Oleyl Oleate and Homologous Wax Esters Synthesized Coordinately from Oleic Acid by Acinetobacter and Coryneform Strains

1996 ◽  
Vol 32 (6) ◽  
pp. 336-342 ◽  
Author(s):  
T. Kaneshiro ◽  
L.K. Nakamura ◽  
J.J. Nicholson ◽  
M.O. Bagby
Keyword(s):  
Oleic Acid ◽  
Wax Esters ◽  
Oleyl Oleate

scholarly journals Low-Temperature Esterification to Produce Oleic Acid-Based Wax Esters Catalyzed by 4-Dodecylbenzenesulfonic Acid

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1471
Author(s):  
Zhenzhen Li ◽  
Wei Liu ◽  
Guolong Yang
Keyword(s):  
Oleic Acid ◽  
Low Temperature ◽  
Inhibitory Effect ◽  
Wax Esters ◽  
Molar Ratio ◽  
Efficient Catalyst ◽  
Dodecylbenzenesulfonic Acid ◽  
Effect Of Water ◽  
Solvent Free Conditions ◽  
Increasing Temperature

Synthesized oleic acid-based wax esters (e.g., cetyl oleate), which can replace spermaceti oil or jojoba oil, have been widely used in the cosmetic, pharmaceutical and other industries. In this work, 4-dodecylbenzenesulfonic acid (DBSA) has been successfully used as an efficient catalyst to synthesize oleic acid-based wax esters through esterification at 40 °C under solvent-free conditions. A 93.6% conversion rate of cetyl alcohol was obtained under optimal conditions: 10 mol% DBSA, a molar ratio of 1.3:1 oleic acid to alcohol, a reaction temperature 40 °C and a reaction time of 4 h. The effect of water content on esterification was investigated, and it was found that the inhibitory effect of water decreased significantly with increasing temperature. Moreover, DBSA-catalyzed esterification could be applied in the production of various oleic acid-based wax esters and excellent conversion (>90%) to esters was obtained under such mild conditions. DBSA-catalyzed low-temperature esterification is an efficient method for the production of liquid wax esters.

Synthesis of oleyl oleate wax esters inArabidopsis thalianaandCamelina sativaseed oil

2015 ◽  
Vol 14 (1) ◽  
pp. 252-259 ◽  
Author(s):  
Tim Iven ◽  
Ellen Hornung ◽  
Mareike Heilmann ◽  
Ivo Feussner
Keyword(s):  
Wax Esters ◽  
Oleyl Oleate

The Distribution of Neutral Lipids in Shark Tissues

1973 ◽  
Vol 53 (3) ◽  
pp. 649-656 ◽  
Author(s):  
J. R. Sargent ◽  
R. R. Gatten ◽  
R. McIntosh
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Neutral Lipid ◽  
Lipid Class ◽  
Deep Sea ◽  
Neutral Lipids ◽  
Wax Esters ◽  
Cholesteryl Esters ◽  
A Minor

Neutral lipid classes were analysed in the livers, muscles and sera of Deania, Centroscymnus, Squalus and Prionace. All three squaloid sharks contained triglycerides and alkyldiacylglycerols and the two deep sea squaloids contained additionally hydrocarbons. Prionace contained triglycerides and hydrocarbons but no alkyldiacylglycerols. For a given species the class compositions of the lipids were similar in liver, muscle and serum, except that serum contained additionally cholesteryl esters and wax esters. Cholesteryl esters in Squalus serum were rich in oleic acid whereas wax esters were very rich in polyunsaturated fatty acids. Squalus serum contained a major and a minor lipoprotein species both of which transport all four neutral lipids in serum. It is concluded that, with the exception of cholesteryl and wax esters in serum, neutral lipids are distributed between shark tissues by a mechanism that is relatively non-specific with respect to lipid class.

scholarly journals Synthesis, Characterization and Optimization of Oleyl Oleate Wax Ester Using Ionic Liquid Catalysts

