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Cat. Number
080458460962715
Chemical Name
Guaiacol
References
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 Ambient in continental US; may vary elsewhere
SMILES 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 Chem 262 6266-6279 (1987).

Doerge, D.R., Divi, R.L., and Churchwell, M.I. Identification of the colored guaiacol oxidation product produced by peroxidases. Anal Biochem 250 10-17 (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. Biochemistry 36 9349-9355 (1997).

Kulmacz, R.J., and Lands, W.E.M. Quantitative similarities in the several actions of cyanide on prostaglandin H synthase. Prostaglandins 29 175-190 (1985).

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Description

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 Chem 262 6266-6279 (1987).

2 Doerge, D.R., Divi, R.L., and Churchwell, M.I. Identification of the colored guaiacol oxidation product produced by peroxidases. Anal Biochem 250 10-17 (1997).

3 Kulmacz, R.J., and Lands, W.E.M. Quantitative similarities in the several actions of cyanide on prostaglandin H synthase. Prostaglandins 29 175-190 (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. Biochemistry 36 9349-9355 (1997).

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