Skip to main content
. 2020 Jul 15;25(14):3223. doi: 10.3390/molecules25143223

Table 2.

Product ions acquired using high-resolution MS/MS for protonated ions of orceins extracted from wool dyed with orchil.

Compound tR, min [M + H]+, m/z Fragment ion, m/z Calc. m/z Formula Diff, ppm Abund %
β/γ-aminoorcein (32) 17.2 485.1718 485.1707 C28H25N2O6 −2.20 100.0
470.1478 470.1472 C27H22N2O6 −1.24 90.3
469.1526 469.1520 C28H23NO6 −1.36 45.4
468.1679 468.1680 C28H24N2O5 0.21 57.0
467.1615 467.1602 C28H23N2O5 −2.91 16.4
457.1760 457.1758 C27H25N2O5 −0.51 14.1
453.1453 453.1445 C27H21N2O5 −1.86 34.2
425.1242 425.1258 C26H19NO5 3.79 25.7
415.1653 415.1652 C25H23N2O4 −0.18 69.5
414.1571 414.1574 C25H22N2O4 0.82 23.8
400.1436 400.1418 C24H20N2O4 −4.52 36.3
399.1367 399.1339 C24H19N2O4 −6.89 26.1
387.1694 387.1703 C24H23N2O3 2.26 23.9
371.1389 371.1390 C23H19N2O3 0.22 18.8
362.1262 362.1261 C21H18N2O4 −0.43 26.2
347.1383 347.1390 C21H19N2O3 2.17 10.9
347.1021 347.1026 C20H15N2O4 1.45 12.9
334.1303 334.1312 C20H18N2O3 2.60 10.2
333.1245 333.1234 C20H17N2O3 −3.35 16.6
283.1083 283.1077 C16H15N2O3 −2.09 7.5
β/γ-aminoorceinimine (33) 17.3 484.1869 484.1867 C28H26N3O5 −0.40 100.0
469.1633 469.1632 C27H23N3O5 −0.20 76.6
468.1669 468.1680 C28H24N2O5 2.25 73.1
467.1836 467.1840 C28H25N3O4 0.78 23.4
467.1615 467.1602 C28H23N2O5 −2.97 22.5
466.1789 466.1761 C28H24N3O4 −5.95 14.0
453.1430 453.1445 C27H21N2O5 3.27 43.9
424.1408 424.1418 C26H20N2O4 2.32 27.5
415.1658 415.1652 C25H23N2O4 −1.28 46.4
414.1585 414.1574 C25H22N2O4 −2.63 21.0
400.1685 400.1656 C24H22N3O3 −7.33 27.4
387.1724 387.1703 C24H23N2O3 −5.30 19.1
361.1419 361.1421 C21H19N3O3 0.63 23.2
346.1209 346.1186 C20H16N3O3 −6.65 21.9
β/γ-hydroxyorcein (44) 21.7 486.1561 486.1547 C28H24NO7 −2.86 54.2
471.1309 471.1313 C27H21NO7 0.87 100.0
470.1231 470.1234 C27H20NO7 0.57 16.9
469.1515 469.1520 C28H23NO6 1.13 59.1
468.1450 468.1442 C28H22NO6 −1.69 20.8
458.1590 458.1598 C27H24NO6 1.77 16.1
454.1285 454.1285 C27H20NO6 −0.07 35.6
440.1488 440.1493 C27H22NO5 1.05 13.6
425.1266 425.1258 C26H19NO5 −1.81 37.2
416.1491 416.1493 C25H22NO5 0.58 63.6
415.1421 415.1414 C25H21NO5 −1.66 30.6
401.1258 401.1258 C24H19NO5 −0.10 37.4
400.1185 400.1179 C24H18NO5 −1.37 23.3
388.1544 388.1543 C24H22NO4 −0.15 40.2
386.1010 386.1023 C23H16NO5 3.37 12.2
