Truxillic acid

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
Truxillic acid
Names
IUPAC name
2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.478
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

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 acid isomers
Isomer a b c d e f
α-truxillic acid
(cocaic acid[8])
COOHHHC6H5HCOOH
γ-truxillic acidCOOHHHC6H5COOHH
ε-truxillic acidHCOOHC6H5HHCOOH
peri-truxillic acidCOOHHC6H5HCOOHH
epi-truxillic acidCOOHHC6H5HHCOOH


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.CS1 maint: uses authors parameter (link)
  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 (1888). "Cinnamic acid polymers obtained from the minor alkaloids of cocaine" (PDF). Berichte der Deutschen Chemischen Gesellschaft. 21: 3372–3376. doi:10.1002/cber.188802102223.
  4. Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta poliniae Pharmaceutica-Drug research. 59 (5): 403–410.
  5. 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.
  6. 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.
  7. Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 8187224657.
  8. "ChemSpider ID 10218892". ChemSpider. Retrieved 15 October 2016.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.