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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.
Chemical data
- Formula
- C28H22O4
- Molecular weight
- 422.5 g/mol
- IUPAC name
- 14-oxahexacyclo[13.9.3.210,13.02,7.019,27.022,26]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,24-triol
- SMILES
- C1CC2=C(C=CC(=C2)O)C3=C(C=C4CCC5=C(C4=C3)C(=C(C=C5)O)OC6=CC=C1C=C6)O
- InChIKey
- MCFLLKAHGNIXPF-UHFFFAOYSA-N
- XLogP
- 6.2
- Polar surface area
- 69.9 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 422.151809184
Show 3 more facts
- found in taxon
- Cavicularia densa
- canonical SMILES
- c1cc2ccc1CCc3cc(ccc3-c4c(ccc5c4-c6cc(c(cc6CC5)O)O2)O)O
- chemical formula
- C₂₈H₂₂O₄
Sources (2)
via Wikidata · CC0
~1 min read
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.