2,2,3-Trimethylcyclopent-3-enylacetonitrile (CAS 15373-31-6) — Woody Top to middle Note Fragrance Ingredient
2,2,3-Trimethylcyclopent-3-enylacetonitrile
CAS 15373-31-6
What Is 2,2,3-Trimethylcyclopent-3-enylacetonitrile?
2,2,3-Trimethylcyclopent-3-enylacetonitrile is a synthetic fragrance ingredient used in modern perfumery. It contributes fresh, woody, and slightly green nuances to fragrances. You’ll encounter it in contemporary citrus and woody compositions where it adds diffusion and lift. This molecule matters because it offers perfumers a unique combination of volatility and tenacity, bridging top and heart notes with its distinctive character.
Safety Profile
USE WITH AWARENESSWhat Does 2,2,3-Trimethylcyclopent-3-enylacetonitrile Smell Like?
This nitrile opens with a crisp, almost metallic freshness reminiscent of crushed green stems, quickly revealing a complex woody-ambery core. As it evolves, the scent develops a pine-like sharpness softened by subtle fruity undertones – imagine the green crunch of a Granny Smith apple meeting the resinous depth of a conifer forest. The dry-down lingers with a clean, slightly musky woodiness that provides excellent diffusion without overwhelming other notes.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a modern woody-ambery bridge between citrus top notes and incense heart notes, contributing to the fragrance’s signature freshness and longevity.
Provides crisp green-woody accents that enhance the ambroxan base, creating the fragrance’s distinctive metallic freshness.
2D Molecular Structure
SMILES: CC1=CCC(CC#N)C1(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
2,2,3-Trimethylcyclopent-3-enylacetonitrile belongs to the nitrile class of fragrance compounds, known for their stability and resistance to oxidation. The molecule features a cyclopentene ring with three methyl groups creating steric hindrance, which influences its odor profile. Synthesis typically involves Diels-Alder reactions followed by nitrile introduction. The rigid cyclic structure contributes to its moderate volatility and distinctive woody-green odor character.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | Approx. 220-230°C (estimated) |
| Density | Approx. 0.9 g/cm³ |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Adds woody freshness |
| Functional Fragrances | 0.1-0.5% | Up to 1% | Used sparingly for lift |
Classic Accords
Tip: Use in trace amounts to brighten woody bases without adding sweetness.
Alternatives & Comparisons
Similar woody character but with more pronounced pine notes and less green freshness.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
GHS Classification
RIFM Assessment
Under review by RIFM for comprehensive safety assessment.
Sustainability
As a synthetic material, this nitrile has consistent quality and doesn’t rely on natural resources. Production typically uses petrochemical feedstocks, though newer green chemistry routes may reduce environmental impact. The molecule’s efficiency at low concentrations makes it relatively sustainable in terms of dosage.
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References
- Bauer et al. (2001). Modern Synthetic Methods in Fragrance Chemistry. Chemistry & Biodiversity. DOI:10.1002/cbdv.200600003
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID60864589
Physical Properties
| Molecular Weight | 149.237 g/mol🔬 EPA CompTox |
| Density | 0.91 g/cm^3🔬 EPA CTX |
| Boiling Point | 225.833 °C🔬 EPA CTX |
| Melting Point | -33.5 °C🔬 EPA CTX |
| Flash Point | 93 °C🔬 EPA CTX |
| Refractive Index | 1.455 Dimensionless📊 OPERA |
| Molar Volume | 169.363 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.96 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.57 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.57 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.99 Log10 unitless📊 OPERA |
| Water Solubility | 0.002 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.574 mmHg🔬 EPA CTX |
| Viscosity | 2.111 cP📊 OPERA |
| Surface Tension | 30.087 dyn/cm📊 OPERA |
| Thermal Conductivity | 137.712 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 | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.928 cm^3/mol📊 OPERA |
| Polarizability | 18.207 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.
