cis-3-Hexenyl methyl carbonate (CAS 67633-96-9) — Green Top Note Fragrance Ingredient
cis-3-Hexenyl methyl carbonate
CAS 67633-96-9
What Is cis-3-Hexenyl methyl carbonate?
cis-3-Hexenyl methyl carbonate is a synthetic fragrance ingredient that mimics the fresh, green scent of crushed leaves. It’s commonly found in perfumes, body care products, and household cleaners where a natural green note is desired. This molecule helps create realistic plant-like aromas without using actual plant extracts, making fragrances more consistent and sustainable. It’s particularly valued for adding the crisp top notes that evoke just-cut grass or garden-fresh herbs.
Safety Profile
GENERALLY SAFEWhat Does cis-3-Hexenyl methyl carbonate Smell Like?
The scent bursts with an intensely green, almost chlorophyll-like freshness reminiscent of snapping a celery stalk or crushing fresh mint leaves. There’s a dewy, watery quality like morning grass, with subtle fruity undertones recalling green apples. The methyl carbonate group adds a sparkling, effervescent lift that prevents the greenness from becoming heavy. As it dries down, it maintains its crisp character without turning bitter, making it unusually stable for a green note. The overall effect is like walking through a vegetable garden after summer rain – vibrant, clean, and alive.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to create the razor-sharp green mango accord, contributing the hyper-realistic ‘just peeled’ vegetal freshness that defines this fragrance’s opening.
Provides the initial leafy burst that complements the violet leaf, giving the impression of dew-covered clover fields at dawn.
Modern reformulations use this to reconstruct the legendary galbanum top note, adding precision to the chaotic green explosion.
Forms the structural backbone of the tomato leaf accord, mimicking the plant’s natural methyl salicylate with added carbonic brightness.
Used in contemporary versions to sharpen the galbanum’s edges while maintaining the icy green floral character of the original.
2D Molecular Structure
SMILES: CC\C=C/CCOC(=O)OC
Chemistry, Properties & Perfumer Guide
The Chemistry
cis-3-Hexenyl methyl carbonate belongs to the ester family, specifically a carbonate ester of leaf alcohol (cis-3-hexenol). The cis configuration is crucial for its fresh green odor, as the trans isomer smells markedly different. Industrially produced via esterification of cis-3-hexenol with methyl chloroformate under controlled conditions, this synthesis allows for high purity and batch consistency. The carbonate group adds stability compared to simple acetate esters, preventing hydrolysis in alkaline formulations while maintaining volatility appropriate for top notes. Its molecular structure combines the green character of leaf alcohol with the sparkling quality imparted by the carbonate moiety.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | ~200 °C (estimated) |
| Density | ~0.95 g/cm³ (estimated) |
| Refractive Index | ~1.43 (estimated) |
| Solubility | Slightly soluble in water, fully miscible in alcohol |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | For sparkling green top notes |
| Functional Products | 0.1-0.5% | Up to 1% | In detergents for fresh linen effect |
| Cosmetics | 0.2-1% | Up to 3% | In shampoos for natural green character |
| Household Cleaners | 0.05-0.2% | Up to 0.5% | For ‘outdoor fresh’ marketing claims |
Classic Accords
Tip: Use with citrus top notes to prevent excessive sharpness – the carbonate’s sparkle harmonizes particularly well with citronellol.
Alternatives & Comparisons
More intense but less stable green note; use when higher impact is needed but beware of hydrolysis in alkaline systems.
For a more floral-green effect with better tenacity, though lacks the crisp carbonic character of the methyl carbonate.
When a woody-green with excellent stability is required, though this is less fresh and more herbal in character.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No restrictions under current IFRA standards (as of 49th Amendment).
RIFM Assessment
RIFM assessment completed – no safety concerns at current use levels.
Sustainability
As a synthetic material, production avoids agricultural land use and seasonal variability of natural green notes. The synthesis from petrochemical precursors has moderate carbon footprint, but high odor potency means minimal quantities are needed. Some manufacturers are exploring bio-based routes using fermentation-derived cis-3-hexenol to improve sustainability. Its stability reduces waste from product degradation compared to less stable green ingredients.
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. ISBN 9781420090869
- Arctander, S. (1969). Perfume and Flavor Chemicals. Allured Publishing. Allured
- IFRA Standards Library IFRA Official
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 67633-96-9Physical Properties
| Molecular Weight | 158.19 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.3🔬 PubChem |
| Boiling Point | 194.2 °C🔬 EPA CompTox |
| Vapor Pressure | 0.2535 mmHg @ 25°C📊 OPERA |
| Flash Point | 75 °C🔬 EPA CompTox |
| Involatility Index | 0.0217💻 Calculated |
| log Kp (skin permeability) | -2.032💻 Calculated |
| SMILES | CCC=CCCOC(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Slow💻 Calculated |
| Persistence Score | 0.9 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | floralgreen• leffingwell |
| Functional Groups | etheralkene💻 RDKit |
Regulatory Status
| IFRA Listed | Yes — see IFRA Standards for category limits⚖️ IFRA 51 |
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: DTXSID3052353
Physical Properties
| Molecular Weight | 158.197 g/mol🔬 EPA CompTox |
| Density | 0.969 g/cm^3🔬 EPA CTX |
| Boiling Point | 194.2 °C🔬 EPA CTX |
| Melting Point | -41.089 °C📊 OPERA |
| Flash Point | 75 °C🔬 EPA CTX |
| Refractive Index | 1.434 Dimensionless📊 OPERA |
| Molar Volume | 164.049 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 1.998 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.998 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.16 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.254 mmHg🔬 EPA CTX |
| Viscosity | 0.952 cP📊 OPERA |
| Surface Tension | 27.891 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 35.53 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 4 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 42.69 cm^3/mol📊 OPERA |
| Polarizability | 16.923 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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