Triclosan
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| Category | Antifungal |
| Catalog number | BBF-05906 |
| CAS | 3380-34-5 |
| Molecular Weight | 289.5 |
| Molecular Formula | C12H7Cl3O2 |
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Description
Triclosan is a broad-spectrum antibacterial and antifungal agent added in consumer products such as toothpaste, soaps, detergents, etc.
Specification
| Synonyms | Cloxifenolum; Irgasan |
| IUPAC Name | 5-chloro-2-(2,4-dichlorophenoxy)phenol |
| Canonical SMILES | C1=CC(=C(C=C1Cl)O)OC2=C(C=C(C=C2)Cl)Cl |
| InChI | 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 |
Properties
| Antibiotic Activity Spectrum | Bacteria; Fungi |
| Melting Point | 55-57°C |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 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. |
| Toxicity | LD50: 3700 mg/kg (Oral, Rat); LD50: 9300 mg/kg (Dermal, Rabbit). |
Reference Reading
1. Triclosan: antimicrobial mechanisms, antibiotics interactions, clinical applications, and human health
Prabin Shrestha, Yongmei Zhang, Wen-Jen Chen, Tit-Yee Wong J Environ Sci Health C Toxicol Carcinog. 2020;38(3):245-268. doi: 10.1080/26896583.2020.1809286.
The large-scale applications of Triclosan in industrial and household products have created many health and environmental concerns. Despite the fears of its drug-resistance and other issues, Triclosan is still an effective drug against many infectious organisms. Knowing the cross-interactions of Triclosan with different antibiotics, bacteria, and humans can provide much-needed information for the risk assessment of this drug. We review the current understanding of the antimicrobial mechanisms of Triclosan, how microbes become resistant to Triclosan, and the synergistic and antagonistic effects of Triclosan with different antibiotics. Current literature on the clinical applications of Triclosan and its effect on fetus/child development are also summarized.
2. Triclosan: An Update on Biochemical and Molecular Mechanisms
Mohammad A Alfhili, Myon-Hee Lee Oxid Med Cell Longev. 2019 May 2;2019:1607304. doi: 10.1155/2019/1607304. eCollection 2019.
Triclosan (TCS) is a synthetic, chlorinated phenolic antimicrobial agent commonly used in commercial and healthcare products. Items made with TCS include soaps, deodorants, shampoos, cosmetics, textiles, plastics, surgical sutures, and prosthetics. A wealth of information obtained from in vitro and in vivo studies has demonstrated the therapeutic effects of TCS, particularly against inflammatory skin conditions. Nevertheless, extensive investigations on the molecular aspects of TCS action have identified numerous adversaries associated with the disinfectant including oxidative injury and influence of physiological lifespan and longevity. This review presents a summary of the biochemical alterations pertaining to TCS exposure, with special emphasis on the diverse molecular pathways responsive to TCS that have been elucidated during the present decade.
3. Preimplantation triclosan exposure alters uterine receptivity through affecting tight junction protein†
Guangzhu Dong, Rundong Sun, Rui Zhang, Yufeng Qin, Chuncheng Lu, Xinru Wang, Yankai Xia, Guizhen Du Biol Reprod. 2022 Jul 25;107(1):349-357. doi: 10.1093/biolre/ioac092.
Triclosan is a broad-spectrum antibacterial agent and widely exists in environmental media and organisms. Triclosan exposure has been reported to have adverse effects on reproduction including embryo implantation disorder. During the embryo implantation window, it is vital that the endometrium develops into a receptive state under the influence of ovarian hormones. However, the effect of triclosan on embryo implantation and endometrial receptivity remains unclear. In the current study, we found a decreased embryo implantation rate, serum estrogen, and progesterone levels in mice exposed to triclosan from gestation days 0.5 to 5.5. Through RNA sequencing (RNA-seq), we identified nearly 800 differentially expressed genes, which were enriched in various pathways, including uterus development, inflammatory response, and immune system processes. Among those enriched pathways, the tight junction pathway is essential for the establishment of the receptive state of the endometrium. Then, genes involved in the tight junction pathway, including Cldn7, Cldn10, and Crb3, were validated by quantitative real-time polymerase chain reaction and the results were consistent with those from RNA-seq. Through immunofluorescence staining and western blotting, we confirmed that the tight junction protein levels of CLDN7 and CRB3 were increased. All these findings suggest that preimplantation triclosan exposure reduces the rate of embryo implantation through upregulating the expression of the tight junction genes and affecting the receptivity of the endometrium. Our data could be used to determine the sensitive time frame for triclosan exposure and offer a new strategy to prevent implantation failure.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H7Cl3O2
Molecular Weight (Monoisotopic Mass): 287.9512 Da
Molecular Weight (Avergae Mass): 289.542 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H7Cl3O2
Molecular Weight (Monoisotopic Mass): 287.9512 Da
Molecular Weight (Avergae Mass): 289.542 Da
LC-MS/MS Spectrum - LC-ESI-QFT , negative
Experimental Conditions
Instrument Type: LC-ESI-QFT
Ionization Mode: negative
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H7Cl3O2
Molecular Weight (Monoisotopic Mass): 287.9512 Da
Molecular Weight (Avergae Mass): 289.542 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H7Cl3O2
Molecular Weight (Monoisotopic Mass): 287.9512 Da
Molecular Weight (Avergae Mass): 289.542 Da
Mass Spectrum (Electron Ionization)
13C NMR Spectrum
Experimental Conditions
Solvent: H2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
