Truxillic acid

Truxillic acid

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Names
IUPAC name 2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid
Identifiers
CAS Number	4462-95-7
Jmol 3D model	Interactive image
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
Vapor pressure	{{{value}}}
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 (C₆H₅)₂C₄H₄(COOH)₂ that yield cinnamic acid on distillation. The two trans alkenes react head-to-tail, and the isolated isomers are called truxillic acids. This products are made by a photochemical cycloaddition:

These compounds can be obtained in a variety of plants.

Truxillic acid isomers

The symmetry of these compounds makes only possible to have 5 possible stereoisomers in nature:

Truxillic acid isomers

Isomer	a	b	c	d	e	f
α-truxillic acid	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

In the next picture is shown the complete structure of these truxillic acids:

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