Vanillylamine

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
3D model (JSmol)	Interactive image
ChemSpider	64127
PubChem CID	70966
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	153.18 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

Vanillylamine is an alkaloid 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]

References

↑ Edward Leete and Mary C. L. Louden (1968). "Biosynthesis of capsaicin and dihydrocapsaicin in Capsicum frutescens". J. Am. Chem. Soc. 90 (24): 6837–6841. PMID 5687710. doi:10.1021/ja01026a049.
1 2 "MetaCyc Pathway: capsaicin biosynthesis". MetaCyc.

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