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. 2022 Sep 12;12(39):25764–25777. doi: 10.1039/d2ra04081f

Identified compounds by HPLC-DAD/ESI-MS2 in defatted hemp seeds.

N° peak RT (min) Compound name Molecular formula UV λmax (nm) Theoretical mass (m/z) Experimental mass (m/z) Error (ppm) Mass fragments (%intensity)
Negative mode [M − H] −
1 13.9 Benzoic acid C7H6O2 222, 285 122.0373 121.0375 1.65 Not fragmented
2 16.1 p-Coumaric acid C9H8O3 230, 295, 310 164.0478 163.0481 1.84 119 (100), 93 (8)
3 17.7 Ferulic acid C10H10O4 225, 292, 315 194.0584 193.0588 2.07 134 (100), 178 (37), 149 (13)
4 19.2 N-trans-caffeoyltyramine isomer C17H16NO4 220, 280, 315 299.1158 298.1161 1.01 135(100), 178(46), 298(45), 161(25), 136(12), 284(6)
5 20.8 N-trans-caffeoyltyramine C17H16NO4 220, 290, 320 299.1158 298.1159 0.34 135(100), 178(43), 161(42), 136(30), 298(16), 256(5), 148(5)
6 23.4 Cannabisin A C34H30O8N2 255 594.2002 593.2014 2.02 593(100), 454(27), 639(21), 523(16), 536(13), 428(11), 482(11)
7 23.7 Cannabisin B C34H32O8N2 225, 250, 285, 310, 335 596.2159 595.2148 −1.85 432(100), 595(93), 485(68), 269(33), 322(30)
8 24.2 N-trans-coumaroyltyramine C17H17O3N 224, 290, 310 283.1208 282.1218 3.54 145(100), 119(85), 282(54), 162(46), 134(14), 240(10)
9 24.6 Cannabisin B isomer 1 C34H32O8N2 255, 310 596.2159 595.2151 −1.34 416(100), 595(99), 269(46), 432(45), 458(30), 485(29), 295(23)
10 24.9 N-feruloyltyramine C18H19O4N 220, 292, 318 313.1314 312.1322 2.56 178(100), 135(45), 297(46), 312(45), 148(12)
11 25.3 Cannabisin B isomer 2 C34H32O8N2 224, 250, 290, 335 596.2159 595.2164 0.84 485(100), 432(40), 322(33), 269(20), 348(9), 456(8), 595 (6)
12 25.9 Demethylgrossamide C35H34N2O8 225, 250, 285, 330 610.2315 609. 2324 1.47 283(100), 446(66), 268(26), 609(9), 377(4)
13 26.4 Cannabisin C C35H34O8N2 220, 245, 292, 320 610.2315 609. 2321 0.98 499(100), 609(95), 446(70), 447(27), 336(20), 269(5)
14 26.9 Cannabisin C isomer C35H34O8N2 220, 280, 335, 410 610.2315 609.2332 2.79 446(100), 485(66), 609(21), 322(19), 472(7), 279(6), 499(6)
15 28.5 Cannabisin D C36H36N2O8 225, 250, 285, 340 624.2472 623.2479 1.12 460(100), 623(94), 283(35), 268(7), 444(9), 499(4)
16 28.9 3,3-Didemethylgrossamide C34H32N2O8 225, 290, 324 596.2159 595.2168 1.51 432(100), 269(99), 458(36), 595(22), 295(10), 338(7), 250(2)
17 29.1 Tri-p-coumaroylspermidine C34H37N3O6 255 583.2688 582.2691 0.52 462(100), 582(87), 342(76), 316(10), 436(11), 299(4), 217(2), 533(2)
18 29.8 Cannabisin E C36H38N2O9 220, 283, 316 642.2577 641.2579 0.31 623(100), 489(90), 281(65), 431(40), 641(30), 591(15), 460(11), 312(12)
