Desoxyhemigossypol 6-methyl ether

The title sesquiterpene [systematic name: 6-methoxy-10-methyl-7-(propan-2-yl)-2-oxatricyclo[6.3.1.0(4,12)]dodeca-1(11),4,6,8(12),9-pentaen-5-ol], C(16)H(18)O(3), was isolated from pathogen-infected stele tissue of Gossypium barbadense. There are two mol­ecules in the asymmetric unit and the dihedral angle between their naphtho­furan systems is 86.48 (2)°. In the crystal, O—H⋯O hydrogen bonds between the hy­droxy groups and etheric O atoms link the mol­ecules into centrosymmetric tetra­mers. These tetra­mers are assembled into (010) layers via stacking inter­actions between the naphtho­furan systems [inter­planar distance 3.473 (3) Å] and short C—H⋯O contacts.