Natural Compounds

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

3α-(5′-Acetoxy-4′-methylpent-2′-cis-enoyloxy)-eremophila-9(10),7(11)-dien-8-one (Isosenescaposone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_993

CAS Registry Number: 69734-55-0 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): −2.0° (589), −2.3° (578), −4.9° (546), −42.8° (436) (c 3.6, CHCl3) [1]

IR (CCl4): 1748, 1720, 1666, 1645, 1630, 1235 [1]

MS: 388.225 [M]+ (13) (calc. for C23H32O5: 388.225), 316 (2), 216 (64), 201 (32), 161 (100), 148 (42), 43 (65) [1]

CD: Δε270 −4.78, Δε233 +12.4 [1]

1H NMR (270 MHz, CHCl3, TMS): 1.00 (3H, d, J = 7, H-15), 1.06 (3H, s, H-14), 1.53 (1H, dddd, J = 4; 14; 15; 11, H-2α), 1.67 (1H, dq, J = 11; 7, H-4α), 1.86 (3H, d, J = ∼1, H-13), 2.04 (3H, s, OAc), 2.11 (3H, d, J = 1.3, H-12), 2.20 (1H, br d, J = 1.3, H-6α), 2.20 (1H, br d, J = 15, H-2β), 2.37 (1H, ddd, J = 14; 4; 2, H-1α), 2.48 (1H, dddd, J = 14; 14; 5; 1.5, H-1β), 2.93 (1H, d, J = ∼0, H-6β), 4.91 (1H,...

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References

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

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