Natural Compounds

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

6β-Angeloyloxy-1α,10β-dihydroxy-furanoeremophil-9-one (1-Deacetyl-2,3-deoxyhilliardinol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1139

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

Biological sources: Senecio andreuxii DC. [1]

C20H26O6: 362.1729

Mp: 127–129°C; colorless needles [1]

[α]D25 +12.7° (CHCl3)

UV (MeOH): 284 (3.7), 218 (3.6) [1]

IR (CHCl3): 3477, 1714, 1673, 1531 [1]

EI-MS: 344 (1), 189 (17), 137 (4), 91 (16), 83 (100), 55 (90) [1]

1H NMR (80 MHz, CDCl3): 1.10 (3H, s, H-14), 1.15 (3H, d, J = 7, H-15), 1.93 (3H, d, J = 1, H-13), 2.00 (3H, dq, J = 1; 1, H-5′), 2.07 (3H, dq, J = 7; 1, H-4′), 3.98 (1H, dd, J = 2.5; 2.5, H-1), 4.00 (2H, br s, OH, exchangeable with D2O), 6.24 (1H, qq, J = 7; 1, H-3′), 7.15 (2H, s, H-6), 7.46 (1H, q, J = 1, H-12) [1]

1H NMR (80 MHz, C5D5N): 1.30 (3H, d, J = 7, H-15), 1.34 (3H, s, H-14), 2.00 (3H, dq, J = 7; 1, H-5′), 2.15 (3H, dq, J = 7; 1, H-4′), 4.43 (1H, dd, J = 2.5; 2.5, H-1β), 6.15 (1H, qq, J = 7; 1, H-3′), 7.16 (1H, q, J = 1,...

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References

  1. 1.
    B. Reyes, G. Delgado, Heterocycles 31, 1405 (1990)CrossRefGoogle Scholar

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