Natural Compounds

2013 Edition
| Editors: Shakhnoza S. Azimova, Ashraf I. Saidkhodzhaev

9α-Acetoxy-6α-(4-hydroxy-benzoyloxy)-5α(H)-dauc-7-en-4β-ol (Lancerotriol 9-Acetate-6-p-hydroxybenzoate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_947

Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Diesters

Biological sources: Ferula sinaica Boiss. [1]

C24H32O6: 416.2199

IR: 3445, 2975, 2885, 1700, 1690 [1]

MS: 417.2251 [M + H]+, 399.2170 [M + H − H2O]+ (100) [1]

1H NMR: 0.80 (3H, d, J = 7, H-13), 0.90 (3H, d, J = 7, H-12), 1.22 (3H, s, H-14), 1.73 (3H, s, H-15), 1.88 (1H, qq, J = 7.0; 7.0, H-11), 2.05 (3H, s, OAc), 2.20 (1H, d, J = 10.0, H-5), 5.40 (1H, br s, H-7), 5.57 (1H, m, H-9α), 5.87 (1H, d, J = 10; 3, H-6); Op-HOBz: 6.82 (2H, d, J = 8.5, H-3′, H-5′), 7.85 (2H, d, J = 8.5, H-2′, H-6′), [1]

13 C NMR [ 1]:

Table 1

C-1

42.1 s

C-9

72.0 d

C-1′

121.7 q

2

41.6 t

10

46.3 t

2′

131.9 d

3

31.5 t

11

36.7 d

3′

115.3 d

4

86.5 s

12

17.3 q

4′

161.0 q

5

54.6 d

13

18.2 q

5′

115.3 d

6

72.4 d

14

18.7 q

6′

131.9 d

7

127.7 d

15

23.5 q

C=O

166.4 s

8

135.6 s

OAc

170.2 s

   
     

21.0 q

   
This is a preview of subscription content, log in to check access.

References

  1. 1.
    A.A. Ahmed, M.H. Abdel-Razek, M.J. Nassur, S. Jzumi, S. Ohta, T. Hirata, Phytochemistry 57(4), 513 (2001)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013