Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one (CAS 34686-71-0) — Sweet Middle Note Fragrance Ingredient
Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one
CAS 34686-71-0
What Is Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one?
Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one is a synthetic fragrance ingredient used in perfumery to create warm, fruity, and slightly woody notes. You might encounter it in fine fragrances, body care products, or candles where a complex, sophisticated fruitiness is desired. This molecule matters because it provides perfumers with a versatile building block that can enhance fruity accords without being overly sweet or cloying, making it valuable for modern unisex and masculine fragrances.
Safety Profile
USE WITH AWARENESSWhat Does Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one Smell Like?
This lactone derivative opens with a juicy, slightly green peach-like fruitiness that evolves into a creamy coconut-milk warmth. As it dries down, the scent develops a woody-amber undertone reminiscent of sun-warmed sandalwood shavings. The overall effect is a sophisticated fruity-woody hybrid with excellent diffusion—like biting into a just-ripe nectarine while standing in a cedar sauna. It has moderate tenacity, lingering as a soft skin scent for 4-6 hours.
2D Molecular Structure
SMILES: CCC=CCC1CCCC(=O)O1
Chemistry, Properties & Perfumer Guide
The Chemistry
Tetrahydro-6-(2-pentenyl)-2H-pyran-2-one belongs to the δ-lactone class, characterized by a six-membered ring with an ester functionality. While not found in nature, it’s structurally related to naturally occurring coconut lactones. Industrial synthesis typically involves the cyclization of unsaturated fatty acid derivatives or the hydrogenation of corresponding pyranones. The pentenyl side chain introduces subtle green nuances that differentiate it from simpler lactones.
Physical & Chemical Properties
| Boiling Point | Not available |
|---|---|
| Density | Not available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 1-3% | Up to 5% | Fruity-woody modifier |
| Personal Care | 0.5-1% | Up to 2% | Skin-safe levels |
Classic Accords
Tip: Use with ionones to create a seamless fruity-woody transition in accords.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No current restrictions under IFRA standards.
RIFM Assessment
Not yet evaluated by RIFM – recommended to follow general lactone safety guidelines.
Sustainability
As a synthetic material, this lactone avoids agricultural land use but requires petrochemical feedstocks. Production typically employs green chemistry principles with high atom economy. Future biotech routes using engineered yeast may offer renewable alternatives while maintaining identical olfactory properties.
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Ingredient Data Sheet
CAS 34686-71-0Physical Properties
| Molecular Weight | 168.23 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.4🔬 PubChem |
| Boiling Point | 238 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0229 mmHg @ 25°C📊 OPERA |
| Flash Point | 113.1 °C🔬 EPA CompTox |
| Involatility Index | 0.0019💻 Calculated |
| log Kp (skin permeability) | -2.022💻 Calculated |
| SMILES | CCC=CCC1CCCC(=O)O1🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.7 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | esteretheralkene💻 RDKit |
| “natural product, can lead to quite remarkable Practically insoluble in water, soluble in similarity and faithful reproduction of odor. Needless to add that this method of operation Powerful oily-fruity, rather fatty and ten- may be considerably less expensive, and it acious odor with floral petal-like notes, There might encourage the perfumer in oflering a is some resemblance to the odor of refine”📖 Arctander | |
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: DTXSID5051492
Physical Properties
| Molecular Weight | 168.236 g/mol🔬 EPA CompTox |
| Density | 0.973 g/cm^3📊 OPERA |
| Boiling Point | 265.539 °C📊 OPERA |
| Melting Point | 1.332 °C📊 OPERA |
| Flash Point | 118.208 °C📊 OPERA |
| Refractive Index | 1.463 Dimensionless📊 OPERA |
| Molar Volume | 174.702 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.229 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.229 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.229 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.79 Log10 unitless📊 OPERA |
| Water Solubility | 0.011 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.01 mmHg📊 OPERA |
| Viscosity | 2.574 cP📊 OPERA |
| Surface Tension | 30.947 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 26.3 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 3 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 48.077 cm^3/mol📊 OPERA |
| Polarizability | 19.059 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.
