Triptolactone

Triptolactone

Common Name: Triptolactone

Synonyms: (3S,3aR,5R,7aR)-3-[3-(6,7-Dihydroxy-2,5-dimethyl-1-naphtyl)-1,1-dimethylpropyl]-octahedro-5,7a-dimethyl-5,3-indenecarbolactone; (+)-Triptolactone

CAS Registry Number: 168706-17-0

InChI: InChI=1S/C29H38O4/c1-17-7-8-20-18(2)24(31)22(30)15-21(20)19(17)9-10-26(3,4)29-14-13-27(5)11-12-28(6,16-23(27)29)25(32)33-29/h7-8,15,23,30-31H,9-14,16H2,1-6H3/t23?,27?,28-,29+/m1/s1

InChIKey: InChIKey=MDIKECAJJPGHJN-CCIRZOMYSA-N

Formula: C29H38O4

Molecular Weight: 450.60962

Exact Mass: 450.27701

NMR Solvent: CDCl3

MHz: 400 (1H); 100 (13C)

Calibration: TMS

NMR references: Morota, T., Aoki, K., Qin, Q., Sugama, K., Xu, L., Maruno, M., Yang, B. (1995) A new nor-triterpenoid, triptolactone, with a novel carbon skeleton from Tripterigium wilfordii. Tetrahedron Lett. 36, 6291-6292.

Species: Tripterygium wilfordii - Morota, T., Aoki, K., Qin, Q., Sugama, K., Xu, L., Maruno, M., Yang, B. (1995) A new nor-triterpenoid, triptolactone, with a novel carbon skeleton from Tripterigium wilfordii. Tetrahedron Lett. 36, 6291-6292.

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 8.06 s
6 7.6 d 8.8
7 7.11 d 8.8
11 (stereochemistry unknown) 2.97 dt 12.9, 4.9
11 (stereochemistry unknown) 3.06 dt, dt 12.9, 4.4
12 1.82 m
15 (stereochemistry unknown) 2.21 ddd 15.4, 12.8, 8.4
15 (stereochemistry unknown) 2.57 dd 15.4, 8.4
16 (stereochemistry unknown) 1.23 m
16 (stereochemistry unknown) 1.62 m
18 1.81 t 3
19 (stereochemistry unknown) 1.61 dd 14, 3
19 (stereochemistry unknown) 2.06 dd 14, 3
21 (stereochemistry unknown) 1.53 dd 12, 4
21 (stereochemistry unknown) 2 m
22 (stereochemistry unknown) 1.43 m
22 (stereochemistry unknown) 1.46 m
23 2.52 s
25 2.42 s
26 1.15 s
27 1.15 s
28 1.01 s
30 1.27 s

Carbon NMR Peaks

Position PPM
1 104.8
2 141.9
3 144.4
4 115.9
5 127.8
6 121.1
7 126.4
8 129.1
9 134.4
10 128
11 25.9
12 39.4
13 40.2
14 110.7
15 27.4
16 40.4
17 41.9
18 45.9
19 31.4
20 38.8
21 35.5
22 31.2
23 10.6
25 19.5
26 23.2
27 24.4
28 25.7
29 179.5
30 26.8