Natural Compounds

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

2α,6α-Diangeloyloxy-5α(H)-dauc-8-en-4β-ol (Jaeschkeanadiol bis-Angelate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_964

Open image in new window

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

Biological sources: Ferula communis L. subsp. communis [1]

C25H38O5: 418.2719

Isolated as 5α(H)-dauc-8-en-2α,4β,6α-triol after conversion by treatment with LiAlH4 [1]

Mp (its triol): 170°C, large cubes [1]

[α]D25 −109° (c 0.88, CH2Cl2) [1]

IR (KBr) (its triol): 3570, 3300, 1670, 1470, 1015, 990, 980, 970 [1]

1H NMR (250 MHz, CDCl3, TMS) (its triol): 0.94 (6H, d, J = 7.1, H-12, H-13), 1.02 (3H, s, H-14), 1.79 (3H, br s, H-15), 2.49 (1H, d, J = 10.5, H-5), 3.76 (1H, d, J = 7.7, H-2), 4.04 (1H, tt, J = 10.5; 10.5; 3.0; 3.0, H-6), 5.71 (1H, br d, J = 7.2, H-9) [1]

13 C NMR (62.89 MHz, acetone-d 6, TMS) (its triol) [ 1]:

Table 1

C-1

47.09 s

C-6

73.34 dc

C-11

39.49 d

2

69.19 dc

7

37.65 tb

12

17.79 qd

3

31.82 tb

8

137.18 s

13

18.77 qd

4

87.91 s

9

127.08 d

14

20.90 qd

5

51.98 d

10

44.78 ta

15

28.63 q

a–dInterchangeable...

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

References

  1. 1.
    G. Appendino, S. Tagliapietra, L. Paglino, G.M. Nano, D. Monti, V. Picci, Phytochemistry 29(5), 1481 (1990)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013