Description
2-Methoxy-4-methylphenol has a characteristic aromatic odor
(sweet, spicy, slightly vanilla-like) and a somewhat bitter taste
(vanilla-like). May be prepared by methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of
vanillin.
Chemical Properties
2-Methoxy-4-methylphenol has a characteristic aromatic odor (sweet, spicy, slightly vanilla-like) and a somewhat bitter
taste (vanilla-like).
Chemical Properties
Clear colorless to slightly yellow liquid
Occurrence
Occurs in beechwood tar; also identified in the essential oils of ylang-ylang, jasmine and anise seeds; it is
one of the active constituents of creosote. Reported found in Gruyere cheese, smoked fish, cured pork, beer, rum, bourbon whiskey,
malt and Scotch whiskey, sherry, white and red wine, cocoa, coffee, tea, mushrooms, mango, pear brandy, malt, wort, dried bonito,
Bourbon vanilla, cuttlefish and green maté.
Uses
2-Methoxy-4-methylphenol is used for blending baking and smoked food flavors.
Uses
2-Methoxy-4-methylphenol is used in preparation of renewable bis(cyanate) esters.
Definition
ChEBI: 2-Methoxy-4-methylphenol is a member of phenols and a member of methoxybenzenes.
Preparation
By methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.
Production Methods
With three distinct oxygenated functional groups (aldehyde, ether, and hydroxyl), VAN can undergo selective hydrodeoxygenation to produce 2- methoxy-4-methylphenol (MMP), a promising candidate for future biofuel applications and its use in fragrances and intermediate in pharmaceutical synthesis. Kumar et al. developed stable, cost-effective Ni nanoparticles supported on montmorillonite (MMT) clay, which was synthesized for eco-friendly, alcohol-mediated catalytic transfer hydrodeoxygenation of VAN to MMP. The Ni(10%)/MMT catalyst achieved >99% VAN conversion and 95.2% MMP selectivity using isopropanol (IPA) as a solvent and hydrogen donor[1].
References
[1] Atul Kumar, Prof. Dr. Rajendra Srivastava, Dr. Rajaram Bal. “Ni Nanoparticles Supported Montmorillonite Clay for Selective Catalytic Transfer Hydrodeoxygenation of Vanillin into 2-Methoxy-4-methylphenol.” ChemCatChem 16 9 (2024).
Aroma threshold values
Detection: 90 ppb. Aroma characteristics at 1.0%: smoky, sweet, phenolic, vanilla, spicy clove with a floral
carnation nuance.
Taste threshold values
Taste characteristics at 1.0 to 1.25 ppm: sweet phenolic, spice, vanilla, medicinal, clove-like, smoky, guaia col-like with a woody, phenolic nuance.
General Description
2-Methoxy-4-methylphenol is the major component of black-ripe table olive aroma. It is the major anti-inflammatory compound in bamboo vinegar. Kinetics of reaction of 2-methoxy-4-methylphenol with chlorine atoms was studied.
Biochem/physiol Actions
Odor at 1.0%
