A potential impurity found in commercial preparations of lindane
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β-BHC

Item No. 24134

Technical Information
Formal Name
1α,2β,3α,4β,5α,6β-hexachloro-cyclohexane
CAS Number
319-85-7
Synonyms
  • β-HCH
  • β-Hexachlorocyclohexane
  • β-Lindane
Molecular Formula
C6H6Cl6
Formula Weight
Purity
≥95%
Formulation
A solid
DMSO: Slightly Soluble
SMILES
Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@@H](Cl)[C@@H]1Cl
InChi Code
InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3+,4+,5-,6-
InChi Key
JLYXXMFPNIAWKQ-CDRYSYESSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    β-BHC is an isomer of the organochlorine pesticide γ-lindane (Item No. 23952) that is a potential impurity found in commercial preparations of lindane.1 It is estrogenic, inducing estrogen receptor α (ERα) and ERβ reporter gene expression in CHO cells expressing the human receptors with 20% relative effective concentration (REC20) values of 3.5 and 1.1 μM, respectively.2 In vitro, β-BHC induces apoptosis of rat Sertoli cells via production of reactive oxygen species (ROS), activation of caspases, and induction of expression of Fas ligand (FasL).3 It is a persistent organic pollutant and levels of total body β-BHC are negatively correlated to plasma testosterone levels in male polar bears.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakajima, M. Biochemical toxicology of lindane and its analogs. J. Environ. Sci. Health B 18(1), 147-172 (1983).

    2. Kojima, H., Katsura, E., Takeuchi, S., et alScreening 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 (2004).

    3. Shi, Y., Song, Y., Wang, Y., et alβ-Benzene hexachloride induces apoptosis of rat Sertoli cells through generation of reactive oxygen species and activation of JNKs and FasL. Environ. Toxicol. 26(2), 124-135 (2011).

    4. Oskam, I.C., Ropstad, E., Dahl, E., et alOrganochlorines affect the major androgenic hormone, testosterone, in male polar bears (Ursus maritimus) at Svalbard. J. Toxicol. Environ. Health 66(22), 2119-2139 (2003).