Natural Compounds

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

2α-Acetoxy-10β-benzoyloxy-6α-(4″-hydroxy-benzoyloxy)-5α(H)-dauc-8-en-4β-ol

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_974

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

Biological sources: Daucus carota L. ssp. carota [1]

C31H36O8: 536.2410

Mp: white powder [1]

[α]D50 +22.8 (c 0.025, CHCl3) [1]

IR (KBr): 3421 (OH), 2963, 2925, 1714 (C=O), 1272, 1164, 770 [1]

CI-MS: 535 [M – H ]+, 519 [M + H – H2O]+, 415 [519 – benzoate]+ [1]

HR-CI-MS: 535.2326 [M – H]+(calc. for C31H34O8, 535.2332) [1]

1H NMR (500 MHz, CDCl3): 0.80 (3H, d, J = 7, H-13), 0.95 (3H, d, J = 7, H-12), 1.85 (1H, qq, J = 7, H-11), 1.86 (3H, s, OAc), 1.93 (1H, d, J = 16, H-3α), 2.12 (1H, dd, J = 6, 16, H-3β), 2.30 (1H, dd, J = 14.5, 10.5, H-7α), 2.71 (1H, d, J = 10.5, H-5), 2.72 (1H,d, J = 14.5, 2.5, H-7β), 5.11 (1H, d, J = 6, H-2), 5.35 (1H, br s, H-9), 5.36 (1H, ddd, J = 10.5, 10.5, 2.5, H-6), 5.77 (1H, br s, H-10α); Op-HOBz: 6.90 (2H, d, J = 8.5, H-3′, H-5′), 7.95 (2H, d, J = 8.5, H-2′, H-6′); OBz: 7.45 (2H, t, J =...

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References

  1. 1.
    A.A. Ahmed, M.M. Bishr, M.A. El-Shanawany, E.Z. Attia, S.A. Ross, P.W. Pare, Phytochemistry 66(14), 1680 (2005)CrossRefGoogle Scholar

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