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Cycloprop-2-ene carboxylic acid
Cycloprop-2-ene carboxylic acid is a mycotoxin found in some mushrooms such as Russula subnigricans.
When ingested, the molecule is known to cause rhabdomyolysis.
In mice, the oral of this molecule is 2.5 mg/kg and poisoning is indicated by an increase in serum creatine phosphokinase activity. Polymerization via the ene reaction abolishes toxicity.
3-(Cycloprop-2-en-1-oyl)oxazolidinones are a class of ‘unusually stable’ derivatives of cycloprop-2-ene carboxylic acid that have been synthesized by Fox et al. As mentioned by Fox et al, this class of ‘unusually stable’ derivatives are dienophiles when involved in a Diels-Alder reaction.
References
References
- "NChemBio.179-comp1". National Center for Biotechnology Information.
- Yan, Ni. (2008-06-01). "Synthesis of Stable Derivatives of Cycloprop-2-ene Carboxylic Acid". The Journal of Organic Chemistry.
- (2009). "Identification of the toxic trigger in mushroom poisoning". Nature Chemical Biology.
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