569-57-3 Usage
Originator
TACE,Merrell ,US ,1952
Manufacturing Process
The following method is described in US Patent 2,430,891. To a solution of 10
parts of tris-p-methoxyphenyl ethylene in 35 to 40 parts of carbon
tetrachloride is added a solution of 2.0 parts of chlorine in 50 parts of carbon
tetrachloride, with stirring, and over a period of ? hour. The carbon
tetrachloride is then removed by distillation on a steam bath and the residual
oil is recrystallized from 250 to 400 parts of methanol, decolorizing with
charcoal or the like if necessary. Tris-p-methoxyphenyl chloroethylene is
obtained in a yield of 65 to 75%. It melts at 113° to 114°C.
Therapeutic Function
Estrogen
Reactivity Profile
CHLOROTRIANISENE may react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with both acids and bases. Various catalysts (such as acids) or initiators can cause very exothermic addition polymerization reactions.
Fire Hazard
Flash point data for CHLOROTRIANISENE are not available. CHLOROTRIANISENE is probably combustible.
Biological Activity
ed50: 2.0 μmglandular kallikrein, a trypsin-like serine protease, has been identified as a major estrogen-induced protein in the rat anterior pituitary. this induction appears to be mediated by increased gene expression since glandular kallikrein mrna is also estrogen-induced. chlorotrianisene is classified as an estrogen agonist.
in vitro
the ed50 of chlorotrianisene were lowered by 3.9-fold. chlorotrianisene inhibited the growth of both p388 and p388/adr cells in a concentration-dependent manner [1].
in vivo
chlorotrianisene markedly varied in its ability to elicit agonist responses on the three measures. on uterine weight and anterior pituitary prolactin, chlorotrianisene behaved as partial agonists. chlorotrianisene also exhibited strikingly less agonist activity on glandular kallikrein than on prl or the uterus. further, the small agonist activity of chlorotrianisene on glandular kallikrein induction differed from that on the uterus or prolactin [2].
references
[1] ramu a, glaubiger d, fuks z. reversal of acquired resistance to doxorubicin in p388 murine leukemia cells by tamoxifen and other triparanol analogues. cancer res. 1984 oct;44(10):4392-5.[2] 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.[3] nulsen ro, carmon wb, hendrick ho. tace (chlorotrianisene), a new estrogen for inhibition of lactation. am j obstet gynecol. 1953 may;65(5):1048-51.
Check Digit Verification of cas no
The CAS Registry Mumber 569-57-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 9 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 569-57:
(5*5)+(4*6)+(3*9)+(2*5)+(1*7)=93
93 % 10 = 3
So 569-57-3 is a valid CAS Registry Number.
InChI:InChI=1/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
569-57-3Relevant articles and documents
UTILIZATION OF TACE INHIBITORS FOR THE TREATMENT OF ACNE
-
, (2010/07/08)
An in vitro method of screening for candidate compounds for the preventive or curative treatment of acne entails determination of the ability of a compound to inhibit the expression or the activity of TACE, and also to the administration of inhibitors of the expression or of the activity of this enzyme, in the treatment of acne.
Competition of mechanisms in the photochemical cleavage of the C-X bond of aryl-substituted vinyl halides
Galli, Carlo,Gentili, Patrizia,Guarnieri, Alessandra,Kobayashi, Shinjiro,Rappoport, Zvi
, p. 9292 - 9299 (2007/10/03)
The photolysis of aryl halides caused homolysis of the carbon-halogen bond and formation of aryl radicals. In contrast, photolysis of vinyl halides can induce both heterolysis of the C-X bond, thereby generating vinyl cations, and homolysis, giving vinyl radicals. Examples of this competition among pathways is reported here for three vinylic precursors, namely, 1,2,2- triphenylbromoethene (1), 1-phenyl-2,2-bis(o-methoxyphenyl)-1-bromoethene (11), and β-bromostyrene (19). Incursion of the photoinduced S(RN)1 process, through the intermediacy of the vinyl radical, is verified in the presence of reducing nucleophiles, such as the enolate ions of ketones, and in part with (EtO)2PO-. Conversely, incursion of the heterolytic path, and intermediacy of the vinyl cation, occurs in the presence of weak electron-donor anions, such as NO2-, N3-, and Cl-. The vinyl cation produced from 19, which is less stable than those derived from 1 and 11, gives phenylacetylene via an E1-type elimination. An estimate is provided for the intramolecular rate of interception of the vinyl cation derived from 11 by the ortho-methoxy groups of the β-o-anisyl substituents. Finally, evidence against a photoinduced electron transfer from RO- ions to vinyl halide 1 is presented.
