Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid.

Abstract:

:Production of conjugated linoleic acids (CLA) using castor oil as starting material involves conversion of ricinoleic acid to methyl 12-mesyloxy-octadec-9-enoate (MMOE) followed by dehydration. This process usually uses 1,8-diazabicyclo-(5.4.0)-undec-7-ene (DBU) as an expensive dehydrating reagent. The present study reports that potassium hydroxide (KOH) can serve as a dehydrating reagent in replacement of DBU. The results showed that conversion of MMOE to CLA catalyzed by KOH was an efficient reaction, with a 77% conversion efficiency at 80 degrees C. The CLA isomeric profile produced in KOH-catalyzed dehydration reaction was similar to that catalyzed by DBU. The CLA mixture produced in KOH-catalyzed dehydration of MMOE at 80 degrees C contained 72% 9c,11t-18:2 and 26% 9c,11c-18:2 while in that catalyzed by DBU, 9c,11t-18:2 and 9c,11c-18:2 accounted for 78 and 16%, respectively. It was found that the temperature of dehydration was an important factor in the determination of CLA isomer composition and yield of conversion. Elevating the temperature from 78 to 180 degrees C decreased not only the conversion efficiency but also production of total c,t-18:2 and c,c-18:2 isomers regardless of dehydration catalyzed by either DBU or KOH. It is concluded that KOH may replace DBU as a dehydrating reagent in conversion of MMOE to CLA when the reaction conditions are optimized.

journal_name

Chem Phys Lipids

authors

Yang L,Huang Y,Wang HQ,Chen ZY

doi

10.1016/s0009-3084(02)00052-x

subject

Has Abstract

pub_date

2002-10-01 00:00:00

pages

23-31

issue

1-2

eissn

0009-3084

issn

1873-2941

pii

S000930840200052X

journal_volume

119

pub_type

杂志文章
  • Interaction of photosensitizers with liposomes containing unsaturated lipid.

    abstract::Small unilamellar liposomes were made of dipalmitoyl-phosphatidylcholine and dioleoyl-phosphatidylcholine, and photosensitized by a symmetrically or an asymmetrically substituted glycosilated tetraphenyl-porphyrin derivative. As differential scanning calorimetry and electron paramagnetic resonance spectroscopy (EPR) r...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2006.10.005

    authors: Voszka I,Budai M,Szabó Z,Maillard P,Csík G,Gróf P

    更新日期:2007-02-01 00:00:00

  • pH responsive delivery of lumefantrine with calcium phosphate nanoparticles loaded lipidic cubosomes for the site specific treatment of lung cancer.

    abstract::The present work aim to develop pH responsive nanosystem comprising lumefantrine with calcium phosphate nanoparticles loaded lipidic cubosomes for the effective treatment of lung cancer. FTIR results showed that, compatibility nature of selected excipients for the synthesis of LF-CaP-Cs. The XRD results showed develop...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2019.03.016

    authors: Sethuraman V,Janakiraman K,Krishnaswami V,Natesan S,Kandasamy R

    更新日期:2019-11-01 00:00:00

  • Isolation and purification of Lea blood-group active and related glycolipids from human plasma of blood-group A Lea individuals.

    abstract::From 81 of human plasma of blood-group A Lea nonsecretors three different Lea blood-group active ceramide pentasaccharides (a total of 4.65 mg) have been isolated, all revealing glucose, galactose, N-acetylglucosamine and fucose in molar ratios of 1 : 2 : 1 : 1 as determined by gas liquid chromatography. A fourth bloo...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(78)90040-3

    authors: Hanfland P,Kladetzky RG,Egli H

    更新日期:1978-09-01 00:00:00

  • Mammalian cardiolipin biosynthesis.

    abstract::Cardiolipin is a major phospholipid in mitochondria and is involved in the generation of cellular energy in the form of ATP. In mammalian and eukaryotic cells it is synthesized via the cytidine-5'-diphosphate-1,2-diacyl-sn-glycerol phosphate pathway. This brief review will describe some of the more recent studies on m...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/j.chemphyslip.2013.10.001

    authors: Mejia EM,Nguyen H,Hatch GM

    更新日期:2014-04-01 00:00:00

  • The apoA-I mimetic peptide 4F protects apolipoprotein A-I from oxidative damage.

