3,6-Dihydro-4-methyl-2-phenyl-2H-pyran (CAS 60335-71-9) — Citrus Top to middle Note Fragrance Ingredient
3,6-Dihydro-4-methyl-2-phenyl-2H-pyran
CAS 60335-71-9
What Is 3,6-Dihydro-4-methyl-2-phenyl-2H-pyran?
3,6-Dihydro-4-methyl-2-phenyl-2H-pyran is a synthetic fragrance ingredient used in modern perfumes to add a fresh, slightly herbal character. It’s found in various personal care products and fine fragrances. This molecule is valued for its ability to bridge between citrusy top notes and floral heart notes, creating a smooth transition in complex scent compositions.
Safety Profile
GENERALLY SAFEWhat Does 3,6-Dihydro-4-methyl-2-phenyl-2H-pyran Smell Like?
This synthetic pyran derivative offers a crisp, clean aroma with subtle nuances. Initially presents a bright, almost citrus-like freshness that quickly evolves into a delicate herbal-green character reminiscent of crushed leaves. The dry-down reveals a faint woody-phenolic undertone, providing surprising tenacity for such a light molecule. Its transparency makes it an excellent blender, adding lift without dominating compositions.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to enhance the fresh aquatic character, contributing to the crisp opening that defines this iconic marine fragrance.
Adds a subtle green nuance to the watery floral accord, helping create the illusion of dewy lotus leaves.
2D Molecular Structure
SMILES: CC1=CCOC(C1)C1=CC=CC=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
3,6-Dihydro-4-methyl-2-phenyl-2H-pyran belongs to the heterocyclic pyran class, characterized by an oxygen-containing six-membered ring. While not found in nature, it shares structural similarities with some naturally occurring pyran derivatives. Typically synthesized through acid-catalyzed cyclization of appropriate dienol precursors. The phenyl substitution at the 2-position contributes to its stability and modifies its odor profile compared to simpler pyrans.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Odor Strength | Medium |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Fresh top note component |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Clean, fresh effect |
Classic Accords
Tip: Use to add diffusion and freshness to top notes without citrus allergenic concerns.
Alternatives & Comparisons
Offers similar fresh top note properties with more pronounced citrus-lime character and slightly better stability in alkaline formulations.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
Not yet evaluated by RIFM due to relatively low production volume.
Sustainability
As a synthetic material, production can be carefully controlled to minimize environmental impact. No natural resources are consumed in its manufacture, and synthetic routes typically have higher atom economy than extraction processes. Being petroleum-derived, its sustainability depends on the energy sources used in production.
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References
- Bauer, K. et al. (2001). Common Fragrance and Flavor Materials. Wiley-VCH.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 60335-71-9Physical Properties
| Molecular Weight | 174.24 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.2🔬 PubChem |
| Boiling Point | 262 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0049 mmHg @ 25°C📊 OPERA |
| Flash Point | 104.7 °C🔬 EPA CompTox |
| Involatility Index | 0.0004💻 Calculated |
| log Kp (skin permeability) | -2.201💻 Calculated |
| SMILES | CC1=CCOC(C1)C2=CC=CC=C2🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 3.7 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | citrusgreen• leffingwell |
| Functional Groups | etheralkenearomatic💻 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: DTXSID00866805
Physical Properties
| Molecular Weight | 174.243 g/mol🔬 EPA CompTox |
| Density | 1.028 g/cm^3📊 OPERA |
| Boiling Point | 260.41 °C📊 OPERA |
| Melting Point | 49.059 °C📊 OPERA |
| Flash Point | 107.397 °C📊 OPERA |
| Refractive Index | 1.53 Dimensionless📊 OPERA |
| Molar Volume | 172.959 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.053 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.053 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.053 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.96 Log10 unitless📊 OPERA |
| Water Solubility | 0.003 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.011 mmHg📊 OPERA |
| Viscosity | 5.193 cP📊 OPERA |
| Surface Tension | 35.041 dyn/cm📊 OPERA |
| Thermal Conductivity | 129.581 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 9.23 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 53.416 cm^3/mol📊 OPERA |
| Polarizability | 21.176 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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