Investigation of 1‐decyne formation in cottonseed oil fried foods

Abstract 1‐Decyne identified in oxidized cottonseed oil was previously thought to originate from oleic acid. However, we have demonstrated that 1‐decyne is a degradative product from the photo‐oxidation of cyclopropenoid fatty acids (CPFA) naturally present in cottonseed oil. Products containing photooxidized cottonseed oil have the distinct off‐flavor of 1‐decyne. Experiments were conducted to identify the factors involved in 1‐decyne formation. Reactions were done under the following conditions: (a) in the dark or under light, (b) with or without removal of CPFA from cotton‐seed oil, (c) in the presence or absence of singlet oxygen quenchers, (d) in the presence or absencc of a hydroperoxide‐reducing agent (triphenylphosphine), and (e) with or without photosensitizers. Methyl sterculate was used as a substrate for studying 1‐decyne formation under photosensitized oxidation conditions in a model system. We have concluded that 1‐decyne is formed by the photo‐oxidation of CPFA utilizing chlorophyll as a photosensitizer. A reaction mechanism for 1‐decyne formation is proposed.

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