High Quality Essential Oils Extracted by an Eco-Friendly Process from Different Citrus Fruits and Fruit Regions

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High Quality Essential Oils Extracted by an Eco-Friendly Process from Different Citrus Fruits and Fruit Regions Rosaria Ciriminna, a Alexandra Fidalgo, b Riccardo Delisi, a Diego Carnaroglio, c,d Giorgio Grillo, d Giancarlo Cravotto, d Alfredo Tamburino, e Laura M. Ilharco, b * Mario Pagliaro a * a Istituto per lo Studio dei Materiali Nanostrutturati, CNR, via U. La Malfa 153, 90146 Palermo PA, Italy; b Centro de Química-Física Molecular and IN-Institute of Nanoscience and Nanotechnology, Instituto Superior Técnico, University of Lisboa, Complexo I, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal; c Milestone Srl, Sorisole, BG, Italy; d Dipartimento di scienza e tecnologia del farmaco, Centre for Nanostructured Interfaces and Surfaces, Università degli Studi di Torino, Torino, Italy; e Legambiente, via Salaria 403, 00199 Rome, Italy. Electronic Supporting Information (Figures S1-S4; Table S1-S3) S1

3600 3200 2800 1800 1600 1400 1200 1000 800 600 Figure S1. DRIFT spectrum of (R)-(+)-Limonene. S2

Orange Orange Orange 3600 3400 3200 3000 2800 2600 3600 3400 3200 3000 2800 2600 3600 3400 3200 3000 2800 2600 Lemon Lemon Lemon 3600 3400 3200 3000 2800 2600 3600 3400 3200 3000 2800 2600 3600 3400 3200 3000 2800 2600 Figure S2. Deconvolution of the DRIFT spectra (3700-2600 cm -1 ) into a sum of Gaussian and Lorentzian components by a non-linear least-squares fitting method. S3

Orange Orange Orange Lemon Lemon Lemon 1900 Figure S3. Deconvolution of the DRIFT spectra (1900-1550 cm -1 ) into a sum of Gaussian and Lorentzian components by a non-linear least-squares fitting method. S4

Orange Orange Orange 1500 1400 1300 1200 1100 1000 900 800 700 1500 1400 1300 1200 1100 1000 900 800 700 Wavenumber cm -1 1500 1400 1300 1200 1100 1000 900 800 700 Lemon Lemon Lemon 1500 1400 1300 1200 1100 1000 900 800 700 Wavenumber cm -1 1500 1400 1300 1200 1100 1000 900 800 700 / Wavenumber cm -1 1500 1400 1300 1200 1100 1000 900 800 700 Figure S4. Deconvolution of the DRIFT spectra (1550-650 cm -1 ) into a sum of Gaussian and Lorentzian components by a non-linear least-squares fitting method. S5

Table S1. Assignments of the spectral band components recovered by deconvolution of the DRIFT spectra (3700-2600 cm -1 ) of EOs from different citrus and parts. Component center / cm -1 Constituent Assignment Orange Lemon Grapef. LOH/HPMFs νo-h 3609 3606 LOH/HPMFs νo-h 3558 3556 3531 3513 3536 LOH/HPMFs νo-h 3491 3460 3453 3383 3415 BOH/HPMFs νo-h 3351 3325 3353 3358 βm ν... as CH 2(chain) 3086 3085 3086 L/βP/LOH/LAc/βM ν as=ch 2 3074 3072 3075 3077 3077 3077 3077 L/βP/βM/LAc/LOH ν s=ch 2 3046 3049 3046 3048 3046 3049 3047 L/βM/γT/PMFs ν=ch 3011 3011 3011 3013 3013 3012 3011 γt/βp ν as=ch 2(ring 4,5) 2982 L/γT/βP/LOH/LAc/βM/Ci/IIm ν asch 3 2966 2966 2965 2967 2968 2966 2967 L/γT/βP/LOH/LAc/βM/Ci ν asch 2 2929 2926 2922 2924 2923 2923 2925 L/γT/βP/LOH/LAc/βM/Ci/IIm ν sch 3 2890 2888 2884 2885 2875 2892 2883 PMFs ν s(o)ch 3 2872 L/γT/βP/LOH/LAc/βM/Ci/IIm ν sch 3 2856 2854 2855 2858 2857 2857 2855 L ν sch 2(ring) 2835 2835 2834 2833 2836 2838 2834 βm/loh/iim ν sch 2 2728 2727 2727 2726 2727 2727 2726 Ci νco-h 2667 2668 2671 2666 2666 2667 ip - in plane; op - out of plane. L - Limonene; βp - β-pinene; γt - γ-terpinene; βm - β-myrcene; LOH - Linalool; LAc - Linalyl acetate; Ci - Citral; BOH - Borneol; PMFs - Polymethoxyflavones; HPMFs - Hydroxylated Polymethoxyflavones; lim - Isoimperatorin. wast e S6

