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;
UNII	1WEZ91E3Z0 ;
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

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]

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

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.
"MetaCyc Pathway: capsaicin biosynthesis". MetaCyc.
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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[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.

[MetaCyc-2] "MetaCyc Pathway: capsaicin biosynthesis". MetaCyc.

[WangYang2009-3] 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.