Synthesis of (±)-3,4-dimethoxybenzyl-4- methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)

Capsinoids exhibit health-promoting properties and are therefore compounds of interest for medical and food sciences. They are minor compounds present in relatively high concentrations in only a few number of pepper cultivars. It is desirable to quantify capsinoids to provide selected cultivars with high capsinoid contents, which can then be employed as health food product. Quantifying low concentrations of capsinoids from pepper fruit requires a precise and selective analytical technique such as HPLC coupled to electrospray ionization - mass spectrometry, with development of an internal standard essential. In this work, the synthesis method of a novel compound analogue of capsinoids, the (±)-3,4-dimethoxybenzyl-4-methyloctanoate, which could be a suitable internal standard for capsinoid determination by electrospray ionization - mass spectrometry is described. (±)-3,4-dimethoxybenzyl-4-methyloctanoate was stable under the analysis conditions and exerted chemical and physical properties similar to those of capsinoids. This internal standard will provide an accurate capsinoid determination by electrospray ionization - mass spectrometry, thus facilitating the pepper breeding programs, screening pepper cultivars and a better understanding of capsinoid biosynthetic pathway.

This study was supported by the National Institute for Agriculture and Food Research and Technology (INIA) and has been co-financed by the European Fund for Regional Development (FEDER) (grant number RTA2011-00118-C02 and RTA2015-00042-C02-00). Also, it was supported for Aragon Government-A16. Author O. Fayos has received research grants from INIA (RTA2011-00118-C02-01).

Capsiate

Dihydrocapsiate

DMBO

Fragmentation pattern

HPLC-MS/MS

Internal standard

Synthesis method

Published