Eugenol
[CAS# 97-53-0]

Identification

• Classification: Organic raw materials >> Ether compounds and their derivatives >> Halogenation, sulfonation, nitration or nitrosation of ethers, ether alcohols, ether phenols
• Name: Eugenol
• Synonyms: 4-Allyl-2-methoxyphenol; 1-Allyl-3-methoxy-4-hydroxybenzene
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20
• CAS Registry Number: 97-53-0
• EC Number: 202-589-1
• FEMA: 2467
• SMILES: COC1=C(C=CC(=C1)CC=C)O

Properties

• Density: 1.066
• Melting point: -12--10 °C
• Boiling point: 254 °C
• Refractive index: 1.54-1.542
• Water solubility: slightly soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319
• Safety Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1B	H317
Aspiration hazard	Asp. Tox.	1	H304
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	2	H401
Acute toxicity	Acute Tox.	5	H303
Flammable liquids	Flam. Liq.	4	H227
Skin mild irritation	Skin Mild Irrit. 99	3	H316
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

The use of eugenol dates back centuries, primarily in traditional medicine and as a spice. French chemist Charles-Frédéric Gerhardt first isolated eugenol from clove oil (*Syzygium aromaticum*) in 1844. This discovery marked a major advance in the understanding of its properties and potential uses.

Eugenol (C10H12O2) is a colorless to pale yellow oily liquid with a distinctive clove smell. It is a phenylpropene that contains a methoxy group and a double bond, which contributes to its aroma and reactivity. Eugenol is slightly soluble in water but readily soluble in organic solvents, making it useful in a variety of applications.

Eugenol is widely used in dentistry for its analgesic and antiseptic properties. It relieves pain and reduces infection in dental treatments such as fillings and root canals. It is combined with zinc oxide to form zinc oxide eugenol (ZOE), which is used in temporary fillings and impression materials. Eugenol is found in over-the-counter products for the treatment of minor burns, insect bites, and muscle aches. Its anesthetic properties provide quick relief from pain, while its antiseptic properties help prevent infection. Eugenol has anti-inflammatory properties and can be used to treat conditions such as arthritis. It also has strong antimicrobial activity, making it effective against bacteria, fungi, and viruses in pharmaceutical formulations.

Eugenol is a key ingredient in perfumes and personal care products, with a warm, spicy scent. It enhances the aroma of a variety of products, including lotions and soaps. In the food industry, eugenol produces a rich, spicy flavor for baked goods, sauces, and condiments. Its use also extends to the tobacco industry, where it flavors cigarettes and cigars for an improved sensory experience.

Eugenol is a natural insect repellent used in sprays and lotions to repel mosquitoes and other insects. Its environmentally friendly properties make it a preferred choice over synthetic insect repellents. Eugenol's antioxidant properties help maintain the quality of cosmetics and pharmaceuticals by preventing oxidation, extending product shelf life. In chemical manufacturing, eugenol is a precursor for the synthesis of various organic compounds, which helps produce drugs and fragrances.

References

2025. Dual catalytic potential of isoeugenol synthase in Asarum sieboldii Miq. (AsIGS): Unveiling isoeugenol preference in vitro and eugenol production in vivo, with insights into hydrogen bonding influence. Gene.
DOI: 10.1016/j.gene.2024.148919

2025. The revealing of the Cyto-genotoxic properties (Allium and MTT) and the effect of chicken meat quality of characterized zein-eugenol nanofibers. Food Chemistry.
DOI: 10.1016/j.foodchem.2024.141043

2008. Dissection of lignin macromolecular configuration and assembly: Comparison to related biochemical processes in allyl/propenyl phenol and lignan biosynthesis. Natural Product Reports, 25(5).
DOI: 10.1039/b510386j