Natural Compounds

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

3α-(5′-Acetoxy-4′-methylpent-2′-cis-enoyloxy)-eremophila-9(10),11(12)-dien-8-one (Senescaposone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_994

CAS Registry Number: 69734-54-9 Open image in new window

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

Biological sources: Senecio scaposus DC. [1]

C23H32O5: 388.2250

Mp: colorless oil [1]

[α]24 (λ, nm): −61.6° (589), −64.4° (578), −74.3° (546), −135.6° (436) (c 4.9, CHCl3) [1]

IR (CCl4): 1746, 1720, 1675, 1647, 1630, 1240 [1]

MS: 388.225 [M]+ (39), 373 (1), 316 (4), 216 (41), 201 (55), 161 (60), 148 (100), 43 (40) [1]

CD: Δε365 = +0.084, Δε347 = +0.34, Δε334 = +0.45, Δε320 = +0.34, Δε311 = +0.17, Δε270 = −0.53, Δε225 = −13.0 [1]

1H NMR (270 MHz, CDCl3, TMS): 1.00 (3H, d, J = 7, H-15), 1.18 (3H, s, H-14), 1.46 (1H, dddd, J = 4; 14; 15; 11, H-2α), 1.78 (3H, br s, H-13), 2.0 (3H, m, H-2β, H-4α, H-6β), 2.28 (1H, ddd, J = 14; 4; 2, H-1α), 2.3 (1H, m, H-6α), 2.59 (1H, dddd, J = 14; 14; 5; 1.5, H-1β), 3.06 (1H, br dd, J = 5.5; 10.5; 1, H-7α), 4.75 (1H, br s, H-12b), 4.96 (1H,...

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References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 17(8), 1337 (1978)CrossRefGoogle Scholar

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