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. 2024 May 16;13(10):1555. doi: 10.3390/foods13101555

Table 3.

Identified compounds in the analyzed by-product extracts.

Peak Number Proposed Compound Molecular Formula RT 1 (min) m/z (Exp) 2 m/z (Theor) 3 Error (ppm) Olive By-Product 4 References
1 Quinic acid C7H12O6 4.03 191.0562 191.0561 0.3 ALP, BLR, BSR [46]
2 3,4-Dihydroxyphenylglycol C8H10O4 5.85 169.0509 169.0506 −1.7 BLR, BSR [49,53]
3 Oxydized hydroxytyrosol C8H8O3 5.90 151.0396 151.0401 3.4 ALP, BLR, BSR [44]
4 Hydrated product of the dialdehydic form of decarboxymethyl elenolic acid isomer 1 C9H14O5 7.41 201.0730 201.0768 19.2 OL [44]
5 Dialdehydic form of decarboxymethyl elenolic acid isomer 1 C9H12O4 7.44 183.0653 183.0663 5.4 BLR [46,48]
6 Oleoside/Secologanoside C16H22O11 7.58 389.1103 389.1089 −3.5 ALP, OL [46,49]
7 1-β-D-Glucopyranosyl acyclodihydroelenolic acid C17H28O11 7.69 407.1574 407.1559 −3.8 ALP, OL [53]
8 Hydrated product of the dialdehydic form of decarboxymethyl elenolic acid isomer 2 C9H14O5 7.69 201.0748 201.0768 10.3 OL [44]
9 Loganic acid C16H24O10 7.73 375.1288 375.1297 2.3 ALP, OL [54]
10 Hydrated product of the dialdehydic form of decarboxymethyl elenolic acid isomer 3 C9H14O5 7.93 201.0764 201.0768 2.1 BLR, BSR, OFWW [44]
11 Hydroxylated product of the dialdehydic form of decarboxymethyl elenolic acid isomer 1 C9H12O5 7.93 199.0598 199.0612 6.8 OL [44,53]
12 7-Epiloganin C17H26O10 8.08 389.1430 389.1453 6.0 OL [55]
13 Hydroxytyrosol C8H10O3 8.14 153.0554 153.0557 2.2 ALP, BLR, BSR [42,44,49]
14 Decarboxylated form of
hydroxyelenolic acid		 C10H14O5 8.23 213.0757 213.0768 5.4 OL, OFWW [44,48]
15 Lamiol C16H26O10 8.24 377.1455 377.1453 −0.4 OL [54]
16 Decarboxymethyl-3,4-dihydroelenolic acid C9H14O4 8.25 185.0819 185.0815 2.2 ALP, OFWW [58]
17 Hydroxylated product of the dialdehydic form of decarboxymethyl elenolic acid isomer 2 C9H12O5 8.33 199.0615 199.0612 −1.3 ALP, OL, BLR, BSR, OFWW [44]
18 Elenolic acid glucoside C17H24O11 8.36 403.1259 403.1246 −3.3 ALP, OL [52]
19 Diosmetin glucoside isomer 1 C20H30O12 8.56 461.1650 461.1664 3.1 OL [54]
20 Verbascoside C29H36O15 8.63 623.1993 623.1981 −1.9 ALP [42,49]
21 Hydroxyoleuropein C25H32O14 8.68 555.1724 555.1719 0.9 OL [46,55]
22 Tyrosol C8H10O2 8.73 137.0590 137.0608 13.4 ALP, BLR, BSR [42,44,49]
23 Hydroxyelenolic acid C11H14O7 8.78 257.0660 257.0667 2.5 ALP, BLR, BSR [48]
24 Apigenin-7-O-rutinoside C27H30O14 8.91 577.1570 577.1563 −1.3 OL [49]
