Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 1, pp. 36−41.
Pleiades Publishing, Ltd., 2014.
Original Russian Text N.A. Lipkovskaya, V.N. Barvinchenko, T.V. Fedyanina, A.A. Rugal’, 2014, published in Zhurnal Prikladnoi Khimii, 2014, Vol. 87,
No. 1, pp. 40−45.
AND INDUSTRIAL ORGANIC CHEMISTRY
Physicochemical Properties of Quercetin and Rutin
in Aqueous Solutions of Decamethoxin
N. A. Lipkovskaya, V. N. Barvinchenko, T. V. Fedyanina, and A. A. Rugal’
Institute of Surface Chemistry, National Academy of Sciences of Ukraine, ul. Generala Naumova, Kiev, Ukraine
Received June 17, 2013
Abstract—The effect of a cationic surfactant, Decamethoxin, on the physicochemical properties of structurally
related natural ﬂ avonoids, quercetin and rutin, was studied by spectrophotometry. The spectral and protolytic
properties and the solubility of quercetin and rutin strongly depend on the Decamethoxin concentration in solu-
tion. The presence of Decamethoxin in the solution favors the tautomeric transition of the enol form of quercetin
to the keto form.
Vegetable ﬂ avonoids rutin (5,7,3',4'-tetrahydroxy-
ﬂ avone-3-rutinoside, Rt) and quercetin (3,5,7,3',4'-pen-
tahydroxyﬂ avone, Q)  exhibit a wide spectrum of
pharmacological properties, which are largely determined
by their high antioxidant activity.
These bioactive polyphenols of vitamin P group are
widely used in medicine owing to angioprotective, gas-
troprotective, diuretic, spasmolytic, antisclerotic, anti-
inﬂ ammatory, and antiviral effects . Extremely low
solubility of rutin and especially quercetin in aqueous
Quercetin: R = H
Rutin: R = rutinose
solutions and body ﬂ uids gives rise to certain problems
in the development of highly effective drugs, because the
solubility is one of the main biopharmaceutical character-
istics largely determining the bioequivalence of a drug .
The following substances are used today for increas-
ing the quercetin solubility: mono- and polysaccharides
(“quercetin granules” and Kvertin drug forms), polyvi-
nylpyrrolidone of molecular weight 12600 (Korvitin), and
phospholipid liposomes (Lipoﬂ avon) . The solubility
of quercetin and rutin also signiﬁ cantly increases in aque-
ous solutions of β-cyclodextrin , polyvinylpyrroilidone
of molecular weight 8000 , and human serum albu-
min  and in micellar solutions of Miramistin cationic
surfactant  owing to the formation of supramolecular
Surfactants are widely used in pharmaceutical tech-
nology as hydrophilizers, solubilizers, emulsiﬁ ers, and
stabilizers . Cationic surfactants combining surface
activity with bactericidal properties are the most promis-
ing for use in pharmaceutical technology. Decamethoxin
(DCM), an antiseptic drug with a wide spectrum of activ-
ity, is a cationic surfactant :