Chili peppers contain signifi cant quantities of vitamins A, C, and E, as well as folic

Chapter 22, Problem 60

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Chili peppers contain signifi cant quantities of vitamins A, C, and E, as well as folic acid andpotassium. They also contain small quantities of capsaicin, the fi ery essence responsible for thehot in hot peppers. The pure substance is in fact quite dangerous: Chemists working withcapsaicin must work in special fi ltered-air enclosures and wear full body protection. One milligramplaced on the skin will cause a severe burn. Although capsaicin has no odor or fl avor of itsown, its pungency in the form of detectable stimulation of the nerves in the mucous membranesof the mouth can be detected even when the substance is diluted to one part in 17 million ofwater. The hottest peppers exhibit about 1y20th of this level of pungency.The structure of capsaicin is shown on p. 1028. Some of the data that were used in its elucidationare presented below. Interpret as much of this information as you can.MS: mYz 5 122, 137 (base peak), 195 (tricky!), 305.IR: n~ 5 972, 1660, 3016, 3445, 3541 cm21.1H NMR: d 5 0.93 (6H, d, J 5 8 Hz), 1.35 (2H, quin, J 5 7 Hz), 1.62 (2H, quin, J 57 Hz), 1.97 (2H, q, J 5 7 Hz), 2.18 (2H, t, J 5 7 Hz), 2.20 (1H, m), 3.85 (3H, s), 4.33 (2H, d,J 5 6 Hz), 5.33 (2H, m), 5.82 (2H, broad s), 6.73 (1H, d, J 5 9 Hz), 6.78 (1H, s), 6.85 (1H, d,J 5 9 Hz) ppm.

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