Truxillic acid
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| Truxillic acid | ||
|---|---|---|
 | ||
| IUPAC name 2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid | ||
| Identifiers | ||
| CAS number | 4462-95-7 | |
| Jmol-3D images | Image 1 | |
| ||
| Properties | ||
| Molecular formula | C18H16O4 | |
| Molar mass | 296.32 g mol−1 | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids (C6H5)2C4H4(COOH)2 that yield cinnamic acid on distillation.[1] The two trans alkenes react head-to-tail, and the isolated isomers are called truxillic acids. This products are made by a photochemical cycloaddition:
These compounds can be obtained in a variety of plants.[2][3]
Truxillic acid isomers
The big symmetry of these compounds makes only possible to have 5 possible stereoisomers in nature:[4][5]
| Isomer | a | b | c | d | e | f |
|---|---|---|---|---|---|---|
| α-truxillic acid | 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 |
In the next picture is shown the complete structure of these truxillic acids:
References
- ↑ Hein, Sara M. (2006). "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data". Journal of Chemical Education 83: 940–942. doi:10.1021/ed083p940.
- ↑ Liebermann (1888). "Cinnamic acid polymers obtained from the minor alkaloids of cocaine". Berichte der Deutschen Chemischen Gesellschaft 21.
- ↑ Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta poliniae Pharmaceutica-Drug research 59 (5): 403–410.
- ↑ Stoermer (1924). "Five stereoisomers have been obtained: alfa-, gamma-, epsilon-, peri- and epi-isomers. Stereochemical configurations". Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen 57B: 15–23.
- ↑ Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 8187224657.
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