From Wikipedia, the free encyclopedia
HPTE
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Names
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Preferred IUPAC name
4,4′-(2,2,2-Trichloroethane-1,1-diyl)diphenol
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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
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Identifiers
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2054671
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ChEBI
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.152.496
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EC Number
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KEGG
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UNII
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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
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C1=CC(=CC=C1C(C2=CC=C(C=C2)O)C(Cl)(Cl)Cl)O
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Properties
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C14H11Cl3O2
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Molar mass
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317.59 g·mol−1
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Hazards
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GHS labelling:
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Warning
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H315,
H319,
H335
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P261,
P264,
P271,
P280,
P302+P352,
P304+P340,
P305+P351+P338,
P312,
P321,
P332+P313,
P337+P313,
P362,
P403+P233,
P405,
P501
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
HPTE, also known as hydroxychlor, p,p'-hydroxy-DDT, or 2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane, is a
metabolite of
methoxychlor, a
synthetic
insecticide related to
DDT.
[1] Like
bisphenol A with similar
chemical structure, HPTE is an
endocrine disruptor which has
estrogenic activity,
[2] and also inhibits
Cholesterol side-chain cleavage enzyme (P450scc, CYP11A1)
[3] and
3α-hydroxysteroid dehydrogenase (3α-HSD).
[4]
References
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^ 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.
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^ 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.
doi:
10.1289/EHP.1002347.
PMC
3018502.
PMID
20826375.
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^ 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.
doi:
10.1016/J.REPROTOX.2011.05.013.
PMID
21664964.
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^ 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.
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Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:
ERX-11
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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