Propane-1,2,3-tricarboxylic acid
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| Propane-1,2,3-tricarboxylic acid | |
|---|---|
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| IUPAC name | Propane-1,2,3-tricarboxylic acid |
| Other names | Tricarballylic acid, carballylic acid, 1,2,3-propanetricarboxylic acid, beta-carboxyglutaric acid |
| Identifiers | |
| CAS number | [99-14-9] |
| PubChem | |
| SMILES | C(C(CC(=O)O)C(=O)O)C(=O)O |
| Properties | |
| Molecular formula | C6H8O6 |
| Molar mass | 176.12 g/mol |
| Appearance | colourless solid |
| Melting point |
156-161 |
| Solubility in water | sl. in water |
| Related compounds | |
| Related compounds | citric acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. The compound is an inhibitor of the enzyme aconitase and interferes with the Krebs cycle.[1]
Esters of propane-1,2,3-tricarboxylic acid are found in natural products such as the mycotoxins fumonisin B1 and B2 and AAL toxin TA and in macrocyclic inhibitors of Ras farnesyl-protein transferase (FPTase) like actinoplanic acid.
It can be synthesized in two steps from fumaric acid.[2]
[edit] References
- ^ Russell, J. B., and N. Forsberg. 1986. Production of tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism. British Journal of Nutrition (1986), 56:153-162 56:153-162. doi:10.1079/BJN19860095
- ^ H. T. Clarke and T. F. Murray (1941). "Tricarballylic Acid". Org. Synth.; Coll. Vol. 1: 523.
