HPTE

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
CAS Number	2971-36-0
3D model (JSmol)	Interactive image
Beilstein Reference	2054671
ChEBI	CHEBI:34025
ChEMBL	ChEMBL196585
ChemSpider	68781
ECHA InfoCard	100.152.496
EC Number	623-854-1
KEGG	C14136
PubChem CID	76302
UNII	H58165YO91
CompTox Dashboard (EPA)	DTXSID8022325
InChI 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
SMILES C1=CC(=CC=C1C(C2=CC=C(C=C2)O)C(Cl)(Cl)Cl)O
Properties
Chemical formula	C14H11Cl3O2
Molar mass	317.59 g·mol^−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
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

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

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. 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. 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.