Cyclopropanecarboxylic acid, (3Z)-3-hexenyl ester (CAS 188570-78-7) — Green Top-Middle Note Fragrance Ingredient
Cyclopropanecarboxylic acid, (3Z)-3-hexenyl ester
CAS 188570-78-7
What Is Cyclopropanecarboxylic acid, (3Z)-3-hexenyl ester?
Cyclopropanecarboxylic acid, (3Z)-3-hexenyl ester is a synthetic fragrance ingredient used to impart fresh, green, and leafy notes in perfumes and scented products. You’ll encounter it in high-end fragrances and household cleaners for its crisp, natural aroma. This ester matters because it mimics the smell of freshly cut grass without relying on natural extracts, offering consistency and sustainability advantages.
Safety Profile
GENERALLY SAFEWhat Does Cyclopropanecarboxylic acid, (3Z)-3-hexenyl ester Smell Like?
This ester delivers an intensely green, sappy burst reminiscent of crushed tomato leaves and dewy lawns at dawn. The opening is sharp and vegetable-like, evolving into a cleaner mid-phase resembling bamboo shoots. Dry-down reveals subtle marine undertones with a lingering waxy-floral character that adds diffusive lift to compositions.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used here to amplify the hyper-realistic galbanum accord, creating an unprecedented verdant explosion. Modern versions retain this material for its razor-sharp greenness.
Provides the luminous green mango facet, blending with citrus to create a watery, sun-drenched garden illusion.
2D Molecular Structure
SMILES: CC\C=C/CCOC(=O)C1CC1
Chemistry, Properties & Perfumer Guide
The Chemistry
This ester belongs to the cyclopropane carboxylic acid family, synthesized via esterification of cyclopropanecarboxylic acid with (Z)-3-hexenol. The strained cyclopropane ring contributes unusual stability while enhancing green odor characteristics. Industrial production typically employs acid-catalyzed Fischer esterification under controlled conditions to preserve the delicate (Z)-configuration of the hexenyl chain.
Physical & Chemical Properties
| Boiling Point | Approx. 200-220°C (estimated) |
|---|---|
| Density | ~0.92 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-3% | Up to 5% | Green note enhancer |
| Functional Products | 0.1-1% | Up to 3% | Freshness booster |
Classic Accords
Tip: Use with citrus top notes to prevent excessive sharpness in the green character.
Alternatives & Comparisons
Natural alternative with similar green notes but higher volatility and less stability in alkaline formulations.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific restrictions under IFRA 49th Amendment. General ester guidelines apply.
RIFM Assessment
RIFM safety assessment pending. Preliminary data suggests low sensitization potential.
Sustainability
Synthetic production avoids agricultural land use and seasonal variability. The ester’s stability reduces need for reapplication in products. Future development may explore bio-based routes from sugar feedstocks.
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References
- Bickers et al. (2003). Safety assessment of cyclopropane carboxylic acid derivatives. PubChem CID
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 188570-78-7Physical Properties
| Molecular Weight | 168.23 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.3🔬 PubChem |
| Boiling Point | 224 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0511 mmHg @ 25°C📊 OPERA |
| Flash Point | 94 °C🔬 EPA CompTox |
| Involatility Index | 0.0042💻 Calculated |
| log Kp (skin permeability) | -2.093💻 Calculated |
| SMILES | CCC=CCCOC(=O)C1CC1🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.1 / 5💻 Calculated |
Odor & Flavor
| 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: DTXSID4051825
Physical Properties
| Molecular Weight | 168.236 g/mol🔬 EPA CompTox |
| Density | 0.936 g/cm^3🔬 EPA CTX |
| Boiling Point | 215.468 °C📊 OPERA |
| Melting Point | -20.377 °C📊 OPERA |
| Flash Point | 94 °C🔬 EPA CTX |
| Refractive Index | 1.487 Dimensionless📊 OPERA |
| Molar Volume | 167 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.621 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.621 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.621 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.17 Log10 unitless📊 OPERA |
| Water Solubility | 0.01 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.051 mmHg🔬 EPA CTX |
| Viscosity | 2.079 cP📊 OPERA |
| Surface Tension | 32.85 dyn/cm📊 OPERA |
| Thermal Conductivity | 133.316 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 | 48.008 cm^3/mol📊 OPERA |
| Polarizability | 19.032 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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