Truxillic acid

Truxillic acid

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
SMILES OC(C1C(C2=CC=CC=C2)C(C(O)=O)C1C3=CC=CC=C3)=O
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]

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 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

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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