Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-5α(H)-dauca-4β,8β,9α-triol (4β,8β,9α-Trihydroxy-6α-p-hydroxybenzoyloxydaucane)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_896

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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]

C22H32O6: 392.2199

[α]D24 +15.8° (c 0.5, MeOH) [1]

IR: 3700, 3620, 3480, 3000, 2440, 1700, 1640, 1580, 1160, 1050 [1]

MS: 349 [M − 43]+ (3), 254 [M − 138]+ (3), 211 [M − 181]+ (10), 121 [benzoate]+ (100) [1]

1H NMR (400 MHz, CDCl3): 0.73 (3H, d, J = 7, H-13), 0.78 (3H, d, J = 7, H-12), 1.16 (3H, s, H-15), 1.18 (3H, s, H-14), 1.78 (1H, dd, J = 10; 4, H-10β), 1.87 (1H, dd, J = 15; 14, H-10α), 3.66 (1H, br t, J = 4, H-9), 5.54 (1H, ddd, J = 10; 6; 2, H-6); Op-HOBz: 6.84 (2H, d, J = 9, H-3′, H-5′), 7.89 (2H, d, J = 9, H-2′, H-6′) [1]

13 C NMR [ 1]:

Table 1

C-1

42.3 s

C-9

69.2 d

C-1′

121.2 s

2

31.3 t

10

43.2 t

2′

131.7 d

3

42.1 t

11

37.0 d

3′

115.2 d

4

86.0 s

12

17.3 q

4′

161.6 s

5

56.2 d

13

18.4 q

5′

115.2 d

6

78.7 d

14

21.2 q

6′

131.7 d

7

42.6 t

15

30.5 q

C=O

166.1 s

8

75...

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References

  1. 1.
    A.A. Ahmed, J. Nat. Prod. 53, 483 (1990)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013