Natural Compounds

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

8β-Angeloyloxy-5β-hydroxy-4α(H)-dauc-9-one (8-Angelate of Felikiol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_859

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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]

C20H32O4: 336.2301

Mp: 106–108°C (petrol – EtOAc) [1]

IR (CHCl3): 3590, 3000, 2940, 2860, 1700, 1450, 1360, 1140, 1040, 850 [1]

MS: 366.2296 [M]+ (calc. for C20H32O4: 336.2300) [1]

EI-MS: 366 [M]+ (1), 277 (1), 253 (4), 236 (10), 218 (6), 193 (36), 175 (33) [1]

1H NMR (90 MHz, CDCl3): 0.95 and 1.02 (each 3H, d, J = 5, H-12, H-13), 1.05 and 1.55 (each 3H, s, H-14, H-15), 2.30 and 2.56 (each 1H, d, J = 12, H-10α, H-10β); OAng: 6.15 (1H, s, H-3′) [1]

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

Table 1

C-1

47.9

C-6

83.5

C-11

27.4

2

205.8

7

47.2

12

21.4b

3

85.1

8

32.4a

13

22.9b

4

37.4

9

25.2

14

23.4c

5

32.8a

10

53.8

15

24.3c

a-cThe assignments for these signals may be reversed

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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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