Triclosan

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H410：Sehr giftig für Wasserorganismen mit langfristiger Wirkung.

• Sicherheit

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P273：Freisetzung in die Umwelt vermeiden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

  P332+P313：Bei Hautreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

Triclosan Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/38:Reizt die Augen und die Haut.
  R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S39:Schutzbrille/Gesichtsschutz tragen.
  S46:Bei Verschlucken sofort ärztlichen Rat einholen und Verpackung oder Etikett vorzeigen.
  S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
  S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S22:Staub nicht einatmen.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

• Beschreibung

  Triclosan is a broad-spectrum antibacterial agent that inhibits bacterial fatty acid synthesis. It is effective against Gram-negative and Gram-positive bacteria, as well as against Mycobacteria. Triclosan is used in a variety of products, including antiseptic soaps, deodorants, and hand washes.

• Chemische Eigenschaften

  Solid

• Physikalische Eigenschaften

  Triclosan is a slightly aromatic high-purity white crystalline powder; Solubility: slightly soluble in water, moderately soluble in dilute alkali, has high solubility in many organic solvents, in water-soluble solvents or surfactants After dissolving, it can be made into a transparent concentrated liquid product.

• Originator

  Anti-Bac,Bentfield Europe BV,Netherlands

• Verwenden

  Bacteriostat and preservative for cosmetic and detergent preparations.

• Verwenden

  anticonvulsant

• Verwenden

  triclosan is a preservative considered to have a low sensitizing potential in leave-on preparations.

• Verwenden

  Used as bacteriostat and preservative for cosmetic and detergent compositions. Antiseptic, disinfectant.

• Definition

  ChEBI: An aromatic ether that is phenol which is substituted at C-5 by a chloro group and at C-2 by a 2,4-dichlorophenoxy group. It is widely used as a preservative and antimicrobial agent in personal care products such as soaps, skin creams, toothpaste and deodo ants as well as in household items such as plastic chopping boards, sports equipment and shoes.

• Indications

  Triclosan is a broad-spectrum antimicrobial compound. It was originally used in soaps, antiperspirants, and cosmetic toiletries as a germicide. Today, triclosan is incorporated into toothpaste because of its wide spectrum of antimicrobial activities and low toxicity.

• Manufacturing Process

  476 g of 4-chloro-2-methoxyphenol(4-chloroguaiacol) and 578 parts of 3,4- dichloro-1-nitrobenzene are melted in 400 ml of diethylene glycoldimethyl ether in a three necked flask fitted with a stirrer and sloping condenser and, at about 120°C, 342 g of 49.6% potassium hydroxide solution are added drop-wise within about 4 h. The inner temperature is kept for 12 h at 140°- 150°C whereby water and slight amounts of organic substances distill off, as partly occured during the dropwise addition of the potassium hydroxide solution. The reaction mixture is then poured into a mixture of water and sodium hydroxide solution, the precipitate is filtered off, dried and recrystallised from benzene. The 2-methoxy-4,2'-dichloro-4'-nitrodiphenyl ether obtained melts at 159°-161°C.
  623 g of 2-methoxy-4,2'-dichloro-4'-nitrodiphenyl ether in 4000 ml of dioxan are catalytically hydrogenated in the presence of 250 g of Raney nickel at room temperature and under normal pressure. After the calculated amount of hydrogen, the Raney nickel is filtered off and the 2-methoxy-4,2'-dichloro-4'- aminodiphenyl ether is precipitated by the addition of water, filtered off, washed and dried, melting point 100°-102°C.
  204 g of well milled 2-methoxy-4,2'-dichloro-4'-aminodiphenyl ether are added to a mixture of 254 ml of concentrated hydrochloric acid and 1600 ml of water, the addition being made at room temperature while stirring well. The suspension formed is cooled to 0°-5°C and at this temperature 225 g of 33% sodium nitrite solution is added under the level of the liquid. The mixture is stirred for another 12 h at 0°-5°C. A solution of 86 g of sodium bisulphate and 60 g of sodium hydroxide in 640 ml of water is added at 80°C to a solution of 400 g of crystallised copper sulfate and 106 g of sodium chloride in 1280 ml of water. The cuprous chloride formed is allowed to settle, the water is poured off and the precipitate is purified by decanting three times with water.
  The residue is dissolved in 640 ml of concentrated hydrochloric acid, the solution is heated to 65°-70°C and the diazo suspension produced above is added while stirring. After cooling, the aqueous phase is poured off, the resin_x0002_like organic phase is taken up in ether, the ether solution is extracted with dilute sodium hydroxide solution, washed neutral, dried over sodium sulphate and concentrated. The residue is distilled under water jet vacuum. The 2- methoxy-4,2',4'-trichlorodiphenyl ether obtained boils at 210°-217°C. 243 g of aluminum chloride are added to the solution of 187.5 g of 2- methoxy-4,2',4'-trichlorodiphenyl ether in 800 ml of benzene and the reaction mixture is boiled for 30 min while stirring. After cooling, it is poured into ice and hydrochloric acid, the benzene phase is separated and extracted with water and sodium hydroxide solution. The mimosa alkaline aqueous phase is separated, the last remains of benzene are removed by blowing in steam, it is then filtered and acidified with hydrochloric acid. The precipitated 2-hydroxy- 4,2',4'-tri-chlorodiphenyl ether is filtered off, washed and dried. After recrystallisation from petroleum ether it melts at 60°-61°C.Model E., Bindler J.; GB Patent No. 1,051,823; Dec. 21, 1966; Assigned: J.R. Geigy AG, Basel

• Trademarks

  Stri-Dex Cleansing Bar (Sterling Health U.S.A.); Stri-Dex Face Wash (Sterling Health U.S.A.).

• Therapeutic Function

  Antiseptic

• Allgemeine Beschreibung

  Chemical structure: diphenyl ether derivative

• Flammability and Explosibility

  Non flammable

• Biochem/physiol Actions

  Irgasan is a broad spectrum antimicrobial agent. 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.

• Mechanism of action

  Triclosan is active against a broad range of oral grampositive and gram-negative bacteria.The primary target of its antibacterial activity is the bacterial cell membrane. High concentrations cause membrane leakage and ultimately lysis of the bacterial cell. Effects at lower concentration are more subtle. Triclosan has been shown to bind to cell membrane targets and inhibit enzymes associated with the phosphotransferase and proton motive force systems.

• Pharmakologie

  Triclosan is retained in dental plaque for at least 8 hours, which in addition to its broad antibacterial property could make it suitable for use as an antiplaque agent in oral care preparations. However, the compound is rapidly released from oral tissues, resulting in relatively poor antiplaque properties as assessed in clinical studies of plaque formation.This observation is further corroborated by a poor correlation between minimal inhibitory concentration values generated in vitro and clinical plaque inhibitory properties of triclosan. Improvement of substantivity was accomplished by incorporation of triclosan in a polyvinyl methyl ether maleic acid copolymer (PVM/MA, Gantrez). With the combination of PVM/MA copolymer and triclosan, the substantivity of the triclosan was increased to 12 hours in the oral cavity.

• Clinical Use

  Triclosan plus copolymer is available in toothpaste. Commercially available dentifrice concentrations contain 0.3% triclosan and 2.0% PVM/MA copolymer.

• Nebenwirkungen

  Triclosan is a preservative used in health care and consumer products, including soaps, deodorants, mouthwashes, toothpastes, cosmetics, and topical medicaments. Ozkaya et al. described a case of suspected immune mediated Cou to triclosan. A 44-year-old female reported experiencing an immediate localized urticarial response after contact with numerous topical products. The use of a toothpaste had also resulted in swelling of her lips, tongue, and breathing difficulties. She also experienced lip swelling after kissing her husband who had used the same product and wheals involving her face after kissing friends on the cheek who had used certain topical products on their faces. The suspected products all contained triclosan 0.2%–0.5%. A severe localized urticarial reaction occurred with open testing to 2% triclosan within 15 minutes. No tests were performed to confirm an immunological mechanism; however, the authors suspected this to be the case because of a positive urticarial response to triclosan within 15 minutes, a history of angioedema to the triclosan-containing toothpaste, and because no immediate reactions were seen in five control subjects who were open tested to 2% triclosan.

• Sicherheitsprofil

  Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mildly toxic by skin contact. Mutation data reported. Ahuman skin irritant. When heated to decomposition itemits toxic fumes of Clí.

• Veterinary Drugs and Treatments

  Found in several products, often with other active ingredients, triclosan’s antibacterial effects may be useful in treating superficial pyodermas.
  Triclosan is a bis-phenol disinfectant/antiseptic. It has a activity against a wide range of organisms, including both gram-positive and gram-negative bacteria and acts via inhibiting bacterial fatty acid synthesis leading to disruption of cell membrane integrity. Triclosan reportedly is not effective against Pseudomonas spp. and may be less effective against staphylococci than either chlorhexidine or ethyl lactate.

• in vitro

  triclosan blocked and displaced [3h] oestradiol binding from oestrogen receptors (er) of mcf7 human breast cancer cells and from recombinant human erα /erβ at low concentrations. triclosan fully dampened the elicitation of the oestrogen-responsive ere-cat reporter gene in mcf7 cells and the activation of growth of mcf7 human breast cancer cells by 10-10 m 17β-oestradiol. additionally, triclosan, on its own, increased the proliferation of oestrogen-dependent mcf7 human breast cancer cells [1].

• in vivo

  balb/c mice were administrated subcutaneously with triclosan daily at 0.8 to 38 mg/kg for 6 weeks. 75% parasitemia was blocked by single subcutaneous injection of triclosan at a dose of 3.0 mg/kg within 24 hours. however, triclosan fully cleared the parasite from circulation with one injection at a dose of 38 mg/kg. no side effects of triclosan were monitored via checking the activities of the enzymes serum glutamate oxaloacetate transaminase and serum glutamate pyruvate transaminase [2].

• Einzelnachweise

  [1]. gee, r., charles, a., taylor, n., & darbre, p. oestrogenic and androgenic activity of triclosan in breast cancer cells. journal of applied toxicology. 2007; 28(1): 78-91.
  [2]. hillyer, c. triclosan offers protection against blood stages of malaria by inhibiting enoyl-acp reductase of plasmodium falciparumm. surolia, a. surolia. nat med 7:167–173, 2001. transfusion medicine reviews. 2002; 16(2): 180-181.

Triclosan Upstream-Materialien And Downstream Produkte

Triclosan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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