Fe-Catalyzed One-Pot Oxidative Cleavage of Unsaturated Fatty Acids into Aldehydes with Hydrogen Peroxide and Sodium Periodate

Conversion of unsaturated fatty acids, FAMEs or triglycerides into the corresponding cyclic organic carbonates involves two reaction steps—double-bond epoxidation and CO2 insertion into the epoxide—that are generally conducted separately. We describe an assisted-tandem catalytic protocol able to carry out carbonation of unsaturated methyl oleate in one-pot without isolating the epoxide intermediate. Methyl oleate carbonate was obtained in 99% yield and high retention of cis-configuration starting from methyl oleate using hydrogen peroxide and CO2 as green reagents, in a biphasic system and in the presence of an ammonium tungstate ionic liquid catalyst with KBr as co-catalyst.

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OZONOLYSIS OF UNSATURATED FATTY ACIDS: I. OZONOLYSIS OF OLEIC ACID

Canadian Journal of Chemistry ◽

10.1139/v61-262 ◽

1961 ◽

Vol 39 (10) ◽

pp. 1956-1963 ◽

Cited By ~ 56

Author(s):

R. G. Ackman ◽

M. E. Retson ◽

L. R. Gallay ◽

F. A. Vandenheuvel

Keyword(s):

Hydrogen Peroxide ◽

Fatty Acids ◽

Oleic Acid ◽

Formic Acid ◽

Unsaturated Fatty Acids ◽

Fission Products ◽

Dicarboxylic Acids ◽

Total Recovery ◽

Subsequent Decomposition ◽

By Products

Ozonolysis of oleic acid in methanol, a reacting solvent, with subsequent decomposition of the ozonide products by hydrogen peroxide in formic acid, gives yields of principal dicarboxylic acid fission products exceeding 95% with a minimum of secondary acidic products. The method is highly reproducible and offers unique advantages in the total recovery of the dicarboxylic acids and the elimination of peroxidic materials. The principal non-acidic by-products were tentatively identified as the Cs alcohols and their formyl esters.

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THE NATURE OF SERUM ANTITRYPSIN

Journal of Experimental Medicine ◽

10.1084/jem.19.5.459 ◽

1914 ◽

Vol 19 (5) ◽

pp. 459-479 ◽

Cited By ~ 14

Author(s):

James W. Jobling ◽

William Petersen

Keyword(s):

Hydrogen Peroxide ◽

Fatty Acids ◽

Fatty Acid ◽

Potassium Iodide ◽

Unsaturated Fatty Acids ◽

Serum Lipase ◽

Enzyme Action ◽

Inhibiting Action

1. The ferment-inhibiting action of the serum is due to the presence of compounds of the unsaturated fatty acids. 2. These fatty acid compounds may be removed from the serum by means of chloroform or ether. 3. Soaps prepared by saponifying the chloroform or ether extracts inhibit the action of trypsin. 4. The anti-enzyme action of the serum can be removed by filtering acid serum through kaolin, and can in part be restored by extracting the kaolin. 5. The decrease in strength of anti-enzyme in old sera is probably due to the action of the serum lipase. 6. Iodin, potassium iodide, or hydrogen peroxide remove the inhibiting action of the serum. 7. Soaps of the unsaturated fatty acids lose their ferment-inhibiting action when heated with serum at 70° C.

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106 Cellulose Coatings Reduce Rancidity of Pecans

HortScience ◽

10.21273/hortsci.35.3.407b ◽

2000 ◽

Vol 35 (3) ◽

pp. 407B-407

Author(s):

E.A. Baldwin ◽

Bruce W. Woods

Keyword(s):

Fatty Acids ◽

Gas Chromatography ◽

Free Fatty Acids ◽

Unsaturated Fatty Acids ◽

Oxidative Cleavage ◽

Carya Illinoinensis ◽

Edible Coatings ◽

Ambient Conditions ◽

Off Flavors ◽

Hydrolysis Of

Pecans (Carya illinoinensis) are full of unsaturated fatty acids, which are subject to oxidative cleavage. This results in the development of rancid off-flavors, which render the nuts unmarketable. For this reason, pecans must be stored under costly refrigerated conditions. Furthermore, pecans usually undergo retail distribution and marketing at ambient conditions, which promote development of off-flavors. Application of cellulose-based edible coatings reduced off-flavor, and improved overall flavor scores while adding shine to the nuts during 14 months of storage under ambient conditions. Development of rancidity involves hydrolysis of glycerides into free fatty acids, oxidation of double bonds of unsaturated fatty acids to form peroxides and then autooxidation of the free fatty acids once the peroxides reach a sufficient level to perpetuate this reaction. One of the products of autooxidation is hexanal which is, thus, a good indicator of rancidity. Analysis of pecans by gas chromatography revealed that hexanal levels were reduced in coated nuts by 5- to over 200-fold compared to uncoated controls, depending on the coating treatment. Some of the coating treatments affected nut color, but overall flavor and appearance were improved by certain formulations.

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