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.
2-Methoxy-4-methylphenol is a clear colorless to slightly yellow liquid or viscous, yeelowish oil, solidifying in the cold. The prismatic crystals melt at 6° C. Sp.Gr. 1.10. B.P. 222° C. Very slightly soluble in water, soluble in
alcohol and oils. Sweet-spicy, phenolic-leathery odor with distinctly Vanilla-1ike undertones, balsamicwarm sweetness, but overall too medicinal to become classified as a versatile, floral-balsamic ingredient.
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.
2-Methoxy-4-methylphenol is used for blending baking and smoked food flavors. Excellent additive and modifier in artificial Ylang-Ylang, Cassie-bases, Jasmin bases, Lily, Gardenia, etc. Finds use in flavor compositions for imitation Vanilla, Clove, various fruit compositions, Rum flavors, etc. and in Nut-Nougat flavor bases. Concentration will be about 0.02 to 1 ppm in the finished consumer product. In beverages, however, it may be as high as 10 to 20 ppm.
ChEBI: 2-Methoxy-4-methylphenol is a member of phenols and a member of methoxybenzenes. It is used in preparation of renewable bis(cyanate) esters.
By methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.
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].
[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).
Detection: 90 ppb. Aroma characteristics at 1.0%: smoky, sweet, phenolic, vanilla, spicy clove with a floral
carnation nuance.
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.
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.
