Cycloprop-2-ene carboxylic acid
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| Names | |
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| Preferred IUPAC name
Cycloprop-2-ene-1-carboxylic acid[1] | |
| Identifiers | |
3D model (JSmol) |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
Infobox references | |
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 dose-dependent rhabdomyolysis.[3]
In mice, the oral LD50 of this molecule is 2.5 mg/kg and poisoning is indicated by an increase in blood creatine phosphokinase levels.
Polymerization via the ene reaction abolishes toxicity.[3]
3-(Cycloprop-2-en-1-oyl)oxazolidinones are a class of ‘unusually stable’ derivatives of the mycotoxin 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]
The pure substance is a hydroscopic white solid that is able to decarboxylate exothermically.[2]
References
- ↑ "NChemBio.179-comp1". The PubChem Project. USA: National Center for Biotechnology Information.
- 1 2 3 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.
- 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.