Truxillic acid

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Truxillic acid
Truxillic acid.svg
Identifiers
CAS number 4462-95-7
Jmol-3D images Image 1
Properties
Molecular formula C18H16O4
Molar mass 296.32 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids (C6H5)2C4H4(COOH)2 that yield cinnamic acid on distillation.[1] The two trans alkenes react head-to-tail, and the isolated isomers are called truxillic acids. This products are made by a photochemical cycloaddition:

Cinnamic Acid CycloAddition

These compounds can be obtained in a variety of plants.[2][3]

Truxillic acid isomers[edit]

The big symmetry of these compounds makes only possible to have 5 possible stereoisomers in nature:[4][5]

DERIVADOS DE ACIDO TRUXILICO Y TRUXINICO.JPG
Truxillic acid isomers
Isomer a b c d e f
α-truxillic acid 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

In the next picture is shown the complete structure of these truxillic acids:

Truxillic acids.svg

References[edit]

  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. 
  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.