Natural Compounds

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

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

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_972

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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]

C29H38O7: 498.2618

Mp: amorphous white powder [1]

[α]D25 +8.8° (c 0.10, CHCl3) [1]

IR (KBr): 3500, 2980, 2960, 1730, 1260, 1164, 1032, 770 [1]

CI-MS: 481 [M + H – H2O]+, 277 [M – benzoate]+ [1]

HR-CI-MS: 481.2585 [M + H – H2O]+ (calc. for C29H37O6, 481.2590) [1]

1H NMR (500 MHz, CDCl3): 0.87 (3H, H-13), 0.89 (3H, H-12), 1.34 (3H, s, H-14), 1.82 (1H, H-11), 1.83 (3H, s, H-15), 1.84 (3H, s, OAc), 1.87 (1H, H-3β), 2.10 (1H, H-3α), 2.23 (1H, H-7α), 2.61 (1H, H-5α), 2.69 (1H, H-7β), 5.07 (1H, H-2β), 5.23 (1H, H-6β), 5.33 (1H, H-9), 5.74 (1H, H-10α); OAng: 1.90 (3H, dq, J = 1.5, 1.5, H-5′), 2.03 (3H, dq, J = 7.3, 1.5, H-4′), 6.20 (1H, qq, J = 7.3, 1.5, H-3′); OBz: 7.45 (2H, H-3″, H-5″), 7.55 (1H, H-4″), 7.95 (2H, H-2″, H-6″) [1]

13 C NMR (125 MHz, CDCl 3) [ 1]:

Table 1

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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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© Springer Science+Business Media New York 2013