Capsicum species, pungent principle

Suzuki, T. and Iwai, K. (1984) Constituents of red pepper species. Chemistry, biochemistry, pharmacology, and food science of the pungent principle of capsicum species, Brossi, A. (Ed.) The Alkaloids, Vol. 23, Academic Press, Orlando, FL, 227-299. 

It is interesting to discuss the SEE of capsaicin next, directly after the discussion of the SEE of vanillin. Capsaicin is an amide (containing isoprene units) derivative of vanillin. Ten parts per milhon can be detected by tasting. Capsaicin is the compound responsible for the pungency (heat) of Jalapena and other peppers. It is the pungent principle in fruit of various species of Capsicum Solanaceae. 

Capsaicin. (E)-N-[i4-Hydroxy-3-methoxyphenyl)-methylJ-S-methyi-d-nonenamide trans-8-methyl-N-vanii-iyl-6-nonenamide N-(4-hydroxy-3-methoxy benzyl)-8-methyluon-Irons-6 -enamide Mioton Zostrix. CjgH-NOj mol wt 305.40. C 70.78%, y 8,91%. N 4.59%, O 15.72%. Pungent principle in fruit of various species of Capsicum. Solanaceae. I soln from paprika and cayenne Thresh, pharm. J. and Trans. 7, 21 (1876) Micko, Z. Nahr. Gen-ussrn. 1, 818 (1898). See Beihtein 13, suppl. I, 322. Early structure study Nelson, J. Am. Chem. Soc. 42, 597 (1920). Synthesis Spath, Darling, Ber. 63, 737 (1930) L. Crombie et al. J. Chem. Soc. 1955, 1025 O. P. Vig et al, Indian J. Chem. 17B, 558 (1979). Constitution and biosynthesis D. 

A number of phenylpropanoids are perceived as pungent by humans and presumably by other organisms. Among these are capsaicin (20), the pungent principle of peppers Capsicum species, Solanaceae) and piperine (21), the pungent principle of black pepper Piper nigrum, Piperaceae) (Fig. 8.9) (Harbome, 1982). 

The pungent principles of the fruits of pepper Capsicum species, Solanaceae) are A-(4-hydroxy-3-methoxybenzyl)al-kyl amides (Fig. 28.6). This plant should not be confused with black pepper. Piper nigrum (Piperaceae) see the discussion of pungent principles of black pepper in Chapter 29). The major and best known of these compounds is capsaicin (12) (Suzuki and Iwai, 1984). Capsaicin and its relatives comprise about 0.5-1.5% of some hot pepper cultivars. Other pepper cultivars have been selected for their very low content of these compounds. Capsaicin is synthesized in the fruit of Capsicum species (Suzuki and Iwai, 1984). 

Tirimann, a. S. L., 1972, Quantitative determination of the pungent principle (capsaicin) of Ceylon chillies (Capsicum species). Analyst (London) 97 372-375. 

Species of red peppers, or Capsicum (Solanaceae), are well-known as spicy ingredients in food, especially in tropical countries. The fruits contain a variable amount of highly pungent principles, the so-called capsaicinoids, which have the general structure iV-(4-hydroxy-3-methoxybenzyl)alkylamides (55). Suzuki and Iwai (186) have provided a recent introductory review. These compounds also have potent pharmacological properties. 

---