15-Vanilloyloxy-dauca-4,8-diene (14-(4′-Hydroxy-3′-methoxybenzoyloxy)dauc-4,8-diene)

Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Monoesters

Biological sources: Ferula hermonis Boiss. [1]

C₂₃H₃₀O₄: 370.2144

Mp: oil [1]

[α]_D −13.0° (c 0.052, MeOH) [1]

UV (MeOH) 302 (3.27) [1]

IR (film): 3394 (OH), 2955, 1711, 1597, 1514, 1462, 1429, 1378, 1282, 1216 [1]

HR-ESI-FT-MS: 369.2080 [M − H]⁺ (calc. for C₂₃H₂₉O₄, 369.2060) [1]

¹ H NMR (CDCl₃): 0.92 (3H, d, J = 6.8, H-12), 0.95 (3H, s, H-14), 0.98 (3H, d, J = 6.8, H-13), 2.06 (1H, m, H-10a), 2.18 (1H, m, H-10b), 2.66 (1H, septet, J = 6.8, H-11), 4.70 (2H, br s, H-14), 5.87 (1H, br t, J = 9.8, H-9); OVan: 3.92 (3H, s, OCH₃), 6.15 (1H, s, 4′-OH), 6.93 (1H, d, J = 8.3, H-5′), 7.56 (1H, d, J = 1.8, H-2′), 7.64 (1H, dd, J = 8.3, 1.7, H-6′) [1]

¹³ C NMR (CDCl₃) [1]:

Table 1

C-1	49.2 s	C-9	128.6 d	C-2′	114.5 d
2	39.1 t	10	40.7 t	3′	146.2 s
3	30.2 t	11	26.8 d	4′	150.0 s
4	141.3 s	12	21.6 q	5′	112.2 d
5	139.4 s	13	22.3 q	6′	124.5 d
6	23.2 t	14