Truxinic acids are any of several stereoisomeric cyclic dicarboxylic acids with the formula (C6H5)2C4H4(COOH)2, found in various plants.[1][2] They are obtained by a photochemical cycloaddition from cinnamic acid,[3] where the two trans alkenes react head-to-head.
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| Names | |
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| IUPAC name
7,7′-Cyclolignane-9,9′-dioic acid
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| Systematic IUPAC name
3,4-Diphenylcyclohexane-1,2-dicarboxylic acid | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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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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Isomers
editTen stereoisomers are possible.[4][5]
| Isomer | a | b | c | d | e | f |
|---|---|---|---|---|---|---|
| ω-truxinic acid | C6H5 | H | COOH | H | COOH | H |
| β-truxinic acid | C6H5 | H | H | COOH | H | COOH |
| neo-truxinic acid | C6H5 | H | COOH | H | H | COOH |
| ζ-truxinic acid | H | C6H5 | COOH | H | COOH | H |
| μ-truxinic acid | H | C6H5 | H | COOH | COOH | H |
| δ-truxinic acid | H | C6H5 | COOH | H | H | COOH |
See also
edit- Truxillic acids, which are isomers of the truxinic acids
References
edit- ^ Liebermann (1888). "Cinnamic acid polymers obtained from the minor alkaloids of cocaine". Berichte der Deutschen Chemischen Gesellschaft. 21: 3372–3376. doi:10.1002/cber.188802102223.
- ^ Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta Poliniae Pharmaceutica-Drug Research. 59 (5): 403–410. PMID 12602803.
- ^ Hein, Sara M. (2006). "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data". Journal of Chemical Education. 83 (6): 940–942. Bibcode:2006JChEd..83..940H. doi:10.1021/ed083p940.
- ^ Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 978-81-87224-65-5.
- ^ M. Freedmana; Y. Mohadgera; J. Rennerta; S. Solowaya; I. Waltchera (1969). "β- and δ-truxinic acids". Organic Preparations and Procedures. 1 (4): 267–269. doi:10.1080/00304946909458397.