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Supporting Information
Synthesis and Antioxidant Activity of Hydroxytyrosol Alkyl-carbonate Derivatives
Ignacio Fernandez-Pastor,† Antonia Fernandez-Hernandez,‡ Francisco Rivas,*,† Antonio Martinez,† Andres GarciaGranados† and Andres Parra*,†
†
Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Granada, Fuentenueva s/n, ES-18071
Granada, Spain
‡
Centro “Venta del Llano” del Instituto Andaluz de Investigacion y Formacion Agraria, Pesquera, Agroalimentaria
y de la Produccion Ecologica (IFAPA), Mengibar, Jaen, Spain
Page S2. HPLC analysis protocol: HPLC protocol for analyzing the composition of the
phenolic extract.
Page S3. Figure S1: HPLC chromatogram of the phenolic extract composition.
Page S4. Figure S2: 13C NMR spectrum of the phenolic extract.
Pages S5-S7. Figures S3, S4, and S5: 1H NMR, 13C NMR and DEPT spectra of 2.
S1
HPLC protocol for analyzing the composition of the phenolic extract.
HPLC study of the phenolic extract composition was carried out with a Waters C18 phase
column (0.4 µm diameter of particle; 150 mm x 3.9 mm) with a flow rate of 1 mL/min, on a
Waters Liquid Chromatograph (HPLC), model Alliance 2690 (Waters, USA). Wavelength of
279 nm was selected for the detection of compounds. The analysis was performed using the
following gradient:
Min 0
Min 15
Min 16
Min 22
Min 23
Min 30
100% A
95% A – 5% B
75% A – 25% B
75% A – 25% B
100% A
100% B
Solvent A is H2O containing 0.1% TFA, and solvent B is CH3CN containing 0.1% TFA.
S2
Figure S1: HPLC chromatogram of the phenolic extract composition.
Retention times: Compound 1, 12.962 min; Compound 2, 16.015 min.
S3
Figure S2: 13C NMR spectrum of the phenolic extract.
S4
Figure S3: 1H NMR spectrum of 2 (CDCl3, 400.45 MHz).
S5
Figure S4: 13C NMR spectrum of 2 (CDCl3, 100.70 MHz).
S6
Figure S5: DEPT spectrum of 2 (CDCl3, 100.70 MHz).
S7