HOT PEPPERS LEAD TO SUICIDES. Maclean's, 119(13), 41. Retrieved from Academic Search Complete database.
28 First Derivitization 200 μL of Capsaicin Standard; evaporate 200 μL of N,N-DMA and 50 μL of TMAH (25%) 10 μL of Methyl-Iodide; (45 °C for 30 minutes) 500 μL of 0.1 M Na2CO3 200 μL CCl4, vortex. Figure 1. TIC of Derivitized Product (CH3-R); 9/29/2010 Abundance Time
34 Part 1. The Isolation and Identification of Capsaicin in Hot Peppers A Variety of Hot Peppers preparation of samples by a drying processes Extraction food processor; cyclohexane pipettes with glass wool GC/MS Analysis Agilent Technologies 6890N GC System with a 5975 inert XL Mass Selective Detector
35 Part 2. Alkylation of the Hydrogens to Produce an Internal Standard 200 μL Capsaicin (95% Pure Pharmaceutical Grade) 1. NNDMA 2. TMAH 3. Methyl Iodide 4. Na2CO3/CCl4 Alkylated Capsaicin