Desmethylchlorotrianisene

{{short description|Chemical compound}}

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| IUPAC_name = (EZ)-4-[2-Chloro-1,2-bis(4-hydroxyphenyl)ethenyl]phenol

| image = Desmethylchlorotrianisene.svg

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| class = Nonsteroidal estrogen

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| CAS_number = 80525-45-7

| CAS_supplemental = (E)-isomer: 80525-45-7
(Z)-isomer: 80525-44-6

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| PubChem = 53325692

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| ChemSpiderID = 25047392

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| synonyms = DMCTA

| C=20 | H=15 | Cl=1 | O=3

| SMILES = OC1=CC=C(/C(C2=CC=C(OC)C=C2)=C(Cl)/C3=CC=C(OC)C=C3)C=C1

| StdInChI_Ref =

| StdInChI = 1S/C20H15ClO3/c21-20(15-5-11-18(24)12-6-15)19(13-1-7-16(22)8-2-13)14-3-9-17(23)10-4-14/h1-12,22-24H

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| StdInChIKey = XQRLRQNJWROVPF-UHFFFAOYSA-N

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Desmethylchlorotrianisene (DMCTA) is a nonsteroidal estrogen which is thought to be the major active metabolite of chlorotrianisene (CTA; TACE).{{Cite journal |vauthors=Ruenitz PC, Toledo MM |date=August 1981 |title=Chemical and biochemical characteristics of O-demethylation of chlorotrianisene in the rat |journal=Biochem. Pharmacol. |volume=30 |issue=16 |pages=2203–7 |doi=10.1016/0006-2952(81)90088-5 |pmid=7295335}}{{Cite book |last=Virgil Craig Jordan |url=https://books.google.com/books?id=7WmLZfGXST0C&pg=PA212 |title=Estrogen/antiestrogen Action and Breast Cancer Therapy |publisher=Univ of Wisconsin Press |year=1986 |isbn=978-0-299-10480-1 |page=212}} It is a 1:1 mixture of cis and trans isomers. DMCTA is produced from CTA via mono-O-demethylation catalyzed by cytochrome P450 enzymes in the liver. CTA is thought to act as a long-lasting prodrug of DMCTA.