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The unique value of 4-ethyl-2-methoxyphenol lies not only in its smoky aroma, but also in the "split personality" behavior of its molecules at the interface. This amphiphilic molecule simultaneously possesses a hydrophobic ethyl benzene ring framework and hydrophilic phenolic hydroxyl and methoxy groups, enabling it to spontaneously assemble into a dynamic monolayer at the gas-water interface. Its π-A isotherm reveals astonishing compressibility. What's particularly rare is that its phenolic hydroxyl groups can precisely anchor on the surface of lignocellulose matrix through specific hydrogen bonds, while the ethyl group acts as a molecular spacer to effectively prevent excessive π-π stacking - this delicate balance makes it an excellent molecular probe for studying the interface compatibility of biomass components, far beyond its traditional understanding as a fragrance or antioxidant.
Additional information of chemical compound:
|
Chemical Formula |
C9H12O2 |
|
Exact Mass |
152.08 |
|
Molecular Weight |
152.19 |
|
m/z |
152.08 (100.0%), 153.09 (9.7%) |
|
Elemental Analysis |
C, 71.03; H, 7.95; O, 21.02 |
|
Melting point |
15℃(lit.) |
|
Boiling point |
234-236℃(lit.) |
|
Density |
1.063 g/mL at 25℃(lit.) |
|
Storage conditions |
2-8℃ |
|
|
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4‑Ethyl‑2‑methoxyphenol,The Chinese name is 4-ethyl-2-methoxyphenol, commonly known as 4-ethylguaiacol. CAS registration number: 2785-89-9, molecular formula: C9H1O2, molecular weight: 152.19, FEMA number: 2436. It is an important phenolic aromatic compound that widely exists in fermented foods, alcoholic beverages, and wood smoke products in nature. It is also an important raw material for the artificial synthesis of fragrances and pharmaceutical intermediates.
This substance is a colorless to pale yellow oily liquid at room temperature, with typical smoky, clove, woody, and mild medicinal aromas. It has a low aroma threshold and a long-lasting fragrance. It is slightly soluble in water and easily soluble in ethanol, propylene glycol, oils, and most organic solvents. It is prone to oxidation and darkening in air, so it is often necessary to avoid light, seal, and add antioxidants during storage and application.
From a molecular structure perspective, its benzene ring contains phenolic hydroxyl (- OH), methoxy (- OCH3), and ethyl (- C2H5) groups simultaneously. This structure endows it with aromatic odor, antioxidant properties, lipophilicity, and chemical reactivity. It can be used directly as a fragrance or as an organic synthesis block to participate in esterification, etherification, sulfonation, coupling and other reactions, thereby extending its applications to various fields such as food, daily chemical, pharmaceutical, and materials.
Main uses in the food industry
The most core and largest application area of this substance is in the food processing industry, where it is widely used as a legal edible spice, flavor enhancer, antioxidant, and quality marker. It has been approved as a natural equivalent flavor by many authorities such as the US FDA, the EU essence Office, and the Chinese GB 2760 Food Additive Standard, and can be safely used for flavoring various foods.
It is a key characteristic flavor substance of whisky, brandy, rum, red wine, sake and some Maotai flavor Baijiu. During the aging process in oak barrels, lignin in the wood degrades and generates phenolic compounds, giving the wine a typical smoky, pungent, woody, and clove complex aroma, which is an important source of flavor recognition for high-end aged wines.
In industrial production, it is often used to simulate the aroma of aged oak barrels and shorten the aging cycle of alcoholic beverages; Enhance the aroma layering of low alcohol wine, blended wine, and fruit wine; Improve the aftertaste of Baijiu, and enhance the coordination of Maotai flavor, Zhai flavor, and Chen flavor; As an evaluation index for the fermentation quality of wine and apple cider.
Seasoning and Flavoring Fermented Foods
Traditional fermented seasonings such as soy sauce, bean paste, oyster sauce, and fish sauce naturally contain 4-ethyl-2-methoxyphenol, which is an important contributing substance to the formation of "sauce aroma, ester aroma, and smoky aroma". In the modern seasoning industry, this compound is used to enhance the richness and fermentation flavor of soy sauce; Improve the base aroma of compound seasonings, hot pot base ingredients, and braised ingredients; Improve the aroma coordination of Fermented bean curd, lobster sauce and pickles.
