Natural Compounds

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

8β-Acetoxy-caryophylla-2(15),5-dien-14-oic Acid (8β-Acetoxy-lychnopholic Acid)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_827

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

Biological sources: Lychnophora martiana Gardner [1]; L. salicifolia Mart. [2]

C17H24O4: 292.1675

[α]24 (λ, nm): + 40.5° (589), + 42.0° (578), + 48.0° (546), + 84.6° (436) (c 3.2, CHCl3) [2]

Mp: 168°C (hexane ether – MeOH) [1]; 170°C (Et2O) [2]

IR (KBr): 3350, 1680, 1630 [1]; 3300–2600, 1690, 1640, 905 [2]

MS: 292 [M]+ [1]

MS: 292.167 [M]+ (0.2), 250 (3), 232 (12), 217 (6), 43 (100) [2]

1H NMR (270 MHz, CDCl3, TMS): 1.05 (3H, s, H-13), 1.19 (3H, s, H-12), 1.6 (2H, m, H-10), 2.2 (3H, m, H-9β, H-7α, H-4b), 2.89 (1H, d, J = 11, H-1α), 3.5 (2H, m, H-7β, H-4a), 4.99 (1H, br s, H-15b), 5.16 (1H, br s, H-15a), 5.70 (1H, dt, J = 11; 6; H-8), 6.29 (1H, dd, J = 10; 6, H-5) [1]

1H NMR(270 MHz): 1.05 (3H, s, H-13), 1.13 (3H, s, H-12), 1.53 (1H, dd, H-10α), 1.64 (1H, dd, H-10β), 1.83 (1H, ddd, H-9), 2.05 (3H, s, OAc), 2.10 (1H,...

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References

  1. 1.
    W. Vichewski, A.P. Lins, W. Herz, R. Murari, Phytochemistry 19(4), 685 (1980)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, C. Zdero, H. Robinson, R.M. King, Phytochemistry 19(11), 2381 (1980)CrossRefGoogle Scholar

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