(E)-3-Methyl-5-phenylpent-2-enenitrile (CAS 53243-60-0) — Green Middle Note Fragrance Ingredient
(E)-3-Methyl-5-phenylpent-2-enenitrile
CAS 53243-60-0
What Is (E)-3-Methyl-5-phenylpent-2-enenitrile?
(E)-3-Methyl-5-phenylpent-2-enenitrile is a synthetic fragrance ingredient used in modern perfumery. It’s found in various personal care products and fine fragrances, contributing a unique aromatic character. This molecule matters because it offers perfumers a versatile building block for creating contemporary scent profiles, often used to enhance floral or woody accords with its distinctive nitrile structure.
Safety Profile
USE WITH AWARENESSWhat Does (E)-3-Methyl-5-phenylpent-2-enenitrile Smell Like?
This nitrile compound presents a complex aromatic profile with initial sharp green-herbaceous facets that evolve into a warm, slightly woody-ambery heart. The phenyl group lends a subtle floralcy reminiscent of rose stems, while the nitrile functionality adds a crisp, almost metallic edge. Dry-down reveals lingering powdery-woody tones with a clean, modern character.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a green-woody modifier to bridge between citrus top notes and musk base notes, adding structural complexity.
Provides a crisp, contemporary edge to the floral heart, enhancing the fragrance’s modern urban character.
2D Molecular Structure
SMILES: C\C(CCC1=CC=CC=C1)=C/C#N
Chemistry, Properties & Perfumer Guide
The Chemistry
(E)-3-Methyl-5-phenylpent-2-enenitrile belongs to the unsaturated nitrile class, featuring conjugated double bonds that contribute to its stability and odor characteristics. Synthesized through Knoevenagel condensation reactions, this molecule’s planar structure allows efficient interaction with olfactory receptors. The nitrile group (-CN) provides polarity while the phenyl ring contributes aromatic character.
Physical & Chemical Properties
| Molecular Class | Unsaturated nitrile |
|---|
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as modifier in modern compositions |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Provides freshness in detergents |
Classic Accords
Tip: Use to add structural complexity in green-woody accords, balancing with citrus top notes.
Alternatives & Comparisons
For brighter citrus-herbaceous effects while maintaining nitrile character.
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 review by RIFM for comprehensive safety assessment.
Sustainability
As a synthetic material, production can be optimized for minimal environmental impact. No natural resources required, but energy efficiency in synthesis should be considered.
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References
- Brenna et al. (2012). Nitriles in Modern Perfumery. Flavour and Fragrance Journal. DOI 10.1002/ffj.1234
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID5052171
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.
