Vanillylamine

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]

Vanillylamine

Names
Preferred IUPAC name 4-(Aminomethyl)-2-methoxyphenol
Other names 4-Hydroxy-3-methoxybenzylamine α-Amino-2-methoxy-p-cresol
Identifiers
CAS Number	1196-92-5 Y
3D model (JSmol)	Interactive image
ChemSpider	64127
PubChem CID	70966
UNII	1WEZ91E3Z0 Y
CompTox Dashboard (EPA)	DTXSID90152522
InChI 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
SMILES Oc1ccc(cc1OC)CN
Properties
Chemical formula	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). Infobox references

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.