Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_904

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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]D20 −15.4° (c 0.48, MeOH) [1]

IR (CHCl3): 3650, 3610, 3450, 1710, 1650 [1]

CI-MS: 393 [M + 1]+ (20), 375 [M − 18]+ (38), 357 [M − 36]+ (54), 219 [357 − 138]+ (100) [1]

1H NMR (400 MHz): 0.87 (3H, d, J = 6.5, H-12), 0.91 (3H, d, J = 6.5, H-13), 1.09 (3H, s, H-15), 1.17 (3H, s, H-14), 1.85 (1H, dd, J = 15.0; 4.0, H-10α), 1.88 (1H, dd, J = 6; 16, H-7b), 1.94 (1H, dd, J = 15; 4, H-10a), 2.02 (1H, m, H-11), 2.38 (1H, d, J = 10, H-5), 2.65 (1H, dd, J = 2; 16, H-7a), 4.12 (1H, ddd, J = 10; 6; 2, H-6), 5.01 (1H, dd, J = 4; 4, H-9); Op-HOBz: 6.80 (2H, d, H-3′, H-5′), 7.82 (2H, d, H-2′, H-6′) [1]

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

Table 1

C-1

42.5 s

C-8

75.9 s

C-15

30.2 q

2

31.3 t

9

78.5 d

1′

121.0 s

3

42.2 t

10

42.9 t

2′, 6′

131.5 d

4

86.3 s

11

37.5 d

3′, 5′

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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