Chemistry:Truxillic acid

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Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids with the formula (C6H5)2C4H4(COOH)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]

Cinnamic Acid CycloAddition

Occurrence and reactions

These compounds are found in a variety of plants, for example in coca.[2][3] 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.[4]

Isomers

Truxillic acid can exist in five isomers.[5][6]

Truxillic and truxinic acid stereo.svg
Truxillic acid isomers
Isomer a b c d e f
α-truxillic acid
(cocaic acid[7])
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
Truxillic acids.svg


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. 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. https://zenodo.org/record/1425537/files/article.pdf. 
  3. Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta poliniae Pharmaceutica-Drug research 59 (5): 403–410. 
  4. 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. 
  5. 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. 
  6. Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 8187224657. 
  7. "ChemSpider ID 10218892". ChemSpider. http://www.chemspider.com/Chemical-Structure.10218892.html. 


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