Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1011

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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]; Cacalia ainsliaeiflora (Franch.) Hand.-Mazz. [2]

C20H26O5: 346.1780

Mp: oil [1]

[α]D +38.5° (c 1.2, CHCl3) [1]

[α]D20 +32.7° (c 0.75, CHCl3) [2]

UV (MeOH): 236 (4.08), 216 (4.15) [2]

IR (KBr): 2500–3400 (br, OH), 1720 (ester carbonyl), 1710 (COOH), 1665, 1634, 1620 (α,β,α′,β′-unsaturated ketone), 1241 (C–O), 980, 915, 733 [1]

EI-MS: 346 [M]+ (1), 246 [M – C4H7COOH]+ (50), 228 [246 – H2O]+ (25), 202 [246 – CO2]+ (80), 201 (60), 173 (32), 135 (36), 115 (50), 91 (74), 83 [C4H7CO]+ (100), 77 (50), 55 (60) [1]

1H NMR (400 MHz, CDCl3): 1.21 (3H, d, J = 6.9, H-15), 1.36 (s, H-14), 1.37 (d, J = 6.8, H-13), 1.66 (m, H-2), 1.72 (m, H-4), 2.20 (m, H-2), 2.33 (H-1), 2.68 (m, H-1), 3.74 (q, H-11), 5.14 (J = 2.8, H-3), 6.20 (s, H-9), 6.94 (s, H-6); OAng:...

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References

  1. 1.
    S. Zhang, G. Zhao, R. Li, G. Lin, Phytochemistry 48(3), 519 (1998)CrossRefGoogle Scholar
  2. 2.
    M. Mao, Z. Jia, Planta Med. 68, 55 (2002)CrossRefGoogle Scholar

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