6β-Acetoxy-7α(H)-eudesmane-1β,4β-diol

Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Eudesmanes (Selinanes) Eudesmanes – Monoesters

Biological sources: Sideritis varoi subsp. varoi, S. varoi subsp. cuatrecasasii [1]; S. varoi subsp. oriensis [2]; S. varoi subsp. nijarensis [3]

C₁₇H₃₀O₄: 298.2144

Mp: colorless gum [1]

[α] ²⁰_D +27.1° (c 1, CHCl₃) [1]

IR (neat): 3450, 1730, 1250 [1]

Found: C, 72.91; H, 10.12; calc. for C₁₇H₂₈O₃: C, 72.82; H, 10.05% [1]

MS: 280 [M − H₂O]⁺ (0.8), 255 (0.8), 238 (5), 220 (100), 202 (34), 192 (6), 187 (25), 177 (61), 159 (80), 145 (32), 133 (54), 129 (38), 105 (45) [1]

¹ H NMR (60 MHz, CDCl₃, TMS): 0.92 (6H, d, J = 6, H-12, H-13), 1.28 (3H, s, H-15), 1.38 (3H, s, H-14), 2.08 (3H, s, OAc), 3.18 (1H, dd, J = 11; 4, H-1), 5.70 (1H, br s, H-6) [1]

¹³ C NMR (20.13 MHz, CDCl₃) [1, 2]:

Table 1

C-1	80.34	C-7	49.57	C-13	20.85
2	28.82	8	21.19	14	13.51
3	40.78	9	39.55	15	20.51
4	71.70	10	39.42	OAc
5	52.98	11	29.65	1′	171.34
6	70.43	12	21.63...