Zinc undecenoate 20% / Undecenoic acid 2% powder

Oleic acid and 10-undecenoic acid were used to esterify corn, tapioca, potato and a waxy potato starch, with a maximum degree of substitution of 2.4 and 1.9 respectively. The thermal and mechanical properties were investigated as a function of the amylopectin content and Mw of starch, and by the fatty acid type. All starch esters had an improved degradation temperature regardless of their botanical origin. While the Tg did increase with increasing amylopectin content and Mw, it decreased with increasing fatty acid chain length. Moreover, films with different optical appearances were obtained by varying the casting temperature. SEM and polarized light microscopy showed that films cast at 20 °C had porous open structures with internal stress, which was absent when cast at higher temperatures. Tensile test measurements revealed that films had a higher Young's modulus when containing starch with a higher Mw and amylopectin content. Besides that, starch oleate films were more ductile than starch 10-undecenoate films. In addition, all films were resistant to water at least up to one month, while some light-induced crosslinking took place. Finally, starch oleate films showed antibacterial properties against Escherichia coli, whereas native starch and starch 10-undecenoate did not.

Abstract licence: CC BY-NC-ND

The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol–ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were confirmed by spectral data. The anti-oxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC 50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.

Abstract licence: CC BY

Polyhydroxyalkanoates (PHAs) are biodegradable and biocompatible biopolymers. These biomaterials have grown in importance in the fields of tissue engineering and tissue reconstruction for structural applications where tissue morphology is critical, such as bone, cartilage, blood vessels, and skin, among others. Furthermore, they can be used to accelerate the regeneration in combination with drugs, as drug delivery systems, thus reducing microbial infections. When cells are cultured under stress conditions, a wide variety of microorganisms produce them as a store of intracellular energy in the form of homo- and copolymers of [R]-hydroxyalkanoic acids, depending on the carbon source used for microorganism growth. This paper gives an overview of PHAs, their biosynthetic pathways, producing microorganisms, cultivation bioprocess, isolation, purification and characterization to obtain biomaterials with medical applications such as tissue engineering.

Abstract licence: CC BY

A two-stage chemostat cultivation was used to investigate the biosynthesis of functionalized medium-chain-length polyhydroxyalkanoate (mclPHA) in the β-oxidation weakened strain of P. putida KTQQ20. Chemostats were linked in sequence and allowed separation of biomass production in the first stage from the PHA synthesis in the second stage. Four parallel reactors in the second stage provided identical growth conditions and ensured that the only variable was the ratio of decanoic acid (C10) to an unusual PHA monomer precursor, such as 10-undecenoic acid (C11:1) or phenylvaleric acid (PhVA). Obtained PHA content was in the range of 10 to 25 wt%. When different ratios of C10 and C11:1 were fed to P. putida, the produced PHA had a slightly higher molar ratio in favor of C11:1 based 3-hydroxy-10-undecenoate. However, in case of PhVA a significantly lower incorporation of 3-hydroxy-5-phenylvalerate over 3-hydroxydecanoate took place when compared to the ratio of their precursors in the feed medium. A result that is explained by a less efficient uptake of PhVA compared to C10 and a 24% lower yield of polymer from the aromatic fatty acid (y_((PHA-M)⁄PhVA)=0.25). In addition, PHA isolated from cultivations with PhVA resulted in the number weight average ¯(M_n ) two times lower than the PHA produced by C10 alone. Detection of products from PhVA metabolism in the culture supernatant showed that uptaken PhVA was not entirely converted into PHA, thus explaining the difference in the yield polymer from substrate. It was concluded that PhVA or its related metabolites increased the chain transfer rate during PHA biosynthesis in P. putida KTQQ20, resulting in a reduction of the polymer molecular weight.

Abstract licence: CC BY