Truxinic acid

Truxinic acid
Names
	IUPAC name 3,4-Diphenyl-1,2-cyclobutanedicarboxylic acid
Identifiers
CAS Number	528-35-8;
3D model (JSmol)	Interactive image;
ChemSpider	233812;
PubChem CID	266036;
	SMILES c1ccc(cc1)C2C(C(C2C(=O)O)C(=O)O)c3ccccc3;
Properties
Chemical formula	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

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]

**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

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References

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.
Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta poliniae Pharmaceutica-Drug research. 59 (5): 403–410.
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.
Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 8187224657.
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)

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[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)

Truxinic acid

Isomers

See also

References