Table 2.
Lowest, highest and mean levels of phenolic and cyclic structures detected in commercial olive oils (mg/kg FW). Retention time (RT) and retention index (RI) are based on an apolar HP-5MS column. The relative intensity (in %) of mass ions is shown in parenthesis. MS spectra included in publicly available databases (DB): [G] Golm Metabolome Database; [H] Human Metabolome Database; [M] MassBank; [N] NIST Chemistry WebBook.
| RT | RI | Compound | Masses | DB | Mean | Low | High |
|---|---|---|---|---|---|---|---|
| 15.05 | 1238 | phenylethyl alcohol | M+ 194(1), 73(100), 103(81), 179(68), 105(24) | [N] | 0.19 | 0.04 | 0.82 |
| 15.40 | 1249 | 3,5-dimethylphenol | M+ 194(39), 179(100), 194(67), 105(16) | [N] | 0.28 | 0.03 | 1.45 |
| 15.64 | 1257 | benzoic acid | M+ 194(4), 179(100), 105(79), 135(62), 77(56) | [G,H,M,N] | 0.44 | 0.02 | 1.32 |
| 17.13 | 1306 | phenylacetic acid | M+ 208, 73(100), 164(21), 193(9), 137(3) | [G,H,M,N] | 0.26 | 0.04 | 0.87 |
| 17.80 | 1329 | catechol | M+ 254(100), 239(30), 151(20), 136(15), 166(13) | [G,H,M,N] | 5.15 | 0.45 | 28.52 |
| 20.34 | 1419 | hydrocinnamic acid | M+ 222(24), 104(100), 207(46), 91(26), 132(4) | [G,H,M,N] | 0.60 | 0.01 | 3.25 |
| 21.62 | 1466 | hydroxybenzoic acid | M+ 282(48), 73(100), 267(18), 179(14), 193(10) | [G,H,M] | 0.47 | 0.03 | 2.36 |
| 21.82 | 1473 | (E)-isoeugenol | M+ 236(42), 206(100), 73(21), 221(19), 179(11), 103(6) | [N] | 0.81 | 0.02 | 4.65 |
| 22.86 | 1513 | salicylic acid | M+ 282, 73(100), 267(92), 135(10), 193(5) | [G,H,N] | 0.17 | 0.01 | 0.49 |
| 23.83 | 1551 | syringaldehyde | M+ 254(45), 224(100), 73(79), 209(45), 239(33) | [N] | 0.04 | 0.03 | 0.07 |
| 24.26 | 1569 | p-tyrosol | M+ 282(19), 179(100), 267(13), 193(12) | [H] | 7.02 | 1.47 | 18.32 |
| 25.23 | 1608 | ligstroside deriv. | M+ 192(100), 177(67), 179(24), 193(19) | – | 4.76 | 0.04 | 18.91 |
| 25.62 | 1624 | methyl homovanillic acid | M+ 268(55), 73(100), 238(75), 209(46), 253(30) | – | 0.05 | 0.02 | 0.14 |
| 25.95 | 1639 | vanillin | M+ 253(71), 223(100), 73(29), 238(22), 165(12) | [N] | 1.28 | 0.03 | 6.12 |
| 27.45 | 1703 | homovanillyl alcohol | M+ 312(33), 73(100), 209(94), 103(22), 179(16) | [N] | 0.61 | 0.01 | 3.05 |
| 28.49 | 1749 | phloretic acid | M+ 308(52), 73(100), 219(71), 293(65), 249(53) | [N] | 0.11 | 0.04 | 0.46 |
| 28.63 | 1755 | vanillic acid | M+ 312(24), 267(49), 297(44), 282(34), 253(28) | [G,H,N] | 0.43 | 0.02 | 2.26 |
| 28.76 | 1761 | hydroxytyrosol | M+ 370(44), 267(100), 193(19), 179(11) | – | 1.47 | 0.27 | 5.35 |
| 29.77 | 1807 | oleuropein deriv. | M+ 340(13), 73(100), 280(96), 193(40), 179(14) | – | 7.19 | 0.17 | 35.98 |
| 30.75 | 1853 | p-coumaric acid | M+ 308(35), 73(100), 293(53), 219(42), 249(23) | [G,H,M,N] | 0.04 | 0.02 | 0.06 |
| 31.44 | 1887 | syringic acid | M+ 342(24), 327(100), 73(67), 312(64), 297(58) | [N] | 0.04 | 0.01 | 0.07 |
| 32.11 | 1919 | (Z)-ferulic acid | M+ 338(49), 73(100), 308(43), 323(37), 249(33) | [G,N] | 0.08 | 0.02 | 0.26 |
| 32.14 | 1921 | (E)-coniferaldehyde | M+ 279(27), 73(100), 248(56), 218(49), 232(14) | [G] | 0.06 | 0.04 | 0.15 |
| 43.86 | 2596 | ligstroside deriv.* | 192(100), 177(26), 179(8) | – | 0.13 | 0.05 | 0.60 |
| 44.12 | 2613 | ligstroside deriv.* | 192(100), 177(22) | – | 0.17 | 0.04 | 0.49 |
| 44.41 | 2633 | ligstroside aglycone (aldehydic form I) | M+ 434(5), 192(100), 177(19), 179(7), 403(3) | – | 4.42 | 0.07 | 25.91 |
| 44.57 | 2644 | ligstroside aglycone (aldehydic form II) | M+ 434(5), 192(100), 177(23), 179(7), 403(3) | – | 0.59 | 0.07 | 3.15 |
| 45.48 | 2706 | ligstroside aglycone deriv.* | 192(100), 177(15), 179(5) | – | 0.34 | 0.03 | 1.51 |
