Natural Compounds

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

6β-Isobutyroyloxy-1α-hydroxy-10αH-furanoeremophil-9-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1187

CAS Registry Number: 55050-48-1 Open image in new window

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

Biological sources: Senecio umbellatus L. [1]; S. hypochoerideus DC. [2]; S. chionophilus Phil. [3]

C19H26O5: 334.1780

Mp: 110–112°C [1]

[α]24 (λ, nm): −30.2° (589), −32.7° (578), −40.1° (546), −107.2° (436) (c 1.16) [1]

IR: 3545, 1682 (α-furanketon), 1745 [1]

MS: 334.178 [M]+ (3.5) (calc. for C19H26O5 334.178), 263 [M – C3H7CO]+ (32), 246 [M – C3H7COOH]+ (46), 228 [246 – H2O]+ (58), 213 [228 – CH3]+ (4), 71 [C3H7CO]+ (100) [1]

1H NMR (100 MHz, CDCl3): 0.88 (3H, d, J = 6.5, H-15), 0.98 (3H, s, H-14), 1.87 (1H, d, J = 1, H-12), 2.38 (1H, d, J = 10, H-6), 4.12 (1H, m, H-1β), 6.37 (1H, s, H-6), 7.38 (1H, q, J = 1, H-10α); OiBu: 1.24 (6H, d, J = 7, H-3′, H-4′), 2.63 (1H, qq, H-2′) [1]

13 C NMR (75.5 MHz, CDCl 3): [ 3]

Table 1

C-1

66.3 d

C-8

146.5 s

C-15

8.8 q

2

32.8 t

9

18...

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References

  1. 1.
    F. Bohlmann, C. Zdero, Chem. Ber. 107, 2912 (1974)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, D. Ehlers, C. Zdero, Phytochemistry 17(3), 467 (1978)CrossRefGoogle Scholar
  3. 3.
    J.-Q. Gu, Y.-H. Wang, S.G. Franzblau, G. Montenegro, B.N. Timmermann, J. Nat. Prod. 67, 1483 (2004)CrossRefGoogle Scholar

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