1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane

HCID 76302CAS 124042-17-7

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Grundinformationen

Standard-SMILES: Oc1ccc(C(c2ccc(O)cc2)C(Cl)(Cl)Cl)cc1
InChIKey: IUGDILGOLSSKNE-UHFFFAOYSA-N
Summenformel: C14H11Cl3O2
Durchschnittliche Molmasse: 317,6 g/mol
Monoisotopische Masse: 315,98246263

Überblick

1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane is a bisphenol. It is functionally related to a 1,1,1-trichloro-2,2-diphenylethane.

Namen und Bezeichner

Bevorzugter Name: 1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane
IUPAC: 4-[2,2,2-trichloro-1-(4-hydroxyphenyl)ethyl]phenol
Englischer Name: 2,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethane
Summenformel: C14H11Cl3O2
Molmasse: 317.59

Namen und Synonyme

Hydroxychlor2,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethanep,p'-Hydroxy-DDT1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane4,4'-(2,2,2-trichloroethane-1,1-diyl)diphenol2,2-Bis(p-hydroxyphenyl)-1,1,1-trichloroethane4,4'-(2,2,2-Trichloroethylidene)diphenolDTXSID8022325NSC 7045Bisdemethylmethoxychlorp,p'-(2,2,2-Trichloroethylidene)diphenol4,4'-Dihydroxydiphenyltrichloroethane

Weitere Namen anzeigen

HPTEdihydroxy-diphenyltrichlorethane-(2,2,2-trichloroethylidene)bis-4,4’-dihydroxydiphenyl-trichloroethanep,p’-(2,2,2-trichloroethylidene)diphenol1 1 1-TRICHLORO-2 2-BIS(4-HYDROXYPHENYL&4,4’-(2,2,2-trichloroethylidene)di-pheno

4,4'-Dihydroxydiphenyl-trichloroethaneBRN 2054671Phenol, 4,4'-(2,2,2-trichloroethylidene)bis-Dihydroxy-diphenyl trichlorethaneDihydroxy-diphenyl trichlorethane [French]AI3-023354,4'-(2,2,2-Trichloroethylidene)bisphenolNSC-7045

Datenbank-Bezeichner

CAS: 124042-17-7、2971-36-0
PubChem CID: 76302
DTXSID: DTXSID8022325
ChEMBL: CHEMBL196585
ChEBI: CHEBI:34025
UNII: H58165YO91
EC Number: 623-854-1
Nikkaji: J42.984H

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 4,9
Polarare Oberfläche (TPSA): 40,5 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 2
Schwere Atome: 19
Formalladung: 0
Komplexität: 255

Experimentelle und physikochemische Eigenschaften

Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt: 204 · 204-208 °C(lit.)
Siedepunkt: 432.99 °C · 432.99°C (rough estimate)
Dichte: 1.3297 · 1.3297 (rough estimate)
Brechungsindex: 1.4521 · 1.4521 (estimate)
storage temp.: -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit: Acetone (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
Aggregatzustand: Solid
pka: 9.4 · 9.40±0.10(Predicted)
Farbe: Pale Pink to Light Purple
Wasserlöslichkeit: 76 mg/L · 76mg/L(temperature not stated)
Stabilität: Hygroscopic
EPA chemische Informationen: 4 · 4,4'-(2,2,2-Trichloroethylidene)bisphenol (2971-36-0)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheit und Schutzausrüstung

Minimum Risk LevelIntermediate Oral: 0.005 mg/kg/day (L134)

Toxikologische Informationen

Health Effects · 1 Eintrag

Animal studies show that HPTE may affect the reproductive system, causing harm to the ovaries, uterus, and mating cycle in females, and the testes and prostate in males, as well as decreased fertility in both sexes. Low dose HPTE exposure may also cause EEG pattern changes. (T10, L167)

Exposure RoutesInternal (Blood)

Toxicity Summary · 1 Eintrag

2,2-bis(p-hydroxyphenyl)-1,1, 1-trichloroethane (HPTE), acts as an estrogen analogue. HPTE is an estrogen receptor alpha agonist, and also acts as an antagonist at the estrogen receptor beta and androgen receptor. HPTE specifically inhibits the P450 cholesterol side-chain cleavage enzyme (P450scc, CYP11A1) resulting in decreased androgen production testicular Leydig cells along with decreased progesterone production by ovarian cells (A7861). HPTE directly inhibit human CYP17A1 activity (17α-hydroxylase/17,20-lyase). The IC50 value of HPTE is 1.13±0.10 uM. The observed changed in EEG patterns as well as tremors, convulsion and seizures with acute methoxychlor/HPTE exposure may be due to the inhibition of key sodium/potassium and calcium channels by HPTE.

Signs and SymptomsHigh levels of methoxychlor/HPTE may cause fatigue, lethargy, tremors, convulsions and seizures. (T10, L167)

Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)

Toxicity DataLD50: 3460 mg/kg (Oral, Rat) (L167)

Sicherheitsdaten

wgk: 2
tsca: TSCA listed
RTECS-Nr.: SN2500000
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Bis-hydroxy-methoxychlor has known human metabolites that include Tris-hydroxy-methoxychlor.

HPTE or 2,2-bis(p-hydroxyphenyl)-1,1, 1-trichloroethane is a biologically active liver metabolite of methoxychlor. Dechlorination and dehydrochlorination reactions occur to a lesser extent. HPTE is excreted mainly in the feces. (L167)

Verwendung und Herstellung

Uses · 1 Eintrag

Methoxychlor (the parent compound of HPTE) is used as an insecticide against flies, mosquitoes, cockroaches, chiggers, and a wide variety of other insects. It is used on agricultural crops and livestock, and in animal feed, barns, grain storage bins, home garden, and on pets. (L167)

General Manufacturing InformationPhenol, 4,4'-(2,2,2-trichloroethylidene)bis-: INACTIVE

Anwendungen · 1 Eintrag

Verwenden2,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethane is an active metabolite of Methoxychlor that acts via the estrogen receptor (ER) to stimulate estrogen response element (ERE)-mediated gene transcription in estrogen-sensitive tissues. 2,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethane is used in epoxy resins and other epoxide compositions as industrial materials and electric insulators.