Cycloprop-2-ene carboxylic acid

Cycloprop-2-ene carboxylic acid
Names
	Preferred IUPAC name Cycloprop-2-ene-1-carboxylic acid
Identifiers
CAS Number	26209-00-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1213481 ;
ChemSpider	21782462 ;
PubChem CID	25241629;
UNII	NN7WE4ADQ8 ;
	InChI InChI=1S/C4H4O2/c5-4(6)3-1-2-3/h1-3H,(H,5,6) Key: DBWAQSJZNKRLLE-UHFFFAOYSA-N ;
	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)
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).
	verify (what is ?)
	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 -1">50 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. https://pubchem.ncbi.nlm.nih.gov/compound/25241629.
↑ ^2.0 ^2.1 ^2.2 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. PMID 18452335.
↑ ^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.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Cycloprop-2-ene carboxylic acid. Read more

[1] "NChemBio.179-comp1". The PubChem Project. USA: National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/compound/25241629.

[Yan08-2] 2.0 ^2.1 ^2.2 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. PMID 18452335.

[mac-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.

[1]

[2]

[3]

Cycloprop-2-ene carboxylic acid

Topic: Chemistry

References