Natural Compounds

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

3β-Acetoxy-eremophila-6,9-dien-8-on-12-oic Acid

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_988

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

Biological sources: Cacalia roborowskii (Maxim.) Ling [1]

C17H22O5: 306.1467

Mp: gum [1]

[α]D +28.6° (c ca. 0.6, CHCl3) [1]

IR (KBr): 2500–3400 (br, bonded OH), 1738 (CH3CO), 1665, 1636, 1615, 1710 (COOH), 1241 (C–O), 980, 915, 732 [1]

FAB-MS: 247 [M – CH3COOH + H]+ (15), 229 [M – CH3COOH – H2O + H]+ (25), 201 [M – CH3COOH – COOH]+ (55), 175 (10), 159 (15), 147 (20), 133 (30), 91 (35), 69 (40), 57 (78), 55 (90), 43 (100) [1]

1H NMR (400 MHz, CDCl3): 1.17 (3H, d, J = 7.0, H-15), 1.34 (3H, s, H-14), 1.37 (3H, d, J = 7.1, H-13), 1.64 (1H, m, H-2a), 1.70 (1H, m, H-4), 2.21 (1H, m, H-2b), 2.01 (3H, s, OAc), 2.33 (2H, m, H-1a), 2.70 (2H, m, H-1b), 3.75 (1H, q, J = 7.1, H-11), 5.07 (1H, J = 2.7, H-3), 6.21 (1H, s, H-9), 6.95 (1H, s, H-6) [1]

NOESY: [1]

Pharm./Biol.: antibacterial activity [1]

References

  1. 1.
    S. Zhang, G. Zhao, R. Li, G. Lin, Phytochemistry 48(3), 519 (1998)CrossRefGoogle Scholar

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