Natural Compounds

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

1α-Acetoxy-6β-(2′-methylacryloyloxy)-10β-hydroxy-furanoeremophilane (2,3-Desoxohilliardinol-[2-methylacrylate])

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1319

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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]

C21H26O7: 390.1679

Mp: colorless oil [1]

IR (CCl4): 3480, 1760, 1745, 1725, 1690, 1640, 1538, 1235 [1]

MS: 390.168 [M]+ (1.5), 348 (5), 304 (4), 262 (15), 178 (100), 177 (72) [1]

1H NMR (270 MHz, CDCl3, TMS): 1.05 (3H, s, H-14), 1.17 (H, d, J = 7, H-15), 1.43 (1H, m, H-3β), 1.63 (1H, m, H-2α), 1.65 (3H, s, OAc), 1.72 (1H, ddq, J = 7; ∼3; ∼3, H-4), 1.91 (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), 7.08 (1H, s, H-6), 7.49 (1H, q, J = 1, H-12); OMeacr: 2.04 (3H, dd, J = ∼1, H-4′), 5.73 (1H, dq, J = ∼1, H-3′b), 6.25 (1H, br s, H-3′a) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 17(8), 1333 (1978)CrossRefGoogle Scholar

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