Truxillic acid
















































Truxillic acid

Truxillic acid.svg
Names

IUPAC name
2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid

Identifiers

CAS Number
  • 4462-95-7

3D model (JSmol)
  • Interactive image

ChemSpider
  • 70589

ECHA InfoCard
100.022.478


PubChem CID
  • 78213


Properties

Chemical formula
C18H16O4

Molar mass
 296.32 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

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



Contents






  • 1 Occurrence and reactions


  • 2 Isomers


  • 3 See also


  • 4 References





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.CS1 maint: Uses authors parameter (link) .mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  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. ^ 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. Retrieved 15 October 2016.









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