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Chemical compound From Wikipedia, the free encyclopedia
Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids with the formula (C6H5C2H2(CO2H)2. They are colorless solids. These compounds are obtained by the [2 + 2] photocycloadditions of cinnamic acid where the two trans alkenes react head-to-tail. The isolated stereoisomers are called truxillic acids.[1] The preparation of truxillic acids provided an early example of organic photochemistry.[2]
Names | |
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IUPAC name
7,8′-Cyclo-8,7′-neolignane-9,9′-dioic acid | |
Systematic IUPAC name
2,4-Diphenylcyclobutane-1,3-dicarboxylic acid | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.022.478 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C18H16O4 | |
Molar mass | 296.322 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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These compounds are found in a variety of plants, for example in coca.[3][4] Incarvillateine, an alkaloid from the plant Incarvillea sinensis, is a derivative of α-truxillic acid.
Upon heating, truxillic acids undergo cracking to give cinnamic acid.[5]
Truxillic acid can exist in five stereoisomers.[6][7]
Isomer | a | b | c | d | e | f |
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α-truxillic acid (cocaic acid[8]) | COOH | H | H | C6H5 | H | COOH |
γ-truxillic acid | COOH | H | H | C6H5 | COOH | H |
ε-truxillic acid | H | COOH | C6H5 | H | H | COOH |
peri-truxillic acid | COOH | H | C6H5 | H | COOH | H |
epi-truxillic acid | COOH | H | C6H5 | H | H | COOH |
Below are the five stereoisomers of truxillic acid, called alpha, gamma, epsilon, peri, and epi. These are shown both in a 2D skeletal diagram with stereocenters indicated and a 3D rendering of the structural geometry of the isomers themselves.
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