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.
In the Vinony graph
Within Vinony's link graph, Cavicularin is referenced by 28 other articles, and connects out to Shikoku, digital object identifier and chemical formula.
It is catalogued under topics including Chembox image size set, Cyclophanes and Dihydrostilbenoids.
Its subject is documented across 5 Wikipedia language editions.
Wikidata facts
- Mass
- 422.151809184
Show 2 more facts
- canonical SMILES
- c1cc2ccc1CCc3cc(ccc3-c4c(ccc5c4-c6cc(c(cc6CC5)O)O2)O)O
- chemical formula
- C₂₈H₂₂O₄
Sources (2)
via Wikidata · CC0
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Encyclopedic overview
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
Excerpted from Wikipedia’s “Cavicularin” article, available under the CC BY-SA 4.0 licence.