9α-​Acetoxy-​2α,​10β-​dihydroxy-​5α-​cinnamoxytaxa-​4(20)​,​11-​dien-​13-​one

9α-​Acetoxy-​2α,​10β-​dihydroxy-​5α-​cinnamoxytaxa-​4(20)​,​11-​dien-​13-​one

Common Name: 9α-​Acetoxy-​2α,​10β-​dihydroxy-​5α-​cinnamoxytaxa-​4(20)​,​11-​dien-​13-​one

Synonyms: 5-​Cinnamoyl-​9-​acetyltaxicin II

CAS Registry Number: 146257-46-7

InChI: InChI=1S/C31H38O7/c1-17-22(33)16-21-27(35)26-18(2)23(38-24(34)13-12-20-10-8-7-9-11-20)14-15-31(26,6)29(37-19(3)32)28(36)25(17)30(21,4)5/h7-13,21,23,26-29,35-36H,2,14-16H2,1,3-6H3/b13-12+/t21-,23-,26-,27+,28+,29-,31+/m0/s1

InChIKey: InChIKey=NLXBXVWBIGYJBM-IRZWYNESSA-N

Formula: C31H38O7

Molecular Weight: 522.63

Exact Mass: 522.2618

NMR Solvent: CDCl3

MHz: 500.0

Calibration: CDCl3 solvent residues 7.25 and 77.0 ppm for proton and carbon respectively.

NMR references: Shi, Q.-W., Lederman, Z., Sauriol, F., McCollum, R.S., and Zamir, L.O. (2004). A Yew in Israel, New Taxane Derivatives†. J. Nat. Prod. 67, 168–173.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.37 dd 7, 2.3
2 4.29 dd 6.4, 2.1
3 3.25 d 6.6
5 5.32 br t 3
6a 2.01 m
6b 1.75 m
7a 1.75 m
7b 1.65 m
9 5.68 d 10
10 5.01 d 10
14a 2.86 dd 19.8, 7
14b 2.26 d 19.8
16 1.27 s
17 1.75 s
18 2.11 s
19 0.96 s
20a 5.43 br s
20b 5.42 br s
CH3CO- 2.16 s
2' 6.41 d 15.9
3' 7.64 d 15.9
Ph-o 7.75 br d 8
Ph-m 7.44 m
Ph-p 7.39 m

Carbon NMR Peaks

Position PPM
1 51.4
2 68
3 44.9
4 143.5
5 78
6 28.8
7 27.5
8 44.5
9 78.9
10 71.9
11 154.7
12 135.4
13 199.9
14 35.6
15 37.7
16 37.7
17 25.5
18 13.8
19 17.4
20 117.6
CH3CO- 20.9
CH3CO- 171.7
Cinn-1 166.3
Cinn-2 117.6
Cinn-3 145.4
Ph-4 134.4
Ph-o 128.3
Ph-m 128.7
Ph-p 130.1