Hexachlorophene

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Structural formula
Structure of hexachlorophene
General
Surname Hexachlorophene
other names
  • 2,2'-methylenebis (3,4,6-trichlorophenol)
  • Nabac
Molecular formula C 13 H 6 Cl 6 O 2
Brief description

light brown solid

External identifiers / databases
CAS number 70-30-4
EC number 200-733-8
ECHA InfoCard 100,000,667
PubChem 3598
ChemSpider 3472
DrugBank DB00756
Wikidata Q425362
Drug information
ATC code

D08 AE01

properties
Molar mass 406.91 g · mol -1
Physical state

firmly

Melting point

164-165 ° C

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 09 - Dangerous for the environment

danger

H and P phrases H: 301-311-410
P: 273-280-301 + 310-312-501
Toxicological data

56 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexachlorophene is a chlorinated Until phenol and a chlorinated hydrocarbon , which as a disinfectant is used.

presentation

Hexachlorophene is produced by the condensation of 2,4,5-trichlorophenol with formaldehyde in the presence of concentrated sulfuric acid.

effect

Hexachlorophene has a strong bactericidal effect against gram-positive bacteria. The growth of Staphylococcus aureus on agar is still prevented by hexachlorophene in a dilution of 1: 8,000,000. In higher concentrations, hexachlorophene is irritating to skin, eyes and mucous membranes, and is neurotoxic and embryotoxic . In test animals, damage to the white matter of the brain and to the spinal cord was found. Taken orally in large amounts , hexachlorophene causes loss of appetite , diarrhea , and paralysis.

use

Hexachlorophene is used as a disinfectant , medicine (for trichophyte and trematode treatment , against acne and hemorrhoids and in the livestock industry) and as a pesticide. It is also used as a microbiocide in cosmetics (banned in the Federal Republic of Germany since 1985), detergents and cleaning agents and as an additive to textiles and plastics. There are also applications in recycling processes (paper, toilet paper, ...).

Admission

Since January 1, 1990, drugs containing hexachlorophene may no longer be placed on the market in Austria. Use in cosmetics has been banned in Germany since 1985. No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Web links

Individual evidence

  1. ↑ Data sheet Hexachlorophene from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
  2. ↑ a b c Entry on 2,2′-methylenebis (3,4,6-trichlorophenol) in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  3. ↑ a b c d Entry on hexachlorophene. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
  4. ↑ Entry on Hexachlorophene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ Entry on hexachlorophene in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  6. ↑ Umweltbundesamt: Fact Sheet Triclosan, Triclocarban, Hexachlorophen ( Memento from November 12, 2011 in the Internet Archive ) (PDF; 35 kB).
  7. ^ Legal information system of the Austrian Federal Chancellery , accessed on October 12, 2013.
  8. ↑ Directorate-General for Health and Food Safety of the European Commission: Entry on Hexachlorophene in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.