Natural Compounds

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

10α-Anisoyloxy-4α(H)-dauc-8-en-5β-ol (Cyclochaenin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_874

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Monoesters

Biological sources: Iva xanthifolia Nutt. (=Cyclachaena xanthifolia) [1]

C23H32O4: 372.2301

The its structure revised [2]

Mp: colorless oil [1]

[α]24 (λ, nm): −89.6° (589), −94.2° (578), −108.3° (546), −197.2° (436) (c 1.0, CHCl3) [1]

IR (CCl4): 1710, 1610, 1510, 845 [1]

MS: 372.230 [M]+ (10) (calc. for C23H32O4: 372.230), 354 [M − H2O]+ (2), 311 [354−⋅C3H7]+ (1), 220 [M − MeOC6H4COOH]+ (6), 205 [220 − ⋅Me]+ (4), 202 [220 − H2O]+ (16), 177 [220 − ⋅C3H7]+ (11), 159 [202 − ⋅C3H7]+ (24), 152 [MeOC6H4COOH]+ (9), 135 [MeOC6H4CO]+ (100), 107 [135 − CO]+ (11), 87 [107 − CH2O]+ (13) [1]

1H NMR (270 MHz, CDCl3, TMS): 0.97 (3H, d, H-13), 1.06 (3H, d, H-12), 1.08 (3H, s, H-14), 1.70 (3H, s, H-15), 1.87 (1H, qq, H-11), 2.37 (1H, m, H-4), 5.31 (1H, br d, H-10), 5.52 (1H, br d, H-9); OAnis: 3.88 (3H, s, OCH3), 6.94 (2H, br...

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References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 18(11), 1892 (1979)CrossRefGoogle Scholar
  2. 2.
    P. Singh, A.K. Sharma, K.C. Joshi, J. Jakupovic, F. Bohlmann, Phytochemistry 24(9), 2023 (1985)CrossRefGoogle Scholar

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