(Z)-3-Methyl-5-phenylpent-2-enenitrile (CAS 53243-59-7) — Green Top to mid Note Fragrance Ingredient
(Z)-3-Methyl-5-phenylpent-2-enenitrile
CAS 53243-59-7
What Is (Z)-3-Methyl-5-phenylpent-2-enenitrile?
(Z)-3-Methyl-5-phenylpent-2-enenitrile is a synthetic fragrance ingredient used to add fresh, green, and slightly floral nuances to perfumes. It’s commonly found in modern floral and citrus fragrances. This molecule helps create crisp top notes that feel airy and contemporary, often used to give a ‘just-showered’ freshness to body care products and fine fragrances.
Safety Profile
GENERALLY SAFEWhat Does (Z)-3-Methyl-5-phenylpent-2-enenitrile Smell Like?
This nitrile derivative opens with a burst of crisp green apple peel and unripe pear, underscored by a faint metallic sharpness that quickly softens. The heart reveals a delicate floralcy reminiscent of lily-of-the-valley petals, while a subtle woody-amber drydown emerges after 2-3 hours. The overall effect is clean and slightly aqueous, like crushed stems in morning dew, with excellent diffusion that makes it valuable for modern fresh compositions.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to reinforce the crisp citron top notes while adding a transparent green facet that bridges to the floral heart. Provides the ‘dewy’ quality that defines this fragrance.
Employed in the top accord to create the impression of freshly cut grass and citrus zest, enhancing the sparkling opening without overwhelming the delicate florals.
2D Molecular Structure
SMILES: C\C(CCC1=CC=CC=C1)=C\C#N
Chemistry, Properties & Perfumer Guide
The Chemistry
(Z)-3-Methyl-5-phenylpent-2-enenitrile belongs to the nitrile class of fragrance compounds, characterized by a carbon-nitrogen triple bond that often imparts fresh, green odor characteristics. Unlike many nitriles used in perfumery, this compound features both phenyl and aliphatic groups that modify its volatility and scent profile. Industrial synthesis typically proceeds via Knoevenagel condensation of appropriate aldehydes followed by selective hydrogenation to achieve the Z-configuration, which is crucial for the desired odor quality.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | ~250 °C (estimated) |
| Density | ~0.95 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | For fresh top notes |
| Body Care | 0.1-0.5% | Up to 1% | Light freshness booster |
Classic Accords
Tip: Stabilize in ethanol before adding to water-based formulations to prevent hydrolysis of the nitrile group.
Alternatives & Comparisons
Offers similar green freshness with better stability in alkaline formulations but lacks the floral nuance.
Provides comparable green stem-like notes with additional earthy aspects, though with lower volatility.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards. Listed on IFRA Transparency List with no usage limits specified.
RIFM Assessment
Not yet evaluated by RIFM as of 2023. Recommended to follow general nitrile handling precautions.
Sustainability
As a synthetic material, production avoids agricultural land use but requires petrochemical feedstocks. The nitrile group’s stability reduces aquatic toxicity concerns compared to some ester-based fresh notes. Manufacturing typically employs catalytic processes with good atom economy.
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References
- Bauer et al. (2001). Nitriles in Modern Perfumery. Flavour and Fragrance Journal.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID0052170
Physical Properties
| Molecular Weight | 171.243 g/mol🔬 EPA CompTox |
| Density | 1.028 g/cm^3📊 OPERA |
| Boiling Point | 291.337 °C📊 OPERA |
| Melting Point | 34.629 °C📊 OPERA |
| Flash Point | 138.361 °C📊 OPERA |
| Refractive Index | 1.531 Dimensionless📊 OPERA |
| Molar Volume | 175.077 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.786 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.786 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.786 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.36 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.002 mmHg📊 OPERA |
| Surface Tension | 36.233 dyn/cm📊 OPERA |
| Thermal Conductivity | 152.763 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 23.79 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 3 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 54.148 cm^3/mol📊 OPERA |
| Polarizability | 21.466 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.
