Natural Compounds

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

10α-Acetoxy-6α-angeloyloxy-8α,9α-epoxy-5α(H)-dauc-4β-ol (Lapiferin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_948

CAS Registry Number: 86992-41-8 Open image in new window

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

Biological sources: Ferula lapidosa Korov. [1]; F. latipinna A. Santos [2]; F. arrigonii E. Bocchieri [3]; F. vesceritensis Coss. et Durieu [4]

C22H34O6: 394.2355

Mp: 137–138°C [1]

[α]D21 −41.6° (c 1.2, CHCl3) [1]

UV 218 (3.96) [1]

IR: 3540, 1740, 1715, 1655, 1230–1260, 970 [1]

MS: 351, 294, 251, 234 [1]

1H NMR: 0.85 (6H, d, J = 7, H-12, H-13), 1.26 (3H, s, H-14), 1.42 (3H, s, H-15), 2.06 (3H, s, OAc), 2.30 (1H, d, J = 10, H-5), 2.86 (1H, d, J = 5.5, H-9), 4.83 (1H, d, J = 5.5, H-10), 5.18 (1H, sextet, J = 10; 10; 3, H-6); OAng: 6.05 (1H, m, H-3′) [1]

13 C NMR [ 2]:

Table 1

C-1

47.3

C-6

69.1

C-11

37.2

2

31.1

7

42.8

12

17.2

3

36.5

8

56.0

13

18.3

4

85.4

9

59.7

14

17.9

5

51.4

10

71.5

15

23.3

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References

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    A.M. Gamal-Eldeen, M.E.F. Hegazy, Nat. Prod. Res. 24, 246 (2010)CrossRefGoogle Scholar

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