Natural Compounds

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

3α-[(E)-3-Methylsulfinylacryloyloxy]-eremophila-1(9),7(11)-dien-8-one (Petasone B)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1058

CAS Registry Number: 211690-99-2 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 −28° (c 1.0, MeOH) [1]

UV (MeOH): 241 (4.56), 276 (3.43) [1]

IR (KBr): 3040, 1725, 1710, 1660, 1625, 1220, 1145, 1060, 995, 890 [1]

EI-MS: 350 [M]+ (12), 216 (72), 161 (100), 148 (32), 55 (32) [1]

HR-EI-MS: 350.1562, (calc. for C19H26O4S, 350.1553) [1]

1H NMR (300 MHz CDCl3): 0.98 (3H, d, J = 6.6, H-15), 1.03 (3H, s, H-14), 1.84 (3H, s, H-13), 2.08 (3H, d, J = 1.8, H-12), 2.18 (1H, dq, J = 13.5; 1.5, H-6b), 2.91 (1H, d, J = 13.5, H-6a), 4.92 (1H, td, J = 11.1; 4.5, H-3), 5.77 (1H, d, J = 1.2, H-9); acyl group: 2.71 (3H, s, S(O)CH3), 6.67 (1H, d, J = 14.7, H-2′), 7.62 (1H, d, J = 14.7, H-3′); signals of H-1; H-2; H-4 – not resolved [1]

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

Table 1

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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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