Long-Chain Polyhydroxyesters from Natural Occurring Aleuritic Acid as Potential Material for Food Packaging

Fatty polyhydroxyesters (C≥16) are present in nature as barrier polymers like cutin in some protective tissues of higher plants. The mimicry of these biopolymers is regarded as a strategy to design nontoxic and fully biodegradable food packaging films and coatings. To obtain cutin inspired materials we have used a natural occurring polyhydroxylated monomer like aleuritic (9,10,16-trihydroxypalmitic) acid and a direct and scalable synthesis route consisting in the noncatalyzed melt-condensation polymerization in air. To reduce the number of hydroxyl groups and to increase hydrophobicity, palmitic acid has been used as a capping agent. Aleuritic-palmitic polyhydroxyesteres films have been obtained and characterized.

[1]  J. Rose,et al.  There's more than one way to skin a fruit: formation and functions of fruit cuticles. , 2013, Journal of experimental botany.

[2]  G. Sandoval,et al.  Oligomerization of 10,16-Dihydroxyhexadecanoic Acid and Methyl 10,16-Dihydroxyhexadecanoate Catalyzed by Lipases , 2013, Molecules.

[3]  R. Gross,et al.  Polymers from fatty acids: poly(ω-hydroxyl tetradecanoic acid) synthesis and physico-mechanical studies. , 2011, Biomacromolecules.

[4]  L. G. Zepeda-Vallejo,et al.  Derivatives of 10,16-Dihydroxyhexadecanoic Acid Isolated from Tomato (Solanum lycopersicum) as Potential Material for Aliphatic Polyesters , 2011, Molecules.

[5]  A. K. Pandey,et al.  Synthesis and characterization of novel value added biodegradable poly(aleuritic acid) from renewable resources (shellac) and invertible amphiphilic behaviors in various solvents , 2010 .

[6]  A. Heredia,et al.  Synthesis and characterization of a plant cutin mimetic polymer , 2009 .

[7]  Haiqing Peng,et al.  Sidewall carboxylic acid functionalization of single-walled carbon nanotubes. , 2003, Journal of the American Chemical Society.

[8]  P. Hatcher,et al.  Evidence for cross-linking in tomato cutin using HR-MAS NMR spectroscopy. , 2003, Phytochemistry.

[9]  G. Hoatson,et al.  Modelling one‐ and two‐dimensional solid‐state NMR spectra , 2002 .

[10]  D. Hachey,et al.  Analysis of diacyl peroxides by Ag+ coordination ionspray tandem mass spectrometry: Free radical pathways of complex decomposition , 2001, Journal of the American Society for Mass Spectrometry.

[11]  A. Aganov,et al.  13C NMR Spectra of organic peroxides , 1982 .

[12]  S. Krimm The infrared spectra of complex molecules, Vol. 1 (3rd ed.), L. J. Bellamy, Halsted Press, a division of John Wiley & Sons, Inc., New York, 1975, 433 pp. $24.00 , 1976 .

[13]  L. J. Bellamy Esters and Lactones , 1975 .

[14]  E. Baker,et al.  The constituent acids of angiosperm cutins , 1970 .

[15]  L. J. Bellamy The infra-red spectra of complex molecules , 1962 .

[16]  W. Davison,et al.  Infrared spectra and crystallinity. Part I. Polyesters , 1955 .

[17]  W. Davison 542. Infra-red absorption of the carbonyl group. Part I. Diacyl peroxides, per-esters, and per-acids , 1951 .