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Formation of formaldehyde and malonaldehyde by photooxidation of squalene
Author(s) -
Yeo H. C. H.,
Shibamoto T.
Publication year - 1992
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02537059
Subject(s) - formaldehyde , chemistry , squalene , acetaldehyde , acetone , irradiation , photochemistry , nuclear chemistry , organic chemistry , ethanol , physics , nuclear physics
Formaldehyde and malonaldehyde were identified upon exposure of squalene to ultraviolet (UV) irradiation at 300 nm. Formaldehyde was derivatized by reaction with cysteamine to form thiazolidine; malonaldehyde was derivatized by reaction with N ‐methylhdyrazine to produce N ‐methylpyrazole. The derivatives were subsequently analyzed with a gas chromatography equipped with a fused silica capillary column and a nitrogen/phosphorus detector. The levels of formaldehyde and malonaldehyde produced increased with irradiation time. The amount of formaldehyde produced reached a maximum of 3.40 nmol/mg squalene after 7 hr irradiation; the maximum amount of malonaldehyde generated, 0.92 nmol/mg, was found after 5 hr of irradiation. Prior to this study, formaldehyde had not been reported as a photoproduct of squalene. Acetaldehyde and acetone were also detected in the irradiated squalen,, which may be formed via a 6‐methyl‐5‐hepten‐2‐one intermediate. 6‐Methyl‐5‐hepten‐2‐one can also undergo breakdown to form malonaldehyde.