1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane
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Grundinformationen
- CAS
1794780-53-2- Standard-SMILES
Oc1ccc(C(c2ccc(O)cc2)C(Cl)(Cl)Cl)cc1- InChIKey
IUGDILGOLSSKNE-UHFFFAOYSA-N- Summenformel
- C14H11Cl3O2
- Durchschnittliche Molmasse
- 317,6 g/mol
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
- 1,1,1-Trichloro-2,2-bi
- Summenformel
- C14H11Cl3O2
- Molmasse
- 317.59494
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
HPTE-d81,1,1-Trichloro-2,2-biBisdeMethylMethoxychlor-d84,4'-Dihydroxydiphenyltrichloroethane-d84,4'-(2,2,2-Trichloroethylidene)diphenol-d82,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethane-d82,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethane-d8 (Major)
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
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 4,9
- Polarare Oberfläche (TPSA)
- 40,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 255
Experimentelle und physikochemische Eigenschaften
LogP3.86
Endocrine DisruptorsPotential endocrine disrupting compound
Physikochemische Eigenschaften
- Schmelzpunkt
- 161 °C · >161°C (dec.)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Heated)
- Aggregatzustand
- Solid
- Farbe
- Off-White to Pale Yellow
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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
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
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.
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
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
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
Verwenden4,4'-(2,2,2-Trichloroethylidene)diphenol-d8, an active metabolite of Methoxychlor that acts via the estrogen receptor (ER) to stimulate estrogen response element (ERE)-mediated gene transc ription 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.
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