    abstract::High density lipoprotein (HDL) is prone to modification by the oxidizing and chlorinating agent hypochlorite anion (OCl-). Oxidation of apolipoprotein (apo) A-I, the major protein in HDL, reduces ABCA-1 mediated cholesterol efflux and other protective responses to HDL. The apoA-I mimetic peptide 4F has been shown to u...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2019.01.009

    authors: White CR,Datta G,Wilson L,Palgunachari MN,Anantharamaiah GM

    更新日期:2019-03-01 00:00:00

  • Biomimetic nitration of the linoleic acid metabolite 13-hydroxyoctadecadienoic acid: isolation and spectral characterization of novel chain-rearranged epoxy nitro derivatives.

    abstract::Nitration of unsaturated fatty acids is a (patho)physiologically important pathway of lipid modification induced by nitric oxide-derived species. We report herein on the unexpected chain rearrangement undergone by (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid (1), a linoleic acid metabolite, when exposed to nitrat...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2007.09.007

    authors: Manini P,Camera E,Picardo M,Napolitano A,d'Ischia M

    更新日期:2008-01-01 00:00:00

  • Influence of temperature on dynamic surface properties of spread DPPC monolayers in a broad range of surface pressures.

    abstract::This work is focused on the study of the dynamic surface properties of spread monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), which is the main component of the pulmonary surfactant (PS), in the region of high surface pressures and at different temperatures. The increase of temperature from 25 to 35 ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2019.104812

    authors: Bykov AG,Guzmán E,Rubio RG,Krycki MM,Milyaeva OY,Noskov BA

    更新日期:2019-12-01 00:00:00

  • Analysis of phospholipid molecular species by liquid chromatography--atmospheric pressure chemical ionisation mass spectrometry of diacylglycerol nicotinates.

    abstract::A method using liquid chromatography - atmospheric pressure chemical ionisation mass spectrometry was evaluated for determining the molecular species composition of phospholipids (phosphatidylcholines from soybean, egg yolk and bovine liver) after conversion to diacylglycerol nicotinate derivatives. The structures cou...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(01)00130-x

    authors: Dobson G,Deighton N

    更新日期:2001-05-01 00:00:00

  • Importance of glycerol and fatty acid residues on the ionic properties of phosphatidylglycerols at the air-water interface.

    abstract::Ionic properties of didodecanoylphosphatidylglycerol (C12PG), didodecanolyphosphatidyl-l'-propanol (C12PP), di-(12-methyl, 13-methyl)-pentadecanoylphosphatidylglycerols (C15PG) and dihexadecanoylphosphatidylglycerol (C16PG) have been studied at the air-water interface using titration experiments at constant ionic stre...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(77)90019-6

    authors: Sacré MM,Tocanne JF

    更新日期:1977-04-01 00:00:00

  • Double layer potential and degree of dissociation in charged lipid monolayers.

    abstract::One of the contributions to the surface potential in charged phospholipid monolayers at air-water interfaces is the double layer potential. In this note several misconceptions found in the literature concerning the relationship between the double layer potential and the degree of dissociation of the lipid polar headgr...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(00)00123-7

    authors: Aguilella VM,Mafé S,Manzanares JA

    更新日期:2000-04-01 00:00:00

  • The role of the ganglioside lipid moiety in the process of ganglioside-cell interactions.

    abstract::The role of the ceramide moiety of gangliosides, together with the deriving aggregative properties of ganglioside in solution, in the process of ganglioside-cell interactions was studied. The natural GM1(stearoyl) and the synthetic GM1(acetyl), containing the stearoyl and acetyl groups as the acyl moiety, respectively...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(92)90048-t

    authors: Bassi R,Sonnino S

    更新日期:1992-07-01 00:00:00

  • Does cholesterol discriminate between sphingomyelin and phosphatidylcholine in mixed monolayers containing both phospholipids?

    abstract::The objective of this work was to examine the interaction of cholesterol with both phosphatidylcholines, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) or 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and sphingomyelins, N-oleoyl-D-sphingomyelin (O-SPM) or N-palmitoyl-D-sphingomyelin (P-SPM), in monolay...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(96)02535-2

    authors: Mattjus P,Slotte JP

    更新日期:1996-06-17 00:00:00

  • Bicontinuous cubic phase: a model for investigating the effects on a lipid bilayer due to a foreign substance.

    abstract::Biological effects of foreign substances are usually caused by their interaction within lipid bilayers with the membrane lipids. It is therefore desirable in many situations to determine the effects and the partition of xenobiotic substances, as well as drugs, added to amphiphile-water systems. Bicontinuous cubic liqu...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(96)02633-3

    authors: Engblom J

    更新日期:1996-12-20 00:00:00

  • Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size.

