Natural Compounds

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

6β-Acetoxy-3β-angeloyloxy-furanoeremophilane (3-O-Angeloyl-6-O-acetylfuranofukinol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1346

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

Biological sources: Farfugium hiberniflorum (Makino) Kitam. (= Ligularia hiberniflora Makino; Kan-tsuwabuki) [1, 2]; Othonna filicaulis L. [3]

C22H30O5: 374.2093

Mp: viscous oil [1]

UV (EtOH) 215 (ε 17000) [1]

IR (CHCl3): 1730, 1710, 1640, 1560, 1235, 1160 [1]; IR: 1720, 1650, 1745, 1240 [3]

MS: 374 [M]+ (2), 124 (100, retro-Diels-Alder fragment), 83 [CH3CH = C(CH3)CO]+ (82), 55 [CH3CH = CCH3]+ (70), 43 [CH3CO]+ (80) [1]

MS: 374.209 [M]+ (25) (calc. for C22H30O5 374.209), 314 [M – CH3COOH]+ (9), 232 [314 – O = C = C(CH3)CH = CH2]+ (15), 231 [314 – C4H7CO]+ (16), 214 [314 – C4H7COOH]+ (12), 199 [214 – CH3]+ (27), 83 [C4H7CO]+ (100) [3]

1H NMR (CDCl3): 0.97 (3H, d, J = 7, H-15), 1.03 (3H, s, H-14), 1.87 (1H, d, J = 1.5, H-11), 1.87 (3H, s, CH3CH = C(CH3)COO-), 1.97 (3H, d, J = 7, CH3CH = C(CH3)COO-),...

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References

  1. 1.
    H. Nagano, T. Takahashi, Bull. Chem. Soc. Jpn. 45, 1935 (1972)CrossRefGoogle Scholar
  2. 2.
    K. Naya, Y. Makiyama, T. Matsuura, N. II, H. Nagano, T. Takahashi, Chem. Lett. 7, 301 (1978)Google Scholar
  3. 3.
    F. Bohlmann, C. Zdero, M. Grenz, Chem. Ber. 107, 3928 (1974)CrossRefGoogle Scholar

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