Autoxidation of methyl linoleate initiated by the ozonide of allylbenzene

Journal Article · Sat Jul 01 04:00:00 EDT 1989 · Lipids; (USA)

DOI:https://doi.org/10.1007/BF02535077· OSTI ID:5404521

Ewing, J C; Cosgrove, J P; Giamalva, D H; Church, D F; Pryor, W A ^[1]

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1. Louisiana State Univ., Baton Rouge (USA)

Allylbenzene ozonide (ABO), a model for polyunsaturated fatty acid (PUFA) ozonides, initiates the autoxidation of methyl linoleate (18:2 ME) at 37 degrees C under 760 torr of oxygen. This process is inhibited by d-alpha-tocopherol (alpha-T) and 2,6-di-tert-butyl-4-methylphenol (BHT). The autoxidation was followed by the appearance of conjugated diene (CD), as well as by oxygen-uptake. The rates of autoxidation are proportional to the square root of ABO concentration, implying that the usual free radical autoxidation rate law is obeyed. Activation parameters for the thermal decomposition of ABO were determined under N2 in the presence of radical scavengers and found to be Ea = 28.2 +/- 0.3 kcal mol-1 and log A = 13.6 +/- 0.2; kd (37 degrees C) is calculated to be (5.1 +/- 0.3) X 10(-7) sec-1. Autoxidation data are also reported for ozonides of 18:2 ME and methyl oleate (18:1 ME).

• OSTI ID: 5404521
• Journal Information: Lipids; (USA), Journal Name: Lipids; (USA) Vol. 24:7; ISSN LPDSA; ISSN 0024-4201
• Country of Publication: United States
• Language: English

Related Subjects

560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
BENZENE
BIOLOGICAL EFFECTS
CARBOXYLIC ACIDS
ENERGY
HEAT
HYDROCARBONS
LINOLEIC ACID
METABOLISM
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
RADICALS