    abstract::The solubilization of biological membranes by detergents has been used as a major method for the isolation and purification of membrane proteins and other constituents. Considerable interest in this field has resulted from the finding that different components can be solubilized selectively. Certain membrane constitue...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2008.11.004

    authors: Toro C,Sanchez SA,Zanocco A,Lemp E,Gratton E,Gunther G

    更新日期:2009-02-01 00:00:00

  • Prediction of the melting points of fatty acids from computed molecular descriptors: a quantitative structure-property relationship study.

    abstract::The aim of these works present in this paper consisted in the development and evaluation of quantitative structure property models (QSPR) for the prediction of the melting points of a series constituted by 62 fatty acids. The best multilinear regressions method (MLR) is used to develop models for the prediction of the...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2011.10.001

    authors: Guendouzi A,Mekelleche SM

    更新日期:2012-01-01 00:00:00

  • Effect of lipid environment on amyloid fibril formation of human serum amyloid A.

    abstract::Human serum amyloid A (SAA) is a precursor protein of AA amyloidosis and a component of high-density lipoproteins (HDLs), thus it is essential to investigate the amyloid fibril formation of SAA under a lipid environment. We used synthetic fragment peptides corresponding to the N-terminal (residues 1-27) and central (r...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2016.11.004

    authors: Tanaka M,Nishimura A,Takeshita H,Takase H,Yamada T,Mukai T

    更新日期:2017-01-01 00:00:00

  • Fluid phase structure of EPC and DMPC bilayers.

    abstract::X-ray diffraction data taken at high instrumental resolution were obtained for EPC and DMPC under various osmotic pressures, primarily at T = 30 degrees C. The headgroup thickness DHH was obtained from relative electron density profiles. By using volumetric results and by comparing to gel phase DPPC we obtain areas AE...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(98)00068-1

    authors: Petrache HI,Tristram-Nagle S,Nagle JF

    更新日期:1998-09-01 00:00:00

  • Properties of unusual phospholipids: I. Synthesis, monolayer investigations and calorimetry of diacylglycerophosphocholines containing monoacetylenic acyl chains.

    abstract::Isomeric diacylglycerophosphocholines containing various octadecynoic acids (4-, 6-, 9-, 12-, 14- and 17-octadecynoic acid) were synthesized and purified to homogeneity. Their behaviour in monolayers, when studied by the Langmuir-Blodgett film balance technique, revealed systematic relationships between structure and ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90086-8

    authors: Rürup J,Mannova M,Brezesinski G,Schmid RD

    更新日期:1994-04-19 00:00:00

  • Structural characterization of polyhydroxy fatty acid nanoparticles related to plant lipid biopolyesters.

    abstract::In the present work, we report the physico-chemical properties and structural characteristics of special polyhydroxy fatty acid nanoparticles after their fusion by means of attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR), X-ray diffraction (XRD), differential scanning calorimetry (DSC), ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2010.01.006

    authors: Heredia-Guerrero JA,Domínguez E,Luna M,Benítez JJ,Heredia A

    更新日期:2010-03-01 00:00:00

  • Observation of ganglioside lactone formation with CD spectrometry.

    abstract::Monolactone (NeuAc1-9NeuAc linkage) formation of a ganglioside, GD1b, was observed at 20 degrees C on solutions ranging in concentration from 0.008 to 1.7 mM and in pH from 2 to 8.1, by following the change of ellipicity at 235 nm, where lactonized gangliosides showed a strong Cotton effect. The lactonization was foun...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90051-5

    authors: Tsuda M,Terabayashi T,Kawanishi Y

    更新日期:1994-03-31 00:00:00

  • Phase state and surface topography of palmitoyl-ceramide monolayers.

    abstract::In cell biology (and in many biophysical) studies there is a natural tendency to consider ceramide as a highly condensed, solid-type lipid conferring rigidity and close packing to biomembranes. In the present work we advanced the understanding of the phase behavior of palmitoyl-ceramide restricted to a planar interfac...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2010.04.008

    authors: Fanani ML,Maggio B

    更新日期:2010-06-01 00:00:00

  • Phospholipid phase transitions: kinetics and structural mechanisms.

    abstract::A brief review is given on the principles and methods used to investigate structural phase transitions in phospholipid supramolecular structures. The conceptual differences of approaches close to and far from equilibrium are addressed, and the consequences in terms of the limits of interpretation for different types o...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/0009-3084(91)90072-j

    authors: Laggner P,Kriechbaum M

    更新日期:1991-03-01 00:00:00

  • Direct observation of the properties of cholesterol in membranes by deuterium NMR.

