2-Methoxy-4-methylphenol

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 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.

Chemical properties

2-Methoxy-4-methylphenol has a characteristic aromatic odor (sweet, spicy, slightly vanilla-like) and a somewhat bitter taste (vanilla-like).

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.

The Uses of 2-Methoxy-4-methylphenol

2-Methoxy-4-methylphenol is used for blending baking and smoked food flavors.

The Uses of 2-Methoxy-4-methylphenol

2-Methoxy-4-methylphenol is used in preparation of renewable bis(cyanate) esters.

Preparation

By methylation of homopyrocatechin using dimethyl sulfate and alkali; also by hydrogenation of vanillin.

Definition

ChEBI: 2-Methoxy-4-methylphenol is a member of phenols and a member of methoxybenzenes.

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%