2021 ◽  
Vol 21 (3) ◽  
pp. 659
Author(s):  
Naowara Al-Arafi ◽  
Nadia Salih ◽  
Jumat Salimon
Keyword(s):  
Ionic Liquid ◽  
Oleic Acid ◽  
Oleyl Alcohol ◽  
Wax Ester ◽  
Esterification Reaction ◽  
Reaction Conditions ◽  
Brønsted Acidic Ionic Liquid ◽  
Acidic Ionic Liquids ◽  
Percentage Yield ◽  
Oleyl Oleate

In this work, the synthesis of oleyl oleate wax ester using Brønsted acidic ionic liquid catalysts was carried out. Confirmation of oleyl oleate molecular structure has been performed using FTIR, NMR, and ESI-MS spectroscopies. The ability of ionic liquid catalysts for catalyzing the esterification reaction of oleic acid and oleyl alcohol to produce oleyl oleate was optimized. The ionic liquid catalyst ([NMP][CH3SO3]) was found to be the best catalyst for the esterification reaction of oleic acid and oleyl alcohol compared with the other acidic ionic liquids studied. The optimal reaction conditions were determined at a reaction time of 8 h; oleic acid to oleyl alcohol mole ratio of 1:1; ([NMP][CH3SO3]) with 9.9 wt.%; and reaction temperature of 90 °C. Under these conditions, the percentage yield of oleyl oleate wax ester was 86%.

Wax esters in fish: Turnover of oleic acid in wax esters and triglycerides of gouramis

Lipids ◽  
1971 ◽  
Vol 6 (8) ◽  
pp. 562-566 ◽  
Author(s):  
D. M. Sand ◽  
Jean L. Hehl ◽  
H. Schlenk
Keyword(s):  
Oleic Acid ◽  
Wax Esters

scholarly journals Thio Wax Ester Biosynthesis Utilizing the Unspecific Bifunctional Wax Ester Synthase/Acyl Coenzyme A:Diacylglycerol Acyltransferase of Acinetobacter sp. Strain ADP1

2005 ◽  
Vol 71 (2) ◽  
pp. 790-796 ◽  
Author(s):  
Stefan Uthoff ◽  
Tim Stöveken ◽  
Nikolaus Weber ◽  
Klaus Vosmann ◽  
Erika Klein ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Specific Activity ◽  
Wax Esters ◽  
Wax Ester ◽  
Mineral Salts ◽  
Relative Specific Activity ◽  
In Vitro Biosynthesis ◽  
Wax Ester Synthase

ABSTRACT The bifunctional wax ester synthase/acyl coenzyme A (acyl-CoA):diacylglycerol acyltransferase (WS/DGAT) from Acinetobacter sp. strain ADP1 (formerly Acinetobacter calcoaceticus ADP1) mediating the biosyntheses of wax esters and triacylglycerols was used for the in vivo and in vitro biosynthesis of thio wax esters and dithio wax esters. For in vitro biosynthesis, 5′His6WS/DGAT comprising an N-terminal His6 tag was purified from the soluble protein fraction of Escherichia coli Rosetta(DE3)pLysS (pET23a::5′His6 atf). By employing SP-Sepharose high-pressure and Ni-nitrilotriacetic acid fast-protein liquid chromatographies, a 19-fold enrichment with a final specific activity of 165.2 nmol mg of protein−1 min−1 was achieved by using 1-hexadecanol and palmitoyl-CoA as substrates. Incubation of purified 5′His6WS/DGAT with 1-hexadecanethiol and palmitoyl-CoA as substrates resulted in the formation of palmitic acid hexadecyl thio ester (10.4% relative specific activity of a 1-hexadecanol control). Utilization of 1,8-octanedithiol and palmitoyl-CoA as substrates led to the formation of 1-S-monopalmitoyloctanedithiol and minor amounts of 1,8-S-dipalmitoyloctanedithiol (59.3% relative specific activity of a 1-hexadecanol control). The latter dithio wax ester was efficiently produced when 1-S-monopalmitoyloctanedithiol and palmitoyl-CoA were used as substrates (13.4% specific activity relative to that of a 1-hexadecanol control). For the in vivo biosynthesis of thio wax esters, the knockout mutant Acinetobacter sp. strain ADP1acr1ΩKm, which is unable to produce fatty alcohols, was used. Cultivation of Acinetobacter sp. strain ADP1acr1ΩKm in the presence of gluconate, 1-hexadecanethiol, and oleic acid in nitrogen-limited mineral salts medium resulted in the accumulation of unusual thio wax esters that accounted for around 1.19% (wt/wt) of the cellular dry weight and consisted mainly of oleic acid hexadecyl thioester as revealed by gas chromatography-mass spectrometry.

