3-(cis-3-Hexenyloxy)propanenitrile (CAS 142653-61-0) — Green Top to middle Note Fragrance Ingredient
3-(cis-3-Hexenyloxy)propanenitrile
CAS 142653-61-0
What Is 3-(cis-3-Hexenyloxy)propanenitrile?
3-(cis-3-Hexenyloxy)propanenitrile is a synthetic fragrance ingredient used to create fresh, green notes in perfumes and scented products. You’ll encounter it in modern floral and citrus fragrances, where it adds a crisp, leafy character. This molecule matters because it provides perfumers with a stable, long-lasting green note that mimics the smell of freshly cut grass or crushed leaves without relying on natural extracts that can vary in quality.
Safety Profile
USE WITH AWARENESSWhat Does 3-(cis-3-Hexenyloxy)propanenitrile Smell Like?
This molecule bursts with an intensely green, almost aggressive leafiness reminiscent of snapping fresh stems or newly mown lawns. The initial sharpness carries a slightly bitter, cucumber-like nuance that evolves into a cleaner, more refined green tea character. Unlike natural leaf alcohols, it maintains remarkable stability throughout the dry-down, transitioning into a soft, mossy base note with subtle earthy undertones. The nitrile group adds a faint metallic edge that distinguishes it from purely herbal green notes.
2D Molecular Structure
SMILES: CC\C=C/CCOCCC#N
Chemistry, Properties & Perfumer Guide
The Chemistry
3-(cis-3-Hexenyloxy)propanenitrile belongs to the nitrile class of compounds, characterized by a cyano group attached to an alkoxy chain. The cis-3-hexenyl moiety provides the characteristic green odor profile found in leaf alcohols. Industrial synthesis typically involves the nucleophilic substitution of 3-chloropropionitrile with cis-3-hexenol under basic conditions. The nitrile group enhances stability against oxidation compared to analogous aldehydes or alcohols, making this compound particularly valuable for functional fragrances requiring longevity.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Odor Threshold | 0.5 ppb (extremely potent) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Powerful green modifier |
| Functional Fragrance | 0.01-0.1% | Up to 0.3% | Freshness booster |
| Household Products | 0.05-0.2% | Up to 0.5% | Green note stabilizer |
Classic Accords
Tip: Use sparingly in citrus accords to prevent overpowering delicate top notes.
Alternatives & Comparisons
The natural alcohol version provides softer green notes but lacks stability and longevity.
Offers similar green character with additional woody aspects, though less intense.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific restrictions under current IFRA standards (Amendment 49).
GHS Classification
RIFM Assessment
Not currently evaluated by RIFM. Recommended for review due to nitrile functionality.
Sustainability
As a fully synthetic material, this compound avoids agricultural land use associated with natural green notes. The production process requires careful waste management due to cyanide-containing precursors. Future green chemistry routes may reduce environmental impact through catalytic methods.
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press.
- IFRA Standards Library (2021). Amendment 49. IFRA Official Site
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID7051717
Physical Properties
| Molecular Weight | 153.225 g/mol🔬 EPA CompTox |
| Density | 0.904 g/cm^3📊 OPERA |
| Boiling Point | 241.771 °C📊 OPERA |
| Melting Point | -12.383 °C📊 OPERA |
| Flash Point | 102.342 °C📊 OPERA |
| Refractive Index | 1.446 Dimensionless📊 OPERA |
| Molar Volume | 170.456 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.713 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 1.713 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.713 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.05 Log10 unitless📊 OPERA |
| Water Solubility | 0.126 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.039 mmHg📊 OPERA |
| Viscosity | 1.858 cP📊 OPERA |
| Surface Tension | 30.903 dyn/cm📊 OPERA |
| Thermal Conductivity | 160.605 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 33.02 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 6 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.461 cm^3/mol📊 OPERA |
| Polarizability | 18.022 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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