4,7-Octadienoic acid, methyl ester, (4E)- (CAS 189440-77-5) — Green Top to middle Note Fragrance Ingredient
4,7-Octadienoic acid, methyl ester, (4E)-
CAS 189440-77-5
What Is 4,7-Octadienoic acid, methyl ester, (4E)-?
4,7-Octadienoic acid, methyl ester, (4E)- is a synthetic fragrance ingredient used in modern perfumery. It contributes to fresh, green, and slightly fruity accords. This molecule is found in niche and avant-garde fragrances where unique green notes are desired. Its importance lies in providing perfumers with a crisp, unsaturated ester character that bridges herbal and fruity olfactory spaces without being overly sweet or heavy.
Safety Profile
GENERALLY SAFEWhat Does 4,7-Octadienoic acid, methyl ester, (4E)- Smell Like?
This unsaturated ester delivers a sharp green opening reminiscent of crushed tomato leaves and unripe kiwi skin, with a subtle metallic edge. The heart reveals a watery cucumber-like freshness layered over a faintly musky undertone. Dry-down is surprisingly persistent for its structure, leaving a clean, slightly waxy green impression akin to the after-scent of snapped pea pods. The (4E)-configuration ensures a brighter, more linear scent profile compared to its (4Z)-isomer.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a hyper-realistic green amplifier, creating the illusion of chlorophyll-rich foliage without floral sweetness. The ester’s sharpness counters the composition’s white florals.
Modern reformulations employ trace amounts to enhance the violet leaf note, adding a contemporary crispness to this classic fougère structure.
2D Molecular Structure
SMILES: COC(=O)CC\C=C\CC=C
Chemistry, Properties & Perfumer Guide
The Chemistry
As an α,β,γ,δ-unsaturated methyl ester, this molecule belongs to the family of aliphatic esters with extended conjugation. The (4E)-configuration creates distinct steric and electronic properties compared to its (4Z)-isomer. Industrial synthesis typically proceeds via Wittig olefination of appropriate aldehyde precursors followed by esterification. The trans-double bond at position 4 contributes to greater stability and a more piercing odor character than cis-configured analogs.
Physical & Chemical Properties
| Boiling Point | Not established |
|---|---|
| Density | Not established |
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 |
Classic Accords
Tip: Stabilize in ethanol before blending to prevent oxidative degradation of the diene system.
Alternatives & Comparisons
For simpler green effects with less metallic character and better stability in alkaline formulations.
When a fruitier, pear-like green note is desired with similar unsaturated ester functionality.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards. No specific use limitations documented.
RIFM Assessment
No public RIFM assessment available. Considered low priority due to limited commercial use.
Sustainability
As a purely synthetic material, production avoids agricultural land use but depends on petrochemical feedstocks. The multi-step synthesis requires careful solvent recovery to minimize environmental impact. Future green chemistry approaches may enable biocatalytic production from renewable resources.
Explore 4,7-Octadienoic acid, methyl ester, (4E)-
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. ISBN 9781420090869
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 189440-77-5Physical Properties
| Molecular Weight | 154.21 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.1🔬 PubChem |
| Boiling Point | 208 °C🔬 EPA CompTox |
| Vapor Pressure | 0.5495 mmHg @ 25°C📊 OPERA |
| Flash Point | 67.3 °C🔬 EPA CompTox |
| Involatility Index | 0.0477💻 Calculated |
| log Kp (skin permeability) | -2.15💻 Calculated |
| SMILES | COC(=O)CCC=CCC=C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Top💻 Calculated |
| Volatility Class | Slow💻 Calculated |
| Persistence Score | 0.5 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | greensweet• leffingwell |
| Functional Groups | esteretheralkene💻 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: DTXSID4051827
Physical Properties
| Molecular Weight | 154.209 g/mol🔬 EPA CompTox |
| Density | 0.914 g/cm^3📊 OPERA |
| Boiling Point | 194.908 °C📊 OPERA |
| Melting Point | -34.091 °C📊 OPERA |
| Flash Point | 71.657 °C📊 OPERA |
| Refractive Index | 1.448 Dimensionless📊 OPERA |
| Molar Volume | 169.287 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.718 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.718 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.718 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.31 Log10 unitless📊 OPERA |
| Water Solubility | 0.009 mol/L📊 OPERA |
| Henry's Law Constant | 0.001 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.474 mmHg📊 OPERA |
| Viscosity | 1.038 cP📊 OPERA |
| Surface Tension | 28.052 dyn/cm📊 OPERA |
| Thermal Conductivity | 140.152 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 26.3 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 5 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.303 cm^3/mol📊 OPERA |
| Polarizability | 17.959 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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