Natural Compounds

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

6α-Vanilloyloxy-8α,9α-epoxy-5α(H)-dauc-4β-ol (6α-Vanillate of 8,9-Epoxy-jaeschkeanadiol; Tenuferinin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_930

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

Biological sources: Ferula jaeschkena Vatke [1]; F. tenuisecta Korov. [2]

C23H32O6: 404.2199

Mp: 104–105°C [1]

[α]D +11.2° (c 3.0, CHCl3) [1]

UV: 262 (4.6), 292 (4.23) [1]; 263 (4.02), 298 (3.69) [2]

IR: 3410, 3150, 2960, 2920, 1690, 1600, 1530, 1470, 1380, 1290, 1130, 1040, 960, 880, 770 [1]

1H NMR (400 MHz): 0.85 and 0.92 (each 3H, d, J = 7.0, H-12, H-13), 1.24 (3H, s, H-14), 1.51 (3H, s, H-15), 1.90 (1H, d, J = 10, H-5), 1.99 (1H, sep, J = 7, H-11), 2.90 (1H, t, J = 8, H-9), 5.40 (1H, td, J = 10; 10; 3, H-6); OVan: 3.98 (3H, s, OCH3), 6.95 (1H, d, J = 8, H-5′), 7.55 (1H, s, 2′), 7.60 (1H, d, J = 8, H-6′) [1]

13 C NMR [ 1]:

Table 1

C-1

44.36 s

C-9

60.92 d

C-1′

122.26 s

2

31.82 t

10

41.87 t

2′

111.96 q

3

40.59 t

11

36.79 d

3′

146.44 s

4

86.03 s

12

17.28 q

4′

150.53 s

5

60.92 d

13

18.42 q

5′

114.97 d

6

70.20 d

14

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References

  1. 1.
    S.N. Garg, S.K. Agarwal, J. Nat. Prod. 51, 771 (1988)CrossRefGoogle Scholar
  2. 2.
    A.I. Saidkhodzhaev, Chem. Nat. Comp. 14, 55 (1978)CrossRefGoogle Scholar

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