Chlorotrianisene

• CAT Number: A000071
• CAS Number: 569-57-3
• Molecular Formula: C23H21ClO3
• Molecular Weight: 380.868
• Purity: ≥95%
• Synonyms: tri-p-anisylchloroethylene, tris(p-methoxyphenyl)chloroethylene, TACE, CTA
• Target: Immunology/Inflammation
• Solubility: >16.1mg/mL in DMSO
• Storage: Store at -20°C
• IUPAC Name: 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
• InChI: InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
• InChIKey: BFPSDSIWYFKGBC-UHFFFAOYSA-N
• SMILES: COC1=CC=C(C=C1)C(=C(C2=CC=C(C=C2)OC)Cl)C3=CC=C(C=C3)OC

Chlorotrianisene is a non-steroidal synthetic estrogen that was used for the treatment of menopause, deficiencies in ovary function, and prostate cancer.

Reference

1: Zhang J, Yang W, Shen Z. [Prevention of bone loss by chlorotrianisene in
oophorectomized rats]. Zhonghua Fu Chan Ke Za Zhi. 1997 Sep;32(9):535-7. Chinese.
PubMed PMID: 9639753.

2: Juedes MJ, Kupfer D. Role of P-450c in the formation of a reactive
intermediate of chlorotrianisene (TACE) by hepatic microsomes from
methylcholanthrene-treated rats. Drug Metab Dispos. 1990 Mar-Apr;18(2):131-7.
PubMed PMID: 1971562.

3: Kupfer D, Bulger WH. Inactivation of the uterine estrogen receptor binding of
estradiol during P-450 catalyzed metabolism of chlorotrianisene (TACE).
Speculation that TACE antiestrogenic activity involves covalent binding to the
estrogen receptor. FEBS Lett. 1990 Feb 12;261(1):59-62. PubMed PMID: 2307235.

4: Powers CA, Hatala MA, Pagano PJ. Differential responses of pituitary
kallikrein and prolactin to tamoxifen and chlorotrianisene. Mol Cell Endocrinol.
1989 Sep;66(1):93-100. PubMed PMID: 2583366.

5: Juedes MJ, Bulger WH, Kupfer D. Monooxygenase-mediated activation of
chlorotrianisene (TACE) in covalent binding to rat hepatic microsomal proteins.
Drug Metab Dispos. 1987 Nov-Dec;15(6):786-93. PubMed PMID: 2893703.

6: Vyshinskaia GV, Murav/’eva NI, Shelsputina ZF, Kuz/’mina ZV, Nikolaeva TG.
[Steroid hormone receptors and cellular proliferative activity following the
short-term use of tamoxifen and chlorotrianisene in breast cancer]. Eksp Onkol.
1985;7(5):66-8. Russian. PubMed PMID: 4065023.

7: Baba S, Janetschek G, Pollow K, Hahn K, Jacobi GH. The effects of
chlorotrianisene (Tace) of kinetics of 3H-testosterone metabolism in patients
with carcinoma of the prostate. Br J Urol. 1982 Aug;54(4):393-8. PubMed PMID:
6810984.

8: Ruenitz PC, Toledo MM. Chemical and biochemical characteristics of
O-demethylation of chlorotrianisene in the rat. Biochem Pharmacol. 1981 Aug
15;30(16):2203-7. PubMed PMID: 7295335.

9: Smith AG, Francis JE. Increased inhibition of hepatic uroporphyrinogen
decarboxylase by hexachlorobenzene in male rats given the oestrogenic drugs
diethylstilboestrol and chlorotrianisene. Biochem Pharmacol. 1981 Jul
1;30(13):1849-53. PubMed PMID: 7271874.

10: Barrabes A, Thanh Haï Duong, Combescot C, Lacroix R. [The influence of
synthetic oestrogens on experimental Schistosoma mansoni parasitosis in hamster:
studies of the effects of hexestrol and chlorotrianisene (author/’s transl)]. Ann
Pharm Fr. 1981 Jun;39(2):141-6. French. PubMed PMID: 6266329.