Triclosan

Abstract

The title compound [systematic name: 5-chloro-2-(2,4-dichlorophenoxy)phenol], C12H7Cl3O2, is a biologically relevant molecule with biocide activity. It crystallizes in the chiral trigonal space group P3(1) with one molecule in the asymmetric unit. As in biological adducts, the two aromatic rings are almost mutually perpendicular, with this structural feature leading to a distribution of the pendant -OH groups to maximize the formation of O-H...O hydrogen bonds. This arrangement leads to a chain of molecules running parallel to the c axis and having a C(2) graph-set motif at its core.

Real-time monitoring of nanomolar binding to a cyclodextrin monolayer immobilized on a Si/SiO2/novolac surface using white light reflectance spectroscopy: The case of triclosan

“…Using the equation described in Section 2.3.1, the corresponding thickness assuming a refractive index of 1.42 for triclosan (Fig. 4a, 12 Stacking of triclosan has been recently documented in its X-ray crystal structure [26] that exhibits offset chains with p-p stacking interactions between the dichlorophenyl ring of one molecule and the chlorophenolyl ring of an adjacent molecule further stabilized by H-bonding between hydroxyl groups. In the present case, we anticipate that the H-bonding is negligible, but the hydrophobic p-p stacking is maximized in the aqueous environment.…”

“…The density of the triclosan layer as determined by XRR measurements (1.356 g/cm 3 ) is smaller than this of the crystalline pure compound as determined by X-ray crystallography (1.59 g/cm 3 ) [26] as expected and in very good agreement with that of the crystalline bCD/triclosan inclusion complex (1.352 g/cm 3 ) also determined by X-ray crystallography [17]. Finally, comparison of the AFM image (not shown) of the Si/SiO 2 /AZ surface before and after DMBUA deposition shows clear differences in grain size and overall morphology between the AZ and the AZ/.DMBUA surfaces, in support of the presence of DMBUA.…”

Conformations and intermolecular interactions pattern in solid chloroxylenol and triclosan (API of anti‐infective agents and drugs). A 35Cl NQR, 1H‐14 N NQDR, X‐ray and DFT/QTAIM study

“…Although the standard X‐ray structural data of chloroxylenol was available, at the moment we took up our study, the structure of triclosan was not known. Recently, Ramos published the data on triclosan structure but at 90 K; however, his results do not provide much information about the weak interactions, which have recently evoked enormous interest as they seem to explain the mechanisms determining biological activity.…”

“…An additional factor is a specific conformation with a dihedral angle of about 90° between the two phenyl rings, adopted by the diphenyl ether of triclosan when bound to inhibitors . The structure published by Ramos was resolved at a temperature much lower than those at which the investigation for inhibitors was made. In view of the above, it would be interesting to check if the adopted conformation in solid state is close to those described for the complexes with inhibitors and, moreover, if it is the same irrespective of temperature.…”

Towards Understanding Drugs on the Molecular Level to Design Drugs of Desired Profiles

“…A valuable example is triclosan (5-chloro-2-(2',4'-dichlorophenoxy)-phenol, TCS) active pharmaceutical ingredient (API) of a known potent wide spectrum of antibacterial, antimicrobial and antifungal agents used in many drugs as well as antiseptic or disinfectant formulations. The crystalline structure of TCS, which crystallizes in the space group P3 1 with one molecule in the asymmetric unit has been solved by XRD and refined to a final R-factor of 2.81% at room temperature [99] and 3.74% at 90 K [100]. The conformation adopted by diphenyl ether of TCS in solid is temperature independent, typical of diphenyl ethers but the opposite to that adopted when it is bound to different inhibitors.…”