2-Methoxy-4-methylphenol Property

Melting point:

5 °C (lit.)

Boiling point:

221-222 °C (lit.)

Density 

1.092 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.537(lit.)

FEMA 

2671 | 2-METHOXY-4-METHYLPHENOL

Flash point:

211 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

10.27±0.18(Predicted)

form 

Liquid

color 

colorless to light yellow

Specific Gravity

1.091.092

Odor

at 10.00 % in dipropylene glycol. spicy clove vanilla phenolic medicinal leathery woody smoky burnt

Odor Type

spicy

Water Solubility 

Slightly soluble in water.

JECFA Number

715

Merck 

14,2571

BRN 

1862340

Dielectric constant

11.0

LogP

1.65

CAS DataBase Reference

93-51-6(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2-methoxy-4-methyl-(93-51-6)

EPA Substance Registry System

Phenol, 2-methoxy-4-methyl- (93-51-6)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-24/25

RIDADR 

2810

WGK Germany 

3

RTECS 

GP1755000

F 

10

TSCA 

Yes

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29095090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Methoxy-4-methylphenol Chemical Properties,Usage,Production

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.

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. 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.

Definition

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.

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%