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. 2021 Mar 23;10(3):500. doi: 10.3390/antiox10030500

Table 3.

Tentative identification of compounds detected in rosemary infusions by UHPLC-ESI-QTOF-MS.

Peak Retention Time (min) [M − H]− Experimental [M − H]− Theorical Error (ppm) MS2 Product Ions Molecular Formula Family Tentative Identification Std ** Ref.
1 2.144 315.0717 315.0722 1.46 108 (42), 109 (38), 152 (100), 153 (41) C13H16O9 Hydroxybenzoic acid Dihydroxybenzoic acid hexoside A –
2 2.260 197.0454 197.0455 0.75 123 (75), 135 (100) C9H10O5 Hydroxybenzoic acid Hydroxydimethoxybenzoic acid B [2,5,20]
3 2.334 167.0344 167.0350 3.49 108 (81), 121 (100), 123 (82), 137 (76) C8H8O4 Hydroxybenzoic acid Hydroxymethoxybenzoic acid (I) C [20]
4 2.467 153.0195 153.0193 −1.09 109 (100) C7H6O4 Hydroxybenzoic acid Protocatechuic acid * A [20]
5 3.141 137.0239 137.0244 3.82 108 (48), 119 (9), 136 (53), 137 (100) C7H6O3 Hydroxybenzaldehyde Dihydroxybenzaldehyde A –
6 3.181 299.0777 299.0772 −1.53 93 (100), 137 (99) C13H16O8 Hydroxybenzoic acid Hydroxybenzoic acid-O-hexoside D [20]
7 3.221 137.0246 137.0244 −1.32 93 (37) C7H6O3 Hydroxybenzoic acid 4-hydroxybenzoic acid * D [20]
8 3.411 339.0719 339.0722 0.76 177 (100), 221 (10) C15H16O9 Coumarin Dihydroxycoumarin hexoside (I) E –
9 3.567 341.0876 341.0878 0.66 135 (61), 161 (20), 179 (100), 221 (25), 281 (30) C15H18O9 Hydroxycinnamic acid Caffeic acid-O-hexoside F [20]
10 3.574 325.0926 325.0929 1.00 119 (49), 163 (100) C15H18O8 Hydroxycinnamic acid Coumaric acid hexoside E –
11 3.667 353.0878 353.0878 0.02 173 (44), 179 (69), 191 (100) C16H18O9 Hydroxycinnamic acid Caffeoylquinic acid * G [5,20]
12 3.811 167.0350 167.0350 −0.10 108 (100), 152 (55) C8H8O4 Hydroxybenzoic acid Hydroxymethoxybenzoic acid (II) C [20]
13 3.874 179.0351 179.0350 −0.65 135 (100) C9H8O4 Hydroxycinnamic acid Caffeic acid * F [1,5,20]
14 3.907 339.0724 339.0722 −0.71 177 (100) C15H16O9 Coumarin Dihydroxycoumarin hexoside (II) E –
15 4.427 305.0706 305.0667 −12.85 59 (43), 97 (100), 225 (40) C15H14O7 Flavan-3-ol Gallocatechin H [2,9,20]
16 4.747 163.0398 163.0400 1.37 119 (100) C9H8O3 Hydroxycinnamic acid p-Coumaric acid * E [20]
17 5.077 463.0877 463.0882 1.09 301 (100) C21H20O12 Flavone/Flavonol Hydroxyluteolin/Quercetin-O-hexoside I [2,5,20]
18 5.371 521.1293 521.1301 1.47 135 (19), 161 (33), 179 (59), 197 (42), 323 (86), 359 (51) C24H26O13 Hydroxycinnamic acid Rosmarinic acid-O-hexoside J [2,5]
19 5.521 593.1517 593.1512 −0.85 285 (65), 151 (22), 593 (100) C27H30O15 Flavone Luteolin-O-rutinoside K [2,5,9,20]
20 5.567 461.0726 461.0726 −0.10 285 (100) C21H18O12 Flavone Luteolin/Scutellarein-O-glucuronide (I) I [1,2,5,9,20]
21 5.641 447.0942 447.0933 −2.04 285 (100) C21H20O11 Flavone Luteolin-7-O-glucoside * I [20]
22 5.898 477.1046 477.1039 −1.56 299 (20), 315 (47), 477 (100) C22H22O12 Flavone Nepitrin I [2,5,9,20]
