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

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

Tracking categories (test):

* SizeSet

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

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

In mice, the oral -1">50 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]

## References

1. ↑ "NChemBio.179-comp1". The PubChem Project. USA: National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=25241629.
2. ↑ 2.0 2.1 Yan, Ni; Liu, Xiaozhong; Pallerla, Mahesh K.; Fox, Joseph M. (2008-06-01). "Synthesis of Stable Derivatives of Cycloprop-2-ene Carboxylic Acid". The Journal of Organic Chemistry 73 (11): 4283–4286. doi:10.1021/jo800042w. ISSN 0022-3263. PMID 18452335.
3. ↑ 3.0 3.1 3.2 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.

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*[CID]: Compound ID