Vanillylamine Explained

Vanillylamine is a chemical compound that is an intermediate in the biosynthesis of capsaicin.^[1] Vanillylamine is produced from vanillin by the enzyme vanillin aminotransferase.^[2] It is then converted with 8-methyl-6-nonenoic acid into capsaicin by the enzyme capsaicin synthase.

Reactions

Acylation of vanillylamine using Schotten-Baumann reactions can provide amide derivatives.^[3] Examples include nonivamide (a component of some pepper sprays), olvanil, and arvanil.

Notes and References

1. Biosynthesis of capsaicin and dihydrocapsaicin in Capsicum frutescens . Edward Leete and Mary C. L. Louden . J. Am. Chem. Soc. . 1968 . 90 . 24 . 6837–6841 . 10.1021/ja01026a049. 5687710 .
2. Web site: MetaCyc Pathway: capsaicin biosynthesis . MetaCyc .
3. Wang. Bo. Yang. Fan. Shan. Yi-Fan. Qiu. Wen-Wei. Tang. Jie. Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system. Tetrahedron. 65. 27. 2009. 5409–5412. 0040-4020. 10.1016/j.tet.2009.04.046.