3414-89-9

Usage

Chemical Properties

Light-tan paste. Soluble in water.

Uses

Emulsifying agent.

InChI:InChI=1/C18H32O2.K/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20);/q;+1/p-1/b7-6-,10-9-;

Upstream product

• 60-33-3 linoleic acid 

Relevant academic research and scientific papers

Linoleic acid and its potassium and sodium salts: A combined experimental and theoretical study

Linoleic acid (cis, cis-9,12-octodecadienoic acid) is the main polyunsaturated -omega 6- essential fatty acid. The conformational behaviour of linoleic acid (LA) in the gas phase was investigated by means of density functional theory (DFT). The structures of conformers of LA were fully optimized by using the B3LYP/6-311++G(d,p) method. The theory showed that the tttttts′CssCs′tt conformation of LA (conformer I) is the more stable than the other conformations. Fourier Transform Infrared (FTIR) and micro-Raman spectra of pure LA in liquid form were recorded in the region 4000–450 and 3500–100 cm?1, respectively. The DFT calculations on the molecular structure and vibrational spectra of the dimer form of most stable conformer of LA were also performed using the same method. The assignment of the vibrational modes was made based on calculated potential energy distributions (PEDs). The simulated spectra of dimer form of LA are in reasonably good agreement with the experimental spectra. The sodium and potassium salts of LA were synthesized and characterized by FTIR and Raman spectroscopy, X-ray diffraction and DFT calculations. Several molecular and electronic properties of LA and its salts such as HOMO-LUMO energies, chemical hardness and electronegativity were also calculated and interpreted.

Fatty acid potassium had beneficial bactericidal effects and removed Staphylococcus aureus biofilms while exhibiting reduced cytotoxicity towards mouse fibroblasts and human keratinocytes

Wounds frequently become infected or contaminated with bacteria. Potassium oleate (C18:1K), a type of fatty acid potassium, caused >4 log colony-forming unit (CFU)/mL reductions in the numbers of Staphylococcus aureus and Escherichia coli within 10 min and a >2 log CFU/mL reduction in the number of Clostridium difficile within 1 min. C18:1K (proportion removed: 90.3%) was significantly more effective at removing Staphylococcus aureus biofilms than the synthetic surfactant detergents sodium lauryl ether sulfate (SLES) (74.8%, p 0.01) and sodium lauryl sulfate (SLS) (78.0%, p 0.05). In the WST (water-soluble tetrazolium) assay, mouse fibroblasts (BALB/3T3 clone A31) in C18:1K (relative viability vs. control: 102.8%) demonstrated a significantly higher viability than those in SLES (30.1%) or SLS (18.1%, p 0.05). In a lactate dehydrogenase (LDH) leakage assay, C18:1K (relative leakage vs. control: 108.9%) was found to be associated with a significantly lower LDH leakage from mouse fibroblasts than SLES or SLS (720.6% and 523.4%, respectively; p 0.05). Potassium oleate demonstrated bactericidal effects against various species including Staphylococcus aureus, Escherichia coli, Bacillus cereus, and Clostridium difficile; removed significantly greater amounts of Staphylococcus aureus biofilm material than SLES and SLS; and maintained fibroblast viability; therefore, it might be useful for wound cleaning and peri-wound skin.

Interaction kinetics of liposome-incorporated unsaturated fatty acids with fatty acid-binding protein 3 by surface plasmon resonance

The role of heart-type fatty acid-binding protein (FABP3) in human physiology as an intracellular carrier of fatty acids (FAs) has been well-documented. In this study, we aimed to develop an analytical method to study real-time interaction kinetics between FABP3 immobilized on the sensor surface and unsaturated C18 FAs using surface plasmon resonance (SPR). To establish the conditions for SPR experiments, we used an FABP3-selective inhibitor 4-(2-(1-(4-bromophenyl)-5-phenyl-1H-pyrazol-3-yl)-phenoxy)-butyric acid. The affinity index thus obtained was comparable to that reported previously, further supporting the usefulness of the SPR-based approach for evaluating interactions between FABPs and hydrophobic ligands. A pseudo-first-order affinity of FABP3 to K+ petroselinate (C18:1 Δ6 cis), K+ elaidate (C18:1 Δ9 trans), and K+ oleate (C18:1 Δ9 cis) was characterized by the dissociation constant (Kd) near micromolar ranges, whereas K+ linoleate (C18:2 Δ9,12 cis/cis) and K+ α-linolenate (C18:3 Δ9,12,15 cis/cis/cis) showed a higher affinity to FABP3 with Kd around 1 × 10-6 M. Interactions between FAPB3 and C18 FAs incorporated in large unilamellar vesicles consisting of 1,2-dimyristoyl-sn-glycero-3- phosphocholine and FAs (5:1 molar ratio) were also analysed. Control DMPC liposomes without FA showed only marginal binding to FABP3 immobilized on a sensor chip while liposome-incorporated FA revealed significant responses in sensorgrams, demonstrating that the affinity of FAs to FABP3 could be evaluated by using the liposome-incorporated analytes. Significant affinity to FABP3 was observed for monounsaturated fatty acids (Kd in the range of 1 × 10-7 M). These experiments demonstrated that highly hydrophobic compounds in a liposome-incorporated form could be subjected to SPR experiments for kinetic analysis.