Triclocarban

Structural formula
General
Surname	Triclocarban
other names	3,4,4'-trichlorocarbanilide TCC 3- (4-chlorophenyl) -1- (3,4-dichlorophenyl) urea
Molecular formula	C 13 H 9 Cl 3 N 2 O
Brief description	white odorless powder
External identifiers / databases
CAS number 101-20-2 EC number 202-924-1 ECHA InfoCard 100.002.659 PubChem 7547 DrugBank DB11155 Wikidata Q416579
properties
Molar mass	315.58 g mol −1
Physical state	firmly
density	1.53 g cm −3 (25 ° C)
Melting point	254-256  ° C
solubility	practically insoluble in water (0.11 mg l −1 at 20 ° C) soluble in polyethylene glycol and acetone
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 410 P: 273-391-501
Toxicological data	3,600 mg kg −1 ( LD 50 ,  rat ,  oral ) 600 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triclocarban is a chemical compound from the group of carbanilide derivatives .

Extraction and presentation

Triclocarban can be obtained by reacting 3,4-dichloroaniline with 4-chlorophenyl isocyanate .

properties

Triclocarban is a white odorless powder that is practically insoluble in water.

use

Triclocarban is used as an antibacterial and preservative in liquid soaps and deodorants. A 1999–2000 study found that triclocarban was found in 84% of soaps sold in the United States. In Europe, the maximum permitted concentration in cosmetic products is 0.2% (Directive 76/768 / EEC, Annex VI, part 1 n ° 23). The effect is based on influencing the cell membranes of the bacteria.

safety instructions

Triclocarban can cause methaemoglobinaemia and should therefore not be used in newborns and infants. When used for vaginal hygiene, erythema multiforme can be induced.

Risk assessment

Triclocarban was included in 2018 by the EU in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's rolling action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of triclocarban were concerns about its widespread use and the possible risk of reproductive toxicity and as a potential endocrine disruptor . The re-evaluation has been running since 2019 and is carried out by France .

literature

• B. Kuch, C. Schneider, JW Metzger: Monitoring of the disinfectants triclosan, triclocarban and hexachlorophene in sewage treatment plants . Ed .: University of Stuttgart. March 2003 ( PDF ).
• M.-F. Yueh, T. Li, RM Evans, B. Hammock, RH Turkey: Triclocarban Mediates Induction of Xenobiotic Metabolism through Activation of the Constitutive Androstane Receptor and the Estrogen Receptor Alpha . In: PLOS ONE . tape 7 , no. 6 , 2012, p. e37705 , doi : 10.1371 / journal.pone.0037705 .

Individual evidence

1. ↑ ^{a b c d e f g} Wolfgang Blaschek, Margitta Albinus: Hager's handbook of pharmaceutical practice . Springer, 1999, ISBN 978-3-540-52688-9 , pp. 1043 ( limited preview in Google Book search).
2. ↑ ^{a b} Data sheet 3,4,4′-Trichlorocarbanilide, 99% from Sigma-Aldrich , accessed on June 27, 2012 ( PDF ).
3. ↑ ^{a b c} Entry on Triclocarban in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
4. ↑ ^{a b} Triclocarban ( Memento of the original from November 28, 2011 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 73 kB), May 24, 2010 Meeting of Scientific Guidance Panel (SGP) Biomonitoring California. 
5. ↑ EU: SCIENTIFIC COMMITTEE ON CONSUMER PRODUCTS SCCP - Opinion on Triclocarban for other uses than as a preservative (PDF; 309 kB).
6. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Triclocarban , accessed on March 26, 2019.