Truxinic acid

Truxinic acid
Names
	IUPAC name 7,7′-Cyclolignane-9,9′-dioic acid
	Systematic IUPAC name 3,4-Diphenylcyclohexane-1,2-dicarboxylic acid
Identifiers
CAS Number	528-35-8; β: 528-34-7;
3D model (JSmol)	Interactive image; μ: Interactive image;
ChemSpider	233812; β: 8119639; μ: 103883278;
PubChem CID	266036;
CompTox Dashboard (EPA)	DTXSID60963283 ;
	InChI InChI=1S/C18H16O4/c19-17(20)15-13(11-7-3-1-4-8-11)14(16(15)18(21)22)12-9-5-2-6-10-12/h1-10,13-16H,(H,19,20)(H,21,22) Key: QVNDSQQNODQYJM-UHFFFAOYSA-N; μ: InChI=1S/C18H16O4/c19-17(20)15-13(11-7-3-1-4-8-11)14(16(15)18(21)22)12-9-5-2-6-10-12/h1-10,13-16H,(H,19,20)(H,21,22)/t13-,14-,15-,16-/m0/s1 Key: QVNDSQQNODQYJM-VGWMRTNUSA-N;
	SMILES c1ccc(cc1)C2C(C(C2C(=O)O)C(=O)O)c3ccccc3; μ: O=C(O)[C@@H]1[C@@H](C(=O)O)[C@@H](c2ccccc2)[C@@H]1c1ccccc1;
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

Ten stereoisomers are possible.^[4]^[5] Of these, the ω and β isomers are meso compounds, while the others form pairs of enantiomers.

**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

↑ 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.
↑ Krauze-Baranowska, Miroslawa (2002). "Truxillic and truxinic acids-occurrence in plant kingdom". Acta Poliniae Pharmaceutica-Drug Research. 59 (5): 403–410. PMID 12602803.
↑ Hein, Sara M. (2006). "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data". Journal of Chemical Education. 83 (6): 940–942. Bibcode:2006JChEd..83..940H. doi:10.1021/ed083p940.
↑ Agarwai, O. P. (2011). Organic Chemistry Reactions and Reagents. Krishna Prakashan Media. ISBN 978-81-87224-65-5.
↑ 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.