Table S2. Assignments of the spectral band components recovered by deconvolution of the DRIFT spectra (1900-1550 cm -1 ) of EOs from different citrus and parts. Component center / cm -1 Constituent Assignment Orange Lemon Grapef. Lac νc=o 1784 1783 1782 1781 1782 1782 1782 IIm νc... O 1746 1744 1742 1743 1746 Ci νc... O 1719 1719 1712 1731 1719 1718 1716 L,βM,βP,LOH,Lac/Ci,PMFs νc=c/νc... O 1678 1678 1677 1678 1677 1678 1676 L νc=c (ring) 1644 1644 1644 1643 1643 1644 1644 Ci νc CCO 1626 1629 1621 γt νc=c (ring) 1613 1613 βm νc... C 1595 1595 1593 1592 1590 1601 1593 ip - in plane; op - out of plane. L - Limonene; βp - β-pinene; γt - γ-terpinene; βm - β-myrcene; LOH - Linalool; LAc - Linalyl acetate; Ci - Citral; BOH - Borneol; PMFs - Polymethoxyflavones; HPMFs - Hydroxylated Polymethoxyflavones; lim - Isoimperatorin. S7

Table S3. Assignments of the spectral band components recovered by deconvolution of the DRIFT spectra (1550-650 cm -1 ) of EOs from different citrus and parts. Component center / cm -1 Constituent Assignment Orange Lemon Grapef. PMFs νc... C (arom ring) 1515 1515 1514 L δch 1454 1452 1452 1458 1453 1453 1451 L/γT/βP/LOH/LAc/βM/Ci/IIm/BOH δ asch 3 1436 1436 1437 1437 1436 1438 1435 1403 1420 1406 1406 1403 βp δ sch 3 1375 1375 1375 1376 1375 1375 1375 IIm δ s(o)ch 2 1353 1348 1351 1348 1349 LOH/βM/IIm δch 2 1330 1329 1330 1329 1330 1328 1330 L δch 2(ring) 1308 1310 1309 1308 1308 1307 1308 PMFs ν asc-o-c 1287 1288 1288 1286 1285 1288 1286 βm 1275 1275 1274 1276 Lac ν asc-o-c (ester) 1258 1255 1254 1257 1251 1255 1254 IIm ν asc-o-c 1242 1242 1242 1242 PMFs ν asc-o-c 1230 1230 1230 1233 1230 1231 1229 PMFs/IIm/LOH/Ci ν sc-o-c/ δc-c=o 1198 1198 1198 1196 1197 1198 1198 βp ν skc-c (isopropyl) 1178 1182 1181 1178 1180 1194 1180 Lac ν sc-o-c (ester) 1151 1156 1155 1156 1154 1154 1155 IIm ν sc-o-c 1147 1148 1147 1147 1146 1146 1146 PMFs ν asc-o-c (6 ring) 1119 1116 1116 IIm/BOH ν asc-o-c (6 rings)/νc-o(h) 1109 1106 1109 1111 1111 1109 1113 IIm ν asc-o-c (5 ring) 1078 1079 1078 1079 1075 1077 1075 L/γT/βP/LOH/LAc/βM/IIm/Ci/BOH νc-c 1051 1051 1050 1049 1052 1051 1050 1038 1038 1037 LAc νc-c 1018 1018 1018 1018 1019 1019 1019 LAc/βM δ ip=ch/δ op=ch 2 990 990 989 988 987 990 989 L/γT/PMFs/IIm δch (ring) 956 956 957 957 955 955 957 γt δch (ring) 953 951 949 L/γT/βP/LOH/LAc/βM/Ci ρch 3 915 915 914 916 915 915 914 L δ op=ch 2/ρCH 3 888 888 888 887 887 887 888 PMFs ρ(o)ch 3 831 833 841 840 837 844 γt ρch 3 816 815 815 L/γT/βM/LAc/LOH δ op=ch 798 798 798 799 799 798 799 788 788 788 786 788 788 L ρch 2(ring) 758 758 758 759 758 759 758 PMFs δ op=ch (ar ring) 721 721 721 IIm δ op=ch (5 ring) 640 640 640 640 640 640 640 ip - in plane; op - out of plane. L - Limonene; βp - β-pinene; γt - γ-terpinene; βm - β-myrcene; LOH - Linalool; LAc - Linalyl acetate; Ci - Citral; BOH - Borneol; PMFs - Polymethoxyflavones; HPMFs - Hydroxylated Polymethoxyflavones; lim - Isoimperatorin. S8