scholarly journals Production of Oleic Acid Based Wax Ester Using Acidic Homogeneous Catalysts

2012 ◽  
Vol 9 (1) ◽  
pp. 99-106 ◽  
Author(s):  
Naowara Al-Arafi ◽  
Jumat Salimon
Keyword(s):  
Oleic Acid ◽  
Oleyl Alcohol ◽  
Specific Activity ◽  
Viscosity Index ◽  
Molar Ratio ◽  
Wax Ester ◽  
Esterification Reaction ◽  
Percentage Yield ◽  
Optimum Reaction ◽  
Oleyl Oleate

Four homogeneous acidic catalysts were tested for their ability to catalyze the esterification reaction of oleic acid and oleyl alcohol to produce oleyl oleate, a wax ester. Sulfuric acid showed relatively higher specific activity. Various reaction parameters were optimised to obtain high percentage yield of oleyl oleate. The optimum condition to produce oeyl oleate was reaction time; 5 h, temperture; 90°C, amount of sulforic acid 0.15 g and molar ratio of oleyl alcohol to oleic acid; 1:1. Percentage yield of wax ester obtained at these optimum reaction conditions was 93.88. Disappearance of carboxylic acid (C=O) peak has confirmed by FTIR with appearance of ester (C=O) peak at 1739 cm−1.1H NMR spectra analyses confirmed the result of oleyl oleate with appearance of ester (-CH2OCOR) at 4.02 ppm and also the13C-NMR confirmed the result with appearance of ester (C=O) peak at 173.2 ppm. The low-temperture behavior of compound synthesized was determined through its pour point (PP), viscosity index (VI) and flash point (FP) values. The results showed that oleyl oleate exhibited the most favorable low-temperture performance of PP, VI and FP with −31°C, 197.5 and 320°C respectively. This is due to increase of the molacular weight thus improve the low temperture property significantly.

A magnetic super lattice

1987 ◽  
Vol 45 ◽  
pp. 360-361 ◽  
Author(s):  
M.D. Bentzon ◽  
J. v. Wonterghem ◽  
A. Thölén
Keyword(s):  
Thermal Decomposition ◽  
Oleic Acid ◽  
Magnetic Fluid ◽  
Magnetic Particles ◽  
Carbon Film ◽  
Thick Layer ◽  
Amorphous Iron ◽  
Super Lattice ◽  
Carrier Liquid ◽  
Median Diameter

We report on the oxidation of a magnetic fluid. The oxidation results in magnetic super lattice crystals. The “atoms” are hematite (α-Fe2O3) particles with a diameter ø = 6.9 nm and they are covered with a 1-2 nm thick layer of surfactant molecules.Magnetic fluids are homogeneous suspensions of small magnetic particles in a carrier liquid. To prevent agglomeration, the particles are coated with surfactant molecules. The magnetic fluid studied in this work was produced by thermal decomposition of Fe(CO)5 in Declin (carrier liquid) in the presence of oleic acid (surfactant). The magnetic particles consist of an amorphous iron-carbon alloy. For TEM investigation a droplet of the fluid was added to benzine and a carbon film on a copper net was immersed. When exposed to air the sample starts burning. The oxidation and electron irradiation transform the magnetic particles into hematite (α-Fe2O3) particles with a median diameter ø = 6.9 nm.

Intestinal Absorption of Iodine131-Labeled Triolein and Oleic Acid in Normal Subjects and in Steatorrhea

1958 ◽  
Vol 34 (5) ◽  
pp. 901-909 ◽  
Author(s):  
Ervin Kaplan ◽  
Bernard D. Edidin ◽  
Robert C. Fruin ◽  
Lyle A. Baker
Keyword(s):  
Oleic Acid ◽  
Intestinal Absorption ◽  
Normal Subjects
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