Chemistry:Truxillic acid

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Truxillic acid
Truxillic acid.svg
Names
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)
ChemSpider
UNII
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).
Infobox references
Tracking categories (test):

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]

Cinnamic Acid CycloAddition

Occurrence and reactions

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]

Isomers

Truxillic acid can exist in five stereoisomers.[6][7]

Truxillic and truxinic acid stereo.svg
Truxillic acid isomers
Isomer a b c d e f
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.

See also

  • Truxinic acids are isomers of the truxillic acids with phenyl groups on adjacent methyne centers.

References

  1. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. (1964). "Topochemistry. II. The photochemistry of trans-cinnamic acids". J. Chem. Soc.: 2000–2013. doi:10.1039/jr9640002000. 
  2. Roth, Heinz D. (1989). "The Beginnings of Organic Photochemistry". Angewandte Chemie International Edition in English 28 (9): 1193–1207. doi:10.1002/anie.198911931. 
  3. Liebermann, C. (1888). "Ueber Cinnamylcocaïn". Berichte der Deutschen Chemischen Gesellschaft 21 (2): 3372–3376. doi:10.1002/cber.188802102223. https://zenodo.org/record/1425537. 
  4. Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta Poliniae Pharmaceutica-Drug Research 59 (5): 403–410. PMID 12602803. 
  5. Hein, Sara M. (2006). "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data". Journal of Chemical Education 83 (6): 940–942. doi:10.1021/ed083p940. Bibcode2006JChEd..83..940H. 
  6. Stoermer, R.; Bachér, F. (1924). "Zur Stereoisomerie der Truxillsäuren und über die Auffindung der letzten Säure dieser Gruppe (VIII.)". Berichte der Deutschen Chemischen Gesellschaft (A and B Series) 57: 15–23. doi:10.1002/cber.19240570105. 
  7. Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 978-8187224655. 
  8. "ChemSpider ID 10218892". ChemSpider. http://www.chemspider.com/Chemical-Structure.10218892.html.