Methyl cis-3-hexenoate (CAS 13894-62-7) — Green Top to mid Note Fragrance Ingredient
Methyl cis-3-hexenoate
CAS 13894-62-7
What Is Methyl cis-3-hexenoate?
Methyl cis-3-hexenoate is a synthetic fragrance ingredient that mimics the fresh, green scent of crushed leaves and unripe fruits. You’ll encounter it in high-end perfumes and body care products that aim for a natural, outdoorsy quality. This ester matters because it delivers an ultra-realistic ‘green’ note without relying on natural extracts, making fragrances more consistent and sustainable. It’s particularly valued in floral and citrus compositions where a crisp, dewy effect is desired.
Safety Profile
GENERALLY SAFEWhat Does Methyl cis-3-hexenoate Smell Like?
A razor-sharp green burst reminiscent of snapping fresh pea pods or torn rhubarb stalks, with an underlying fruity sweetness like underripe kiwi. The top note is aggressively verdant – think of the sappy smell when pruning hedges – which rapidly softens into a watery, cucumber-like freshness. Unlike harsher green notes, it maintains a rounded quality throughout evaporation, ending with a faint melon rind character in the dry-down. Exceptionally diffusive in the first 30 minutes, it behaves like nature’s version of a green laser beam – precise, intense, but never shrill.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to create the piercing green mango accord, lending hyper-realistic freshness to the tropical fruit theme. The ester’s crisp edge prevents the composition from becoming cloying.
Modern reformulations employ this synthetic to replace natural galbanum, delivering the iconic crushed-leaf effect with greater stability and lower allergen risk.
2D Molecular Structure
SMILES: CC\C=C/CC(=O)OC
Chemistry, Properties & Perfumer Guide
The Chemistry
Methyl cis-3-hexenoate belongs to the ester family, synthesized via acid-catalyzed esterification of cis-3-hexenoic acid with methanol. The cis configuration at the double bond is crucial for odor quality – the trans isomer smells markedly different. Industrial production often starts from butadiene, which undergoes hydroformylation and subsequent oxidation to yield the precursor acid. Unlike many green-smelling compounds, it lacks the sulfurous or aldehydic harshness typical of the genre, owing to its saturated ester group that tempers the vegetative character.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | ~195-200 °C (estimated) |
| Density | ~0.89 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Green accent in floral bouquets |
| Functional Fragrances | 0.1-0.5% | Up to 1% | Shampoos and shower gels for fresh effects |
Classic Accords
Tip: Use at 0.1% in alcohol bases to prevent excessive sharpness – it’s more potent than most green synthetics.
Alternatives & Comparisons
For sharper, more metallic green effects without fruity undertones. Preferred in masculine fougères.
When a greener, grassier effect is needed, though less tenacious and more alcohol-soluble.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not restricted under current IFRA standards (as of 50th Amendment).
RIFM Assessment
RIFM evaluation confirms safe use at reported industry levels with good margin of safety.
Sustainability
As a fully synthetic material, production avoids agricultural land use and seasonal variability. The petrochemical starting materials are offset by the ingredient’s high potency – only tiny amounts are needed compared to natural extracts. Recent advances allow some manufacturers to use bio-based methanol from renewable sources.
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References
- Arctander, S. (1969). Perfume and Flavor Chemicals. Montclair, NJ.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 13894-62-7Physical Properties
| Molecular Weight | 128.17 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 1.5🔬 PubChem |
| Boiling Point | 168 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.417💻 Calculated |
| SMILES | CCC=CCC(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 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: DTXSID80893694
Physical Properties
| Molecular Weight | 128.171 g/mol🔬 EPA CompTox |
| Density | 0.915 g/cm^3📊 OPERA |
| Boiling Point | 149.851 °C📊 OPERA |
| Melting Point | -47.165 °C📊 OPERA |
| Flash Point | 51.237 °C📊 OPERA |
| Refractive Index | 1.428 Dimensionless📊 OPERA |
| Molar Volume | 141.18 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.092 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.092 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.092 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 3.76 Log10 unitless📊 OPERA |
| Water Solubility | 0.031 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 4.2 mmHg📊 OPERA |
| Viscosity | 0.75 cP📊 OPERA |
| Surface Tension | 26.31 dyn/cm📊 OPERA |
| Thermal Conductivity | 137.61 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 | 3 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 36.312 cm^3/mol📊 OPERA |
| Polarizability | 14.395 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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