The traditional wood smoking process will produce harmful substances such as polycyclic aromatic hydrocarbons, and the use of smoke essence with this substance as the core can significantly improve food safety while ensuring aroma. It is widely used for:
Smoked meat, smoked sausages, smoked fish, bacon, ham and other meat products; Smoked dried tofu, vegetarian meat and other plant-based protein products; Barbecue seasoning powder, smoked potato chips, casual snacks.
Baking food, coffee, and chocolate flavor modification
In the baking field, 4 ‑ ethyl guaiacol can provide warm baking fragrance, woody fragrance and a slight sense of vanilla. It is often used in combination with vanillin, ethyl maltol and eugenol for bread, cake, biscuits, coffee essence, cocoa products, etc., to improve the fullness and durability of the overall flavor.
The phenolic hydroxyl structure endows it with certain free radical scavenging ability and inhibits lipid peroxidation, which can delay oil oxidation and prevent meat products from spoiling. It is used as an auxiliary antioxidant in some oily foods, fried foods, and meat products. When combined with vitamin E, tea polyphenols, rosemary extract, etc., it can enhance the preservation effect.
Food analysis standard
Due to its iconic role in fermented foods and alcoholic beverages, this compound is often used as a standard for GC-MS, GC-O, HPLC analysis, for quality control, origin identification, and flavor fingerprint construction of soy sauce, wine, whiskey, and other products.
This section mainly refers to sources:
Sigma‑Aldrich. 4‑Ethyl‑2‑methoxyphenol Analytical Standard Product Sheet. 2025.
FooDB. Compound: 4‑Ethyl‑2‑methoxyphenol (FDB019887). https://foodb.ca/
Chinese National Standard GB 2760-2014 Food Safety National Standard for the Use of Food Additives
NIST Chemistry WebBook. Phenol, 4‑ethyl‑2‑methoxy‑ (CAS 2785‑89‑9).
Use in daily chemical essence and personal care products
This material has a unique smoky woody fragrance. It is a typical base note fragrance fixing component in the daily chemical essence formula, and is widely used in perfume, aromatherapy, cleaning products, air fresheners, candles, fabric care products, etc.
Perfume and fragrance products
In perfume blending, it is often used in: woody, oriental, leather, tobacco perfume to enhance the deep, warm, smoke feeling; As an important base fragrance component of men's perfume, it can enhance the sense of composure and duration of fragrance retention; Compound with sandalwood, cedar, patchouli, coumarin, vanilla, etc. to construct a high-end fragrance structure.
Personal care and cleaning products
Due to its gentle aroma and certain antibacterial properties, it is used in soap, shower gel, shampoo, hair conditioner, body lotion, hand sanitizer, etc., giving the product a woody medicinal and smoky aroma, while also improving its oxidative stability.
Home fragrances and environmental products
In aromatherapy essential oils, rattan aromatherapy, candles, air fresheners, and car fragrances, it can create a natural, warm, and stable indoor atmosphere, especially suitable for autumn and winter fragrances and wooden home styles.
Antioxidant stabilizer for daily chemical products
The phenolic structure can inhibit the oxidation and discoloration of oils, plant extracts and active ingredients in cosmetics, extend the shelf life of products, and serve as an auxiliary antioxidant in cream, lotion and essential oil products.
This section mainly refers to sources:
Leffingwell & Associates. Odor and Uses of 4‑Ethyl‑2‑methoxyphenol.
MarketPublishers. Global 4‑Ethyl‑2‑methoxyphenol Market Report 2024‑2030.
ChemicalBook. 4‑Ethyl‑2‑methoxyphenol: Properties, Uses and Production.
Applications in the fields of medicine, health products, and biological activity
4-Ethyl-2-methoxyphenol is not only a fragrance, but also an important pharmaceutical intermediate with certain biological activity. It has research value in the fields of expectorant, anti-inflammatory, antibacterial, antioxidant, neuroprotective, etc.
