Natural Compounds

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

1α-Acetoxy-6β-isobutyroyloxy-10β-hydroxy-furanoeremophil-9-one (2,3-Desoxohilliardinol-isobutyrate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1316

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

Biological sources:Senecio mauricei Hilliard et Burtt [1]; S. dryophyllus Meyen et Walp. [2]

C21H28O7: 392.1835

Mp: colorless oil [1]

IR (CCl4): 3460, 1760, 1745, 1735, 1690, 1535, 1235 [1]

MS: 392.183 [M]+ (1), 350 (6), 304 (5), 262 (17), 177 (100) [1]

1H NMR (270 MHz, CDCl3, TMS): 1.03 (3H, s, H-14), 1.17 (H, d, J = 7, H-15), 1.43 (1H, m, H-3β), 1.63 (1H, m, H-2α), 1.64 (3H, s, OAc), 1.72 (1H, ddq, J = 7; ∼3; ∼3, H-4), 1.96 (3H, d, J = 1, H-13), 2.28 (1H, br dd, J = ∼12; ∼14; ∼3, H-3α), 2.33 (1H, br dd, J = 2.5; ∼14; ∼12, H-2β), 3.99 (1H, s, OH), 4.77 (1H, dd, J = 2.5; 2.5, H-1), 7.01 (1H, s, H-6), 7.47 (1H, q, J = 1, H-12); OiBu: 1.28 (3H, d, J = 7, H-4′), 1.30 (3H, d, J = 7, H-3′), 2.72 (1H, qq, J = 7; 7, H-2′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 17(8), 1333 (1978)CrossRefGoogle Scholar
  2. 2.
    S. Dupre, M. Grenz, J. Jakupovic, F. Bohlmann, H.M. Niemeyer, Phytochemistry 30(4), 1211 (1991)CrossRefGoogle Scholar

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