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.
^ ^a ^b "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.

[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.

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