Derivatives of 10,16-Dihydroxyhexadecanoic Acid Isolated from Tomato (Solanum lycopersicum) as Potential Material for Aliphatic Polyesters

Daniel Arrieta-Baez,L Gerardo Zepeda-Vallejo,Miguel Cruz-Carrillo,Mayra Beatriz Gómez-Patiño

doi:10.3390/molecules16064923

Abstract

The main monomer of tomato cuticle, 10,16-dihydroxyhexadecanoic acid (or 10,16-dihydroxypalmitic acid; 10,16-DHPA), was isolated and used to efficiently synthesize two different monomers (16-hydroxy-10-oxo-hexadecanoic and 7-oxohexa-decanedioic acids) in addition to a dimer and linear and branched trimers. These compounds were fully characterized using NMR and MS techniques and could be used as starting materials for the synthesis of a wide range of chemicals and bio-polyesters, particularly the latter due to their physical properties, non-toxicity, and relative abundance among raw materials.

Highlights

There is a great need to develop chemistry that is based on the use of biodegradable and renewable resources [1]
The present work describes the use of 10,16-DHPA to efficiently synthesize the 16-dihydroxy10-oxo-hexadecanoic acid [13,16,25], 7-oxohexadecanendioic acid [26], as well as a dimer and linear and branched trimer compounds. These products were characterized by nuclear magnetic resonance (NMR) and mass spectrometry (MS) and they could be used as starting materials in the preparation of different aliphatic polyesteres with potential industrial applications
We found 10,16-DHPA as the main isomer isolated from tomato cutin according to the mass analysis from different derivatives (Table 1)

Summary

Introduction

There is a great need to develop chemistry that is based on the use of biodegradable and renewable resources [1]. The present work describes the use of 10,16-DHPA to efficiently synthesize the 16-dihydroxy10-oxo-hexadecanoic acid (a monomer present in lime cuticle) [13,16,25], 7-oxohexadecanendioic acid [26], as well as a dimer and linear and branched trimer compounds These products were characterized by nuclear magnetic resonance (NMR) and mass spectrometry (MS) and they could be used as starting materials in the preparation of different aliphatic polyesteres with potential industrial applications

Results and Discussion

Preparation and Characterization OF Dimer 7 and Trimer 8

Preparation of Linear Trimer

General

Synthesis

Conclusions