Search

AROMATICINE (SYSTEMATIC NAME: 4a,8-dimethyl-3-methyl-ene-3,3a,4,4a,7a,8,9,9a-octa-hydro-azuleno[6,5-b]furan-2,5-dione), C(15)H(18)O(3), is a natural lactone isolated from Amblyopappus pusillus. The mol-ecular structure and conformation agree with the results of Romo, Joseph-Nathan & Díaz [(1964 ▶). Tetra-hedron, 20, 79-85]. The fused-ring system contains a seven-membered ring in a twist-boat conformation and two five-membered rings trans fused in envelope conformations.

The mol-ecular conformation of the title compound, C(10)H(8)O(4), isolated from Laretia acualis, is stabilized by a strong intra-molecular hydrogen bond between the hydroxyl and carbonyl groups. The crystal packing shows π-π stacking inter-actions. The chromene (4H-1-benzopyran-4-one) unit is essentially planar.