Natural Compounds

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

3α-[(E)-3-Methylsulfinylacryloyloxy]-8β-hydroxy-7αH-eremophila-1(9),7(11)-diene (Petasinol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1059

CAS Registry Number: 211691-01-9 Open image in new window

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

Biological sources: Petasites formosanus Kitam. [1]

C19H28O4S: 352.1709

Mp: colorless amorphous solid [1]

[α]D25 +25° (c 1.0, MeOH) [1]

UV (MeOH) 261 (4.19) [1]

IR (KBr): 3440, 3020, 1710, 1650, 1625, 1220, 1150, 1050, 890 [1]

EI-MS: 352 [M]+ (4), 335 (10), 278 (20), 216 (22), 200 (100), 185 (72), 150 (96), 145 (82)

HR-EI-MS: 352.1705 (calc. for C19H28O4S, 352.1709) [1]

1H NMR (300 MHz CDCl3): 0.84 (3H, d, J = 6.6, H-15), 1.00 (3H, s, H-14), 1.71 (3H, s, H-13), 4.06 (2H, d, J = 9.6, H-6), 4.72 (1H, br s, H-12a), 4.87 (1H, br s, H-12b), 4.91 (1H, td, J = 11.0; 4.8, H-3), 5.43 (1H, d, J = 1.2, H-9); acyl group: 2.69 (3H, s, S(O)CH3), 6.64 (1H, d, J = 14.7, H-2′), 7.57 (1H, d, J = 14.7, H-3′); signals of H-1; H-2; H-4; H-6 – not resolved [1]

13 C NMR (75 MHz, CDCl 3): [ 1]

Tab...

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References

  1. 1.
    Y.-L. Lin, C.-H. Mei, S.-L. Huang, Y.-H. Kuo, J. Nat. Prod. 61, 887 (1998)CrossRefGoogle Scholar

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