Molecular structure of Guaiacol, CAS Number: 90-05-1
Guaiacol (CAS 90-05-1)
Alternate Names:
2-Methoxyphenol
Application:
Guaiacol is a phenolic natural product and reducing co-substrate for COX reactions
CAS Number:
90-05-1
Purity:
>98%
Molecular Weight:
124.14
Molecular Formula:
C7H8O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
QUICK LINKS
Ordering Information
Description
Technical Information
Safety Information
SDS & Certificate of Analysis
Guaiacol is a natural compound found in Guaiac resin and lignin oxidation. It acts as a co-substrate for cyclooxygenase (COX) enzymes, which are peroxidases that use heme iron for oxidation. This means that Guaiacol can be readily oxidized by COX enzymes. The color yield per peroxide at 470 nm is 6,650 (M peroxide reduced)-1 cm-1. For every mole of hydroperoxide reduced by the peroxidase, two moles of guaiacol are oxidized. The resulting guaiacol chromophore can be used to measure hydroperoxidase activity using colorimetric methods.
Guaiacol (CAS 90-05-1) References
- Formation of guaiacol in chocolate milk by the psychrotrophic bacterium Rahnella aquatilis. | Jensen, N., et al. 2001. Lett Appl Microbiol. 33: 339-43. PMID: 11696092
- An unexpected side reaction in the guaiacol assay for peroxidase. | Taurog, A., et al. 1992. Anal Biochem. 205: 271-7. PMID: 1443572
- Polymerization of guaiacol and a phenolic beta-O-4-substructure by Trametes hirsuta laccase in the presence of ABTS. | Rittstieg, K., et al. 2003. Biotechnol Prog. 19: 1505-9. PMID: 14524712
- A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.). | Saini, RK. and Hassanali, A. 2007. J Chem Ecol. 33: 985-95. PMID: 17404820
- Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina. | Deng, ZS., et al. 2008. Org Lett. 10: 1119-22. PMID: 18284247
- Crystal structure of guaiacol and phenol bound to a heme peroxidase. | Murphy, EJ., et al. 2012. FEBS J. 279: 1632-9. PMID: 22093282
- Simultaneous analysis of guaiacol and vanillin in a vanilla extract by using high-performance liquid chromatography with electrochemical detection. | Takahashi, M., et al. 2013. Biosci Biotechnol Biochem. 77: 595-600. PMID: 23470765
- Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII). | Scozzafava, A., et al. 2015. J Enzyme Inhib Med Chem. 30: 586-91. PMID: 25373500
- Structural characterization of lignin: a potential source of antioxidants guaiacol and 4-vinylguaiacol. | Azadfar, M., et al. 2015. Int J Biol Macromol. 75: 58-66. PMID: 25603142
- Hydrodeoxygenation of Guaiacol over Ceria-Zirconia Catalysts. | Schimming, SM., et al. 2015. ChemSusChem. 8: 2073-83. PMID: 26036450
- Simultaneous Quantification of Chlorpheniramine, Phenylephrine, Guaifenesin in Presence of Preservatives with Detection of Related Substance Guaiacol in their Cough Syrup by RP-HPLC and TLC-Densitometric Methods. | Boltia, SA., et al. 2019. J Chromatogr Sci. 57: 552-559. PMID: 30994883
- Establishment of quantitative PCR assays for the rapid detection of Alicyclobacillus spp. that can produce guaiacol in apple juice. | Li, H., et al. 2021. Int J Food Microbiol. 360: 109329. PMID: 34275638
- Guaiacol augments quorum quenching potential of ciprofloxacin against Pseudomonas aeruginosa. | Mangal, S., et al. 2022. J Appl Microbiol. 133: 2235-2254. PMID: 35984044
- Oxidation of guaiacol by lignin peroxidase. Role of veratryl alcohol. | Koduri, RS. and Tien, M. 1995. J Biol Chem. 270: 22254-8. PMID: 7673205
Substrate of:
Enzyme.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Guaiacol, 25 g | sc-205337 | 25 g | $25.00 | |||
Guaiacol, 50 g | sc-205337C | 50 g | $36.00 | |||
Guaiacol, 100 g | sc-205337A | 100 g | $56.00 | |||
Guaiacol, 500 g | sc-205337B | 500 g | $143.00 |