Triclocarban

Names

[ CAS No. ]:
101-20-2

[ Name ]:
Triclocarban

[Synonym ]:
3,4,4'-Trichlorocarbanilide
N-(4-Chlorophenyl)-N'-(3,4-dichlorophenyl)carbamimidic acid
3,4,4′-Trichlorocarbanilide
Methanol, 1-[(4-chlorophenyl)amino]-1-[(3,4-dichlorophenyl)imino]-, (Z)-
3,4,4'-trichlorodiphenylurea
Urea, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-
cusiter
MFCD00013254
Triclocarban
Nobacter
genoface
GR DMVMR CG DG
Procutene
Carbanilide, 3,4,4'-trichloro-
TCC
CUTISAN
N-(4-Chlorophenyl)-N-(3,4-dichlorophenyl)-Urea
EINECS 202-924-1
1-(4-Chlorophenyl)-3-(3,4-dichlorophenyl)urea
3,4,4-Trichlorocarbanilide
N-(4-Chlorophenyl)-N'-(3,4-dichlorophenyl)urea

Biological Activity

[Description]:

Triclocarban is an antimicrobial agent used in personal cleaning products.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[Target]

Bacterial[1]

[In Vitro]

Triclocarban at 300 nM potentiates the cytotoxicity of 300 µM H2O2 in rat thymocytes. 300 nM triclocarban itself does not increase the population of death cells, it facilitates the process of cell death induced by H2O2, resulting in further increase in the population of dead cells[1]. Triclocarban exertes estrogenic activities by inducing luciferase activities in an ER reporter gene assay, promoting the proliferation of the MCF-7 cells, up-regulating the expression of pS2 and down-regulating ERα expression at both the mRNA and protein levels in the MCF-7 cells[2].

[In Vivo]

Triclocarban is absorbed significantly from soap used during showering in human subjects and that its Cmax in their whole blood ranges from 23 nM to 530 nM[1]. Gestational triclocarban exposure does not affect the ability of dams to carry offspring to term but triclocarban exposure during lactation has adverse consequences on the survival of offspring[3].

[Animal admin]

Rats: Sprague Dawley rats are provided control, 0.2% weight/weight (w/w), or 0.5% w/w triclocarban -supplemented chow through a series of 3 experiments that limited exposure to critical growth periods: gestation, gestation and lactation, or lactation only (cross-fostering) to determine the susceptible windows of exposure for developmental consequences[3].

[References]

[1]. Kanbara Y, et al. Nanomolar concentration of triclocarban increases the vulnerability of rat thymocytes to oxidative stress. J Toxicol Sci. 2013 Feb;38(1):49-55.

[2]. Huang H, et al. The in vitro estrogenic activities of triclosan and triclocarban. J Appl Toxicol. 2014 Sep;34(9):1060-7.

[3]. Kennedy RC, et al. Early life triclocarban exposure during lactation affects neonate rat survival. Reprod Sci. 2015 Jan;22(1):75-89.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
475.3±55.0 °C at 760 mmHg

[ Melting Point ]:
254-256 °C(lit.)

[ Molecular Formula ]:
C₁₃H₉Cl₃N₂O

[ Molecular Weight ]:
315.582

[ Flash Point ]:
241.2±31.5 °C

[ Exact Mass ]:
313.978058

[ PSA ]:
41.13000

[ LogP ]:
5.66

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.630

[ Storage condition ]:
Refrigerator

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents strong bases.

[ Water Solubility ]:
<0.1 g/100 mL at 26 ºC

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
N

[ Risk Phrases ]:
R50/53

[ Safety Phrases ]:
S60-S61

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
FE1250000

[ Hazard Class ]:
9.0

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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