| 46.08 | 2749 | ligstroside aglycone deriv.* | 192(100), 177(22), 179(5) | – | 0.49 | 0.04 | 1.96 |
| 46.39 | 2770 | oleuropein deriv.* | 280(100), 193(35), 179(14) | – | 0.09 | 0.02 | 0.36 |
| 46.66 | 2790 | oleuropein deriv.* | 280(100), 192(74), 177(16) | – | 0.08 | 0.02 | 0.27 |
| 46.92 | 2809 | oleuropein aglycone (aldehydic form) | M+ 522(3), 280(100), 193(18), 179(4), 267(3) | – | 3.48 | 0.07 | 20.45 |
| 47.00 | 2814 | ligstroside deriv. | M+ 492(3), 192(100), 177(29), 280(13), 209(4), 461(2) | – | 0.81 | 0.03 | 4.66 |
| 47.08 | 2820 | ligstroside deriv. | M+ 492(2), 192(100), 177(30), 461(21), 209(14), 280(9) | – | 0.52 | 0.03 | 2.91 |
| 47.32 | 2837 | ligstroside deriv. | M+ 492(1), 192(100), 177(16), 179(5), 209(2), 280(1) | – | 2.57 | 0.07 | 14.28 |
| 47.67 | 2863 | ligstroside deriv.* | 192(100), 177(18), 355(10), 179(8) | – | 0.23 | 0.03 | 1.15 |
| 47.77 | 2870 | oleuropein deriv.* | 280(100), 193(26), 179(4) | – | 0.25 | 0.01 | 1.22 |
| 47.91 | 2881 | ligstroside deriv.* | 192(100), 177(38), 179(19) | – | 0.08 | 0.02 | 0.26 |
| 47.98 | 2886 | ligstroside deriv.* | 192(100), 177(16), 179(6) | – | 0.46 | 0.03 | 2.27 |
| 48.07 | 2893 | ligstroside deriv.* | 192(100), 177(18), 179(9) | – | 0.20 | 0.02 | 1.01 |
| 48.40 | 2918 | oleuropein deriv.* | 280(100), 193(23), 179(6), 267(4), 519(4) | – | 0.73 | 0.04 | 3.82 |
| 48.63 | 2935 | oleuropein deriv.* | 280(100), 193(44), 192(41) | – | 0.05 | 0.01 | 0.08 |
| 49.07 | 2968 | oleuropein deriv.* | 280(100), 193(28), 179(8), 355(7) | – | 0.14 | 0.02 | 0.66 |
| 49.13 | 2973 | oleuropein deriv.* | 280(100), 193(28), 179(14) | – | 0.10 | 0.02 | 0.37 |
| 49.22 | 2979 | oleuropein deriv. | M+ 580(2), 280(100), 193(21), 179(5), 267(4) | – | 0.33 | 0.03 | 1.80 |
| 49.27 | 2984 | oleuropein deriv. | M+ 549(5), 280(100), 193(27), 179(8), 267(4) | – | 0.31 | 0.03 | 1.68 |
| 49.35 | 2989 | oleuropein deriv. | M+ 551(2), 280(100), 193(21), 179(4), 519(1) | – | 0.88 | 0.04 | 4.94 |
| 49.46 | 2998 | oleuropein deriv. | M+ 551(2), 280(100), 193(19), 179(4), 519(1) | – | 6.32 | 0.08 | 36.78 |
| 49.79 | 3023 | oleuropein deriv. | M+ 551(2), 280(100), 193(18), 179(5), 267(4) | – | 0.47 | 0.02 | 2.62 |
| 49.98 | 3038 | oleuropein deriv.* | 280(100), 355(30), 193(20), 368(4) | – | 0.30 | 0.02 | 1.60 |
| 50.04 | 3043 | oleuropein deriv.* | 280(100), 193(18), 179(5), 355(2) | – | 0.64 | 0.04 | 3.43 |
| 50.15 | 3051 | oleuropein deriv.* | 280(100), 193(17), 179(7), 267(5) | – | 0.23 | 0.01 | 1.16 |
| 51.78 | 3182 | luteolin | M+ 559(100), 73(54), 487(8), 272(7) | [G,H] | 0.05 | 0.01 | 0.09 |
| 53.26 | 3306 | pinoresinol | M+ 502(59), 223(100), 73(75), 209(56), 235(43) | – | 0.08 | 0.02 | 0.16 |
| 53.34 | 3313 | β-sitosterol | M+ 486(25), 129(100), 357(97), 396(92), 73(63), 381(40) | [G,H,N] | 0.12 | 0.03 | 0.24 |
| 53.76 | 3348 | acetoxipinoresinol | M+ 560(18), 276(100), 245(53), 73(37), 209(34), 261(20) | – | 1.06 | 0.04 | 5.40 |
| 55.59 | 3509 | uvaol | M+ 496(89), 216(100), 73(58), 203(51), 188(25), 161(24) | – | 0.32 | 0.02 | 0.96 |
| 56.65 | 3607 | oleanolic acid | M+ 585(6), 203(100), 73(53), 320(35), 189(33), 482(24) | [G,H] | 1.36 | 0.05 | 3.77 |
| Total Phenolics | 59.96 | 4.22 | 286.99 | ||||
| oleuropein structures | 21.61 | 0.72 | 117.21 | ||||
| ligstroside structures | 15.78 | 0.52 | 79.08 | ||||
| tyrosols | 8.49 | 1.74 | 23.67 | ||||
| phenolic acids | 2.69 | 0.36 | 11.56 | ||||
| alcohols | 7.04 | 0.58 | 38.49 | ||||
| aldehydes | 1.37 | 0.10 | 6.34 | ||||
| lignans | 1.13 | 0.07 | 5.56 | ||||
| flavonoids | 0.05 | 0.03 | 0.09 |
* no molecular peak detected; – no database MS spectrum available