Rosas, Julieta;Martinez, Joel O.;Alonso, Pedro;Miranda, Rene;Velasco, Luis;Rubio-Perez, Laura;Perez, Francisco J. published 《Alternative mass spectrometry techniques for the validation of the fragmentation pattern of capsaicin and dihydrocapsaicin》. The research results were published in《Rapid Communications in Mass Spectrometry》 in 2019.Recommanded Product: N-Vanillylnonanamide The article conveys some information:
Rationale : Capsaicinoids are prevalent secondary metabolites in many natural and synthetic pharmacol. compounds To date, several soft ionization studies related to capsaicinoids have been reported; they all proposed a common fragmentation pattern based on a rearrangement of the aromatic double bonds and the fragmentation of the various positional acyl chains. However, the mechanism has never been validated by high-resolution analyses. Consequently, in this work, a validated fragmentation mechanism of the main capsaicinoids, capsaicin (1) and dihydrocapsaicin (2), is offered. Methods : In order to propose and validate a common electron ionization (EI) fragmentation mechanism for the target analytes, the following mass spectrometric methods were employed: collision-induced dissociation (CID) by means of linked scans (LS), reinforcing the methodol. by high-resolution mass spectrometry (HRMS), in addition to appropriate deuterium-labeled experiments performed using gas chromatog./mass spectrometry (GC/MS) and direct anal. in real time (DART). Results : In a first stage, a common EI fragmentation pattern comprising two pathways was proposed for compounds 1 and 2; then, the suggested mechanism was validated by CID-LS together with HRMS complemented by DART-deuterium-labeling studies. The obtained results are indicative that the corresponding mol. ions were conveniently observed, m/z 305 and m/z 307; it is worth noting that the common base peak is in correspondence with a tropylium ion derivative (m/z 137), as a consequence of a McLafferty rearrangement. In addition to these highlighted fragments, other common ions, m/z 122 and m/z 94, and their corresponding trajectory, were confirmed using the same approach. Finally, the proposed mechanism was complementarily validated by deuterium-labeling studies, taking into account the two exchangeable hydrogens present in the phenolic and the amidic moieties. Conclusions : A common validated EI fragmentation pattern for both capsaicin and dihydrocapsaicin was established using appropriated mass spectrometric methods together with convenient hydrogen/deuterium labeling. This study provides a new alternative to validate mechanisms of fragmentation of important natural products. And N-Vanillylnonanamide (cas: 2444-46-4) was used in the research process.
N-Vanillylnonanamide(cas:2444-46-4) is also called pelargonic acid vanillylamide or PAVA.Recommanded Product: N-Vanillylnonanamide Similar to capsaicin, nonivamide can activate the TRPV1 receptor, thus, stimulate the firing rate of dopaminergic neurons in the ventral tegmental area of the brain and to increase the expression of the serotonin receptor gene HTR2A.
Reference:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics