Eugenol (CAS 97-53-0) — Spicy Top Note Fragrance Ingredient
Eugenol
CAS 97-53-0
What Is Eugenol?
Eugenol is a naturally occurring aromatic compound found in cloves, cinnamon, and bay leaves. It’s what gives these spices their warm, spicy character and is widely used in both food flavorings and perfumery. This molecule matters because it’s a cornerstone of oriental and spicy fragrance families, adding depth and warmth to everything from holiday candles to luxury perfumes.
Safety Profile
USE WITH AWARENESS
What Does Eugenol Smell Like?
Eugenol bursts forth with an intense, spicy-clove character – think of biting into a whole clove with its medicinal warmth and peppery bite. The top note carries a phenolic sharpness that quickly mellows into a sweet, woody heart reminiscent of carnations and old apothecary cabinets. In drydown, it reveals surprising floral facets with a vanillic softness, leaving a trail that’s both comforting and sophisticated. The evolution lasts hours, transitioning from aggressive spice to a skin-like warmth.
Scent Profile
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Eugenol provides the fiery clove-cinnamon heart that defines this oriental legend, creating addictive warmth against amber and florals.
Used in moderation here to add spicy depth to the lavender-citrus opening, demonstrating its versatility in classic fougères.
Eugenol’s floral side enhances the tuberose, mimicking the natural clove-like facets found in the living flower.
Provides subtle spicy texture to the woody-iris accord, showing how eugenol can work in minimalist compositions.
Amplifies the explosive pepper-cinnamon effect while preventing the blend from becoming too sweet.
2D Molecular Structure
SMILES: COC1=C(O)C=CC(CC=C)=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
Eugenol (4-allyl-2-methoxyphenol) is a phenylpropanoid belonging to the allylbenzene class. Naturally abundant in clove bud oil (up to 90%), it’s typically isolated via steam distillation or synthesized from guaiacol. Industrial production often involves the isomerization of isoeugenol or allylation of catechol derivatives. The molecule’s chirality isn’t usually considered in perfumery as commercial eugenol is racemic. Its phenolic OH group makes it moderately polar (XLogP~2.3), explaining both its solubility in alcohol and its ability to form hydrogen bonds with olfactory receptors.
Physical & Chemical Properties
| Boiling Point | 254 °C |
|---|---|
| Melting Point | -7.5 °C |
| Flash Point | 104 °C |
| Density | 1.067 g/cm³ |
| Vapor Pressure | 0.01 mmHg at 25°C |
| Refractive Index | 1.541 |
| Solubility | 1.8 g/L in water, miscible in ethanol |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Use sparingly due to sensitization risk |
| Home Fragrance | 1-3% | Up to 8% | Provides warmth in candles/diffusers |
| Functional Products | 0.1-0.5% | Up to 1% | Mouthwashes/toothpaste applications |
| Flavorings | 10-100 ppm | Up to 500 ppm | Key clove flavor component |
Classic Accords
+ Lavender + Coumarin = Fougère
+ Rose + Cinnamon = Spicy Floral
+ Citrus + Oakmoss = Chypre
Tip: Pre-dilute to 10% in ethanol to prevent crystallization in alcohol-based perfumes.
Alternatives & Comparisons
Less phenolic, more floral character; preferred when a softer clove effect is needed without medicinal harshness.
Modern captive with similar warmth but reduced sensitization potential and better stability in soap applications.
Esterified version with sweeter, fruitier profile and lower irritation potential for sensitive skin formulas.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. IFRA, REACH, EU Cosmetics Regulation standards update periodically. Consult current IFRA Standards Library before formulating. Not legal or regulatory advice.
IFRA Status
Restricted under IFRA 49th Amendment: Maximum 0.5% in leave-on products, 2.5% in rinse-off due to sensitization potential.
EU Allergen Declaration
Must be declared when present ≥0.001% in leave-on, ≥0.01% in rinse-off (EU Regulation No 1223/2009 Annex III).
