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.[2]

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.

References

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