Cis-3-Hexenol (Leaf Alcohol) (CAS 928-96-1) — Green Top Note Fragrance Ingredient
Cis-3-Hexenol (Leaf Alcohol)
CAS 928-96-1
What Is Cis-3-Hexenol (Leaf Alcohol)?
Cis-3-Hexenol, often called ‘leaf alcohol’, is the molecule that gives freshly cut grass its vibrant green scent. You encounter it in everything from perfumes to flavored foods and household cleaners. This natural compound matters because it’s one of the most authentic ways perfumers recreate the smell of nature – a single drop can transform a fragrance with the crispness of a summer garden.
Safety Profile
USE WITH AWARENESS
What Does Cis-3-Hexenol (Leaf Alcohol) Smell Like?
Cis-3-Hexenol bursts with the juicy verdancy of crushed tomato leaves and dewy lawn clippings. Its piercing top note has a slightly bitter, chlorophyll-like intensity that mellows into a softer green tea character. Unlike many green notes, it maintains remarkable freshness throughout evaporation rather than turning musty. The dry-down reveals subtle fruity undertones reminiscent of unripe kiwi, with a clean, almost metallic finish that prevents cloying sweetness.
Scent Profile
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
The reformulated version uses cis-3-hexenol to create its legendary galbanum opening – amplifying the sensation of snapping green stems with photorealistic precision.
Ellena employs it to mimic the sappy greenness of unripe mangoes, blending with carrot seed for an aqueous green effect.
Used sparingly here to add a dewy freshness to the violet leaf, preventing the composition from becoming too powdery.
The sharp green attack relies on cis-3-hexenol to contrast the iris heart, like morning frost on metal.
A masterclass in green accords, using cis-3-hexenol to recreate the tartness of tomato vines in sunlight.
2D Molecular Structure
SMILES: CC\C=C/CCO
Chemistry, Properties & Perfumer Guide
The Chemistry
Cis-3-Hexenol is a six-carbon unsaturated alcohol with the hydroxyl group on the third carbon. It’s part of the ‘green leaf volatiles’ (GLVs) emitted by damaged plants as a defense mechanism. Industrially produced via selective hydrogenation of cis-3-hexenal or through biotechnological routes using lipase enzymes. The cis-configuration at the double bond is crucial – the trans isomer smells markedly different. Recent advances allow enantioselective synthesis to produce the (Z)-3-hexenol form with 99% purity for perfumery applications.
Physical & Chemical Properties
| Boiling Point | 157 °C |
|---|---|
| Density | 0.849 g/cm³ |
| Flash Point | 56 °C |
| Vapor Pressure | 0.7 mmHg at 25°C |
| Solubility | Slightly soluble in water, miscible with alcohols |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Powerful green modifier |
| Functional Fragrance | 0.01-0.1% | Up to 0.3% | Air fresheners, detergents |
| Flavor | 1-5 ppm | Up to 10 ppm | Green tea, vegetable flavors |
Classic Accords
+ Rose Oxide + Blackcurrant = Modern Rose
+ Calone + Melon = Aquatic Fantasy
Tip: Stabilize in ethanol before adding to aqueous systems to prevent rapid degradation.
Alternatives & Comparisons
Less intense, more fruity green character. Preferred when a softer leafy note is needed without the sharpness.
Synthetic alternative with greater tenacity and less bitterness, though lacks the natural freshness.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. IFRA, REACH, EU Cosmetics Regulation standards update periodically. Consult current IFRA Standards Library before formulating. Not legal or regulatory advice.
IFRA Status
Not restricted under current IFRA standards (Amendment 49).
EU Allergen Declaration
Not listed in EU allergen regulation (EC) No 1223/2009.
GHS Classification
H319
RIFM Assessment
RIFM evaluation concludes safe use at current industry levels (2016 assessment).
Sustainability
While naturally occurring, most commercial cis-3-hexenol is synthesized from petrochemical precursors. Emerging bio-based production methods use plant-derived fatty acids as feedstock. Biodegradation occurs readily in the environment (95% in 28 days per OECD 301F). The molecule’s potency means very small quantities are needed, reducing ecological footprint.
Explore Cis-3-Hexenol (Leaf Alcohol)
Browse essential oils and aroma compounds.
Affiliate disclosure: we may earn a small commission at no extra cost to you.
Industry & Science Data
References
- Matsui K. (2006). Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism. Current Opinion in Plant Biology. PMID 16603411
- Burdock GA. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. ISBN 9781439852296
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Mar 2026.
Ingredient Data Sheet
CAS 928-96-1Physical Properties
| Molecular Weight | 100.16 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 1.3🔬 PubChem |
| Boiling Point | 156.5 °C🔬 EPA CompTox |
| Vapor Pressure | 1.6951 mmHg @ 25°C📊 OPERA |
| Flash Point | 54.4 °C🔬 EPA CompTox |
| Involatility Index | 0.1826💻 Calculated |
| log Kp (skin permeability) | -2.388💻 Calculated |
| SMILES | CCC=CCCO🔬 PubChem |
Volatility & Performance
| Fragrance Note | Top💻 Calculated |
| Volatility Class | Moderate💻 Calculated |
| Persistence Score | 0.5 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | freshgrassygreen• leffingwell |
| Functional Groups | alcoholalkene💻 RDKit |
| “Powerful and intensely green, grassy odor. It appears more grassy-green and foliage-green, less fruity than the trans-2-Hexenol.”📖 Arctander | |
| 3-Hexen-1-ol has an intense, green odor, not as strong as the corresponding aldehyde, and a characteristic herbaceous, leafy odor on dilution.📖 Fenaroli | |
Sensory Thresholds
| Odor Detection Threshold | 0.0797 ppm (n=6)📖 van Gemert |
Regulatory Status
| FEMA Number | FEMA 2563⚖️ FEMA GRAS |
| GRAS Status | Generally Recognized as Safe⚖️ FEMA GRAS |
| IOFI Classification | Nature Identical📖 Fenaroli |
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: DTXSID6022137
Physical Properties
| Molecular Weight | 100.161 g/mol🔬 EPA CompTox |
| Density | 0.848 g/cm^3🔬 EPA CTX |
| Boiling Point | 156.5 °C🔬 EPA CTX |
| Melting Point | -27.859 °C📊 OPERA |
| Flash Point | 50.358 °C🔬 EPA CTX |
| Refractive Index | 1.443 Dimensionless📊 OPERA |
| Molar Volume | 118.697 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.313 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 1.313 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.313 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.65 Log10 unitless📊 OPERA |
| Water Solubility | 0.164 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 1.695 mmHg🔬 EPA CTX |
| Viscosity | 2.286 cP📊 OPERA |
| Surface Tension | 27.044 dyn/cm📊 OPERA |
| Thermal Conductivity | 152.183 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 20.23 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 3 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 31.439 cm^3/mol📊 OPERA |
| Polarizability | 12.463 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.
Related Research
- Coriander herb oil (CAS 8008-52-4) — Green Top Note Fragrance Ingredient
- 4-Ethylbenzaldehyde (CAS 4748-78-1) — Sweet Heart to base Note Fragrance Ingredient
- Alcohols, C6-12, ethoxylated (5 > EO < 20) (CAS 68439-45-2) — Citrus N/A Note Fragrance Ingredient
- Sodium hydroxide (CAS 1310-73-2) — Citrus N/A Note Fragrance Ingredient
