Truxinic acid explained

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! width="140 px" style="background:Lavender; color:Black"

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

See also

• Truxillic acids, which are isomers of the truxinic acids

Notes and References

1. Liebermann. Cinnamic acid polymers obtained from the minor alkaloids of cocaine. Berichte der Deutschen Chemischen Gesellschaft. 1888. 21. 10.1002/cber.188802102223. 3372–3376.
2. Krauze-Baranowska. Miroslawa. Truxillic and truxinic acids-occurrence in plant kingdom. Acta Poliniae Pharmaceutica-Drug Research. 2002. 59. 5. 403–410. 12602803 .
3. Hein, Sara M. . An Exploration of a Photochemical Pericyclic Reaction Using NMR Data . Journal of Chemical Education . 83 . 940–942 . 2006 . 6 . 10.1021/ed083p940. 2006JChEd..83..940H .
4. Book: Agarwai, O. P.. Organic Chemistry Reactions and Reagents. 2011. Krishna Prakashan Media. 978-81-87224-65-5.
5. M. Freedmana . Y. Mohadgera . J. Rennerta . S. Solowaya . I. Waltchera . β- and δ-truxinic acids. Organic Preparations and Procedures. 1969. 1. 4. 267–269. 10.1080/00304946909458397.