19 30.2 Grossamide K C28H29NO7 225, 288, 325 491.1949 490.1957 1.63 472(100), 490(43), 460(34), 488(2)
20 31.3 Cannabisin M C34H32N2O8 223, 285, 315 596.2159 595.2147 −2.04 298(100), 595(57), 430(17), 427(5), 547(4)
21 31.5 3,3′-demethyl-heliotropamide C34H32N2O8 223, 285, 315 596.2159 595.2168 1.51 107(100), 298(49), 595(23)
22 31.7 Unnamed condensed trilignanamide C51H47N3O12 222, 278, 315 893.3160 892.3164 0.44 430(100), 595(85), 593(55), 727(24), 485(11), 322(11), 892(9)
23 32.0 Cannabisin Q C34H32N2O8 290, 320 596.2159 595.2154 −0.84 298(100), 595(42), 296(7), 178(1)
24 32.3 Cannabisin F C36H36N2O8 225, 290 624.2472 623.2478 0.96 460(100), 623(61), 297(35), 486(29), 352(5)
25 33.4 Isocannabisin N C35H34N2O9 225, 294, 312 610.2315 609.2298 −2.79 609(100), 296(41), 312(25), 417(17), 446(5), 176(4), 581(3)
26 34.2 Grossamide C36H36N2O8 226, 285, 322 624.2472 623.2485 2.08 623(100), 460(77), 591(47), 297(32), 471(30), 551(23), 432(17), 486(15), 428(11), 282(11)
27 34.5 Cannabisin O C54H53N3O12 229, 315 935.3629 934.3641 1.28 Not fragmented
28 35.4 Unnamed lignanamide — 228, 312 — 589.2366 — 426 (100), 261(10), 443(8), 589(7), 255(7), 279(5), 163(5)
29 39.4 Dihydrocannabinol C21H28O2 272 312.2089 311.2092 0.96 293(100), 311(82), 223(59), 275(41), 201(26), 235(20), 171(15)
30 40.7 Cannabidiol (CBD) C21H30O2 280 314.2246 313.2257 3.51 313(100), 201(96), 171(36), 295(34), 277(26), 202(14), 165(6), 172(5), 183(2), 129(0,5)
31 44.2 Cannabielsoic acid C22H29O5 280 374.2099 373.2105 1.61 205(100), 329(94), 311(84), 373(56), 271(35), 173(16), 259(8)
32 45.2 Sinapic acid C11H12O5 275 224.0690 223.0697 3.13 225(100), 223(34), 195(36), 125(35), 179(24), 221(20), 163(18), 206(16), 164(12), 155(17)
33 45.9 Cannabidiolic acid (CBDA) C22H30O4 224, 270, 310 358.2144 357.2141 −0.84 339(100), 357(21), 340(19), 341(11), 311(7), 313(5), 289(3), 179(2), 271(1), 245(1)
 
Positive mode [M + H]+
1 13.9 Benzoic acid C7H6O2 222, 285 122.0373 123.0376 2.44 123(100), 95(74), 122(20), 79(17), 97(15), 107(14), 96(12), 20(7)
4 19.2 N-trans-caffeoyltyramine isomer C17H16NO4 220, 280, 315 299.1158 300.1155 −0.99 163(100), 138(18), 300(16), 121(10), 145(4)
5 20.8 N-trans-caffeoyltyramine C17H16NO4 220, 290, 320 299.1158 300.1160 0.67 163(100), 300(18), 138(15), 121(7), 145(5)
6 23.4 Cannabisin A C34H30N2O8 255 594.2002 595.2011 1.51 458(100), 595(18), 459(5)
7 23.7 Cannabisin B C34H32N2O8 225, 250, 285, 310, 335 596.2159 597.2167 1.34 460(100), 597(11), 432(5), 350(3), 295(1)
8 24.2 N-trans-coumaroyltyramine C17H17NO4 224, 290, 310 283.1208 284.1214 2.11 147(100), 284(30), 148(14), 119(2)