GHS Classification
H317 May cause allergic skin reaction
H319 Eye irritation
RIFM Assessment
RIFM assessment confirms skin sensitization potential at high doses but safe at IFRA-restricted levels with proper labeling.
Sustainability
Most commercial eugenol is now synthesized from petrochemical sources despite natural abundance, as synthetic routes are more consistent and avoid clove crop fluctuations. Green chemistry approaches using lignin-derived guaiacol are emerging. The shift from natural extraction reduces pressure on clove-growing regions but increases carbon footprint from manufacturing.
Explore Eugenol
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Industry & Science Data
References
- PubChem Compound Summary for Eugenol CID 3314
- IFRA Standards Library 49th Amendment IFRA 49
- Surburg & Panten (2006). Common Fragrance and Flavor Materials. Wiley-VCH.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Mar 2026.
Ingredient Data Sheet
CAS 97-53-0Physical Properties
| Molecular Weight | 164.2 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2🔬 PubChem |
| Boiling Point | 253.9 °C🔬 EPA CompTox |
| Vapor Pressure | 0.01 mmHg @ 25°C📊 OPERA |
| Flash Point | 103.9 °C🔬 EPA CompTox |
| Involatility Index | 0.0008💻 Calculated |
| log Kp (skin permeability) | -2.282💻 Calculated |
| SMILES | COC1=C(C=CC(=C1)CC=C)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 3.1 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | drypungentsmokyspicy• leffingwell |
| Functional Groups | phenoletheralkenearomatic💻 RDKit |
| “Powerful, warm-spicy, rather dry and almost sharp odor, drier and harder than that of Clove bud oil, less peppy-woody than that of Clove leaf oil.”📖 Arctander | |
| Eugenol has a strong aromatic odor of clove and a spicy, pungent taste. It darkens and thickens on exposure to air.📖 Fenaroli | |
Flavor Notes (Arctander)
| “Eugenol is in no way a substitute for Clove bud oil in flavors, but it may add to the strength and give a clove-like note to combination-spice flavors. With a Clove leaf oil price of U.S. \$ 2.20 to 3.30 per kilo (1967-1968) there is no interest in promoting synthetic methods of making Eugenol. This”📖 Arctander |
Sensory Thresholds
| Odor Detection Threshold | 0.3493 ppm (n=40)📖 van Gemert |
Regulatory Status
| IFRA Listed | Yes — see IFRA Standards for category limits⚖️ IFRA 51 |
| EU Annex III | Listed (restricted)⚖️ IFRA 51 |
| FEMA Number | FEMA 2467⚖️ FEMA GRAS |
| GRAS Status | Generally Recognized as Safe⚖️ FEMA GRAS |
| IOFI Classification | Nature Identical📖 Fenaroli |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID9020617
Physical Properties
| Molecular Weight | 164.204 g/mol🔬 EPA CompTox |
| Density | 1.065 g/cm^3🔬 EPA CTX |
| Boiling Point | 249.67 °C🔬 EPA CTX |
| Melting Point | -8.836 °C🔬 EPA CTX |
| Flash Point | 111.948 °C🔬 EPA CTX |
| Refractive Index | 1.536 Dimensionless📊 OPERA |
| Molar Volume | 156.283 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 6.368 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.375 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.375 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.72 Log10 unitless📊 OPERA |
| Water Solubility | 0.019 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 0.028 mmHg🔬 EPA CTX |
| Viscosity | 5.782 cP📊 OPERA |
| Surface Tension | 37.025 dyn/cm📊 OPERA |
| Thermal Conductivity | 148.274 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 29.46 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 3 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 48.72 cm^3/mol📊 OPERA |
| Polarizability | 19.314 Å^3📊 OPERA |
Data Sources:
🔬 EPA Experimental data from U.S. EPA CompTox Chemicals Dashboard & CTX APIs. 📊 OPERA Predicted using EPA's OPERA QSAR models. 💻 Computed Calculated from SMILES using RDKit.
