Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1317

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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]

C21H26O8: 406.1628

Mp: 122°C (ether–petrol), colorless crystals [1]

[α]24 (λ, nm): +98° (589), +103° (578), +121° (546), +265° (436), +814° (365)(c 1.49, CHCl3) [1]

IR (CCl4): 3460, 1750, 1692, 1535 [1]

MS: 406.163 [M]+ (10), 346 (3), 336 (6), 321 (5), 318 (12), 276 (33), 258 (35), 177 (91), 71 (100) [1]

CD: Δε312 = +3.9, Δε270 = −1.1, Δε241 = −4.8 [1]

1H NMR (270 MHz, CDCl3, TMS): 1.02 (3H, s, H-14), 1.23 (H, d, J = 7, H-15), 1.69 (3H, s, OAc), 1.94 (3H, d, J = 1, H-13), 2.21 (1H, dq, J = 7; 1, H-4), 3.33 (1H, dd, J = 4; 1, H-3), 3.61 (1H, dd, J = 5; 4, H-2), 4.00 (1H, s, OH), 4.97 (1H, d, J = 5, H-1), 7.02 (1H, s, H-6), 7.49 (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

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