Natural Compounds

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

6β-Acetoxy-eremophila-1(10),7(8),11(12)-trien-9-one (Cinalyratol Acetate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_995

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

Biological sources: Cineraria albicans N.E.Br., C. Dieterlenii E.Phillips, C. decipiens Harv., C. lydrata DC. [1]; C. fructiculorum Hutch. et Taylor, C. parvifolia Burtt Davy [2]; C. geifolia L., C. britteniae Hutch. et R.A. Dyer. [3]

C17H22O3: 274.1569

Mp: colorless oil [1]

[α]24 (λ, nm): +106.5° (589), +114.1° (578), +141.4° (546), +560.7° (436) (c 1.4, CHCl3) [1]

IR (CCl4): 1745, 1675, 1630, 1600, 1235, 990 [1]

MS: 274 [M]+ (0.1), 232.146 (20) (calc. for C15H20O2), 214 (100), 199 (69), 190 (43) [1]

1H NMR (270 MHz, CHCl3, TMS): 1.00 (3H, s, H-14), 1.02 (3H, d, J = 7, H-15), 1.60 (3H, m, H-3), 1.75 (1H, m, H-4), 2.02 (3H, br s, H-13), 2.04 (3H, s, OAc), 2.31 (2H, m, H-2), 5.38 (1H, br s, H-12b), 5.81 (1H, br s, H-12a), 5.95 (1H, s, H-6), 6.26 (1H, s, H-8), 7.08 (1H, t, J = 4, H-1) [1]

References

  1. 1.
    F. Bohlmann, W.-R. Abraham, Phytochemistry 17(9), 1629 (1978)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, P. Singh, J. Jakupovic, Phytochemistry 21(10), 2531 (1982)CrossRefGoogle Scholar
  3. 3.
    L. Lehmann, J. Jakupovic, F. Bohlmann, L. Vincent, Phytochemistry 27(10), 3307 (1988)CrossRefGoogle Scholar

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