Natural Compounds

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

6α-(4′-Hydroxy-benzoyloxy)-4β-hydroxy-5α(H)-dauc-8-en-2-one (Ferutionone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_902

CAS Registry Number: 126617-09-2 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters

Biological sources: Ferula jaeschkeana Vatke [1]

C22H28O5: 372.1937

Mp: 93–94°C [1]

[α]D +28.5° (c 1.4, CHCl3) [1]

UV (EtOH): 210, 240, 260, 275 [1]

IR (KBr): 3410, 2960, 2860, 1705, 1685, 1645, 1440, 1260, 1145, 940 [1]

MS: 372.1969 [M]+ (calc. for C22H28O5: 372.4624), 354 [M − H2O]+, 329 [M − C3H7]+, 234 [M − C7H5O2]+, 191 [M − C7H5O2 − C3H7]+, 163 [M − C7H5O2 − C3H7 − CO]+, 137 [C7H5O3]+, 135 [163 − CO]+, 121 [C7H5O2]+ (100), 107, 93, 77, 55, 28 [1]

1H NMR (60 MHz, CDCl3, TMS): 0.85 (3H, d, J = 7, H-12), 0.95 (3H, d, J = 7, H-13), 1.54 (3H, s, H-14), 1.91 (3H, s, H-15), 2.62 (2H,br d, J = 10, H-3), 5.32 (1H, t, J = 10; 3, H-6), 5.56 (1H, t, J = 6.5, H-9); Op-HOBz: 6.8 (2H, d, J = 8, H-3′, H-5′), 7.8 (2H, d, J = 8, H-2′, H-6′) [1]

13 C NMR (62.89MHz, CDCl 3, TMS) [ 1]:

Table 1

C-1

43.2

C-9

129.4

C-1′

147.2

2

217.3

10...

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References

  1. 1.
    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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