4-Acetoxy-3-pentyltetrahydropyran (CAS 18871-14-2) — Woody Middle Note Fragrance Ingredient
4-Acetoxy-3-pentyltetrahydropyran
CAS 18871-14-2
What Is 4-Acetoxy-3-pentyltetrahydropyran?
4-Acetoxy-3-pentyltetrahydropyran is a synthetic fragrance ingredient used in modern perfumery. It’s found in niche and designer fragrances where unique woody-floral effects are desired. This molecule matters because it helps create sophisticated scent profiles that evolve beautifully on skin, offering perfumers a versatile building block for contemporary compositions.
Safety Profile
USE WITH AWARENESSWhat Does 4-Acetoxy-3-pentyltetrahydropyran Smell Like?
This synthetic molecule unfolds with an intriguing duality – opening with crisp, almost ozonic freshness that quickly melds into a rounded woody-heart. Imagine the first snap of green bamboo shoots wrapped in velvety sandalwood undertones. As it dries down, it reveals subtle lactonic nuances reminiscent of coconut husk and warm skin, creating an intimate sillage that lingers close to the body. The evolution from bright top to creamy base makes it particularly valuable for modern unisex fragrances seeking complexity without heaviness.
2D Molecular Structure
SMILES: CCCCCC1COCCC1OC(C)=O
Chemistry, Properties & Perfumer Guide
The Chemistry
4-Acetoxy-3-pentyltetrahydropyran belongs to the tetrahydropyran class of oxygen-containing heterocycles, modified with an acetoxy group at position 4 and a pentyl chain at position 3. The molecule is typically synthesized through acid-catalyzed cyclization of appropriate pentyl-substituted diols followed by selective acetylation. The stereochemistry at the 3-position significantly impacts its odor profile, with different enantiomers exhibiting varying intensity and character.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Adds woody complexity |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Used sparingly for subtle effects |
Classic Accords
Tip: Use in conjunction with ionones to enhance its woody-floral character without overpowering delicate top notes.
Alternatives & Comparisons
Offers similar woody-amber characteristics with greater stability in functional products.
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
Under evaluation by RIFM as of 2023.
Sustainability
As a synthetic material, 4-Acetoxy-3-pentyltetrahydropyran has minimal environmental impact during production compared to naturally derived ingredients. Its synthesis can be optimized for atom economy, reducing waste. Being petroleum-derived, its carbon footprint depends on energy sources used in manufacturing, but it requires no agricultural land or water resources.
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Physicochemical Properties
DTXSID: DTXSID7044556
Physical Properties
| Molecular Weight | 214.305 g/mol🔬 EPA CompTox |
| Density | 0.976 g/cm^3🔬 EPA CTX |
| Boiling Point | 261.2 °C🔬 EPA CTX |
| Melting Point | 7.127 °C📊 OPERA |
| Flash Point | 104 °C🔬 EPA CTX |
| Refractive Index | 1.452 Dimensionless📊 OPERA |
| Molar Volume | 218.965 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.45 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 3.821 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.821 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.56 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.004 mmHg🔬 EPA CTX |
| Viscosity | 4.545 cP📊 OPERA |
| Surface Tension | 31.388 dyn/cm📊 OPERA |
| Thermal Conductivity | 137.42 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 35.53 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 5 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 59.117 cm^3/mol📊 OPERA |
| Polarizability | 23.436 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.
