Natural Compounds

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

8β-(2′,3′-Epoxy-angeloyloxy)-dauca-3,9-dione (8-Epoxyangelate of Webiol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_887

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

Biological sources: Ferula linkii Webb et Berthel. [1]

C20H28O5: 348.1937

Mp: 82–84°C (petrol – EtOAc) [1]

UV 242 [1]

IR (CHCl3): 3075, 3000, 2950, 2920, 2860, 1740, 1715, 1690, 1625, 1600, 1455, 1410, 1370, 1320, 1270, 1150, 1100, 995, 855 [1]

MS: 232.1442 [M − C5H8O3]+ (calc. for C15H20O2: 232.1464) [1]

EI-MS: 348 [M]+, 333, 320, 232, 207, 189, 149, 121 [1]

1H NMR (200 MHz, CDCl3): 1.08 and 1.12 (each 3H, d, J = 5, H-12, H-13), 1.17 (3H, s, H-14), 1.64 (3H, s, H-15); OEpang: 1.36 (3H, d, J = 5, H-5′), 1.44 (3H, s, H-4′), 3.09 (1H, s, J = 5, H-3′) [1]

X-ray: [1]

13 C NMR (50.32 MHz, CDCl 3) [ 1]:

Table 1

C-1

43.5

C-6

174.0

C-11

25.5

2

207.0

7

41.4

12

20.3*

3

87.4

8

49.1

13

20.7*

4

40.3

9

204.5

14

21.6

5

21.3

10

174.0

15

30.1

*The assignments for these signals may be reversed [1]

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References

  1. 1.
    J.G. Diaz, B.M. Fraga, A.G. Gonzalez, M.G. Hernandez, A. Perales, Phytochemistry 25(5), 1161 (1986)CrossRefGoogle Scholar

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