    abstract::The properties of cholesterol in bilayers of egg phosphatidylcholine (PC) were investigated directly by means of 2H-NMR of specifically-deuterated species (C3, C7, C26, C27). Quadrupole splittings were a measure of molecular ordering, and relaxation times T1 and T2e were indicators of rates of motion. The importance o...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(82)90072-x

    authors: Taylor MG,Akiyama T,Saitô H,Smith IC

    更新日期:1982-12-01 00:00:00

  • Amphiphilic effects of dibucaine HCl on rotational mobility of n-(9-anthroyloxy)stearic acid in neuronal and model membranes.

    abstract::We studied dibucaine's effects on specific locations of n-(9-anthroyloxy)palmitic acid or stearic acid (n-AS) within phospholipids of synaptosomal plasma membrane vesicles isolated from bovine cerebral cortex (SPMV) and model membranes. Giant unilamellar vesicles (GUVs) were prepared with total lipids (SPMVTL) and mix...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2006.12.002

    authors: Lee YH,Park NS,Kwon JD,Park JS,Shin GB,Lee CS,Jung TS,Choi NJ,Yoon JH,Ok JS,Yoon UC,Bae MK,Jang HO,Yun I

    更新日期:2007-03-01 00:00:00

  • Luliconazole loaded lyotropic liquid crystalline nanoparticles for topical delivery: QbD driven optimization, in-vitro characterization and dermatokinetic assessment.

    abstract::Fungal infections are an important cause of morbidity and pose a serious health concern especially in immunocompromised patients. Luliconazole (LUL) is a topical imidazole antifungal drug with a broad spectrum of activity. To overcome the limitations of conventional dosage forms, LUL loaded lyotropic liquid crystallin...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2020.105028

    authors: Mahmood A,Rapalli VK,Waghule T,Gorantla S,Singhvi G

    更新日期:2021-01-01 00:00:00

  • Translational diffusion measurements of a fluorescent phospholipid between MDCK-I cells support the lipid model of the tight junctions.

    abstract::The diffusion of a lipid fluorescent analogue across tight junctions in MDCK-I cells was studied by FRAP measurements. Cells were labelled with C6-NBD-PC at the apical cell membrane. Transepithelial resistance of MDCK-I cells was found to be higher than 3000 omega x cm2, which indicates the presence of a very tight ep...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90066-3

    authors: Grebenkämper K,Galla HJ

    更新日期:1994-05-23 00:00:00

  • Effects of oxygenated sterol on phospholipid bilayer properties: a molecular dynamics simulation.

    abstract::The properties of dipalmitoylphosphatidylcholine (DPPC):6-ketocholestanol bilayer at 50 mol% sterol were studied using the molecular dynamics simulation technique. Our simulations were performed at constant pressure and temperature on a nanosecond time scale. Data from this simulation were compared to the results of o...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(01)00160-8

    authors: Smondyrev AM,Berkowitz ML

    更新日期:2001-07-01 00:00:00

  • A DSC and FTIR spectroscopic study of the effects of the epimeric coprostan-3-ols and coprostan-3-one on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes: Comparison with their 5-cholesten analogues.

    abstract::We present the results of a comparative differential calorimetric and Fourier transform infrared spectroscopic study of the effect of cholesterol and five analogues on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes. These sterols/steroids differ in both the nature...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2015.03.002

    authors: Benesch MG,Lewis RN,Mannock DA,McElhaney RN

    更新日期:2015-05-01 00:00:00

  • The yeast sphingolipid signaling landscape.

    abstract::Sphingolipids are recognized as signaling mediators in a growing number of pathways, and represent potential targets to address many diseases. The study of sphingolipid signaling in yeast has created a number of breakthroughs in the field, and has the potential to lead future advances. The aim of this article is to pr...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/j.chemphyslip.2013.10.006

    authors: Montefusco DJ,Matmati N,Hannun YA

    更新日期:2014-01-01 00:00:00

  • Thermodynamic and structural effects of propranolol on DPPC liposomes.

    abstract::Some thermodynamic and structural aspects of propranolol-DPPC liposomes interaction were investigated by DSC and X-ray diffraction: the lamellar arrangement of the lipid matrix remains intact even at high concentrations of the drug (until 1:1 drug/lipid molar ratio). However, the bilayer thickness increases significan...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(90)90171-m

    authors: Albertini G,Donati C,Phadke RS,Ponzi Bossi MG,Rustichelli F

    更新日期:1990-09-01 00:00:00