Natural Compounds

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

3α-[(Z)-3-Methylsulfinylacryloyloxy]-eremophila-1(10),7(11)-dien-8-one (Petasone A)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1057

CAS Registry Number: 211690-98-1 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]

C19H26O4S: 350.1553

Mp: colorless oil [1]

[α]D25 +40° (c 1.0, MeOH) [1]

UV (MeOH): 243 (4.47), 276 (3.22) [1]

IR (KBr): 3040, 1710, 1660, 1635, 1210, 1150, 1050, 815 [1]

EI-MS: 350 [M]+ (5), 334 (8), 216 (100), 201 (54), 161 (100), 54 (70) [1]

HR-EI-MS: 350.1560, (calc. for C19H26O4S, 350.1553) [1]

1H NMR (300 MHz CDCl3): 0.93 (3H, d, J = 6.9, H-15), 1.04 (3H, s, H-14), 1.80 (3H, s, H-13), 2.04 (3H, d, J = 1.5, H-12), 2.13 (1H, dq, J = 13.5; 1.5, H-6a), 2.91 (1H, d, J = 13.5, H-6a), 4.83 (1H, td, J = 11.1; 4.8, H-3), 5.73 (1H, d, J = 1.5, H-9); acyl group: 2.79 (3H, s, S(O)CH3), 6.24 (d, J = 10.2, H-2′), 6.96 (d, J = 10.2, H-3′); signals of H-1; H-2; H-4 – not resolved [1]

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

Table 1

C-1

29.8

C-8...

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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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