An organochlorine antiseptic and antibacterial biocide
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Hexachlorophene

Item No. 23948

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2'-methylenebis[3,4,6-trichloro-phenol
CAS Number
70-30-4
Synonyms
  • Nabac
  • NSC 9887
  • NSC 49115
Molecular Formula
C13H6Cl6O2
Formula Weight
406.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:4): 0.2 mg/ml
λmax
300 nm
SMILES
ClC1=CC(Cl)=C(O)C(CC2=C(Cl)C(Cl)=CC(Cl)=C2O)=C1Cl
InChi Code
InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2
InChi Key
ACGUYXCXAPNIKK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    Hexachlorophene is an organochlorine antiseptic and antibacterial biocide.1,2,3,4 It is active against S. aureus (MIC = 1.56 μg/ml), E. faecium isolates from fresh produce (MICs = 5-50 mg/L), Salmonella isolates from meats (MICs = 2.5-25 mg/L), and Pseudomonas isolates from slaughterhouse surfaces (MICs = ≤0.0025-≤0.25 mg/L). Hexachlorophene inhibits severe acute coronavirus 2 (SARS-CoV-2) endoribonuclease (nsp15) in a FRET assay (IC50 = 1.6 µM) and inhibits SARS-CoV-2 replication in infected Vero CCL-81 cells (IC50 = 0.91 µM).5 Hexachlorophene inhibits infection of mouse astrocytoma delayed brain tumor (DBT) cells by mouse hepatitis virus (MHV; IC50 = 1.2 μM).6 Hexachlorophene also inhibits recombinant human glutathione transferases P1-1 and A3-3 (IC50s = 9.7 and <0.16 μM, respectively) and activates KCNQ1- and KCNE1 subunit-containing voltage-gated potassium Kv7 channels expressed in CHO cells (EC50 = 4.61 μM).7,8 In vivo, hexachlorophene is toxic to fasted and non-fasted rats with LD50 values of 215 and 165 mg/kg, respectively.9 It reduces R. solani-induced fruit rot in cucumber plants when applied at a concentration of 4.4 kg/ha.10

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Conradi, R.A., Vander Wyk, J.C., and Bowlus, S.B. Alkenylidene bisphenols, a new class of bisphenol bactericide. J. Med. Chem. 22(8), 1000-1002 (1979).

    2. Burgos, J.G., Aguayo, C.L., Pulido, R.R., et al. Multilocus sequence typing and antimicrobial resistance in Enterococcus faecium isolates from fresh produce. Antonie Van Leeuwenhoek 105(2), 413-421 (2014).

    3. Garrido, A.M., Burgos, J.G., Márquez, L.F., et al. Biocide tolerance in Salmonella from meats in Southern Spain. Braz. J. Microbiol. 46(4), 1177-1181 (2015).

    4. Lerma, L.L., Benomar, N., Casado Muñoz, M.d.C., et al. Correlation between antibiotic and biocide resistance in mesophilic and psychrotrophic Pseudomonas spp. isolated from slaughterhouse surfaces throughout meat chain production. Food Microbiol. 51, 33-44 (2015).

    5. Chen, J., Farraj, R.A., Velazquez, D.L., et al. Reversible and irreversible inhibitors of coronavirus Nsp15 endoribonuclease. The Journal of Biological Chemisty 11, 105341 (2023).

    6. Cao, J., Forrest, J.C., and Zhang, X. A screen of the NIH Clinical Collection small molecule library identifies potential anti-coronavirus drugs. Antiviral Res. 114, 1-10 (2015).

    7. Musdal, Y., Hegazy, U.M., Aksoy, Y., et al. FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. Chem. Biol. Interact. 205(1), 53-62 (2013).

    8. Zheng, Y., Zhu, X., Zhou, P., et al. Hexachlorophene is a potent KCNQ1/KCNE1 potassium channel activator which rescues LQTs mutants. PLoS One 7(12):e51820, (2012).

    9. Dashiell, O.L., and Kenney, G.L., Jr. The effects of fasting on the acute oral toxicity of nine chemicals in the rat. J. Appl. Toxicol. 4(6), 320-325 (1984).

    10. Sciumbato, G.L., and Hegwood, C.P., Jr. Use of elevated fungicide rates to control cucumber fruit rot under multiple harvesting conditions. Plant Dis. Rep. 63(6), 482-485 (1979).