Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-4β-hydroxy-5α(H)-dauc-8-en-10-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_903

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

Biological sources: Ferula sinaica Boiss. [1]

C22H28O5: 372.1937

[α]D +12.9° (c 1.12, CHCl3) [1]

IR (CHCl3): 3610, 1780, 1650 [1]

CI-MS: 372 [M]+ (1), 329 [M − 43]+ (38), 235 [M − 138]+ (41), 138 [benzoic acid]+ (20), 121 [benzoate]+ (55), 84 (100) [1]

1H NMR (400 MHz, CDCl3): 0.85 (3H, d, J = 6.5, H-12), 0.87 (3H, d, J = 6.5, H-13), 1.40 (3H, s, H-14), 1.63 (1H, m, H-11), 2.02 (3H, br s, H-15), 2.47 (1H, ddd, J = 1; 5; 17, H-7b), 2.57 (1H, d, J = 10, H-5), 3.03 (1H, ddd, J = 1; 3; 17, H-7a), 5.84 (1H, ddd, J = 10; 5; 3, H-6), 6.03 (1H, br s, H-9); Op-HOBz: 6.90 (2H, d, H-3′, H-5′), 7.92 (2H, d, H-2′, H-6′) [1]

13 C NMR (67.9 MHz, CDCl 3): [ 1]

Table 1

C-1

55.7 s

C-8

151.2 s

C-15

28.3 q

2

31.2 t

9

128.5 d

1′

121.5 s

3

38.4 t

10

209.7 s

2′, 6′

131.9 d

4

84.8 s

11

31.8 d

3′, 5′

115.5 d

5

50.4 d

12

18.3 q*

4′

161.4 s

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References

  1. 1.
    A.A. Ahmed, Phytochemistry 30(4), 1207 (1991)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013