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72779

Sigma-Aldrich

Triclosan

97.0-103.0% (active substance, GC)

Synonym(s):

Triclosan, 5-Chloro-2-(2,4-dichlorophenoxy)phenol, Irgasan

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About This Item

Empirical Formula (Hill Notation):
C12H7Cl3O2
CAS Number:
3380-34-5
Molecular Weight:
289.54
Beilstein:
2057142
EC Number:
222-182-2
MDL number:
MFCD00800992
UNSPSC Code:
12352132
PubChem Substance ID:
57652433
NACRES:
NA.85

biological source

synthetic

Quality Level

200

Assay

97.0-103.0% (active substance, GC)

form

powder or crystals

impurities

≤0.1% Water (Karl Fischer)

color

white

mp

55-59 °C

solubility

1 M NaOH: 5% at 25 °C, faintly turbid to clear (colorless solution)

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

SMILES string

Oc1cc(Cl)ccc1Oc2ccc(Cl)cc2Cl

InChI

1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H

InChI key

XEFQLINVKFYRCS-UHFFFAOYSA-N

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General description

Chemical structure: diphenyl ether derivative

Application

A component of cefsulodin-irgasan-novobiocin selection medium for Yersinia, a human pathogen that may contaminate animal-source food products.

Biochem/physiol Actions

It is an inhibitor of the enoyl-ACP (acyl-carrier protein) reductase component of type II fatty acid synthase (FAS-II) in bacteria and Plasmodium. It also inhibits mammalian fatty acid synthase (FASN), and may have anticarcinogenic activity.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H319,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kathleen Dittmann et al.
Antimicrobial resistance and infection control, 8, 122-122 (2019-08-02)
Recent publications have raised concerns of reduced susceptibilities of clinical bacterial isolates towards biocides. This study presents a comparative investigation of the susceptibility of livestock-associated Methicillin-resistant Staphylococcus aureus (LA-MRSA), hospital-acquired MRSA (HA-MRSA) and community-aquired MRSA (CA-MRSA) to the commonly used
Cale T Anger et al.
Environmental science & technology, 47(4), 1833-1843 (2013-01-17)
When discharged into surface waters via wastewater effluents, triclosan, the antimicrobial agent in handsoaps, and chlorinated triclosan derivatives (CTDs, formed during disinfection with chlorine) react photochemically to form polychlorinated dibenzo-p-dioxins. To evaluate the historical exposure of waters to these compounds
Wai Keat Chang et al.
Annals of surgery, 255(5), 854-859 (2012-04-04)
To determine the efficacy and safety of triclosan-impregnated sutures. Surgical-site infections (SSIs) produce considerable morbidity and increase health care costs. A potential strategy to decrease the rates of SSIs may be the use of triclosan-impregnated sutures. These have been endorsed
Joseph V Rodricks et al.
Critical reviews in toxicology, 40(5), 422-484 (2010-04-10)
Triclosan (2,4,4'-trichloro-2'-hydroxy-diphenyl ether) is an antibacterial compound that has been used in consumer products for about 40 years. The tolerability and safety of triclosan has been evaluated in human volunteers with little indication of toxicity or sensitization. Although information in
Markus K Diener et al.
Lancet (London, England), 384(9938), 142-152 (2014-04-11)
Postoperative surgical site infections are one of the most frequent complications after open abdominal surgery, and triclosan-coated sutures were developed to reduce their occurrence. The aim of the PROUD trial was to obtain reliable data for the effectiveness of triclosan-coated
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