HPTE
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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 | |
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3D model (JSmol) |
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Beilstein Reference | 2054671 |
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ECHA InfoCard | 100.152.496 |
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InChI
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Properties | |
Chemical formula | C14H11Cl3O2 |
Molar mass | 317.59 g·mol−1 |
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Hazard statements | H315, H319, H335 |
Precautionary statements | 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 their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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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- See also
- Receptor/signaling modulators
- Estrogens and antiestrogens
- Androgen receptor modulators
- Progesterone receptor modulators
- List of estrogens
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