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HPTE

From Wikipedia, the free encyclopedia
HPTE
Names
Preferred IUPAC name
4,4′-(2,2,2-Trichloroethane-1,1-diyl)diphenol
Other names
p,p'-Hydroxy-DDT
Hydroxychlor
2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane
1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane
Identifiers
3D model (JSmol)
2054671
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.152.496Edit this at Wikidata
EC Number
  • 623-854-1
KEGG
UNII
  • InChI=1S/C14H11Cl3O2/c15-14(16,17)13(9-1-5-11(18)6-2-9)10-3-7-12(19)8-4-10/h1-8,13,18-19H
    Key: IUGDILGOLSSKNE-UHFFFAOYSA-N
  • InChI=1S/C14H11Cl3O2/c15-14(16,17)13(9-1-5-11(18)6-2-9)10-3-7-12(19)8-4-10/h1-8,13,18-19H
    Key: IUGDILGOLSSKNE-UHFFFAOYSA-N
  • C1=CC(=CC=C1C(C2=CC=C(C=C2)O)C(Cl)(Cl)Cl)O
Properties
C14H11Cl3O2
Molar mass317.59 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315,H319,H335
P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

HPTE, also known ashydroxychlor,p,p'-hydroxy-DDT, or2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane, is ametabolite ofmethoxychlor, asyntheticinsecticide related toDDT.[1] Likebisphenol A with similarchemical structure, HPTE is anendocrine disruptor which hasestrogenic activity,[2] and also inhibitsCholesterol side-chain cleavage enzyme (P450scc, CYP11A1)[3] and3α-hydroxysteroid dehydrogenase (3α-HSD).[4]

References

[edit]
  1. ^Leung-Gurung, Lucie; Escalante Cobb, Priscilla; Mourad, Faraj; Zambrano, Cristina; Muscato, Zachary; Sanchez, Victoria; Godde, Kanya; Broussard, Christine (4 July 2018)."Methoxychlor metabolite HPTE alters viability and differentiation of embryonic thymocytes from C57BL/6 mice".Journal of Immunotoxicology.15 (1):104–118.doi:10.1080/1547691X.2018.1474978.PMC 6120686.PMID 29973080.
  2. ^Hewitt, Sylvia C.; Korach, Kenneth S. (January 2011)."Estrogenic Activity of Bisphenol A and 2,2-bis(p-Hydroxyphenyl)-1,1,1-trichloroethane (HPTE) Demonstrated in Mouse Uterine Gene Profiles".Environmental Health Perspectives.119 (1):63–70.Bibcode:2011EnvHP.119...63H.doi:10.1289/EHP.1002347.PMC 3018502.PMID 20826375.
  3. ^Akgul, Yucel; Derk, Raymond C.; Meighan, Terence; Rao, K. Murali Krishna; Murono, Eisuke P. (July 2011). "The methoxychlor metabolite, HPTE, inhibits rat luteal cell progesterone production".Reproductive Toxicology.32 (1):77–84.Bibcode:2011RepTx..32...77A.doi:10.1016/J.REPROTOX.2011.05.013.PMID 21664964.
  4. ^Mao, Baiping; Wu, Chengyun; Zheng, Wenwen; Shen, Qiuxia; Wang, Yiyan; Wang, Qiufan; Lin, Han; Li, Xiaoheng; Sun, Jianliang; Ge, Ren-Shan (September 2018). "Methoxychlor and its metabolite HPTE inhibit rat neurosteroidogenic 3α-hydroxysteroid dehydrogenase and retinol dehydrogenase 2".Neuroscience Letters.684:169–174.doi:10.1016/j.neulet.2018.08.008.PMID 30107201.S2CID 52004606.
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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