Organic Chemistry By: Jordan de Jong & Owen Rowe-Codner Triclocarban Organic Chemistry By: Jordan de Jong & Owen Rowe-Codner

C13H9Cl3N2O

History Triclocarban has been used as effective antiseptics in soap since the 1960's! Not stated who synthesized this molecule.

Synthesis of Triclocarban There are two commercial routes used for the production of triclocarban, using the reaction of isocyanates with nucleophiles such as amines to form ureas. 4-chlorophenylisocyanate is reacted with 3,4-dichloroaniline 3,4-dichlorophenylisocyanate is reacted with 4-chloroaniline The purity specification in the draft USP monograph for triclocarban is: not less than 97.0% w/w. The purity of commercial production is greater 98% w/w.[1 -a colorless crystalline compound that is the main nitrogenous breakdown product of protein metabolism in mammals and is excreted in urine.

Problems associate with the molecule… 1) Resistant Bacteria Problems associate with the molecule… This substance is not very soluble in water, but is fat-soluble and easily able to cross cell membranes. Once inside the cell, triclocarban poisons a specific enzyme that many bacteria and funguses need for survival. This prevents the bacteria from manufacturing fatty acids it needs for building cell membranes and other vital functions. Humans don't have this enzyme, so triclocarban is harmless to them. One molecule of triclocarban permanently disables an ENR molecule, which explains why it has powerful antibiotic action even at very low concentrations. The highly specific way that triclocarban kills has researchers concerned about its role in fostering antibiotic-resistant strains of bacteria. Researchers have recently demonstrated that mutations in the bacterial gene that produces ENR can produce triclocarban-resistant bacteria. It is now so widespread in the environment, it's likely that new antibiotics targeting ENR would be ineffective.

2) Pregnant Women Pycke, a research scientist at Arizona State University (ASU), states that there is a growing body of evidence showing that the compound can lead to developmental and reproductive problems in animals and potentially in humans. Also, some research suggests that the additives could contribute to antibiotic resistance, a growing public health problem. Widespread exposure to these compounds could cause a subtle but large-scale shift in birth sizes. Mr. Pycke explains how this molecule transfers throughout the body, “We looked at the exposure of pregnant women and their fetuses to triclocarban, one of the most commonly used germ-killers in soaps and other everyday products,” says Benny Pycke, Ph.D. “We found triclocarban in all of the urine samples from the pregnant women that we screened. We also detected it in about half of the umbilical cord blood samples we took, which means it transfers to fetuses. Triclocarban was also in many of the samples.”

Side effects of Triclocarban Abnormalities with endocrine/thyroid/hormone system Weakening of the immune system Birth Defects Uncontrolled cell growth Weight loss

Properties Boiling Point 344.2°C at 760 mmHg Melting Point 254°C to 256°C Appearance White crystals or powder Molecular weight 315.59 Polar or Non-Polar Polar

Uses in society… -This compound is used in more than 2,000 everyday products marketed as antimicrobial. Soaps, cosmetics, Dental care, Deodorant, First aid care, Other personal care, Kitchen ware, Children’s toy, Clothes… It is “more than play” for these pre-school toys, when these children are being exposed to this molecule. For babies, it is especially dangerous as their bodies are building an immune system and being exposed to germs during the initial years is, beneficial! Derivatives Triclosan, similar in its uses and mechanism of action to triclocarban, is an antibacterial and antifungal agent found in consumer products.

Citations… http://www.acs.org/content/acs/en/pressroom/newsreleases/2014/august/pregn ant-women-and-fetuses-exposed-to-antibacterial-compounds-face-potential-health- risks.html http://antoine.frostburg.edu/chem/senese/101/consumer/faq/triclosan.shtml https://pubchem.ncbi.nlm.nih.gov/compound/Triclocarban#section=Probable- Routes-of-Human-Exposure http://www.home-remedies-pure-and-simple.com/Antibacterial-Soap.html