Introduction
Phenols, also known as phenolic acids, are aromatic organic compounds with the formula C6H5OH. They are usually volatile white crystalline solid. The molecules consist of phenyl group bonded to hydroxyl group. As precursors to many materials and useful compounds, phenols are important industrial products, which are mainly used for synthesis of plastics and related materials. Phenols are also essential for the productions of polycarbonates, epoxy resins, phenolic resins, nylons, detergents, herbicides such as phenoxy herbicides and many pharmaceutical preparations.
Applications
Medical use: Phenol is a common precursor for a large number of drugs, the most notable is aspirin. Phenol liquids are often used for permanent treatment of ingrown toe and finger nails, which is a procedure called chemical matrixectomy and has become a choice for chemical matrixectomies performed by podiatrists. Phenol is also used as a preservative for certain vaccines. Phenol spray is used medicinally to help get relief from sore throats. It is an active ingredient of some oral analgesics, such as Chloraseptic spray, which is commonly used for the temporary treatment for pharyngitis.
Biochemistry use: The ortho-isobornyl phenol derivatives 4-methyl-2,6-diisobornylphenol possesses antithrombotic and antiplatelet properties under conditions of intravascular thrombosis and acute cerebral ischemia. 4-Methyl-2,6-diisobornylphenol can prevent intravascular thrombosis by reducing platelet aggregation and improving antiplatelet activity of the vascular wall. Thus, 4-methyl-2,6-diisobornylphenol is a new promising compound that produces significant effects on the thrombovascular homeostasis and characterized by low toxicity. Radioprotective and anticlastogenic properties of the phenol derivative monoterpene thymol (TOH) are studied by using gamma irradiation in Swiss albino mice. Gamma-irradiated mice pretreated with TOH for three consecutive days show a significant decrease in LPO levels and antigenictoxicity. This effect may be attributed to several possible mechanisms, such as the normalization of intracellular antioxidant levels and free radical scavenging activity.
Organic chemistry: DCC reactions between N-arylglycine esters and phenols can occur by copper catalysis using DTBP as an oxidant. Under optimized conditions, a series of N-arylglycine esters are successfully reacted with various phenols or 1,3,5-trimethoxybenzenes to give the desired α-aryl α-amino acid esters, which have High ortho regioselectivities with excellent yields.
Fig.1. Dehydrogenative cross-coupling reaction between N-aryl α-amino acid esters and phenols or phenol derivative
Phenol derivatives can undergo chemoselective reaction in HRP-catalyzed polymerization in aqueous acetone. The polymer is cross-linked at a lower temperature. The resulting polymer has a methacryloyl group in the side chain and thus is expected to have various applications as a highly reactive polymer. For example, the polymer is subjected to photochemical hardening, indicating that this polymer may be used as a new photosensitive material.
Fig.2. Chemoselective polymerization of a phenol derivative
References
- Salman M, Zhu Z Q, Huang Z Z. Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters[J]. Organic letters, 2016, 18(7): 1526-1529.
- Uyama H, Lohavisavapanich C, Ikeda R, et al. Chemoselective polymerization of a phenol derivative having a methacryl group by peroxidase catalyst[J]. Macromolecules, 1998, 31(2): 554-556.
