Cavicularin
Sign in to saveCavicularin is a natural phenolic secondary metabolite isolated from the liverwort Cavicularia densa. This macrocycle is unusual because it was the first compound isolated from nature displaying optical activity solely due to the presence of planar chirality and axial chirality. The specific rotation for (+)-cavicularin is +168.2°. It is also a very strained molecule. The para-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat boat-like geometry. This type of angle strain in aromatic compounds is normally reserved for synthetic cyclophanes.
Wikidata facts
- Mass
- 422.151809184
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- canonical SMILES
- c1cc2ccc1CCc3cc(ccc3-c4c(ccc5c4-c6cc(c(cc6CC5)O)O2)O)O
- chemical formula
- C₂₈H₂₂O₄
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Article
2 sectionsContents
- Total synthesis
- References
Cavicularin is a natural phenolic secondary metabolite isolated from the liverwort Cavicularia densa. This macrocycle is unusual because it was the first compound isolated from nature displaying optical activity solely due to the presence of planar chirality and axial chirality. The specific rotation for (+)-cavicularin is +168.2°. It is also a very strained molecule. The para-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat boat-like geometry. This type of angle strain in aromatic compounds is normally reserved for synthetic cyclophanes.
thumb|none|227px|Cavicularin, three-dimensional representation