Natural Compounds

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

3α-Senecioyloxy-7βH-eremophila-9(10),11(12)-dien-8-one (Senecioyloxy-petasol; 3α-O-Senecioylsencathenon)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1073

CAS Registry Number: 69734-56-1 Open image in new window

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

Biological sources: Petasites hybridus (L.) (= P. officinalis Moench) [1, 2]; Senecio cathcartensis O. Hoffm. [3]; Hoehnephytum imbricatum (Gardner) Cabrera [4]

C20H28O3: 316.2039

Mp: colorless oil [3]

UV (cyclohexane) 225 [1]

IR (CCl4): 1713, 1676, 1648, 1627 [1]; (CCl4): 1720, 1680, 1650, 1630 [3]

MS: 316.2033 [M]+ (calc. for C20H28O3: 316.2038) [1]

MS: 316.204 [M]+ (7) (calc. for C20H28O3), 216 [M − C4H7COOH]+ (31), 201 [216 − ⋅CH3]+ (15), 148 [216 − Isopren]+ (100), 83 [C4H7CO]+ (52) [3]

HPLC: [1, 2]

1H NMR (360 MHz, CDCl3, TMS): 0.95 (3H, d, J = 7, H-15), 1.24 (3H, s, H-14), 1.48 (1H, dtd, J = 5; 14; 11, H-2ax), 1.61 (1H, dq, J = 11; 7, H-4ax), 1.75 (3H, s, H-13), 1.87 (1H, dd, J = 13; 14.5, H-6ax), 2.03 (1H, dd, J = 13; 4.5, H-6eq), 2.24 (1H, dd, J = 14; 4.5, H-2eq...

This is a preview of subscription content, log in to check access

References

  1. 1.
    M. Neuenschwander, A. Neuenschwander, E. Steinegger, P. Engel, Helv. Chim. Acta 62, 609 (1979)CrossRefGoogle Scholar
  2. 2.
    B. Debrunner, M. Neuenschwander, R. Brenneisen, Pharm. Acta Helv. 70, 167 (1995)CrossRefGoogle Scholar
  3. 3.
    F. Bohlmann, C. Zdero, Phytochemistry 17(8), 1337 (1978)CrossRefGoogle Scholar
  4. 4.
    F. Bohlmann, M. Ahmed, H. Robinson, R.M. King, Phytochemistry 20(5), 1157 (1981)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013