Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serve as a reducing co-substrate for COX reactions.1 The color yield per peroxide at 470 nm is 6,650 (M peroxide reduced)-1 cm-1.2,3,4 Two moles of guaiacol are oxidized for each mole of hydroperoxide reduced by the peroxidase. The resulting guaiacol chromophore can be used for the colorimetric determination of hydroperoxidase activity.
1
Markey, C.M., Alward, A., Weller, P.E., et al. Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities. J Biol Chem2626266-6279(1987).
2
Doerge, D.R., Divi, R.L., and Churchwell, M.I. Identification of the colored guaiacol oxidation product produced by peroxidases. Anal Biochem25010-17(1997).
3
Kulmacz, R.J., and Lands, W.E.M. Quantitative similarities in the several actions of cyanide on prostaglandin H synthase. Prostaglandins29175-190(1985).
4
Marquez, L.A., and Dunford, H.B. Mechanism of the oxidation of 3,5,3',5'-tetramethylbenzidine by myeloperxidase determined by transient-and steady-state kinetics. Biochemistry369349-9355(1997).
Formal Name
2-methoxy phenol
CAS Number
90-05-1
Molecular Formula
C7H8O2
Formula Weight
124.1
Formulation
A colorless liquid
Purity
≥98%
λmax
220, 277 nm
Stability
1 year
Storage
Room temperature
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
COc1ccccc1O
Background Reading
Markey, C.M., Alward, A., Weller, P.E., et al. Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities. J Biol Chem2626266-6279(1987).
Doerge, D.R., Divi, R.L., and Churchwell, M.I. Identification of the colored guaiacol oxidation product produced by peroxidases. Anal Biochem25010-17(1997).
Marquez, L.A., and Dunford, H.B. Mechanism of the oxidation of 3,5,3',5'-tetramethylbenzidine by myeloperxidase determined by transient-and steady-state kinetics. Biochemistry369349-9355(1997).
Kulmacz, R.J., and Lands, W.E.M. Quantitative similarities in the several actions of cyanide on prostaglandin H synthase. Prostaglandins29175-190(1985).