9 24.6 Cannabisin B isomer 1 C34H32N2O8 255, 310 596.2159 597.2151 −1.34 460(100), 432(32), 597(25), 295(13), 350(7), 418(5), 279(5)
10 24.9 N-feruloyltyramine C17H17NO4 220, 292, 318 313.1314 314.1319 1.59 177(100), 314(28), 145(13), 178(13), 313(9), 117(1)
11 25.3 Cannabisin B isomer 2 C17H17NO4 224, 250, 290, 335 596.2159 597.2164 0.84 460(100), 597(7), 350(3), 187(3), 131(1), 295(2), 323(2)
12 25.9 Demethylgrossamide C35H34N2O8 225, 250, 285, 330 610.2315 611.2318 0.49 474(100), 611(51), 446(20), 350(16), 309(7), 591(5), 187(3)
13 26.4 Cannabisin C C35H34N2O8 220, 245, 292, 320 610.2315 611.2297 −2.94 474(100), 611(30), 446(21), 364(12), 309(5), 201(4)
14 26.9 Cannabisin C isomer C35H34N2O8 220, 280, 335, 410 610.2315 611.2317 0.33 474(100), 611(48), 446(21), 472(12), 350(7), 337(4), 309(4), 454(3)
15 28.5 Cannabisin D C36H36N2O8 225, 250, 285, 340 624.2472 625.2479 1.12 488(100), 460(31), 625(20),364(19), 323(9), 201(5), 297(2), 244(1), 439(1)
16 28.9 3,3-Didemethylgrossamide C34H32N2O8 225, 290, 324 596.2159 597.2170 1.84 434(100), 297(49), 597(44), 279(41), 323(25), 251(15), 460(14), 233(6), 271(5)
17 29.1 Tri-p-coumaroylspermidine C34H37N3O6 255 583.2688 584.2691 0.51 438(100), 420(73), 584(17), 204(14), 275(7), 565(4), 534(3)
18 29.8 Cannabisin E C36H38N2O9 220, 283, 316 642.2577 643.2586 1.40 643(100), 462(80), 282(17), 625(15), 338(10), 341(9), 325(7), 489(7)
19 30.2 Grossamide K C28H29NO7 225, 288, 325 491.1949 492.1929 −4.06 462(100), 493(57), 325(45), 463(13), 337(9), 307(7), 293(1)
20 31.3 Cannabisin M C34H32N2O8 223, 285, 315 596.2159 597.2164 0.84 297(100), 434(82), 597(52), 300(30), 337(17), 187(17), 533(16), 460(15), 279(14)
21 31.5 3,3′-demethyl-heliotropamide C34H32N2O8 223, 285, 315 596.2159 597.2167 1.34 523(100), 297(45), 597(42), 458(33), 337(21), 853(20)
22 31.7 Unnamed condensed trilignanamide C51H47N3O12 222, 278, 315 893.3160 894.3171 1.23 894(00), 757(99), 484(30), 729(28), 374(10), 647(10), 594(10), 429(4)
23 32.0 Cannabisin Q C34H32N2O8 290, 320 596.2159 597.2162 0.50 297(100), 597(31), 460(24), 434(21), 187(21), 279(11), 233(5), 251(5)
24 32.3 Cannabisin F C36H36N2O8 225, 290 624.2472 625.2453 −3.03 462(100), 625(70), 325(44), 307(12), 351(8), 293(5), 201(2)
25 33.4 Isocannabisin N C35H34N2O9 225, 294, 312 610.2315 611.2319 0.65 448(100), 611(80), 311(64), 314(35), 187(33), 474(25), 293(14), 177(13), 591(8), 409(6)
26 34.2 Grossamide C36H36N2O8 226, 285, 322 624.2472 625.2481 1.44 625(100), 462(93), 325(57), 351(42), 307(30), 488(25), 293(15),292(5), 626(5)
27 34.5 Cannabisin O C54H53N3O12 229, 315 935.3629 936.3609 −2.13 799(100), 538(36), 634(30), 771(21), 512(15), 936(12), 675(8), 388(6)