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

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Natural Compounds

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CAS Registry Number: 469-26-1

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

Biological sources: Petasites hybridus (= P. officinalis Moench) [1–5]; 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] 22D +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]

1 H 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]

1 H 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 (1H, d, J = 11, H-6), 3.07 (1H,...

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Editor information

Editors and Affiliations

  1. S.Yu. Yunusov Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Republic of Uzbekistan, Tashkent, Republic of Uzbekistan

    Shakhnoza S. Azimova

  2. S.Yu. Yunusov Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Republic of Uzbekistan, Tashkent, Republic of Uzbekistan

    Ashraf I. Saidkhodzhaev

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(2013). 3α-Angeloyloxy-eremophila-9(10),7(11)-dien-8-one (Iso-Petasin; Isopetasin). In: Azimova, S.S., Saidkhodzhaev, A.I. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0539-9_1009

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