Cycloprop-2-ene carboxylic acid

Cycloprop-2-ene carboxylic acid is a mycotoxin found in some mushrooms such as Russula subnigricans.^[3]

Cycloprop-2-ene carboxylic acid

Skeletal formula of cycloprop-2-ene carboxylic acid
Names
Preferred IUPAC name Cycloprop-2-ene-1-carboxylic acid[1]
Identifiers
CAS Number	26209-00-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1213481 Y
ChemSpider	21782462 Y
PubChem CID	25241629
CompTox Dashboard (EPA)	DTXSID201028873
InChI InChI=1S/C4H4O2/c5-4(6)3-1-2-3/h1-3H,(H,5,6) Y Key: DBWAQSJZNKRLLE-UHFFFAOYSA-N Y
SMILES C1(C=C1)C(=O)O
Properties
Chemical formula	C4H4O2
Molar mass	84.074 g·mol−1
Melting point	40–41 °C (104–106 °F; 313–314 K)[2]
log P	−0.816
Acidity (pKa)	4.246
Basicity (pKb)	9.751
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

When ingested, the molecule is known to cause rhabdomyolysis.^[3]

In mice, the oral LD₅₀ 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]

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.^[2]