Natural Compounds

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

6β-(2′-Methylbutyroyloxy)-10βH-furanoeremophil-1-one (6β-(2′-Methylbutyryloxy)-senberginone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1237

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Eremophilanes – Furanoeremophilanes – Monoesters

Biological sources: Senecio auricula Bourg. var. major Wk. [1]

C20H28O4: 332.1988

Mp: colorless oil [1]

IR: 1710, 1630, 1450, 1370, 1180, 1140, 1090, 1010, 950, 740 [1]

GC-EI-MS: 332 [M]+ (3), 248 (6), 233 (2), 230 (40), 215 (13), 188 (14), 146 (100), 125 (46), 91 (10), 85 (31), 57 (40), 55 (10), 41 (15) [1]

1H NMR (300 MHz, CDCl3): 0.97 (3H, s, H-14), 0.98 (3H, d, J = 7.5, H-15), 1.80 (3H, br s, H-13), 6.02 (1H, br s, H-6), 7.07 (1H, br s, H-12); OMeBu: 0.96 (3H, t, H-4′), 1.22 (3H, d, H-5′), 1.81 (2H, ddq, H-3′), 2.42 (1H, m, H-2′) [1]

13 C NMR (75 Hz, CDCl 3) [ 1]:

Table 1

C-1

209.0

C-7

116.0

C-14

17.8*

2

36.0

8

149.8

15

14.8

3

29.8

9

22.3

OMeBu

176.6

4

30.3

10

51.1

 

41.2

5

44.1

11

119.4

 

26.4

6

67.9

12

138.4

 

17.0*

7

116.0

13

8.2

 

11.7

*Signals may be interchanged within the same column

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References

  1. 1.
    P. Torres, J. Ayala, C. Grande, M.J. Macias, M. Grande, Phytochemistry 47(1), 57 (1998)CrossRefGoogle Scholar

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