Vanillylamine

Vanillylamine
Names
Preferred IUPAC name
4-(Aminomethyl)-2-methoxyphenol
Other names
4-Hydroxy-3-methoxybenzylamine
α-Amino-2-methoxy-p-cresol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H11NO2/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,10H,5,9H2,1H3
    Key: WRPWWVNUCXQDQV-UHFFFAOYSA-N
  • InChI=1/C8H11NO2/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,10H,5,9H2,1H3
    Key: WRPWWVNUCXQDQV-UHFFFAOYAK
  • Oc1ccc(cc1OC)CN
Properties
C8H11NO2
Molar mass 153.181 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

  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.