(Z)-Hex-3-enyl 2-methylbutyrate (CAS 53398-85-9) — Green Top to middle Note Fragrance Ingredient
(Z)-Hex-3-enyl 2-methylbutyrate
CAS 53398-85-9
What Is (Z)-Hex-3-enyl 2-methylbutyrate?
(Z)-Hex-3-enyl 2-methylbutyrate is a synthetic fragrance ingredient that mimics the fresh, green scent of crushed leaves. You’ll find it in perfumes, body care products, and household cleaners where a natural, outdoorsy green note is desired. This molecule matters because it captures the vibrant essence of nature without relying on plant extracts, making fragrances more sustainable and consistent in quality.
Safety Profile
GENERALLY SAFEWhat Does (Z)-Hex-3-enyl 2-methylbutyrate Smell Like?
This molecule bursts with the sharp, sappy greenness of freshly torn grass blades, evolving into a rounded fruitiness reminiscent of green apples. The initial punch of chlorophyll-like intensity mellows into a soft herbal sweetness, like basil stems crushed between fingers. During dry-down, it maintains a crisp vegetal character with subtle tropical undertones – imagine unripe bananas and young bamboo shoots. The overall effect is remarkably lifelike, as if bottling the moment when morning dew evaporates from a vegetable garden.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to create the photorealistic green mango accord, contributing to the fragrance’s vibrant opening that mimics sun-warmed fruit plucked straight from the tree.
Enhances the dewy violet leaf heart with its crisp, wet greenery effect, adding dimensionality to the classic fougère structure.
2D Molecular Structure
SMILES: CC\C=C/CCOC(=O)C(C)CC
Chemistry, Properties & Perfumer Guide
The Chemistry
(Z)-Hex-3-enyl 2-methylbutyrate belongs to the ester class, specifically a 2-methylbutyrate ester of (Z)-3-hexenol. While the (Z)-3-hexenol moiety occurs naturally as ‘leaf alcohol’ in plants, this particular ester is primarily synthetic. Industrial production typically involves esterification of (Z)-3-hexenol with 2-methylbutyric acid under acidic conditions. The Z-configuration at the 3-position is crucial for odor quality, as the E-isomer exhibits markedly different sensory properties. This chiral specificity makes stereoselective synthesis important for fragrance applications.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Odor Threshold | 0.5 ppb in water |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-1% | Up to 3% | For fresh top notes |
| Functional Fragrance | 0.05-0.5% | Up to 1% | In detergents and cleaners |
Classic Accords
Tip: Use with citrus oils to prevent excessive sharpness in green compositions.
Alternatives & Comparisons
For a more straightforward green note without fruity undertones, though less tenacious.
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 confirms safe use at current industry levels.
Sustainability
As a synthetic molecule, this compound avoids agricultural land use while accurately reproducing natural scent profiles. Production typically utilizes green chemistry principles with high atom economy. Unlike some natural extracts, it doesn’t contribute to deforestation or require seasonal harvesting, making supply more reliable and environmentally consistent.
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. ISBN 9781439828873
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID5052177
Physical Properties
| Molecular Weight | 184.279 g/mol🔬 EPA CompTox |
| Density | 0.882 g/cm^3📊 OPERA |
| Boiling Point | 224.274 °C📊 OPERA |
| Melting Point | -53.378 °C📊 OPERA |
| Flash Point | 82.831 °C📊 OPERA |
| Refractive Index | 1.441 Dimensionless📊 OPERA |
| Molar Volume | 207.583 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.748 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.748 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.748 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.5 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.115 mmHg🔬 EPA CTX |
| Viscosity | 1.735 cP📊 OPERA |
| Surface Tension | 27.015 dyn/cm📊 OPERA |
| Thermal Conductivity | 134.586 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 | 6 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 54.802 cm^3/mol📊 OPERA |
| Polarizability | 21.725 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.
