Truxinic acid
Names
IUPAC name
7,7′-Cyclolignane-9,9′-dioic acid
Systematic IUPAC name
3,4-Diphenylcyclohexane-1,2-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • c1ccc(cc1)C2C(C(C2C(=O)O)C(=O)O)c3ccccc3
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

Ten stereoisomers are possible.[4][5]

Truxinic acid isomers
Isomer a b c d e f
ω-truxinic acidC6H5HCOOHHCOOHH
β-truxinic acidC6H5HHCOOHHCOOH
neo-truxinic acidC6H5HCOOHHHCOOH
ζ-truxinic acidHC6H5COOHHCOOHH
μ-truxinic acidHC6H5HCOOHCOOHH
δ-truxinic acidHC6H5COOHHHCOOH

See also

References

  1. ↑ 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.
  2. ↑ Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta Poliniae Pharmaceutica-Drug Research. 59 (5): 403–410. PMID 12602803.
  3. ↑ Hein, Sara M. (2006). "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data". Journal of Chemical Education. 83 (6): 940–942. Bibcode:2006JChEd..83..940H. doi:10.1021/ed083p940.
  4. ↑ Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 978-81-87224-65-5.
  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.
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