Phenol conjugation

Phenol is absorbed readily after inhalation exposure. Eight subjects were exposed to phenol vapors (1.6-5.2 ppm) for 8 hours (Piotrowski 1971). Subjects were exposed through a face mask in order to eliminate the possibility of percutaneous absorption. The concentration of phenol in inhaled and exhaled air was determined, and urine was analyzed for total phenol (phenol and phenol conjugates). 

Although mammals all metabolize phenol to the same metabolites, the amounts of each metabolite vary between species. For example, in the old world monkeys and prosimians, sulfation is the major phenol conjugation pathway, while in the new world monkeys, glucuronidation predominates (Mehta et al. 

Levels of total urinary phenol (phenol plus phenol conjugates) measured at the end of the workshift correlated with atmospheric phenol concentrations, suggesting that this measurement may be useful in predicting recent exposure to phenol vapor. 

Ramli JB, Wheldrake JF. 1981. Phenol conjugation in the desert hopping mouse, Notomys alexis. Comp Biochem Physiol 69C 379-381. 

This resulted in an enthalpy of reaction 39 of ca 70 klmol". While this is much larger than what would be predicted for the correction due to nitroso-phenol conjugation and the energies of most hydrogen bonds, the value for the related reaction for p-nitrophenol (equation 40) is the rather comparable 80 klmol". ... 

Legaz, M.E., de Armas, R., Pinon, D., Vicente, C. Relationships between phenolics, conjugated polyamines and sensitivity of sugar cane to smut (Ustilago scitaminea). J Exp Bot 1998 49 1723-1728. 

Disposition in the Body. Rapidly absorbed from the gastrointestinal tract and readily penetrates the skin. It is metabolised by conjugation to yield phenyl glucuronide and phenyl sulphate small amounts are oxidised to catechol and quinol which are also conjugated. Oxidation of these metabolites to quinones may tint the urine green. Acid-labile phenol conjugates are present endogenously in serum at concentrations of about 0.1 pg/ml. Phenol is a metabolite of benzene. 

Sulfate formation has also been demonstrated in a variety of other Invertebrates including spiders, scorpions and ticks (7), although the arachnids appear to possess no alternative glycosTde mechanism for phenol conjugation. 

P2. Pelkan, H. F., and Whipple, G. H., Studies of liver function. III. Phenol conjugation as influenced by liver injury and insufficiency. /. Biol. Chem. 60, 513 (1922). 

When the lone-pair electrons of oxygen in phenol conjugate with the ring, there is charge separation ... 

Species preparation analysis Hydroxymethyl Epoxides Diols Phenols Conjugates Comments Ref. 

Obied H et al (2008) Biosynthesis and biotransformations of phenol-conjugated oleosidic secoiridoids from Olea europaea L. Nat Prod Rep 25 1167-1179... 

Variations in the phenolic acid levels during growth and development of vegetables and cereals are not so homogeneous as those reported for fleshy fruits. It depends mainly on two parameters the nature of the plant organ (leaves, tubers, grains, etc.) and the subcellular localization of the phenolic conjugates that accumulate either as soluble forms in the vacuole or linked to the cell wall. 

Kurihara, U. Urinary metabolites from gamma- and beta-BHC in the mouse Chloro-phenol conjugates. 3rd Intemat. S)mip. Chem. Toxicol. Aspects of Environ. Qual., Tokyo, Japan (19-22 Nov. 1973). 

One of the compoimds commonly determined as its Phase 1 metabolite is benzene, whieh is metabolized to phenol in the body (see Chapter 23, Section 23.13 and Figure 23.16). The phenol metabolic product of benzene is measured in urine, usually by gas chromatography. The urine sample is treated with perchlorie aeid to hydrolyze phenol conjugates and the phenol is extracted into diisopropyl ether for ehromatographic analysis. Two other metabolic products of benzene, trans,trans-mueonie aeid and S-phenyl mercapturic acid, are now commonly measured as more-speeifie biomarkers of benzene exposure. 

---