Natural Compounds

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

3α-Angeloyloxy-eremophila-9(10),7(11)-dien-8-one (Iso-Petasin; Isopetasin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1009

CAS Registry Number: 469-26-1 Open image in new window

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

Biological sources: Petasites hybridus (= P. officinalis Moench) [1, 2, 3, 4, 5]; P. fragrans (Vill.) C. Presl [6]; P. formosanus Kitam. [7, 8]; P. kablikianus Tausch. ex Bercht. [9]; Senecio cuneatus Sch. Bip. [10]; S. integrifolius (L.) Claivr. ssp. aucheri (DC.) V.A. Matthews [11]; S. polyodon DC. [12]

C20H28O3: 316.2038

Mp: 89–91°C [1]

[α]D22 +28.6° (CHCl3) [1]

UV (cyclohexane): 234, 269 [1]

IR (CCl4): 1712, 1665, 1628 [1]; (neat): 1710, 1675, 1650, 1630, 890 [6]

MS: 316.2036 [M]+ (calc. for C20H28O3: 316.2038) [1]

HPLC [1, 4, 5]

1H NMR (360 MHz, CDCl3, TMS): OAng: 1.89 (3H, q, J = 1.4, H-5′), 1.99 (3H, qq, J = 7.1; 1.4, H-4′), 6.06 (1H, qq, J = 7.1; 1.4, H-3′) [1]

1H NMR (100 MHz, CDCl3, TMS): 0.98 (3H, d, J = 6.6, H-15), 1.26 (3H, s, H-14), 1.74 (3H, s, H-13), 2.93...

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