Natural Compounds

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

2β-Angeloyloxy-5α(H)-dauc-8-ene-4β,6α-diol (2β-O-Angeloyl Akichenol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_853

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

Biological sources: Ferula jaeschkeana Vatke [1]

C20H32O4: 336.2301

Mp: gum [1]

[α]D40 +6.6° (c 1.0, CHCl3) [1]

UV (MeOH) 220 [1]

IR (neat): 3400, 2980, 1720, 1640, 1440, 1365, 1210, 1150, 1060, 1020, 960, 930 [1]

MS: 318 [M − H2O]+ (8.4), 293 [M − C3H7]+ (4.4), 300 [M − 2H2O]+ (7.2), 236 [M − angelic acid]+ (8.6), 235 (11.3), 193 (30), 175 (35), 147 (25), 121 (20), 83 (100), 71 (35), 55 (60) [1]

Found: C, 70.62; H, 9.45; calc. for C20H32O4: C, 71.43; H, 9.52% [1]

TLC: CHCl3 – MeOH (49:1), Rf 0.32 [1]

1H NMR (400 MHz, CDCl3, TMS): 0.92 (3H, d, J = 7, H-12), 0.99 (3H, d, J = 7, H-13), 1.09 (3H, s, H-14), 1.56 (1H, dd, J = 14; 10, H-7a), 1.61 (1H, m, H-10α), 1.81 (3H, s, H-15), 2.12 (1H, dd, J = 14.5; 2, H-3a), 2.18 (1H, dd, J = 14; 8, H-10β), 2.20 (1H, d, J = 10, H-5), 2.21 (1H, qq, J = 7, H-11), 2.23 (1H, dd,...

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References

  1. 1.
    S.N. Garg, K. Vishwapaul, S.N. Rastogi, Phytochemistry 29(2), 531 (1990)CrossRefGoogle Scholar

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