Oligomerization of 10,16-dihydroxyhexadecanoic acid and methyl 10,16-dihydroxyhexadecanoate catalyzed by lipases.
The main monomer of tomato cuticle, 10,16-dihydroxyhexadecanoic acid (10,16-DHPA) and its methyl ester derivative (methyl-10,16-dihydroxyhexadecanote; methyl-10,16-DHHD), were used to study their oligomerization reactions catalyzed by five lipases: Candida antarctica lipase B (CAL-B), Rhizomucor miehei lipase (RM), Thermomyces lanuginosus lipase (TL), Pseudomonas cepacia lipase (PCL) and porcine pancreatic lipase (PPL). For 10,16-DHPA, optimum yields were obtained at 60 °C using toluene and 2-methyl-2-butanol (2M2B) as solvent, while for methyl-10,16-DHHD the bests yields were obtained in toluene and acetonitrile. Both reactions leaded to linear polyesters according to the NMR and FT-IR analysis, and there was no data indicating the presence of branched polymers. Using optimized conditions, poly(10,16-DHPA) and poly(methyl-10,16-DHHD) with Mw = 814 and Mn = 1,206 Da, and Mw = 982 and Mn = 860 Da, respectively, were formed according to their MALDI-TOF MS and ESI-MS data. The self-assembly of the polyesters obtained were analyzed by AFM.
Instituto Politécnico Nacional-ENCB, Carpio y Plan de Ayala S/N, Col. Casco de Santo Tomas, México, D.F., CP 11340, Mexico.
M Beatriz
MB
Gómez-Patiño
Julia
J
Cassani
María Eugenia
ME
Jaramillo-Flores
L Gerardo
LG
Zepeda-Vallejo
Georgina
G
Sandoval
Manuel
M
Jimenez-Estrada
Daniel
D
Arrieta-Baez
D002384:Catalysis; D008049:Lipase / Q000737:chemistry*; D018551:Solanum lycopersicum / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010169:Palmitic Acids / Q000737:chemistry* / Q000378:metabolism; D011108:Polymers / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
C474391:10,16-dihydroxyhexadecanoic acid; D010169:Palmitic Acids; D011108:Polymers; D012997:Solvents; D008049:Lipase