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Truxillic acid

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Truxillic acid
Names
IUPAC name
2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid
Identifiers
3D model (JSmol)
ECHA InfoCard 100.022.478 Edit this at Wikidata
  • OC(C1C(C2=CC=CC=C2)C(C(O)=O)C1C3=CC=CC=C3)=O
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).

Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids with the formula (C6H5)2C4H4(COOH)2 that yield cinnamic acid on distillation.[1] They are obtained by a photochemical cycloaddition from cinnamic acid, where the two trans alkenes react head-to-tail. The isolated stereoisomers are called truxillic acids.

Cinnamic Acid CycloAddition
Cinnamic Acid CycloAddition

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

Isomers

These compounds have four chiral carbon atoms, which looks like there should be 16 (24) stereoisomers. However, the symmetry of the molecule allows for only five possibilities:[4][5]

Truxillic acid isomers
Isomer a b c d e f
α-truxillic acid
(cocaic acid[6])		 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

Derivatives

Incarvillateine, an alkaloid from the plant Incarvillea sinensis, is a derivative of α-truxillic acid.

See also

References

  1. ^ 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.
  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.
  3. ^ Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta poliniae Pharmaceutica-Drug research. 59 (5): 403–410.
  4. ^ 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.
  5. ^ Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 8187224657.
  6. ^ "ChemSpider ID 10218892". ChemSpider. Retrieved 15 October 2016.
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