384.1234 384.1204 C21H20O7 −7.71 12.5
373.1311 373.1309 C23H19NO4 −0.40 21.9
372.1236 372.1230 C23H18NO4 −1.64 12.8
363.1113 363.1101 C21H17NO5 −3.28 33.5
348.0864 348.0866 C20H14NO5 0.57 19.3
346.1429 346.1438 C22H20NO3 2.57 15.8
334.1078 334.1074 C20H16NO4 −1.11 25.9
293.1053 293.1046 C18H15NO3 −2.46 17.3
264.1032 264.1019 C17H14NO2 −4.96 14.4
α-aminoorceinimine (45) 21.9 362.1499 362.1499 C21H20N3O3 −0.08 100.0
347.1264 347.1264 C20H17N3O3 0.04 73.8
346.1318 346.1312 C21H18N2O3 −1.85 47.4
345.1461 345.1472 C21H19N3O2 4.01 19.2
345.1230 345.1234 C21H17N2O3 1.19 10.3
344.1391 344.1394 C21H18N3O2 0.81 17.6
332.1031 332.1030 C19H14N3O3 −0.42 19.7
331.1078 331.1077 C20H15N2O3 −0.27 33.1
330.1245 330.1237 C20H16N3O2 −2.39 38.3
302.1047 302.1050 C19H14N2O2 0.93 26.3
293.1297 293.1284 C18H17N2O2 −4.26 17.5
278.1283 278.1288 C17H16N3O 1.62 24.0
264.1140 264.1131 C16H14N3O −3.41 12.0
262.1099 262.1101 C17H14N2O 0.76 9.3
239.1055 239.1053 C14H13N3O −0.80 30.4
β/γ-aminoorceinimine (46) 22.0 484.1868 484.1867 C28H26N3O5 −0.28 100.0
469.1629 469.1632 C27H23N3O5 0.60 61.5
468.1668 468.1680 C28H24N2O5 2.58 71.4
467.1783 467.1840 C28H25N3O4 12.18 17.6
466.1775 466.1761 C28H24N3O4 −3.05 11.1
453.1436 453.1445 C27H21N2O5 1.94 26.5
452.1613 452.1605 C27H22N3O4 −1.70 25.1
424.1422 424.1418 C26H20N2O4 −0.94 17.8
415.1630 415.1652 C25H23N2O4 5.30 16.6
400.1664 400.1656 C24H22N3O3 −2.05 12.5
361.1429 361.1421 C21H19N3O3 −2.10 24.1
346.1196 346.1186 C20H16N3O3 −2.83 8.2
β/γ-aminoorcein (47) 22.3 485.1721 485.1707 C28H25N2O6 −2.94 100.0
470.1473 470.1472 C27H22N2O6 −0.30 86.1
469.1511 469.1520 C28H23NO6 1.83 35.2
468.1681 468.1880 C28H24N2O5 −0.21 53.5
467.1602 467.1602 C28H23N2O5 −0.06 14.5
457.1762 457.1758 C27H25N2O5 −0.87 15.7
453.1442 453.1445 C27H21N2O5 0.73 29.4
425.1266 425.1258 C26H19NO5 −1.79 20.7
415.1657 415.1652 C25H23N2O4 −1.28 63.2
414.1575 414.1574 C25H22N2O4 −0.17 21.0
400.1412 400.1418 C24H20N2O4 1.50 34.6
399.1371 399.1339 C24H19N2O4 −7.97 22.0
387.1697 387.1703 C24H23N2O3 1.58 28.0
371.1387 371.1390 C23H19N2O3 0.86 14.9
362.1262 362.1261 C21H18N2O4 −0.30 22.5
347.1375 347.1390 C21H19N2O3 4.26 7.6
347.1022 347.1026 C20H15N2O4 1.24 19.5
334.1302 334.1312 C20H18N2O3 2.90 9.0
333.1238 333.1234 C20H17N2O3 −1.17 12.0
283.1068 283.1077 C16H15N2O3 3.21 4.4
α-aminoorcein (49) 22.7 363.1342 363.1339 C21H19N2O4 −0.73 75.2
