Natural Compounds

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

6α-Salicyloyloxy-5α(H)-dauc-8-en-4β-ol (Salicyloyl of Jaeschkeanadiol; 6α-[2-Hydroxy-benzoyloxy]-4β-hydroxy-dauc-8-ene; Jaeskeanadiol Salicylate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_919

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

Biological sources: Ferula elaeochytris Korov. [1]; F. rigidula DC. [2]; F. jaeschkeana Vatke [3]

C22H30O4: 358.2144

Mp: amorphous [1]; 210–213°C [3]

UV (MeOH): 220, 249, 280, 340 [1]; (MeOH): 325, 280, 250 [3]

IR (KBr): 3470, 3360, 2980, 2880, 1680, 1610, 1585, 1550, 1480, 1375, 1295, 1235, 1160, 1095, 950, 750, 700 [1]; (KBr): 3450, 3360, 2970, 2870, 1670, 1610, 1580, 1370, 1295, 1230, 1160, 950 [3]

MS: 358 [M]+ (85), 340 [M − (OH + H)]+ (5), 315 [M − 43]+ (88), 220 [jaeschkeanadiol − (OH + H)]+ (20), 202 [jaeschkeanadiol − 2(OH + H)]+ (40), 137 [salicylic acid − 1]+ (95), 121 [salicyloyl acylium ion]+ (100) [1]

MS: 358.3825 [M]+ (calc. for C22H30O4: 358.4788), 340 [M − H2O]+, 315 [M − C3H7]+, 220 [M − C7H5O2 − H2O]+, 202 [M − C7H5O2 − 2 × H2O]+, 137 [C7H5O3 − 1]+, 121 [C7H5O2]+ [3]

1H NMR(200 MHz): 0.85...

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References

  1. 1.
    M. Miski, A. Ulubelen, T.J. Mabry, Phytochemistry 22(10), 2231 (1983)CrossRefGoogle Scholar
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    M. Miski, J. Jakupovic, Phytochemistry 29(1), 173 (1990)CrossRefGoogle Scholar
  3. 3.
    T.K. Razdan, B. Qadri, M.A. Qurishi, M.A. Khuroo, P.K. Kachroo, Phytochemistry 28(12), 3389 (1989)CrossRefGoogle Scholar

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