Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Differential Partitioning of Bioantioxidants in Edible Oil-Water and Octanol-Water Systems: Linear Free Energy Relationships

Freiria-Gandara, J., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Diaz, C.
J. Chem. Eng. Data 2018, 63, 8, 2999-3007
ABSTRACT
Partition coefficients, PW O, of antioxidants (AOs) between edible oils and water are scarce in the literature, despite that AOs are widely used to control lipid oxidation and the oxidative stress in cells. PW O values have a great importance to predict the efficiency and distribution of bioactives at different levels of biological organization from binary oil-water systems to living cells. Here, we determined the partition coefficients, PW O, of four series of potent, natural AOs of increasing lipophilicity between vegetable oils (olive, soybean, and corn) and water and, for the sake of comparison, between octanol-water, PW OCT. Results indicate that the contribution of the -CH2 groups to the overall lipophilicity of the AO is the same irrespective of the oil employed. The PW O values were compared with PW OCT values, and linear relationships were obtained for each series of AOs. Results indicate that, in general, PW O values cannot be predicted from the PW OCT values, making necessary to determine the PW O values for each oil and antioxidant.
Compounds
# Formula Name
1 C10H10O4 methyl 3-(3,4-dihydroxyphenyl)-2-propenoate
2 C9H10O4 ethyl protocatechuate
3 C11H14O4 butyl protocatechuate
4 C13H18O4 hexyl protocatechuate
5 C10H12O4 propyl protocatechuate
6 C10H12O4 2-(3,4-dihydroxyphenyl)ethyl acetate
7 C12H14O4 propyl 3-(3,4-dihydroxyphenyl)-2-propenoate
8 C17H24O4 octyl 3-(3,4-dihydroxyphenyl)-2-propenoate
9 C16H24O4 2-(3,4-dihydroxyphenyl)ethyl octanoate
10 C11H14O4 2-(3,4-dihydroxyphenyl)ethyl propionate
11 C14H20O4 2-(3,4-dihydroxyphenyl)ethyl hexanoate
12 C11H12O4 ethyl 3-(3,4-dihydroxyphenyl)-2-propenoate
13 C9H10O5 ethyl gallate
14 C11H14O5 butyl gallate
15 C8H8O4 methyl protocatechuate
16 C8H8O5 benzoic acid, 3,4,5-trihydroxy-, methyl ester
17 C10H12O5 propyl 3,4,5-trihydroxybenzoate
18 C15H22O5 benzoic acid, 3,4,5-trihydroxy-, octyl ester
19 C8H18O octan-1-ol
20 H2O water
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 1 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 1; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 12
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 12 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 12; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 7
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 7 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 7; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 8
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 8 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 8; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 16
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 16 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 16; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 13
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 13 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 13; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 17
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 17 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 17; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 14
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 14 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 14; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 18
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 18 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 18; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 6
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 6 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 6; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 10
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 10 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 10; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 11
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 11 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 11; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 9
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 9 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 9; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 15
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 15 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 15; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 2
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 2 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 2; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 5
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 5 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 5; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 3
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 3 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 3; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1
  • POMD
  • 4
  • 19
  • 20
  • Amount concentration (molarity), mol/dm3 - 4 ; Liquid - 19
  • Temperature, K; Liquid - 19
  • Pressure, kPa; Liquid - 19
  • Mole fraction - 4; Liquid - 20
  • Liquid - 19
  • Liquid - 20
  • Shake-flask
  • 1