Natural Compounds

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

6α,10α-Diangeloyloxy-5α(H)-dauc-8-ene-2β,4β-diol (Tingitanol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_967

CAS Registry Number: 95342-43-1 Open image in new window

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

Biological sources: Ferula tingitana L. [1]

C25H38O6: 434.2668

Mp: amorphous [1]

IR (KBr): 3470, 2960, 2920, 2860, 1700, 1680, 1450, 1380, 1345, 1260, 1230, 1150, 1115, 1075, 1030, 950, 840, 750 [1]

MS: 434 [M]+ (1), 416 [M − 18]+ (2), 391 [M − 43]+ (2), 334 [M − angeloyloxy]+ (25), 317 (12), 291 (60), 216 (75), 120 (100), 83 (85) [1]

Found: C, 69.5; H, 8.8; calc. for C25H38O6: C, 69.1; H, 8.8% [1]

1H NMR (200 MHz, CDCl3): 0.88 (3H, d, J = 7, H-13 or H-12), 0.92 (3H, d, J = 7, H-12 or H-13), 1.14 (3H, s, H-14), 1.55 (1H, dd, J = 10; 12, H-3β), 1.78 (3H, br s, H-15), 2.2 (2H, m, H-3α, H-7α), 2.52 (1H, d, J = 10, H-5α), 2.72 (1H, br t, J = 13, H-7β), 3.58 (1H, dd, J = 8; 10, H-2α), 5.07 (1H, d, J = 8, H-10β), 5.35 (1H, dt, J = 3; 10; 12, H-6β), 5.74 (1H, br d, J = 8, H-9); 2 × OAng:...

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References

  1. 1.
    M. Miski, A. Ulubelen, T.J. Mabry, W.H. Watson, I. Vickovic, M. Holub, Tetrahedron 40, 5197 (1984)CrossRefGoogle Scholar

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