Natural Compounds

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

8α-Acetoxy-caryophyllen-14-oic Acid

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_829

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

Biological sources: Lychnophora salicifolia Mart. [1]

C17H24O4: 292.1675

Mp: 170°C (Et2O), colorless crystals [1]

[α]24 (λ, nm): +40.5° (589), +42.0° (578), +48.0° (546), +84.6° (436) (c 3.2, CHCl3) [1]

IR (CCl4): 3300–2600, 1690, 1640, 905 [1]

MS: 292.167 [M]+ (0.2) (C17H24O4), 250 (3), 232 (12), 217 (6), 43 (100) [1]

1H NMR (270 MHz, CDCl3, TMS, in parentheses are signals of the second conformer): 1.05 (1.00) (3H, s, H-13), 1.13 (1.14) (3H, s, H-12), 1.53 (1H, dd, J = 10; 10.5, H-10α), 1.64 (1H, dd, J = 10; 10.5, H-10β), 1.83 (1.78) (1H, ddd, J = 10.5; 10, H-9), 2.05 (2.06) (3H, s, OAc), 2.10 (1H, dd, J = 10; 12, H-7α), 2.15–2.6 (4H, m, H-3α, H-3β, H-4α, H-4β), 2.68 (1H, br ddd, J = 10.5; 10; 10, H-1), 3.13 (2.96) (1H, dd, J = 6; 12, H-7β), 4.89 (4.97) (1H, br s, H-15b), 5.01 (5.11) (1H, br s, H-15a), 5.17 (5.00)...

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References

  1. 1.
    F. Bohlmann, C. Zdero, H. Robinson, R.M. King, Phytochemistry 19(11), 2381 (1980)CrossRefGoogle Scholar

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