(3-Z)-3,12-Tridecadienenitrile (CAS 124071-43-8) — Green Top to middle Note Fragrance Ingredient
(3-Z)-3,12-Tridecadienenitrile
CAS 124071-43-8
What Is (3-Z)-3,12-Tridecadienenitrile?
(3-Z)-3,12-Tridecadienenitrile is a synthetic fragrance ingredient used in modern perfumery. It’s found in niche and avant-garde fragrances where unique green-metallic effects are desired. This molecule creates intriguing olfactory effects that can’t be achieved with traditional natural materials, making it valuable for innovative scent compositions.
Safety Profile
USE WITH AWARENESSWhat Does (3-Z)-3,12-Tridecadienenitrile Smell Like?
This unsaturated nitrile delivers a sharp, green-metallic character reminiscent of freshly crushed stems and unripe fruits. The initial impression is intensely vegetal with cucumber-like freshness, evolving into a more complex heart with waxy, fatty undertones. The dry-down reveals subtle marine aspects with lingering green persistence. At low concentrations, it adds remarkable diffusion and lift to floral compositions.
2D Molecular Structure
SMILES: C=CCCCCCCC\C=C/CC#N
Chemistry, Properties & Perfumer Guide
The Chemistry
(3-Z)-3,12-Tridecadienenitrile belongs to the unsaturated nitrile class, synthesized through controlled hydrocyanation of conjugated dienes. The Z-configuration at the 3-position is crucial for its characteristic odor profile. As a synthetic material, it’s produced via catalytic processes that ensure stereochemical purity. The conjugated diene-nitrile structure makes it highly reactive olfactively while maintaining good stability in formulations.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used for green-metallic effects |
| Functional Fragrance | 0.01-0.1% | Up to 0.3% | For freshness in detergents |
Classic Accords
Tip: Use at trace levels to add lift to green-floral compositions without dominating.
Alternatives & Comparisons
Similar green-metallic character but with more pronounced cucumber aspects and less fatty undertones.
Natural alternative providing green notes though with different metallic quality and higher cost.
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
Limited safety assessment available from RIFM due to specialized usage.
Sustainability
As a synthetic material, this nitrile has minimal environmental impact in production compared to natural alternatives requiring agricultural resources. Its potency means very small quantities are needed in formulations, reducing overall chemical load. Manufacturing can be optimized for atom economy given its specialized application.
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Ingredient Data Sheet
CAS 124071-43-8Physical Properties
| Molecular Weight | 191.31 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 4.7🔬 PubChem |
| Boiling Point | 266 °C🔬 EPA CompTox |
| Vapor Pressure | 0.006 mmHg @ 25°C📊 OPERA |
| Flash Point | 133.4 °C🔬 EPA CompTox |
| Involatility Index | 0.0005💻 Calculated |
| log Kp (skin permeability) | -0.53💻 Calculated |
| SMILES | C=CCCCCCCCC=CCC#N🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 5 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | alkene💻 RDKit |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID401341489
Physical Properties
| Molecular Weight | 191.318 g/mol🔬 EPA CompTox |
| Density | 0.841 g/cm^3📊 OPERA |
| Boiling Point | 278.256 °C📊 OPERA |
| Melting Point | -7.338 °C📊 OPERA |
| Flash Point | 130.136 °C📊 OPERA |
| Refractive Index | 1.463 Dimensionless📊 OPERA |
| Molar Volume | 225.215 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.991 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.991 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.991 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.9 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.003 mmHg📊 OPERA |
| Viscosity | 2.744 cP📊 OPERA |
| Surface Tension | 29.988 dyn/cm📊 OPERA |
| Thermal Conductivity | 158.255 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 | 9 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 61.973 cm^3/mol📊 OPERA |
| Polarizability | 24.568 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.
