<Suppliers Price>

Chlorotrianisene

Names

[ CAS No. ]:
569-57-3

[ Name ]:
Chlorotrianisene

[Synonym ]:
1-chloro-1,2,2-tris(p-methoxyphenyl)ethene
TACE
1,1',1''-(1-chloro-1-ethenyl-2-ylidene)tris[4-methoxy-benzene]
Chlortrianisestrol
Merbentul
Chlorestrolo
Chlorotrianisene
Tris-(4-methoxy-phenyl)-vinylchlorid
chloro-tris-(4-methoxy-phenyl)-ethene
Chlorotrianizen
Chlor-tris-(4-methoxy-phenyl)-aethen
Chlortrianisen
Chloortrianisestrol
1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
Chlorotrianisine
Chlortrianizen
2-Chlor-1,1,2-tris-(4-methoxy-phenyl)-aethylen

Biological Activity

[Description]:

Chlorotrianisene is a long-acting non-steroidal estrogen and an orally active estrogen receptor modulator. Chlorotrianisene exhibits antiestrogenic activity. Chlorotrianisene potently inhibits the enzyme COX-1 and inhibits platelet aggregation in whole blood[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR
Research Areas >> Cardiovascular Disease
Research Areas >> Endocrinology
Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

Estrogen receptor[1] COX-1[2]


[In Vitro]

Comparison of intracellular estrogen receptor (ER) affinities of Chlorotrianisene with respective rat uterine cytosolic ER affinities has initially suggested the potential for activation of ER as a mechanism of growth stimulation. Chlorotrianisene exhibits concentration dependent cell growth stimulation with an EC50 of 28 nM and a Ki of 500 nM in MCF-7 cells[1].

[In Vivo]

The incubation of Chlorotrianisene with rat liver microsomes and NADPH generates a reactive intermediate which binds covalently to proteins. Intermediate may inactivate the uterine estrogen receptors (ER). The incubation of Chlorotrianisene with rat liver microsomes and NADPH in the presence of rat uteri, under conditions which generate intermediate, markedly decreased the binding capacity of the ER for [3H]estradiol (E2)[3].

[References]

[1]. Ruenitz PC, et al. Estrogenic tamoxifen derivatives: categorization of intrinsic estrogenicity in MCF-7 cells. J Steroid Biochem Mol Biol. 1997 Nov-Dec;63(4-6):203-9.

[2]. Lounkine E, et al. Large-scale prediction and testing of drug activity on side-effect targets. Nature. 2012 Jun 10;486(7403):361-7.

[3]. Kupfer D, et al. 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.

Chemical & Physical Properties

[ Density]:
1.168g/cm3

[ Boiling Point ]:
514.2ºC at 760mmHg

[ Melting Point ]:
114-116ºC

[ Molecular Formula ]:
C23H21ClO3

[ Molecular Weight ]:
380.86400

[ Flash Point ]:
164.1ºC

[ Exact Mass ]:
380.11800

[ PSA ]:
27.69000

[ LogP ]:
5.86780

[ Index of Refraction ]:
1.591

[ Storage condition ]:
-70°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KV0600000
CHEMICAL NAME :
Ethylene, chlorotris(p-methoxyphenyl)-
CAS REGISTRY NUMBER :
569-57-3
BEILSTEIN REFERENCE NO. :
1891845
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C23-H21-Cl-O3
MOLECULAR WEIGHT :
380.89
WISWESSER LINE NOTATION :
1OR DYGUYR DO1&R DO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
37 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors Behavioral - changes in motor activity (specific assay)
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 11,489,1967
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg/89W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - tumors Reproductive - Tumorigenic effects - testicular tumors
REFERENCE :
AMPLAO AMA Archives of Pathology. (Chicago, IL) V.50(4)-69, 1950-60. For publisher information, see APLMAS. Volume(issue)/page/year: 50,750,1950 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
48 mg/kg
SEX/DURATION :
female 14 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
OBGNAS Obstetrics and Gynecology. (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.1- 1953- Volume(issue)/page/year: 8,399,1956 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,139,1979 TOXICOLOGY REVIEW ACRSAJ Advances in Cancer Research. (Academic Press, Inc., 465 S. Lincoln Dr., Troy, MO 63379) V.1- 1953- Volume(issue)/page/year: 1,173,1953 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84523 No. of Facilities: 14 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1134 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84523 No. of Facilities: 18 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 229 (estimated) No. of Female Employees: 114 (estimated)

Safety Information

[ WGK Germany ]:
3

[ RTECS ]:
KV0600000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds