1β-Acetoxy-9α-benzoyloxy-15-cinnamoyloxy-4α,6α-dihydroxy-dihydroagarofuran

1β-Acetoxy-9α-benzoyloxy-15-cinnamoyloxy-4α,6α-dihydroxy-dihydroagarofuran

Common Name: 1β-Acetoxy-9α-benzoyloxy-15-cinnamoyloxy-4α,6α-dihydroxy-dihydroagarofuran

Synonyms: TWHR-1

CAS Registry Number:

InChI: InChI=1S/C33H38O9/c1-21(34)40-25-17-18-31(4,38)33-28(36)24(30(2,3)42-33)19-26(41-29(37)23-13-9-6-10-14-23)32(25,33)20-39-27(35)16-15-22-11-7-5-8-12-22/h5-16,24-26,28,36,38H,17-20H2,1-4H3/b16-15+/t24-,25+,26-,28-,31+,32+,33+/m1/s1

InChIKey: InChIKey=HFAVLOIYMYQWNG-GVTWWSSXSA-N

Formula: C33H38O9

Molecular Weight: 578.64942

Exact Mass: 578.251583

NMR Solvent: CDCl3

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

Calibration: TMS

NMR references: 1H, 13C - Nakano, K., Oose, Y., Masuda, Y., Kamada, H., Takaishi, Y. (1998) Terpenoids in transformed root culture of Tripterygium wilfordii. Phytochemsitry 49, 1821-1824

Species: Tripterygium wilfordii - Nakano, K., Oose, Y., Masuda, Y., Kamada, H., Takaishi, Y. (1998) Terpenoids in transformed root culture of Tripterygium wilfordii. Phytochemsitry 49, 1821-1824

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 5.5 b 11.2, 4.4
2 2.04 m
3beta 1.78 m
3alpha 1.98 dd 12.7, 4.9
6 4.81 d 5.4
7 2.31 t 3.4
8alpha 2.25 dd 13.7, 2.9
8beta 2.47 ddd 13.7, 7.8, 3.4
9 5.68 d 7.3
15a 4.73 d 12.2
15b 4.95 d 12.2
Me 1.45 s
Me 1.58 s
Me 1.61 s
Me 1.68 s
4-OH 3.22 s
6-OH 5.18 d 5.4
Aromatic (position unknown; 10 H) 7.75 m
Cinnamoyl moiety (double bond?) 6.5 d 16.6
Cinnamoyl moiety (double bond?) 7.78 d 16.6

Carbon NMR Peaks

Position PPM
1 72.5
2 23.6
3 37.1
4 73
5 91.2
6 79.2
7 49.9
8 34.2
9 68.4
10 53.4
11 84.7
12 30
13 26.6
14 23.3
15 65
1-OAc (CH3) 20.6
CH=CH (cinnamoyl moiety) 117.2
CH=CH (cinnamoyl moiety) 146.2
Carbonyl (position unknown) 165.2
Carbonyl (position unknown) 166.4
Carbonyl (position unknown) 169.7