Cycloprop-2-ene carboxylic acid

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Cycloprop-2-ene carboxylic acid
Skeletal formula of cycloprop-2-ene carboxylic acid Cycloprop-2-ene carboxylic acid (SVG).svg
Skeletal formula of cycloprop-2-ene carboxylic acid
Names
Preferred IUPAC name
Cycloprop-2-ene-1-carboxylic acid [1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C4H4O2/c5-4(6)3-1-2-3/h1-3H,(H,5,6) Yes check.svgY
    Key: DBWAQSJZNKRLLE-UHFFFAOYSA-N Yes check.svgY
  • C1(C=C1)C(=O)O
Properties
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).
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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 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 etal, 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.
  2. 1 2 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. PMC   3132478 . PMID   18452335.
  3. 1 2 3 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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