Natural Compounds

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

6α-Isovaleroyloxy-5α(H)-dauc-8(15)-ene-4β,9α,10α-triol (6-Isovalerate of Isolancerotetrol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_909

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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]

C20H34O5: 354.2406

IR: 3580, 3460, 3070, 3000, 2950, 2920, 2860, 1705, 1640, 1460, 1380, 1365, 1290, 1230, 1160, 1050, 1000, 975, 910, 830 [1]

MS: 311 [M − C3H7]+ (2), 252 (2), 234 (10), 209 (27), 191 (59), 173 (16), 163 (13) [1]

1H NMR (360 MHz, CDCl3): 0.90 and 0.92 (each 3H, d, J = 2.7, H-12 or H-13), 1.20 (3H, s, H-14), 5.08 and 5.27 (1H, s, H-15), 5.32 (1H, ddd, J = 10.4; 2, H-6); OiVal: 0.97 and 0.99 (each 3H, d, J = 3, H-4′, H-5′), 3.68 and 4.31 (each 1H, d, J = 3, H-2′) [1]

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

Table 1

C-1

46.3

C-8

143.6

C-15

115.1

2

31.7

9

77.1

1′

173.3

3

36.8

10

74.1

2′

44.1

4

86.4

11

37.0

3′

25.7

5

45.0

12

17.6

4′

22.5

6

71.6

13

18.3

5′

22.5

7

40.4

14

21.2

   
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References

  1. 1.
    B.M. Fraga, M.G. Hernandez, J.G. Diaz, A.G. Gonzales, P. Gonzales, Phytochemistry 25(12), 2883 (1986)CrossRefGoogle Scholar

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