Taxine B

Taxine B

Common Name: Taxine B

Synonyms:

CAS Registry Number: 1361-51-9

InChI: InChI=1S/C33H45NO8/c1-18-23(36)17-33(40)29(38)27-19(2)24(42-25(37)16-22(34(7)8)21-12-10-9-11-13-21)14-15-32(27,6)30(39)28(41-20(3)35)26(18)31(33,4)5/h9-13,22,24,27-30,38-40H,2,14-17H2,1,3-8H3

InChIKey: InChIKey=XMZFIBDTPOUHMW-UHFFFAOYSA-N

Formula: C33H45N1O8

Molecular Weight: 583.71

Exact Mass: 583.3145

NMR Solvent: CDCl3

MHz: 400.0

Calibration:

NMR references: Ettouati, L., Ahond, A., Poupat, C., and Potier, P. (1991). Révision Structurale de la Taxine B, Alcaloïde Majoritaire des Feuilles de l’If d’Europe, Taxus baccata. J. Nat. Prod. 54, 1455–1458.

Species: Taxus

Notes: This compounds structure has been source of considerable confusion. The NMR reference cited corrected this, see article for details (note language: French). J values rounded to nearest half number in reference. Unsure of the multiplicity description of proton at position 5 in reference due to language, therefore left blank. Aromatic protons not well described.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 3.98 d 7
3 3.17 d 7
5 5.1
6 1.57 m
7 1.78 m
7 1.37 m
9 4.28 d 9.5
10 5.85 d 9.5
14 2.65 s
16 1.52 s
17 1.25 s
18 2.15 s
19 1.13 s
20 5.4 s
20 5.35 s
2' 2.92 dd 16, 7
2' 2.53 dd 16, 7
3' 3.85 t 7
MeCO 2.22 s
NMe2 2.22 s
2" 6" 7.32 m
3" 5" 7.32 m
4" 7.32 m

Carbon NMR Peaks

Position PPM
1 77.9
2 71.6
3 46.8
4 144
5 78.2
6 29.1
7 26.4
8 45.6
9 75.3
10 76.6
11 153.5
12 139.1
13 199.9
14 44.5
15 42.3
16 20.5
17 34.2
18 13.9
19 17.9
20 118.1
1' 171.3
2' 38.3
3' 66.5
COMe 170.2
MeCO 21.2
NMe2 42.3
1" 138.5
2" 6" 128.2
3" 5" 128.7
4" 127.6