348.1106 348.1105 C20H16N2O4 −0.41 100.0
347.1145 347.1152 C21H19N2O4 2.06 58.7
346.1298 346.1312 C21H18N2O3 3.93 30.1
346.1063 346.1074 C21H16NO4 3.01 11.0
345.1232 345.1234 C21H17N2O3 0.41 18.8
335.1400 335.1400 C20H19N2O3 −2.78 2.3
333.0876 333.0870 C19H13N2O4 −1.81 19.1
332.0918 332.0917 C20H14NO4 −0.21 46.7
331.1063 331.1077 C20H15N2O3 4.14 42.1
330.1108 330.1125 C21H16NO3 5.03 21.2
303.0900 303.0890 C19H13NO3 −3.35 67.2
293.1289 293.1285 C18H17N2O2 −1.39 4.8
292.1209 292.1206 C18H16N2O2 −0.83 9.5
279.1128 279.1128 C17H15N2O2 0.03 27.5
265.0969 265.0969 C16H13N2O2 0.80 7.4
240.0892 240.0893 C14H12N2O2 0.43 51.9
β/γ-hydroxyorcein (56) 26.6 486.1548 486.1547 C28H24NO7 −0.31 40.7
471.1310 471.1313 C27H21NO7 0.63 100.0
469.1517 469.1520 C28H23NO6 0.52 74.3
468.1438 468.1442 C28H22NO6 0.82 23.3
458.1594 458.1598 C27H24NO6 0.90 22.6
454.1285 454.1285 C27H20NO6 0.09 41.9
440.1501 440.1493 C27H22NO5 −2.00 12.9
425.1246 425.1258 C26H19NO5 2.77 28.8
416.1487 416.1493 C25H22NO5 1.31 83.8
401.1259 401.1258 C24H19NO5 −0.22 45.8
400.1187 400.1179 C24H18NO5 −1.91 28.1
388.1543 388.1543 C24H22NO4 −0.02 43.8
384.1189 384.1204 C21H20O7 3.72 17.1
373.1306 373.1309 C23H19NO4 0.75 13.7
372.1236 372.1230 C23H18NO4 −1.45 13.5
363.1104 363.1101 C21H17NO5 −0.87 13.8
348.0860 348.0866 C20H14NO5 1.95 14.0
346.1432 346.1438 C22H20NO3 1.67 22.0
334.1068 334.1074 C20H16NO4 1.79 24.1
292.0975 292.0968 C18H14NO3 −2.17 9.5
264.1015 264.1019 C17H14NO2 1.72 13.9
α-hydroxyorcein (58) 27.3 364.1184 364.1179 C21H18NO5 −1.17 30.9
349.0946 349.0945 C20H15NO5 −0.45 79.6
348.0867 348.0866 C20H14NO5 −0.10 29.5
347.1152 347.1152 C21H17NO4 −0.07 45.6
346.1079 346.1074 C21H16NO4 −1.60 40.5
336.1232 336.1230 C20H18NO4 −0.49 15.1
334.0717 334.0710 C19H12NO5 −2.12 8.8
332.0919 332.0917 C20H14NO4 −0.43 55.3
331.0841 331.0839 C20H13NO4 −0.49 38.9
318.1132 318.1125 C20H16NO3 −2.32 16.2
303.0897 303.0890 C19H13NO3 −2.22 54.6
294.1126 294.1125 C18H16NO3 −0.34 100.0
293.1049 293.1046 C18H15NO3 −0.95 37.8
279.0892 279.0890 C17H13NO3 −0.57 81.4
266.1173 266.1176 C17H16NO2 0.98 57.6
266.0816 266.0816 C16H12NO3 −1.69 8.0
251.0938 251.0941 C16H13NO2 1.22 30.5
250.0868 250.0863 C16H12NO2 −2.33 25.9
241.0736 241.0733 C14H11NO3 −0.96 25.9
226.0862 226.0863 C14H12NO2 0.21 16.4
212.0706 212.0706 C13H10NO2 0.27 38.9