AND POLYMERIC MATERIALS
Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 3, pp. 460−464.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © E.I. Khizhan, A.I. Khizhan, G.A. Tikhonova, V.Yu. Maslova, 2012, published in Zhurnal Prikladnoi Khimii, 2012, Vol. 85, No. 3,
Antioxidant Activity of Arylhydrazones
in Sunﬂ ower Oil Oxidation
E. I. Khizhan
, A. I. Khizhan
, G. A. Tikhonova
, and V. Yu. Maslova
Donetsk National University, Donetsk, Ukraine
Litvinenko Institute of Physical Organic and Coal Chemistry,
National Academy of Sciences of Ukraine, Donetsk, Ukraine
Received October 19, 2011
Abstract—Antioxidant properties of arylhydrazones in sunﬂ ower oil oxidation and regular trends in variation of
the antioxidant activity of arylhydrazones in the process in comparison with ethybenzene oxidation were examined.
The mechanism of the inhibiting effect of such com-
mon effective antioxidants as phenols and aromatic
amines on oxidation with food fats and oils, polymeric
materials, and biological systems is characterized by
certain speciﬁ c features . These features are deter-
mined by complex multicomponent composition of real
systems, by the ratio of primary and secondary oxidation
products, and by the possibility of conjugate oxidation of
separate components. Furthermore, natural composites
frequently contain impurities that can affect the overall
oxidation rate, acting as initiators, catalysts, antioxidants,
or synergists. As a result, in real systems, compared to
model hydrocarbons, the inhibitor activity can be fully
lost, weakened, or, on the contrary, enhanced.
Purposeful search for new effective oxidation inhibi-
tors is primarily based on the known mechanisms of the
antioxidant action. According to the radical-chain oxida-
tion theory, any compound with a high reducing power
toward participants of the oxidation process can act as
antioxidant. Among such substances are compounds of
the arylhydrazone series . Interest in arylhydrazones
(AHs) as promising antioxidants is due to a number of
objective reasons: presence of an amino group similar
in properties to that in aromatic amines, but with a more
labile bond; practically unlimited synthetic possibilities
for varying the compound composition; pronounced
physiological activity; lower toxicity compared to amines.
Compounds of the hydrazone series find diverse
applications in laboratory and industrial practice.
Hydrazones serve as starting substances for preparing
various heterocyclic compounds and identifying
carbonyl compounds. Antioxidant properties of
compounds of this class are used in motion-picture
and photographic industry . Thanks to the capability
to absorb solar radiation, some of them are included
into formulations for coating glasses and protecting
skin from sunburns. However, the most valuable
property of compounds of the hydrazone series is
their physiological activity. Drugs based on hydrazone
(Ftivazide, Soluzide, Larusane) play noticeable role in
tuberculosis chemotherapy . Particular attention is
given to search for antitumor agents among hydrazone
derivatives. Quinolinohydrazones of some heterocyclic
aldehydes inhibit the development of malignant tumors.
Salicylaldehyde benzoylhydrazone inhibits the DNA
synthesis in cells of radiation-sensitive tissues and is an
effective low-toxicity radioprotector .
Nikolaevskii et al. [5, 6] found that arylhydrazones
of aromatic and heterocyclic aldehydes are effective in-
hibitors of the oxidation of a model hydrocarbon system,
ethylbenzene. They terminate oxidation chains, reacting
with peroxy radicals generated from the substrate in the
course of its oxidation.