6α-(4′-Hydroxy-benzoyloxy)-4β-hydroxy-5α(H)-dauc-8-en-2-one (Ferutionone)

CAS Registry Number: 126617-09-2

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

Biological sources: Ferula jaeschkeana Vatke [1]

C₂₂H₂₈O₅: 372.1937

Mp: 93–94°C [1]

[α]_D +28.5° (c 1.4, CHCl₃) [1]

UV (EtOH): 210, 240, 260, 275 [1]

IR (KBr): 3410, 2960, 2860, 1705, 1685, 1645, 1440, 1260, 1145, 940 [1]

MS: 372.1969 [M]⁺ (calc. for C₂₂H₂₈O₅: 372.4624), 354 [M − H₂O]⁺, 329 [M − C₃H₇]⁺, 234 [M − C₇H₅O₂]⁺, 191 [M − C₇H₅O₂ − C₃H₇]⁺, 163 [M − C₇H₅O₂ − C₃H₇ − CO]⁺, 137 [C₇H₅O₃]⁺, 135 [163 − CO]⁺, 121 [C₇H₅O₂]⁺ (100), 107, 93, 77, 55, 28 [1]

¹ H NMR (60 MHz, CDCl₃, TMS): 0.85 (3H, d, J = 7, H-12), 0.95 (3H, d, J = 7, H-13), 1.54 (3H, s, H-14), 1.91 (3H, s, H-15), 2.62 (2H,br d, J = 10, H-3), 5.32 (1H, t, J = 10; 3, H-6), 5.56 (1H, t, J = 6.5, H-9); Op-HOBz: 6.8 (2H, d, J = 8, H-3′, H-5′), 7.8 (2H, d, J = 8, H-2′, H-6′) [1]

¹³ C NMR (62.89MHz, CDCl₃, TMS) [1]:

Table 1

C-1	43.2	C-9	129.4	C-1′	147.2
2	217.3	10	41.8	2′	128.7
3	40.3