Natural Compounds

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

3α-Angeloyloxy-11-hydroxy-eremophila-9(10),6(7)-dien-8-one (Petasitin; 3α-[(Z)-2-Methyl-2-butenoyloxy]-11-hydroxyeremophila-6,9-dien-8-one)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1022

CAS Registry Number: 19887-90-2 Open image in new window

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

Biological sources: Petasites japonicus (Siebold et Zucc.) Maxim. [1, 2]; P. formosanus Kitam. [3]

C20H28O4: 332.4339

Mp: viscous oil [2]

[α]D22 −26.2° (c 1.0, MeOH) [2]

TLC: benzene – ethyl acetate, 10:1, Rf 0.2 [2]

UV (EtOH) 235 (14200) [1]

IR (film): 3460, 1710, 1632, 1665, 1617, 1235 [1]

1H NMR (CDCl3): 1.16 (3H, d, J = 7, H-15), 1.25 (3H, s, H-14), 1.90* (3H, s, H-13), 2.05* (3H, s, H-12), 4.95 (1H, m, H-3), 6.15 (1H, t, J = 1, H-9), 6.93 (1H, s, H-6); OAng: 1.50 (each 3H, each s, H-4′, H-5′), 6.13 (1H, q, J = 5, H-3′), * – assignments may be interchanged [1]

1H NMR (60 MHz, CDCl3): 1.16 (3H, s, J = 7.0, H-15), 1.25 (3H, s, H-14), 1.50 (3H×2, each s, H-12, H-13), 1.90 (3H, s, H-5′), 2.05 (3H, d, J = 7.0, H-4′), 4.95 (1H, m, W1/2= 14, H-3), 6.13 (1H, q, J = 7.0,...

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References

  1. 1.
    K. Naya, I. Takagi, Tetrahedron Lett. 9, 629 (1968)CrossRefGoogle Scholar
  2. 2.
    I. Takagi, Y. Tazuke, K. Naya, Bull. Chem. Soc. Jpn. 50, 3320 (1977)CrossRefGoogle Scholar
  3. 3.
    Y.-L. Lin, C.-H. Mei, S.-L. Huang, Y.-H. Kuo, J. Nat. Prod. 61, 887 (1998)CrossRefGoogle Scholar

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