Antioxidation effect was examined with 14 kinds of α-thio derivatives of acetic acid, 4 kinds of α-thio derivatives and 14 kinds of β-thio derivatives of propionic acid, 9 kinds of mercaptal, 4 kinds of thiodifatty acid, and six miscellaneous compounds, with methyl oleate as the substrate.
In general, propionic acid derivatives were better than acetic acid derivatives, and the β-thio derivatives of propionic acid were better than the α-thio derivatives. 3-Alkylthiopropionic acids were all effective, the effect decreasing in the order of butyl, octyl, dodecyl, propyl, and ethyl. None of the thiodifatty acids was effective while mercaptal derivatives of vanillin showed fairly strong effect, This latter effect was heightened by the addition of their synergist, phosphoric acid or ascorbic acid stearate. Vanillalacetone was also a strong antioxidant. The effect of 3-arylthiopropionic acid decreased in the order of 3-methoxy-4-hydroxyphenyl, benzyl,
p-hydroxyphenyl, 3, 4-dimethoxyphenyl, phenyl,
p-tolyl,
p-methoxyphenyl, and
p-methoxypeezyl, and 3-(3-methoxy-4-hydroxyphenylthio)propionic acid was equally effective as the commercial antioxidant. Protocatechualdehyde mercaptal-3, 3-dipropionic acid had stronger effect than commercial antioxidant but its toxicity was stronger, minimum lethal dose in mice being 0.11-0.12g./kg. by subcutaneous injection.
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