Cycloprop-2-ene carboxylic acid

Cycloprop-2-ene carboxylic acid

Systematic name Cycloprop-2-ene-1-carboxylic acid^[1]
Identifiers
PubChem	25241629
ChemSpider	21782462^Y
ChEMBL	CHEMBL1213481^Y
Jmol-3D images	Image 1 Image 2
SMILES OC(=O)C1C=C1 C1=CC1C(=O)O
InChI InChI=1S/C4H4O2/c5-4(6)3-1-2-3/h1-3H,(H,5,6)^Y Key: DBWAQSJZNKRLLE-UHFFFAOYSA-N^Y InChI=1/C4H4O2/c5-4(6)3-1-2-3/h1-3H,(H,5,6) Key: DBWAQSJZNKRLLE-UHFFFAOYAV
Properties
Molecular formula	C₄H₄O₂
Molar mass	84.07 g mol⁻¹
Exact mass	84.021129372 g mol^-1
log P	-0.816
Acidity (pK_a)	4.246
Basicity (pK_b)	9.751
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cycloprop-2-ene carboxylic acid is a toxic molecule found in some mushrooms such as Russula subnigricans and Tricholoma equestre.^[2]

When ingested, the molecule is known to cause rhabdomyolysis.^[2]

In mice, by oral injection, the molecule is lethal at 2.5 mg/kg of body mass and poisoning is indicated by an increase in serum creatine phosphokinase activity. Polymerization at high concentrations via ene reaction abolishes toxicity.^[2]

References

^ "NChemBio.179-comp1". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=25241629.
^ ^a ^b ^c Matsuura, Masanori; Saikawa, Yoko; Inui, Kosei; Nakae, Koichi; Igarashi, Masayuki; Hashimoto, Kimiko; Nakata, Masaya (2009). "Identification of the toxic trigger in mushroom poisoning". Nature Chemical Biology 5 (7): 465–7. doi:10.1038/nchembio.179. PMID 19465932.