4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)- (CAS 58461-27-1) — Green Top to middle Note Fragrance Ingredient
4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)-
CAS 58461-27-1
What Is 4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)-?
4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)- is a synthetic fragrance ingredient primarily used in perfumery. It contributes to fresh, green, and slightly woody accords. You might encounter it in modern floral or citrus fragrances where it adds naturalistic complexity. This molecule matters because it helps perfumers create lifelike green notes without relying on natural extracts, offering consistency and sustainability advantages over plant-derived materials.
Safety Profile
GENERALLY SAFEWhat Does 4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)- Smell Like?
This molecule delivers a crisp, dewy green character reminiscent of freshly crushed leaves with subtle citrus undertones. The initial burst has a sappy, almost unripe fruit quality that evolves into a cleaner, more refined green note. As it dries down, a faint woody-musky undertone emerges, providing excellent tenacity for a green note. The overall effect bridges the gap between sharp galbanum and softer violet leaf, making it versatile for modern green accords.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to reinforce the legendary green galbanum note, adding contemporary freshness while maintaining the classic’s sharp vegetal character.
Contributes to the luminous green mango accord, enhancing the fruity-green illusion without overpowering the delicate citrus top notes.
2D Molecular Structure
SMILES: CC(C)=CCC(CO)C(C)=C
Chemistry, Properties & Perfumer Guide
The Chemistry
This unsaturated alcohol belongs to the terpenoid family, featuring both hydroxyl and alkene functional groups. While not found in nature, its structure mimics compounds found in green plants. Industrial synthesis typically involves palladium-catalyzed coupling reactions to construct the carbon skeleton, followed by selective oxidation. The molecule’s stereochemistry significantly impacts its odor profile, with different isomers exhibiting varying intensity of green character.
Physical & Chemical Properties
| Appearance | Colorless liquid |
|---|---|
| Boiling Point | Estimated 200-220°C |
| Density | ~0.89 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Green note modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Freshness booster |
Classic Accords
Tip: Use with citrus materials to prevent excessive sharpness in green compositions.
Alternatives & Comparisons
More intense grassy-green character when a stronger natural leaf effect is desired.
For softer green effects with floral undertones and better stability in soap applications.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
Under review by RIFM, preliminary data suggests low sensitization potential.
Sustainability
As a synthetic material, this molecule reduces pressure on natural resources while offering consistent quality. Production typically uses petrochemical feedstocks, though bio-based routes are being explored. Its potency means relatively small quantities are needed, reducing environmental load compared to some natural alternatives.
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References
- Bauer et al. (2001). Modern Synthetic Methods in Fragrance Chemistry. Chemistry & Biodiversity. DOI:10.1002/cbdv.200600001
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 58461-27-1Physical Properties
| Molecular Weight | 154.25 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3🔬 PubChem |
| Boiling Point | 229 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.511💻 Calculated |
| SMILES | CC(=CCC(CO)C(=C)C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
Odor & Flavor
| