Triclosan

Triclosan (TRY-klo-san) is a white crystalline powder with antimicrobial properties that make it a useful ingredient in soaps, cosmetics, acne medications, deodorants, foot sprays and foot powders, toothpastes, and mouthwashes. It acts as an antimicrobial by inhibiting the action of an enzyme called enoyl-acyl carrier-protein reductase (ENR) that bacteria and fungi need to survive. The enzyme is used in the synthesis of fatty acids from which cell membranes are constructed. Having lost the ability to manufacture cell walls, bacteria and fungi die. The ENR enzyme is not present in humans, so triclosan has no effect on the human body. 

Triclosan is also known by the following names 5-chloro-2-(2,4-dichlorophenoxy)phenol trichloro-2 -hydroxydiphenyl-ether and 2,4,4 -trichloro-2 -hydroxydiphenyl ether. 

Two procedures are available for the synthesis of triclosan. In one, i,4-dichloro-2-nitrobenzene (C6H3C12N03) is 

Triclosan. Red atoms are oxygen white atoms are hydrogen black atoms are carbon and green atoms are chlorine. Dark gray sticks are double bonds other sticks are single bonds, publishers 

Soaking socks in a bacteria that grow on feet 

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The most common use of 2-(2, 4 -dichlorophenoxy)-5-chlorophenol (2,4,4 -trichloro 2 -phenoxyphenol) is in the personal care products market, where it is commonly known as triclosan and is the active antibacterial in underarm deodorants. It has also found some acceptance as an antibacterial component of plastic mattress covers. 

Oral Cleansing Products. Toothpastes and mouthwashes are considered cosmetic oral cleansers as long as claims about them are restricted to cleaning or deodorization. Because deodorization may depend on reduction of microbiota in the mouth, several antimicrobial agents, either quaternaries, such as benzethonium chloride [121 -54-0] or phenoHcs, such as triclosan [3380-35-5] are permitted. Products that include anticaries or antigingivitis agents or claim to provide such treatment are considered dmgs. 

An antimicrobial agent that reduces dental plaque and can be deUvered effectively from toothpaste is a combination of Triclosan [3380-34-5] (0.2% in the toothpaste) and zinc citrate (0.5%) (7). This agent influenced plaque accumulation and reduced the incidence of gingival bleeding in clinical tests. Additional dentifrices for improved gingival health are in the offing. 

Triclosan is a broad-spectrum antibacterial and antifungal agent. It is an ingredient in toothpastes and mouthwashes, detergents, laundry soaps, and cosmetics. It kills germs by interfering with the enzyme necessary for fatty-acid synthesis. 

Once widely used in over-the-counter products, hexachlorophene is now available by prescription only, due to incidents of overdose in infants in France during the 1970s. It has been largely replaced by the related compound triclosan. 

Antibacterial soaps usually contain triclosan or triclocarban as the active antibacterial ingredient. 

The antibacterial agent triclosan is added to kill plaque-forming microbes. 

Sicorten Plus (Novartis 1986)-comb. with triclosan... 

Ci,)Hi,N503S2 37539-03-0) see Cefatrizine 2-amino-2, 4,4 trichlorodiphenyJ ether (C12HXCI3NO 56966-52-6) see Triclosan 2-amino-3,5,6-trifluoro-4-methoxybenzonitriIe (CXH5F3N2O 114214-46-9) see Moxifloxacin hydrochloride... 

Thomas PM, Foster GD (2005) Tracking acidic pharmaceuticals, caffeine, and triclosan through TFIE wastewater treatment process. Environ Toxicol Chem 24(l) 25-30... 

Phenolics, e.g. tar acids (clear soluble phenolics), non-coal tar (chloroxylenol), bisphenol (triclosan)... 

Bisphenols are composed of two phenolic groups connected by various linkages. Hydroxy halogenated derivatives, such as hexachlorophane (Fig. 10.7D) and triclosan, are the most active microbiologically, but are bacteriostatic at use-concentrations and have little antipseudomonal activity. The use of hexachlorophane is also limited by its serious toxicity. Both hexachlorophane and trichlosan have limited application in medicated soaps and washing creams. 

The oxidation of triclosan was initiated by oxidation to the PhO radical. In analogy with reactions established in biomimetic synthesis, this nnderwent coupling to produce biphenyl ethers and biphenyls that were oxidized further to diphenoquinones (Zhang and Huang 2003). 

Zhang H, C-H Huang (2003) Oxidative transformation of triclosan and chlorophene by manganese dioxides. Environ Sci Technol 37 2421-2430. 

As an illustrated example of these ideas presented thus far we show in Scheme 4.8 and Figure 4.14 the conventional synthesis plan for triclosan and its corresponding synthesis tree diagram. 

Figure 4.14 Synthesis tree for triclosan synthesis plan shown in Scheme 4.8. Molecular weights for each species are shown within parentheses.

For a linear plan the pseudo-overall yield as defined above is numerically close to the multiplicative product of the reaction yields. The difference between the two values diminishes as the reaction yields approach 1 as would be expected. However, for complex plans with several converging branches this alternative definition becomes less useful. For the triclosan branch equation (4.16) yields 0.405 (40.5%) for the pseudo-overall yield. 

Table 4.6 Summary of reaction and overall material efficiency performances for the production of triclosan according to the tree diagram shown in Figure 4.14. of 1 mole...

Figure 4.15 shows the same synthesis tree for triclosan as given before in Figure 4.14 with some modifications made and added geometric parameters superimposed. The... 

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