Truxinic acid

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Truxinic acid
Truxinic acid skeletal.svg
Names
IUPAC name
3,4-Diphenyl-1,2-cyclobutanedicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
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

Truxinic acids are any of several stereoisomeric cyclic dicarboxylic acids with the formula (C6H5)2C4H4(COOH)2, found in various plants.[1][2] They are obtained by a photochemical cycloaddition from cinnamic acid,[3] where the two trans alkenes react head-to-head.

Isomers[edit]

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 ten possibilities, of which six have been described in literature:[4][5]

Truxillic and truxinic acid stereo.svg
Truxinic acid isomers
Isomer a b c d e f
ω-truxinic acid C6H5 H COOH H COOH H
β-truxinic acid C6H5 H H COOH H COOH
neo-truxinic acid C6H5 H COOH H H COOH
ζ-truxinic acid H C6H5 COOH H COOH H
μ-truxinic acid H C6H5 H COOH COOH H
δ-truxinic acid H C6H5 COOH H H COOH

See also[edit]

References[edit]

  1. ^ 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.
  2. ^ Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta poliniae Pharmaceutica-Drug research. 59 (5): 403–410.
  3. ^ 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.
  4. ^ Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 8187224657.
  5. ^ M. Freedmana, Y. Mohadgera, J. Rennerta, S. Solowaya, I. Waltchera (1969). "β- and δ-truxinic acids". Organic Preparations and Procedures. 1 (4): 267–269. doi:10.1080/00304946909458397.CS1 maint: uses authors parameter (link)