Natural Compounds

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

6-Isobutyroyloxy-furanoeremophil-1(2)-en-9-one (Isoadenostylone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1174

CAS Registry Number: 18883-10-8 Open image in new window

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

Biological sources: Adenostyles alliariae (Gouan) Kern. [1, 2, 3]

C19H24O4: 316.1675

Mp: 92–94°C [1]

[α]D24 ±0° (CHCl3) [1]

UV (EtOH): 284 (4.16), 243 (3.61) [1]

ORD: [θ]252 −29°⋅ 10−3; [θ]239 0°; [θ]225 +34.3° ⋅ 10−3 (p) [3]

CD: Δε239 −11.79 [3]

IR (CCl4): 1738, 1685, 1631, 1601, 1535, 1150 [2]

MS: 316 [M]+ [1]

1H NMR: 0.90 (3H, d, J = 7.2, H-15), 1.06 (3H, s, H-14), 2.00 (3H, d, J = 1.0, H-13), 5.80 (2H, br s, H-1, H-2), 6.26 (1H, s, H-6), 7.40 (1H, d, J = 1.0, H-12); OiBu: 1.18 (3H, d, J = 7.0, H-4′), 1.21 (3H, d, J = 7.0, H-3′), 7.40 (1H, m, H-2′) [2]

1H NMR (100 MHz, CDCl3, TMS): 0.90 (3H, J = 7.2, H-14), 1. 07 (1H, J = 7.2, H-4), 1.06 (3H, H-15), 2.00 (3H, J = 1.0; ≠ 0, H-13), 3.16 (1H, W = ∼6.0, H-10), 6.26 (1H, J ≠ 0, H-6), 7.40 (1H, J = 1.0; ≠ 0, H-12) [3]

References

  1. 1.
    J. Harmantha, Z. Samek, L. Novotny, V. Herout, F. Sorm, Tetrahedron Lett. 12, 1409 (1968)CrossRefGoogle Scholar
  2. 2.
    J. Harmantha, Z. Samek, L. Novotny, V. Herout, F. Sorm, Collect. Czech. Chem. Commun. 34, 1739 (1969)CrossRefGoogle Scholar
  3. 3.
    Z. Samek, J. Harmantha, L. Novotny, F. Sorm, Collect. Czech. Chem. Commun. 34, 2792 (1969)CrossRefGoogle Scholar

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