9α-Acetoxy-6α-(4-hydroxy-benzoyloxy)-5α(H)-dauc-7-en-4β-ol (Lancerotriol 9-Acetate-6-p-hydroxybenzoate)

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

Biological sources: Ferula sinaica Boiss. [1]

C₂₄H₃₂O₆: 416.2199

IR: 3445, 2975, 2885, 1700, 1690 [1]

MS: 417.2251 [M + H]⁺, 399.2170 [M + H − H₂O]⁺ (100) [1]

¹ H NMR: 0.80 (3H, d, J = 7, H-13), 0.90 (3H, d, J = 7, H-12), 1.22 (3H, s, H-14), 1.73 (3H, s, H-15), 1.88 (1H, qq, J = 7.0; 7.0, H-11), 2.05 (3H, s, OAc), 2.20 (1H, d, J = 10.0, H-5), 5.40 (1H, br s, H-7), 5.57 (1H, m, H-9α), 5.87 (1H, d, J = 10; 3, H-6); Op-HOBz: 6.82 (2H, d, J = 8.5, H-3′, H-5′), 7.85 (2H, d, J = 8.5, H-2′, H-6′), [1]

¹³ C NMR [1]:

Table 1

C-1	42.1 s	C-9	72.0 d	C-1′	121.7 q
2	41.6 t	10	46.3 t	2′	131.9 d
3	31.5 t	11	36.7 d	3′	115.3 d
4	86.5 s	12	17.3 q	4′	161.0 q
5	54.6 d	13	18.2 q	5′	115.3 d
6	72.4 d	14	18.7 q	6′	131.9 d
7	127.7 d	15	23.5 q	C=O	166.4 s
8	135.6 s	OAc	170.2 s
			21.0 q