beta-endosulfan

Synonyms: "Endosulfan I", "Benzoepin", "Thionex", "beta-Thionex", "beta-Thiodan", "Endosulfan B".

Source: beta-endosulfan is a persistant isomer of the insecticide endosulfan.

Identifiers:

IUPAC Name: (1R,2S,8R,9S)-1,9,10,11,12,12-hexachloro-4,6-dioxa-5lambda4-thiatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide
CAS Number: 959-98-8
PubChem ID: 12309460
InChiKey: RDYMFSUJUZBWLH-AZVNHNRSSA-N
Canonical SMILES: C1C2C(COS(=O)O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl

Structural Properties:

Molecular Formula: C₉H₆Cl₆O₃S
Molecular Weight: 406.904

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 4
Number of atoms different from hydrogen: 19

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Abalis IM, Eldefrawi ME, Eldefrawi AT. 1985. High-affinity stereospecific binding of cyclodiene insecticides and gamma-hexachlorocyclohexane to gamma-aminobutyric acid receptors of rat brain. Pesticide Biochemistry & Physiology 24(1):95-102. DOI: 10.1016/0048-3575(85)90118-X. URL: https://www.sciencedirect.com/science/article/pii/004835758590118X.
Kojima H, Katsura E, Takeuchi S, Niiyama K, Kobayashi K. 2004. Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. Environ Health Perspect 112(5):524-531. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1241915/Scippo ML, Argiris C, Van De Weerdt C, Muller M, Willemsen P, Martial J, Maghuin-Rogister G. 2004. Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors. Anal Bioanal Chem 378(3):664-669. DOI: 10.1007/s00216-003-2251-0. URL: https://link.springer.com/article/10.1007/s00216-003-2251-0.
Soto AM, Chung KL, Sonnenschein C. 1994. The pesticides endosulfan, toxaphene and dieldrin have estrogenic properties in human estrogen-sensitive cells. Environ Health Perspect 102(4):380-383. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1566957/.
Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO. 1995. The E-SCREEN assay as a tool to identify estrogens: An update on estrogenic environmental pollutants. Environ Health Perspect 103 (Suppl. 7):113-122. DOI: 10.2307/3432519 . URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1518887/.