2-Methoxy-4-(tetrahydro-4-methylene-2H-pyran-2-yl)phenol (CAS 128489-04-3) — Woody Middle Note Fragrance Ingredient
2-Methoxy-4-(tetrahydro-4-methylene-2H-pyran-2-yl)phenol
CAS 128489-04-3
What Is 2-Methoxy-4-(tetrahydro-4-methylene-2H-pyran-2-yl)phenol?
2-Methoxy-4-(tetrahydro-4-methylene-2H-pyran-2-yl)phenol is a synthetic fragrance ingredient used in perfumery to create unique woody-spicy accords. It is found in niche fragrances where complex, modern scent profiles are desired. This molecule matters because it offers perfumers a novel building block that bridges traditional phenolic warmth with contemporary woody-pyrannic structures, allowing for innovative scent designs that stand out in crowded markets.
Safety Profile
USE WITH AWARENESSWhat Does 2-Methoxy-4-(tetrahydro-4-methylene-2H-pyran-2-yl)phenol Smell Like?
This synthetic phenol presents an intriguing duality – opening with sharp medicinal overtones reminiscent of clove oil’s eugenolic bite, then unfolding into a warmer heart where the tetrahydro-4-methylene-2H-pyran moiety introduces a dry, woody character with subtle fruity undertones. The dry-down reveals a persistent phenolic base with whispers of smoked tea leaves and distant leather. Unlike simpler phenols, the pyran ring adds dimensionality that prevents the scent from becoming one-dimensional or overly aggressive.
2D Molecular Structure
SMILES: COC1=C(O)C=CC(=C1)C1CC(=C)CCO1
Chemistry, Properties & Perfumer Guide
The Chemistry
As a synthetic phenol derivative, this molecule combines a methoxy-substituted phenolic ring with a tetrahydro-4-methylene-2H-pyran substituent at the para position. The structure suggests potential formation via Friedel-Crafts alkylation of guaiacol derivatives with dihydropyran precursors. The methylene group adjacent to the pyran oxygen creates electron density that influences both the molecule’s reactivity and olfactory properties. While exact synthesis routes are proprietary, the presence of both phenolic and cyclic ether functionalities suggests careful control of reaction conditions would be required to prevent polymerization.
Physical & Chemical Properties
| Boiling Point | Not available |
|---|---|
| Density | Not available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as woody-phenolic modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Limited use due to intensity |
Classic Accords
Tip: Use sparingly in woody bases to add phenolic complexity without overwhelming the composition.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions identified. General phenolic compound guidelines apply.
RIFM Assessment
No RIFM assessment publicly available for this specific compound.
Sustainability
As a synthetic material, this compound avoids natural resource depletion concerns but requires petrochemical feedstocks. The multi-step synthesis likely has moderate energy requirements. Being used at low concentrations minimizes environmental impact in finished products. No known biodegradation data available.
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Ingredient Data Sheet
CAS 128489-04-3Physical Properties
| Molecular Weight | 220.26 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2🔬 PubChem |
| Boiling Point | 314 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 160.9 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.624💻 Calculated |
| SMILES | COC1=C(C=CC(=C1)C2CC(=C)CCO2)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 9.6 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | phenoletheralkenearomatic💻 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: DTXSID50888936
Physical Properties
| Molecular Weight | 220.268 g/mol🔬 EPA CompTox |
| Density | 1.148 g/cm^3📊 OPERA |
| Boiling Point | 266 °C🔬 EPA CTX |
| Melting Point | 77.043 °C📊 OPERA |
| Flash Point | 164.096 °C📊 OPERA |
| Refractive Index | 1.558 Dimensionless📊 OPERA |
| Molar Volume | 191.205 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.31 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.47 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.449 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.55 Log10 unitless📊 OPERA |
| Water Solubility | 0.009 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Viscosity | 27.543 cP📊 OPERA |
| Surface Tension | 42.904 dyn/cm📊 OPERA |
| Thermal Conductivity | 141.233 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 | 2 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 61.643 cm^3/mol📊 OPERA |
| Polarizability | 24.437 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.