25 Dihydrooleuropein C25H36O13 8.94 543.2075 543.2083 1.5 ALP [47]
26 Aldehydic form of decarboxymethyl elenolic acid C10H16O5 8.95 215.0910 215.0925 6.8 ALP, BLR, BSR, OFWW [44,48]
27 Hydroxyoleuropein aglycone isomer 1 C19H22O9 9.38 393.1190 393.1191 0.3 BLR, BSR [48]
28 Dialdehydic form of decarboxymethyl elenolic acid isomer 2 C9H12O4 9.45 183.0658 183.0663 2.5 ALP, BLR, BSR [46,48]
29 Luteolin glucoside C21H20O11 9.45 447.0937 447.0933 −0.9 ALP, OL [49]
30 Apigenin-7-O-glucoside C21H20O10 9.48 431.0981 431.0984 0.7 OL [49]
31 Dialdehydic form of decarboxymethyl elenolic acid isomer 3 C9H12O4 9.50 183.0657 183.0663 3.0 OFWW [46,48]
32 Diosmetin glucoside isomer 2 C22H22O11 9.62 461.1090 461.1089 −0.2 OL [54]
33 Oleuropein C25H32O13 9.88 539.1809 539.1771 −7.1 ALP, BSR, OL [49]
34 Hydroxyoleuropein aglycone isomer 2 C19H22O9 10.54 393.1203 393.1191 −3.1 BLR, BSR [48]
35 Hydroxydecarboxymethyl oleuropein aglycone C17H20O7 10.77 335.1133 335.1136 1.0 ALP, BLR, BSR [48,53]
36 Elenolic acid C11H14O6 11.19 241.0716 241.0718 0.6 ALP, BLR, BSR, OL [48,49]
37 Hydroxyoleuropein aglycone isomer 3 C19H22O9 11.72 393.1181 393.1191 2.6 BSR [48]
38 Luteolin C15H10O6 12.09 285.0406 285.0405 −0.5 ALP, BLR, BSR, OL [42,44,48,49]
39 Oleacein/Decarboxymethyl oleuropein aglycone C17H20O6 12.26 319.1190 319.1187 0.9 ALP, BSR [44,48,49]
40 Hydrated oleuropein aglycone C19H24O8 12.58 379.1397 379.1398 0.4 ALP, BLR, BSR [44]
41 Hydroxyoleuropein aglycone isomer 4 C19H22O9 12.88 393.1193 393.1191 −0.4 BLR, BSR [48]
42 Oleuropein aglycone isomer 1 C19H22O8 13.16 377.1250 377.1242 −2.2 ALP, BLR, BSR [44,49]
43 Oleuropein aglycone isomer 2 C19H22O8 13.66 377.1259 377.1242 −4.6 ALP, BSR [44,49]
44 Apigenin C15H10O5 13.85 269.0451 269.0455 1.7 OL [44,48,49]
45 Diosmetin C16H12O6 14.12 299.0552 299.0561 3.0 OL [52]
46 Oleuropein aglycone isomer 3 C19H22O8 14.85 377.1253 377.1242 −2.8 ALP, BSR [44,49]
47 Methyl jasmonate C13H20O3 17.34 223.1320 223.1340 8.8 OL [59]
48 Dihydroxyoleanolic acid isomer 1 C30H48O5 18.67 487.3421 487.3429 1.7 OL [60]
49 Dihydroxyoleanolic acid isomer 2 C30H48O5 19.92 487.3410 487.3429 4.0 OL [60]
50 Hydroxy-oxo-oleanolic acid C30H46O4 25.02 469.3304 469.3323 4.1 OL [54]
51 Maslinic acid C30H48O4 25.42 471.3491 471.3480 −2.1 ALP, BSR, OL [52]
52 Oleanolic acid C30H48O3 31.68 455.3505 455.3531 5.7 OL [52]

1 Retention time; 2 Experimental; 3 Theoretical; 4 OL: olive leaf; ALP: “alpeorujo”; BLR: borras liquid residue; BSR: borras solid residue; OFWW: olive fruit washing water.