Vanillylamine

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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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

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