(E,Z)-2,6-Nonadien-1-ol acetate (CAS 68555-65-7) — Green Top to middle Note Fragrance Ingredient
(E,Z)-2,6-Nonadien-1-ol acetate
CAS 68555-65-7
What Is (E,Z)-2,6-Nonadien-1-ol acetate?
(E,Z)-2,6-Nonadien-1-ol acetate is a synthetic fragrance compound that mimics the fresh, green aroma of cucumber and melon rinds. It’s used in fine fragrances, body care products, and some food flavorings to add crisp, watery freshness. This ingredient matters because it provides a photorealistic ‘just-cut’ cucumber note that’s difficult to achieve with natural extracts, allowing perfumers to create ultra-realistic aquatic and green accords.
Safety Profile
USE WITH AWARENESSWhat Does (E,Z)-2,6-Nonadien-1-ol acetate Smell Like?
This molecule bursts with the exact scent of freshly sliced cucumber – watery, green, and slightly sweet like the white flesh near the rind. The top note is intensely crisp with melon-like undertones, evolving into a heart that recalls dew-covered cucumber vines at dawn. As it dries down, it maintains remarkable freshness while revealing a subtle floral character reminiscent of cucumber blossoms. The dry-down is clean and slightly waxy, like the after-smell of hands that have handled garden-fresh cucumbers.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Jean-Claude Ellena used this cucumber-mimetic to create the illusion of rain-drenched vegetation, pairing it with cardamom and ginger for a photorealistic monsoon garden effect.
The aquatic freshness in this classic relies on cucumber-like molecules including (E,Z)-2,6-nonadienol acetate to achieve its dewy, just-showered effect.
2D Molecular Structure
SMILES: CC\C=C/CC\C=C\COC(C)=O
Chemistry, Properties & Perfumer Guide
The Chemistry
(E,Z)-2,6-Nonadien-1-ol acetate is an unsaturated fatty alcohol ester with cis-trans isomerism at the 2,6 positions. The E,Z configuration is crucial for its characteristic cucumber aroma. Industrially produced via acetylation of the corresponding alcohol, which is typically obtained through hydroformylation of 1,3-butadiene followed by selective hydrogenation. The stereochemistry presents synthesis challenges – the commercial product usually contains an isomeric mixture where the E,Z form dominates for olfactory performance.
Physical & Chemical Properties
| Boiling Point | ~220 °C (estimated) |
|---|---|
| Density | ~0.89 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used sparingly for fresh top notes |
| Body Care | 0.1-0.5% | Up to 1% | Adds crispness to shower gels |
| Functional Fragrance | 0.01-0.1% | Up to 0.5% | Masking agent in cleaners |
Classic Accords
Tip: Stabilize in ethanol before adding to aqueous systems to prevent hydrolysis of the acetate group.
Alternatives & Comparisons
The non-acetylated form provides stronger green character but less diffusion and more vegetative aspects.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions currently apply to this material (as of Amendment 49).
RIFM Assessment
RIFM has evaluated this material and found it safe for use at current industry levels.
Sustainability
As a synthetic material, this avoids agricultural land use but requires petrochemical feedstocks. Modern production routes aim for atom economy in the hydroformylation steps. Some manufacturers are exploring bio-based routes using fermentation-derived intermediates.
Explore (E,Z)-2,6-Nonadien-1-ol acetate
Browse essential oils and aroma compounds.
Browse on iHerb →Affiliate disclosure: we may earn a small commission at no extra cost to you.
References
- Bauer et al. (2001). Cucumber aroma constituents. Journal of Agricultural and Food Chemistry. DOI: 10.1021/jf010030e
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID20904430
Physical Properties
| Molecular Weight | 182.263 g/mol🔬 EPA CompTox |
| Density | 0.912 g/cm^3📊 OPERA |
| Boiling Point | 236.422 °C📊 OPERA |
| Melting Point | -30.307 °C📊 OPERA |
| Flash Point | 91.845 °C📊 OPERA |
| Refractive Index | 1.459 Dimensionless📊 OPERA |
| Molar Volume | 200.821 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.612 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.612 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.612 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.79 Log10 unitless📊 OPERA |
| Water Solubility | 0.002 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.035 mmHg📊 OPERA |
| Viscosity | 1.78 cP📊 OPERA |
| Surface Tension | 28.023 dyn/cm📊 OPERA |
| Thermal Conductivity | 141.544 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 | 54.901 cm^3/mol📊 OPERA |
| Polarizability | 21.764 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.
