2380-23-6Relevant academic research and scientific papers
Transformation of Unsaturated Fatty Acids/Esters to Corresponding Keto Fatty Acids/Esters by Aerobic Oxidation with Pd(II)/Lewis Acid Catalyst
Senan, Ahmed M.,Zhang, Sicheng,Zeng, Miao,Chen, Zhuqi,Yin, Guochuan
, p. 6912 - 6918 (2017/08/21)
Utilization of renewable biomass to partly replace the fossil resources in industrial applications has attracted attention due to the limited fossil feedstock with the increased environmental concerns. This work introduced a modified Wacker-type oxidation for transformation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, in which Cu2+ cation was replaced with common nonredox metal ions, that is, a novel Pd(II)/Lewis acid (LA) catalyst. It was found that adding nonredox metal ions can effectively promote Pd(II)-catalyzed oxidation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, even much better than Cu2+, and the promotional effect is highly dependent on the Lewis acidity of added nonredox metal ions. The improved catalytic efficiency is attributed to the formation of heterobimetallic Pd(II)/LA species, and the oxidation mechanism of this Pd(II)/LA catalyst is also briefly discussed.
Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation
Ebert, Cynthia,Felluga, Fulvia,Forzato, Cristina,Foscato, Marco,Gardossi, Lucia,Nitti, Patrizia,Pitacco, Giuliana,Boga, Carla,Caruana, Paolo,Micheletti, Gabriele,Calonghi, Natalia,Masotti, Lanfranco
, p. 38 - 45 (2012/11/07)
Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas' rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned.
Anti-inflammatory constituents of the Red Alga Gracilaria verrucosa and their synthetic analogues
Hung, The Dang,Hye, Ja Lee,Eun, Sook Yoo,Shinde, Pramod B.,Yoon, Mi Lee,Hong, Jongki,Dong, Kyoo Kim,Jung, Jee H.
, p. 232 - 240 (2008/12/22)
A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11-deoxyprostaglandins (1-4), a ceramide (5), and a C16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-α) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.
8-Hydroxyoctadec-10(Z)-enoic Acid in Diospyros montana Seed Oil
Rauf, Abdul,Ahmad, M. S.,Osman, S. M.
, p. 283 (2007/10/02)
The seed glycerides of Diospyros montana contain mainly C16 and C18 fatty acids and a hitherto unknown minor component (5.4percent) characterised as 8-hydroxyoctadec-10(Z)-enoic acid.
