Natural Compounds

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

15-(4′-Hydroxy-benzoyloxy)-dauca-4,8-diene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_906

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

Biological sources: Ferula hermonis Boiss. [1]

C22H28O3: 340.2038

Mp: oil [1]

[α]D +13.9° (c 0.03, MeOH) [1]

UV (MeOH) 286 (2.67) [1]

IR (film): 3357, 2956, 2931, 1713, 1608, 1592, 1514, 1545, 1374, 1278 [1]

HR-ESI-FT-MS: 339.1961 [M − H]+ (calc. for C22H29O3, 339.1955) [1]

1H NMR (CDCl3): 0.93 (3H, d, J = 6.9, H-12), 0.95 (3H, s, H-14), 0.98 (3H, d, J = 7.0, H-13), 2.06 (1H, m, H-10a), 2.19 (1H, m, H-10b), 2.66 (1H, septet, J = 6.8, H-11), 4.69 (2H, d, J = 13.0, H-15), 5.85 (1H, br t, J = 6.2 Hz, H-9); Op-HOBz: 6.33 (1H, s, 4′-OH), 6.88 (2H, d, J = 8.6Hz, H-3′, H-5′), 7.96 (2H, d, J = 8.0 Hz, H-2′, H-6′) [1]

13 C NMR (CDCl 3) [ 1]:

Table 1

C-1

49.2 s

C-9

128.5 d

C-1′

122.6 s

2

38.6 t

10

40.3 t

2′

131.9 d

3

29.8 t

11

26.4 d

3′

115.2 d

4

141.3 s

12

21.2 q

4′

160.2 s

5

139.4 s

13

21.8 q

5′

115.2 d

6

22.8 t

14

23.4 q

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References

  1. 1.
    A.M. Galal, E.A. Abourashed, S.A. Ross, M.A. El. Sohly, M.S. Al-Said, F.S. El-Feraly, J. Nat. Prod. 64, 399 (2001)CrossRefGoogle Scholar

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