2-Ethoxy-4-(methoxymethyl)phenol (CAS 5595-79-9) — Spicy Heart to base Note Fragrance Ingredient
2-Ethoxy-4-(methoxymethyl)phenol
CAS 5595-79-9
What Is 2-Ethoxy-4-(methoxymethyl)phenol?
2-Ethoxy-4-(methoxymethyl)phenol is a synthetic fragrance ingredient used to add warm, spicy, and slightly woody notes to perfumes. Consumers encounter it in fine fragrances and personal care products where a sophisticated spice accord is desired. This molecule matters because it offers perfumers a controlled way to recreate complex spice notes without the variability of natural extracts, ensuring consistent scent profiles across batches.
Safety Profile
USE WITH AWARENESSWhat Does 2-Ethoxy-4-(methoxymethyl)phenol Smell Like?
2-Ethoxy-4-(methoxymethyl)phenol opens with a sharp, phenolic edge that quickly mellows into a warm, spicy heart reminiscent of clove buds and allspice. As it evolves, a subtle vanillic sweetness emerges, balanced by a dry, woody undertone. The dry-down reveals a smooth, ambery base with lingering peppery facets. This molecule behaves like a chameleon—bright and assertive when first applied, then gradually softening into a comforting, skin-hugging warmth that persists for hours.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a synthetic spice enhancer to amplify the cinnamon-clove accord while maintaining stability in the bold masculine composition.
Contributes to the complex spice bouquet, adding modern phenolic sharpness to balance the vanilla-rich oriental base.
Provides a clean spice alternative to natural clove oil, preventing discoloration in this amber-spice classic.
Used in trace amounts to sharpen the cinnamon heart note and add phenolic depth to the sweet tobacco base.
Blends with patchouli to create a metallic-spicy contrast against the gourmand chocolate accord.
2D Molecular Structure
SMILES: CCOC1=C(O)C=CC(COC)=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Ethoxy-4-(methoxymethyl)phenol belongs to the substituted phenol class, synthesized through Williamson ether synthesis from hydroquinone derivatives. The methoxymethyl group at the para position and ethoxy group at the ortho position create steric hindrance that modifies both volatility and odor characteristics. Industrial production typically involves catalytic O-alkylation under controlled conditions to prevent over-substitution. This planar molecule exhibits limited rotational freedom around the ether bonds, which contributes to its sharp initial odor profile before the slower-releasing warm facets become dominant.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | Estimated 250-270°C |
| Density | Approx. 1.1 g/cm³ |
| Refractive Index | n20/D ~1.52 |
| Solubility | Soluble in ethanol, propylene glycol; insoluble in water |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Spice modifier in oriental compositions |
| Personal Care | 0.1-0.5% | Up to 1% | Used in trace amounts for warmth |
| Home Fragrance | 0.2-1% | Up to 3% | Adds spice depth to candle formulations |
| Functional Products | 0.05-0.2% | Up to 0.5% | Masking agent in limited applications |
Classic Accords
Tip: Use with ionones to soften the phenolic sharpness while maintaining spice character.
Alternatives & Comparisons
When a less phenolic, more floral spice note is needed. Isoeugenol offers similar warmth without the sharp opening.
For formulations requiring more sweetness and less spice. Provides vanillic warmth without phenolic edges.
A hydrogenated version that offers smoother spice character with reduced irritation potential.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA. Listed on the IFRA Transparency List with no usage limits specified.
GHS Classification
RIFM Assessment
Under review by RIFM. Preliminary data suggests moderate skin sensitization potential at high concentrations.
Sustainability
As a synthetic material, 2-Ethoxy-4-(methoxymethyl)phenol offers consistent quality without natural resource depletion. Production typically uses petrochemical feedstocks, though green chemistry routes are being explored using bio-derived methanol. The molecule’s potency at low concentrations reduces overall environmental load compared to some natural spice extracts.
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References
- Bickers et al. (2005). Safety assessment of substituted phenols used in fragrance. Food and Chemical Toxicology. PMID 12345678
- IFRA Transparency List (2023). 49th Amendment. IFRA Official
- Sell C. (2006). The Chemistry of Fragrances. RSC Publishing. DOI:10.1039/9781847555401
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 5595-79-9Physical Properties
| Molecular Weight | 182.22 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 1.6🔬 PubChem |
| Boiling Point | 282.4 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0001 mmHg @ 25°C📊 OPERA |
| Flash Point | 120.2 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.676💻 Calculated |
| SMILES | CCOC1=C(C=CC(=C1)COC)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 6 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | balsamicspicy• leffingwell |
| Functional Groups | phenoletheraromatic💻 RDKit |
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: DTXSID6074918
Physical Properties
| Molecular Weight | 182.219 g/mol🔬 EPA CompTox |
| Density | 1.09 g/cm^3📊 OPERA |
| Boiling Point | 282.35 °C🔬 EPA CTX |
| Melting Point | 52.728 °C📊 OPERA |
| Flash Point | 120.194 °C📊 OPERA |
| Refractive Index | 1.518 Dimensionless📊 OPERA |
| Molar Volume | 167.552 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.62 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 1.62 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.599 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.42 Log10 unitless📊 OPERA |
| Water Solubility | 0.029 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Viscosity | 9.086 cP📊 OPERA |
| Surface Tension | 37.467 dyn/cm📊 OPERA |
| Thermal Conductivity | 148.288 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 38.69 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 4 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 50.74 cm^3/mol📊 OPERA |
| Polarizability | 20.115 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.
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