Natural Compounds

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

3α-Angeloyloxy-7βH-eremophila-9(10),11(12)-dien-8-one (Petasin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1008

CAS Registry Number: 26577-85-5 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, 3, 4, 5, 6, 7, 8]; P. albus Gaertn. [9]; P. fragrans (Vill.) C. Presl [10]; P. formosanus Kitam. [11, 12]; P. japonicus (Siebold et Zucc.) Maxim. [13]; Hoehnephytum imbricatum (Gardner) Cabrera [14]; Senecio congestus (R. Br.) DC. [15]; S. integrifolius (L.) Claivr. ssp. aucheri (DC.) V.A. Matthews [16]; S. polyodon DC. [17]

C20H28O3: 316.2038

Mp: viscous oil [8]

[α]D24 +39.6° (c 1.08, CHCl3) [13]

UV (cyclohexan) 225.5 [2]

IR (CCl4): 1710, 1676, 1647, 1626 [2]; (neat) : 1710, 1675, 1650, 1630, 890 [10]

MS: 316.2042 [M]+ (calc. for C20H28O3: 316.2038) [2]

HPLC [2, 7, 8]

1H NMR (360 MHz, CDCl3, TMS): 0.99 (3H, d, J = 7, H-15), 1.26 (3H, s, H-14), 1.52 (1H, dtd, J = 5; 14; 11, H-2ax), 1.69 (1H,...

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