Natural Compounds

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

1β-Acetoxy-7αH-eremophila-9(10),11(13)-dien-3-on-12-oic Acid

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_983

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

Biological sources: Haeckeria pholidota (F. Muell.) J. H. Willis [1]

C17H22O5: 306.1467

C18H24O5: 320.1624 (methyl ester: 1β-Acetoxy-7αH-eremophila-9(10),11(13)-dien-3-on-12-oic acid methyl ester)

Mp: isolated as its methyl ester [1]

IR (CCl4) (methyl ester): 1740, 1725 [1]

MS (methyl ester): 320 [M]+ (0.2), 260.141 [M − HOAc]+ (100) (calc. for C16H20O3: 260.141), 228 (32), 213 (41), 204 (96), 189 (96), 172 (92), 145 (84), 119 (56), 91 (61) [1]

TLC (methyl ester): Et2O – petrol (1:3) [1]

HPLC (methyl ester): MeOH – H2O (3:1), Rt 5.6 min [1]

1H NMR (400 MHz, CDCl3, TMS) (methyl ester): 1.00 (3H, s, H-14), 1.04 (3H, d, J = 7, H-15), 1.29 (1H, dd, J = 13; 12, H-6b), 1.99 (3H, s, OAc), 2.02 (1H, dt, J = 13; 2; 2, H-6a), 2.06 (1H, ddd, J = 11; 17; 2, H-8b), 2.28 (1H, ddddd, J = 2; 3; 17; 6.5, H-8a), 2.69...

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References

  1. 1.
    C. Zdero, F. Bohlmann, A. Anderberg, R.M. King, Phytochemistry 30(8), 2643 (1991)CrossRefGoogle Scholar

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