Basic information
- Standard SMILES
Oc1ccc(C(c2ccc(O)cc2)C(Cl)(Cl)Cl)cc1- InChIKey
IUGDILGOLSSKNE-UHFFFAOYSA-N- Molecular formula
- C14H11Cl3O2
- Average molar mass
- 317.6 g/mol
- Monoisotopic mass
- 315.98246263
Overview
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.
Names & identifiers
- Preferred name
- 1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane
- IUPAC
- 4-[2,2,2-trichloro-1-(4-hydroxyphenyl)ethyl]phenol
- English name
- 2,2-Bis(4-hydroxyphenyl)-1,1,1-trichloroethane
- Molecular formula
- C14H11Cl3O2
- Molecular weight
- 317.59
Names & synonyms
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
Show more names
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
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 255
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 204 · 204-208 °C(lit.)
- Boiling point
- 432.99 °C · 432.99°C (rough estimate)
- Density
- 1.3297 · 1.3297 (rough estimate)
- refractive index
- 1.4521 · 1.4521 (estimate)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Acetone (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.4 · 9.40±0.10(Predicted)
- color
- Pale Pink to Light Purple
- Water Solubility
- 76 mg/L · 76mg/L(temperature not stated)
- Stability
- Hygroscopic
- FDA UNII
- 58165 YO91 · H58165YO91
- EPA Substance Registry System
- 4 · 4,4'-(2,2,2-Trichloroethylidene)bisphenol (2971-36-0)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H335-H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 2500000 · SN2500000
- TSCA
- TSCA listed
Safety & regulation
GHS classification
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.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety & protection
Minimum Risk LevelIntermediate Oral: 0.005 mg/kg/day (L134)
Toxicology
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.
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)
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SN2500000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H315-H335-H319
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
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)
Uses & manufacturing
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
Applications
Uses2,2-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.
Upstream & downstream products
Downstream products
Suppliers10 total
艾吉析科技（上海）有限公司17717235263 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
上海珈得尔化学技术有限公司021-4007787-550 400-7787-550 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
上海传芊化工科技中心15869524721 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
Additional notes
DefinitionChEBI: 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.
Related reactions
4 records
Linked notes
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