Synthetic expectorant and cough suppressant drugs
This compound is an important intermediate for the preparation of guaiacol based expectorants. It can be used to prepare commonly used clinical drugs such as potassium guaiacol sulfonate and calcium guaiacol sulfonate through sulfonation, salt formation, and other reactions. It is used for phlegm accumulation and cough caused by colds, bronchitis, chronic obstructive pulmonary disease, etc., by diluting sputum and promoting expectoration.
Synthesis of anti-inflammatory and analgesic drug derivatives
This substance can undergo esterification reactions with nonsteroidal anti-inflammatory drugs such as ibuprofen and aspirin, forming a prodrug with higher lipid solubility and lower irritation. It has both anti-inflammatory, analgesic, and expectorant effects and is suitable for symptoms of respiratory inflammation accompanied by fever and pain.
Research on Antioxidant and Neuroprotective Activities
Modern pharmacological studies have shown that this substance can scavenge DPPH and ABTS free radicals, inhibit lipid peroxidation and the release of inflammatory factors TNF alpha and IL-6, and exhibit neuroprotective potential in cell models. It is considered a potential lead compound for anti neuroinflammation, anti cerebral ischemia, and improving cognitive function.
Synthetic external antibacterial and skin care preparations
It has a certain inhibitory effect on Staphylococcus aureus, Escherichia coli, Candida albicans, etc. It can be used as an auxiliary ingredient in external disinfection and antibacterial products, as well as in soothing skincare products, acne removal products, oral care products, etc.
Veterinary drugs and feed additives
In animal husbandry, it can be used as a flavor improver and antioxidant to improve feed palatability, reduce oil oxidation, and have a certain auxiliary protective effect on the respiratory health of livestock and poultry.
This section mainly refers to sources:
ACS Omega. A New Efficient Method for Isolation of 4‑Ethyl‑2‑methoxyphenol from Lignin Pyrolysis Oil. 2021.
Journal of Agricultural and Food Chemistry. Biological Activities of 4‑Ethylguaiacol and Derivatives.
Entropy Chemistry Database Pharmaceutical applications and synthetic routes of 4-ethyl-2-methoxyphenol.
Smolecule. 4‑Ethyl‑2‑methoxyphenol: Pharmacological Activities.
Applications in the fields of organic synthesis, chemical engineering, and materials
Due to the presence of active phenolic hydroxyl groups in the molecule, this substance is an important intermediate in organic synthesis and can participate in various classical organic reactions, resulting in a large number of high value-added products.
Synthetic spice esters and ether derivatives
Through esterification and etherification, 4-ethyl-2-methoxyphenyl acetate, benzoate, methyl ether, ethyl ether, etc. can be produced. These derivatives have softer aroma and higher stability, and are widely used in food and daily chemical essence.
Synthetic dyes, pesticides, and additives
Phenolic structures can be used as coupling components in diazotization reactions for the preparation of small amounts of aromatic dyes; It can also be used as a pesticide intermediate for synthesizing fungicides, insecticides, and plant growth regulators.
Polymer materials and resin modification
It can be used as a phenolic monomer to participate in the synthesis of phenolic resins, epoxy resins, and polyurethane, improving the material's oxidation resistance, heat resistance, and mechanical strength; It can also be used as a chain transfer agent and stabilizer in plastic and rubber processing.
Biomass refining and lignin conversion
This substance is one of the main products of lignin pyrolysis and liquefaction, and has received widespread attention in the fields of biomass energy, bio based chemicals, and bio aviation fuels in recent years. It is an important target product for achieving high-value utilization of agricultural and forestry waste.
This section mainly refers to sources:
Industrial & Engineering Chemistry Research. Lignin‑Derived Phenolic Compounds: 4‑Ethylguaiacol.
Journal of Analytical and Applied Pyrolysis. Formation of 4‑Ethyl‑2‑methoxyphenol from Lignin.
IChemistry. Overview of Chemical Applications of 4-Ethyl-2-methoxyphenol
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