Natural Compounds

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

15-Vanilloyloxy-dauca-4,8-diene (14-(4′-Hydroxy-3′-methoxybenzoyloxy)dauc-4,8-diene)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_934

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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]

C23H30O4: 370.2144

Mp: oil [1]

[α]D −13.0° (c 0.052, MeOH) [1]

UV (MeOH) 302 (3.27) [1]

IR (film): 3394 (OH), 2955, 1711, 1597, 1514, 1462, 1429, 1378, 1282, 1216 [1]

HR-ESI-FT-MS: 369.2080 [M − H]+ (calc. for C23H29O4, 369.2060) [1]

1H NMR (CDCl3): 0.92 (3H, d, J = 6.8, H-12), 0.95 (3H, s, H-14), 0.98 (3H, d, J = 6.8, H-13), 2.06 (1H, m, H-10a), 2.18 (1H, m, H-10b), 2.66 (1H, septet, J = 6.8, H-11), 4.70 (2H, br s, H-14), 5.87 (1H, br t, J = 9.8, H-9); OVan: 3.92 (3H, s, OCH3), 6.15 (1H, s, 4′-OH), 6.93 (1H, d, J = 8.3, H-5′), 7.56 (1H, d, J = 1.8, H-2′), 7.64 (1H, dd, J = 8.3, 1.7, H-6′) [1]

13 C NMR (CDCl 3) [ 1]:

Table 1

C-1

49.2 s

C-9

128.6 d

C-2′

114.5 d

2

39.1 t

10

40.7 t

3′

146.2 s

3

30.2 t

11

26.8 d

4′

150.0 s

4

141.3 s

12

21.6 q

5′

112.2 d

5

139.4 s

13

22.3 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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