23 5.908 577.1561 577.1563 0.32 269 (100) C27H30O14 Flavone Apigenin-O-rutinoside K [20]
24 6.188 359.0775 359.0772 −0.71 135 (7), 161 (100), 179 (12), 197 (52) C18H16O8 Hydroxycinnamic acid Rosmarinic acid * J [1,2,5,9,20]
25 6.291 609.1825 609.1825 0.00 301 (100) C28H34O15 Flavanone Hesperidin * L [2,5,9]
26 6.454 461.1091 461.1089 −0.35 283 (32), 297 (10), 461 (100) C22H22O11 Flavone Homoplantaginin I [1,2,5,9]
27 6.568 461.0728 461.0726 −0.53 285 (100) C21H18O12 Flavone Luteolin/Scutellarein-O-glucuronide (II) I [1,2,5,9,20]
28 7.061 503.0840 503.0831 −1.75 285 (44), 399 (100) C23H20O13 Flavone Tetrahydroxyflavone-O-acetylglucuronide (I) I [1,2,5,9]
29 7.314 503.0833 503.0831 −0.36 285 (100), 399 (11) C23H20O13 Flavone Tetrahydroxyflavone-O-acetylglucuronide (II) I [1,2,5,9]
30 7.741 503.0828 503.0831 0.63 285 (100), 443 (14) C23H20O13 Flavone Tetrahydroxyflavone-O-acetylglucuronide (III) I [1,2,5,9]
31 8.365 345.1715 345.1707 −2.18 301 (100) C20H26O5 Phenolic diterpene (Epi)(iso)Rosmanol (I) M [2,5,9,20]
32 8.571 403.1765 403.1762 −0.68 281 (34), 299 (18), 341 (15), 359 (100) C22H28O7 Phenolic diterpene Rosmanol derivative M –
33 8.691 345.1719 345.1707 −3.34 283 (44), 301 (100) C20H26O5 Phenolic diterpene (Epi)(iso)Rosmanol (II) M [2,5,9,20]
34 8.718 313.0716 313.0718 0.52 283 (100), 298 (83) C17H14O6 Flavone Cirsimaritin N [2,5,20]
35 8.798 345.1711 345.1707 −1.02 283 (100), 301 (19) C20H26O5 Phenolic diterpene (Epi)(iso)Rosmanol (III) M [2,5,9,20]
36 8.848 331.1918 331.1915 −0.96 283 (26), 287 (12), 331 (100) C20H28O4 Phenolic diterpene Carnosic acid isomer M [2,5,9,20]
37 8.961 283.0610 283.0612 0.70 268 (100) C16H12O5 Flavone Genkwanin * O [2,5,9,20]
38 9.051 387.1819 387.1813 −1.49 179 (8), 283 (43), 343 (100) C22H28O6 Pyranochromanone Isocalolongic acid M –
39 9.345 343.1550 343.1551 0.29 299 (34), 343 (100) C20H24O5 Phenolic diterpene Rosmadial/Safficinolide (I) M [2,9,20]
40 9.445 359.1864 359.1864 0.00 283 (89), 284 (100), 285 (49), 300 (52), 317 (64) C21H28O5 Phenolic diterpene Epirosmanol methyl ether M [2]
41 9.488 329.1766 329.1758 −2.33 285 (100) C20H26O4 Phenolic diterpene Carnosol M [2,9,20]
42 9.591 343.1552 343.1551 −0.30 315 (55), 343 (100) C20H24O5 Phenolic diterpene Rosmadial/Safficinolide (II) M [2,9,20]
43 9.725 315.1957 315.1966 2.76 285 (100) C20H28O3 Phenolic diterpene Rosmaridiphenol M [2,9]
44 9.838 331.1912 331.1915 0.86 287 (100) C20H28O4 Phenolic diterpene Carnosic acid * M [2,5,9,20]

*, Confirmed by reference standard. **, Reference standard used for quantification or semi-quantification: A: Protocatechuic acid, B: Syringic acid, C: Vanillic acid, D: 4-hydroxybenzoic acid, E: p-Coumaric acid, F: Caffeic acid, G: Chlorogenic acid, H: Catechin, I: Luteolin-7-O-glucoside, J: Rosmarinic acid, K: Rutin, L: Hesperidin, M: Carnosic acid, N: Hesperetin, O: Genkwanin.