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
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).
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.

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. "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.
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