69778 Triclosan - AK Scientific
 
 
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  Catalog ID # 69778
Triclosan
, 98% (HPLC)
 
5-Chloro-2-(2,4-dichlorophenoxy)phenol
Irgasan




IDENTITY
CAS Registry #:[3380-34-5]
MDL Number:MFCD00800992
MF:C12H7Cl3O2
MW:289.5418
EINECS:222-182-2
BRN:2057142
SPECIFICATIONS & PROPERTIES
Purity:98% (HPLC)
Physical Form:White to off-white crystalline powder or flakes
Melting Point:54-59°C
Boiling Point:280-290°C
Shipping:Normal Temperature

BIOLOGICAL INFO
Solubility:H2O: insoluble; DMSO: 15mg/mL; MeOH: 25mg/mL

REVIEW

 At in-use concentrations, triclosan acts as a biocide, with multiple cytoplasmic and membrane targets. At lower concentrations, however, triclosan appears bacteriostatic and is seen to target bacteria mainly by inhibiting fatty acid synthesis. Triclosan binds to bacterial enoyl-acyl carrier protein reductase enzyme (ENR), which is encoded by the gene FabI. This binding increases the enzyme's affinity for nicotinamide adenine dinucleotide (NAD+). This results in the formation of a stable ternary complex of ENR-NAD+-triclosan, which is unable to participate in fatty acid synthesis. Fatty acids are necessary for reproducing and building cell membranes. Humans do not have an ENR enzyme, and thus are not affected. Some bacterial species can develop low-level resistance to triclosan at its lower bacteriostatic concentrations because of FabI mutations, which results in a decrease of triclosan's effect on ENR-NAD+ binding, as shown in Escherichia coli and Staphylococcus aureus. Another way for these bacteria to gain low-level resistance to triclosan is to overexpress FabI. Some bacteria have innate resistance to triclosan at low, bacteriostatic levels, such as Pseudomonas aeruginosa, which possesses multi-drug efflux pumps that ''pump'' triclosan out of the cell.[18] Other bacteria, such as some of the Bacillus genus, have alternative FabI genes (FabK) to which triclosan does not bind and hence are less susceptible.

REFERENCES
[1]Russell AD (2004). ''Whither triclosan?''. J. Antimicrob. Chemother. 53 (5): 693-5. doi:10.1093/jac/dkh171. PMID 15073159.
[2] Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO (1999). ''Mechanism of triclosan inhibition of bacterial fatty acid synthesis''. J. Biol. Chem. 274 (16): 11110-4. doi:10.1074/jbc.274.16.11110. PMID 10196195.
[3] Fan F, Yan K, Wallis NG, et al. (2002). ''Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus''. Antimicrob. Agents Chemother. 46 (11): 3343-7. doi:10.1128/AAC.46.11.3343-3347.2002. PMC 128739. PMID 12384334.
[4] Slater-Radosti C, Van Aller G, Greenwood R, et al. (2001). ''Biochemical and genetic characterization of the action of triclosan on Staphylococcus aureus''. J. Antimicrob. Chemother. 48 (1): 1-6. doi:10.1093/jac/48.1.1. PMID 11418506.

Risk Description(s)
R36/38:Irritating to eyes and skin
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment

Safety Description(s)
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39:Wear eye/face protection.
S46:If swallowed, seek medical advice immediately and show this container or label.
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions/Safety data sheets.


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CATEGORIES

 APIs and Bioactives > Antibacterials, Fungicides

USEFUL LINKS

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