41194-37-0Relevant academic research and scientific papers
Suberin structure in potato periderm: Glycerol, long-chain monomers, and glyceryl and feruloyl dimers
Graca, Jose,Pereira, Helena
, p. 5476 - 5483 (2000)
Suberin in extractive-free potato periderm amounts to 25% determined by NaOCH3 methanolysis. Monomeric composition is characterized by glycerol (20% of monomers), long-chain α,ω-diacids, ω-hydroxyacids, alkanoic acids, and alkan-1-ols, with predominance of octadec-9-enodioic acid and 18-hydroxyoctadec-9-enoic acid (39 and 15% of long-chain monomers, respectively). Aromatic hydroxycinnamyl monomers were also present (2-catalyzed methanolysis solubilized ~10% of suberin aliphatics. GC-MS analysis showed the presence of monomers, dimers, and trimers (87, 12, and 1% of identified compounds, respectively). A total of 26 dimers were identified by EIMS: monoacylglyceryl esters of α,ω-diacids, ω-hydroxyacids, and alkanoic acids (with predominance of the 1- and 2-isomers of the monoacylglyceryl ester of the octadec-9-enodioic acid), as well as feruloyl esters of ω-hydroxyacids and alkan-1-ols and a small quantity of a monoferuloylglycerol. Following a discussion of suberin macromolecular structure, it is proposed that in suberized cell walls, the polyaliphatic polymers have a three-dimensional development ensured by glycerol and exist independently from the associated polyaromatics.
Lipidic polyols using thiol-ene/yne strategy for crosslinked polyurethanes
Pham, Phuoc Dien,Lapinte, Vincent,Raoul, Yann,Robin, Jean-Jacques
, p. 1597 - 1606 (2014/05/06)
Oleic acid and α,ω-diacid were converted into propargylic esters followed by thiol-ene/yne coupling (TEC/TYC) functionalization in presence of mercaptoethanol. The multiradical addition on fatty esters leads to the formation of lipidic polyols (OH1 and OH2), as judged by 1H NMR and mass spectroscopies as well as by size exclusion chromatography. The crosslinking reaction between TEC/TYC-based polyols and 4,4′-methylene bis(phenylisocyanate) isocyanate reactant was monitored by FTIR experiment and reaction parameters were optimized. By differential scanning calorimetry, relatively high glass transitions are measured corresponding to structure with little or without dangling chain. Moreover, the thermal stability of the resulting plant oil-based polyurethane materials (PU1 and PU2) were found to be fully consistent with that of other lipidic PUs respecting a three-step process. Thanks to TYC methodology, fatty α,ω-diacid produces lipidic polyol without dangling chain and lipidic thermoset PU with relatively high T g.
Design, synthesis, and activity of membrane-disrupting bolaphiles
Jayasuriya, Nimal,Bosak, Stanislav,Regen, Steven L.
, p. 5844 - 5850 (2007/10/02)
Four new classes of bolaphiles ("double-headed" single-chain surfactants) have been prepared, via condensation of an homologous series of linear saturated, olefinic, and acetylenic α,ω-dicarboxylic acids with hexaethylene glycol, and evaluated for their ability to induce the release of 5(6)-carboxyfluorescein (CF) entrapped within large unilamellar vesicles derived from 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). Operationally, the membrane-disrupting activity of the bolaphiles has been found to vary by a factor of ca. 100, when the total number of carbon atoms which separate the carboxylate moieties range from 12 to 24; the most active bolaphile is approximately three times more active than Triton X-100. When the affinity of the bolaphiles toward POPC membranes is considered, the intrinsic membrane-disrupting activity varies by a factor of ca. 230. A "loop" model is proposed to account for the general trends in bolaphile activity that are observed, where the depth of loop penetration and loop width are presumed to be the key factors involved in determining membrane-disrupting activity. The potential utility of these surfactants as antimicrobial agents, and as anti-HIV agents in particular, is briefly discussed.
