Natural Compounds

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

3β,6β-Disenecioyloxy-10βH-furanoeremophilane (bis(3-Methyl-2-butenoyl)-10βH-furanoeremophilane)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1411

CAS Registry Number: 59806-53-0 Open image in new window

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

Biological sources: Othonna intermedia Compton [1]; Petasites niveus [2]

C25H34O5: 414.2406

Mp: colorless oil [2]

[α]D22 −80.8° (CHCl3, c 1.07) [2]

UV (cyclohexane) 218 (4.23) [2]

IR: 1720 (C = O), 1625 [1]

IR (film): 1717, 1651, 1572 [2]

MS: 414.240 [M]+ (6) (calc. for C25H34O5: 414.241) [1]

HPLC [1]

1H NMR (C6D6): 0.96 (3H, d, J = 7, H-15), 1.92 (3H, d, J = 1, H-13), 2.82 (2H, dd, J = 16; 6, H-9), 5.28 (1H, m, J = 15, H-3), 6.32 (1H, br s, H-6), 6.92 (1H, br s, H-12) [1]

1H NMR (CDCl3 / C6D6): 0.97, 0.96 (3H, d, J = 7.0, H-15), 1.04, 1.06 (3H, s, H-14), 2.18, 2.10 (3H, d, J = 1.3, Me cis to −C(O)O− at C-3), 2.21, 2.13 (3H, d, J = 1.2, Me cisto H at C-6), 5.37, 5.62 (1H, ddd, J = 10; 5; 5, H-3), 5.66, 5.66 (1H, m, =CHC(O)O− at C-3), 5.73, 5.75 (1H, m, =CHC(O)O− at...

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References

  1. 1.
    F. Bohlmann, A. Suwita, Chem. Ber. 109, 1230 (1976)CrossRefGoogle Scholar
  2. 2.
    A. Guerriero, F. Pietra, Phytochemistry 21(12), 2887 (1982)CrossRefGoogle Scholar

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