Natural Compounds

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

3α-Angeloyloxy-1α-hydroxy-1αH-furanoeremophil-9-one (1α-Hydroxyeurypsonol Angelate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1124

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

Biological sources: Senecio smithii DC. [1]

C20H26O5: 346.1780

Mp: 150°C (colorless crystals, Et2O–petrol) [1]

[α]24 (λ, nm): −0.8° (589), −1.3° (578), −3.4° (546), −28.0° (436), −149.1° (365) (c 0.95, CHCl3) [1]

IR (CHCl3): 3520, 1715, 1670, 1545 (α-furan ketone) [1]

MS: 346.178 [M]+ (3), 246 [M – C4H7COOH]+ (6), 228 [246 – H2O]+ (8), 213 [228 – Me]+, 163 [C10H11O2]+ (100), 83 [C4H7CO]+ (26), 55 [83 – CO] (62) [1]

1H NMR (400, MHz, CDCl3): 0.89 (3H, s, H-14), 0.98 (3H, d, J = 7, H-15), 1.51 (1H, ddd, J = 2.5; 12; 11, H-2α), 1.86 (1H, dq, J = 7, H-4), 2.01 (3H, br s, H-13), 2.44 (1H, d, J = 11, H-10), 2.47 (1H, ddd, J = 5; 12; 5, H-2β), 2.53 (1H, d, J = 17, H-6a), 2.73 (1H, d, J = 17, H-6b), 4.26 (1H, br ddd, J = 11.5; 5, H-1β), 4.92 (1H, ddd, J = 11; 5; 11, H-3β), 7.43 (1H, br s, H-12); OAng:...

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References

  1. 1.
    F. Bohlmann, C. Zdero, R.M. King, H. Robinson, Phytochemistry 20(10), 2389 (1981)CrossRefGoogle Scholar

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