Jan 1, 1968

Autoxidation of saturated fatty acids. II. The determination of the site of hydroperoxide groups in autoxidizing methyl palmitate

Lipids
M H BrodnitzI S Fagerson

Abstract

The monohydroperoxides of methyl palmitate oxidized at 150C were concentrated, purified, and reduced to yield a mixture of isomers of monohydroxy palmitate. No evidence of unsaturation in these molecules could be obtained, and no direct method for the resolution or identification of the individual isomers was found. Nuclear magnetic resonance (NMR) spectroscopy of the reduced esters suggested that the hydroxy groups were not located at either end of the chain of the fatty ester.To establish the location of the initial oxidative attack on saturated esters, the reduced esters of oxidized methyl palmitate were chemically cleaved at the location of the hydroxy group by means of chromium trioxide oxidation and by the Beckmann transformation. The resulting mono- and dibasic fatty acids were methylated and analyzed by gas chromatography. This analysis indicated that the oxidation of methyl palmitate did not occur selectively at one location along the ester. Although all carbon atoms can apparently be oxidized, preferential oxidation was observed toward the center of the molecule.

  • References1
  • Citations4

References

  • References1
  • Citations4

Citations

Mentioned in this Paper

Chromium product (pharmacologic preparation)
Hydrogen Peroxide
Magnetic Resonance Imaging
Methylate
Oxidation
Cleaved Cell
Saturated Fat
Palmitate
Chemicals
Esters

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Bone Marrow Neoplasms

Bone Marrow Neoplasms are cancers that occur in the bone marrow. Discover the latest research on Bone Marrow Neoplasms here.

IGA Glomerulonephritis

IgA glomerulonephritis is a chronic form of glomerulonephritis characterized by deposits of predominantly Iimmunoglobin A in the mesangial area. Discover the latest research on IgA glomerulonephritis here.

Cryogenic Electron Microscopy

Cryogenic electron microscopy (Cryo-EM) allows the determination of biological macromolecules and their assemblies at a near-atomic resolution. Here is the latest research.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

LRRK2 & Immunity During Infection

Mutations in the LRRK2 gene are a risk-factor for developing Parkinson’s disease. However, LRRK2 has been shown to function as a central regulator of vesicular trafficking, infection, immunity, and inflammation. Here is the latest research on the role of this kinase on immunity during infection.

Antiphospholipid Syndrome

Antiphospholipid syndrome or antiphospholipid antibody syndrome (APS or APLS), is an autoimmune, hypercoagulable state caused by the presence of antibodies directed against phospholipids.

Meningococcal Myelitis

Meningococcal myelitis is characterized by inflammation and myelin damage to the meninges and spinal cord. Discover the latest research on meningococcal myelitis here.

Alzheimer's Disease: MS4A

Variants within membrane-spanning 4-domains subfamily A (MS4A) gene cluster have recently been implicated in Alzheimer's disease by recent genome-wide association studies. Here is the latest research.