Natural Compounds

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

10α-Cinnamoyloxy-4α(H)-dauca-2,8-dien-5β-ol (10α-Cinnamoyloxy-2,3-dehydrocarotol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_882

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

Biological sources: Blainvillea acmella L. [1]

C24H30O3: 366.2195

Mp: colorless oil [1]

[α]D −198°( c 0.05, CHCl3) [1]

IR (CCl4): 3600, 1710, 1640 [1]

MS: 366.219 [M]+ (1), 218 [M − cinnamic acid]+ (10), 200 [218 − H2O]+ (9), 185 [200 − Me]+ (4), 175 [218 − C3H7]+ (12), 131 [PhCH = CHCO]+ (100), 103 [131 − CO]+ (26), 77 [103 − C2H2]+ (18) [1]

1H NMR (400 MHz, CDCl3, TMS): 1.09 (3H, d, J = 7, H-12), 1.12 (3H, s, H-14), 1.75 (3H, br s, H-15), 1.84 (1H, dqq, J = 7; 7; 7, H-11), 2.05 (1H, m, H-6b), 2.18 (1H, m, H-6a), 2.38 (1H, m, H-7b), 2.50 (1H, m, H-4), 2.55 (1H, m, H-7a), 5.33 (1H, m, H-10), 5.37 (1H, m, H-2), 5.48 (1H, m, H-9), 5.71 (1H, br d, J = 3; 6, H-3); OCinn: 6.33 (1H, d, J = 16, H-8′), 7.38 (3H, m, H-3′, H-5′, H-4′), 7.50 (2H, m, H-2′, H-6′), 7.62 (1H, d, J = 16, H-7′) [1]

1H NMR (400 MHz, 60°, CDCl3,...

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References

  1. 1.
    P. Singh, A.K. Sharma, K.C. Joshi, J. Jakupovic, F. Bohlmann, Phytochemistry 24(9), 2023 (1985)CrossRefGoogle Scholar

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