Natural Compounds

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

3β-Acetoxy-6β-isovaleroyloxy-furanoeremophil-1(10)-ene (3β-Acetoxy-6β-isovaleryloxyeuryopsin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1331

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

Biological sources:Senecio subumbellatus Phil. [1]

C22H30O5: 374.2093

[α]D24 −33° (c 0.1, CHCl3) [1]

IR (CCl4): 1745 [1]

MS: 374.209 [M]+ (0.8) (calc. for C22H30O5: 374.209), 272 (39), 212 (71), 197 (70), 123 (100), 85 (80) [1]

HPLC: MeOH – H2O (9:1), Rt 8.3 min [1]

1H NMR (400 MHz, CDCl3): 0.94 (3H, d, J = 7, H-15), 1.10 (3H, s, H-14), 1.82 (3H, d, J = 1.5, H-13), 2.04 (3H, s, OAc), 3.04 (1H, d, J = ∼1; 17, H-9b), 3.40 (1H, br d, J = 2.5; 17, H-9a), 5.18 (1H, ddd, H-3), 5.53 (1H, dt, J = 5; 2, H-1), 6.18 (1H, dd, J = 2.5; ∼1, H-6), 7.02 (1H, br s, H-12); OiVal: 0.99 (6H, d, J = ∼7, H-4′, H-5′), 2.12 (1H, m, H-3′), 2.20 (1H, dd, J = 13; ∼7, H-2′b), 2.28 (1H, dd, J = 13; ∼7, H-2′a) [1]

References

  1. 1.
    J. Jakupovic, M. Grenz, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(8), 2691 (1991)CrossRefGoogle Scholar

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