5-O-Acetyltaxinine M

5-O-Acetyltaxinine M

Common Name: 5-O-Acetyltaxinine M

Synonyms: Taxumairol R

CAS Registry Number: 244167-04-2

InChI: InChI=1S/C37H44O15/c1-18-26(48-19(2)38)15-28(49-20(3)39)36(17-46-33(44)24-12-10-9-11-13-24)29(18)30(50-21(4)40)25-14-27(43)35(8)37(45,34(25,7)16-47-35)32(52-23(6)42)31(36)51-22(5)41/h9-13,25-26,28-32,45H,1,14-17H2,2-8H3/t25-,26-,28?,29-,30+,31-,32-,34-,35+,36?,37-/m0/s1

InChIKey: InChIKey=XUMIEQQAVQWNBJ-QDGPANNTSA-N

Formula: C37H44O15

Molecular Weight: 728.74

Exact Mass: 728.268

NMR Solvent: CDCl3

MHz: 300.0

Calibration: TMS

NMR references: Shi, Q., Oritani, T., Sugiyama, T., Murakami, R., and Wei, H. (1999). Six New Taxane Diterpenoids from the Seeds of Taxus chinensis var. mairei and Taxus yunnanensis. J. Nat. Prod. 62, 1114–1118.

Shen, Y.C., Prakash, C.V.S., and Hung, M.C. (2000). Taxane diterpenoids from the root bark of Taiwanese yew Taxus mairei. J. Chin. Chem. Soc. 47, 1125–1130.

Species: Taxus

Notes: Proton NMR data takenf rom Shi et al., 1999 while carbon NMR data taken from Shen et al., 2000.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.43 br d 12
2 6.11 dd 9.6, 2.7
3 3.43 d 9.6
5 5.31 s
6a 2.26 m
6b 1.67 m
7 5.45 dd 10.7, 6.3
9 5.31 s
10 5.31 s
14α 2.55 d 18.7
14β 3.02 dd 18.7, 12
16a 4.09 d 8
16b 3.62 d 8
17 1.27 s
18 1.17 s
19a 5.2 d 12.6
19b 4.43 d 12.6
20a 4.67 s
20b 5.42 s
CH3CO- 2.17 s
CH3CO- 2.13 s
CH3CO- 2.12 s
CH3CO- 2.01 s
Ph 8.15 d 7.1
Ph 7.6 t 7.1
Ph 7.5 t 7.1

Carbon NMR Peaks

Position PPM
1 48.7
2 69.4
3 39.7
4 140.8
5 74.2
6 37
7 68.2
8 49.7
9 70.2
10 63.7
11 80.2
12 91.6
13 204.7
14 34.4
15 49.5
16 82.1
17 15.5
18 12
19 60.9
20 115.7
OAc-2 170.4
OAc-2 20.3
OAc-5 169.6
OAc-5 22.7
OAc-7 168
OAc-7 20.7
OAc-9 172.5
OAc-9 20.8
OAc-10 168.7
OAc-10 21.2
OCOC6H5 166.6
i-C6H5 129.2
O-C6H5 130
M-C6H5 128.6
P-C6H5 133.6