derivatives of 10,16-dihydroxyhexadecanoic acid isolated from tomato (solanum lycopersicum) as potential material for aliphatic polyesters衍生品的16-dihydroxyhexadecanoic酸分离番茄(茄属植物lycopersicum)作为潜在的脂肪族聚酯材料.pdfVIP

Molecules 2011, 16, 4923-4936; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Derivatives of 10,16-Dihydroxyhexadecanoic Acid Isolated from Tomato (Solanum lycopersicum) as Potential Material for Aliphatic Polyesters Daniel Arrieta-Baez *, Miguel Cruz-Carrillo, Mayra Beatriz Gómez-Patiño and L. Gerardo Zepeda-Vallejo Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas-IPN, Prolongación de Carpio y Plan de Ayala S/N, Colonia Santo Tomás, D.F. 11340, Mexico * Author to whom correspondence should be addressed; E-Mail: danielarrieta@; Tel.: +52-55-5729-6300 Ext. 62345. Received: 6 May 2011; in revised form: 1 June 2011 / Accepted: 10 June 2011 / Published: 15 June 2011 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. Keywords: cutin; tomato; 16-hydroxyacids; dimer; trimer 1. Introduction There is a great need to develop chemistry that is based on the use of biodegradable and renewable resource