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protoanemonin
Sign in to saveAlso known as 5-methylene-2(5H)-furanone
Protoanemonin (sometimes called anemonol or ranunculol) is a toxin whose glycosidic precursor ranunculin is found in many plants of the buttercup family (Ranunculaceae). When the plant is wounded or macerated, ranunculin is enzymatically broken down into glucose and protoanemonin. This toxin's ability to inhibit both gram positive and gram negative bacteria is linked to the presence of a 5-membered lactone ring with a highly reactive double bond system.
Chemical data
- Formula
- C5H4O2
- Molecular weight
- 96.08 g/mol
- IUPAC name
- 5-methylidenefuran-2-one
- SMILES
- C=C1C=CC(=O)O1
- InChIKey
- RNYZJZKPGHQTJR-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 26.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
~3 min read
Encyclopedic overview
5 sectionsContents
- Biological pathway
- Toxicity
- Safety
- Synthesis
- References
Protoanemonin (sometimes called anemonol or ranunculol) is a toxin whose glycosidic precursor ranunculin is found in many plants of the buttercup family (Ranunculaceae). When the plant is wounded or macerated, ranunculin is enzymatically broken down into glucose and protoanemonin. This toxin's ability to inhibit both gram positive and gram negative bacteria is linked to the presence of a 5-membered lactone ring with a highly reactive double bond system.
==Biological pathway==
Excerpted from Wikipedia’s “protoanemonin” article, available under the CC BY-SA 4.0 licence.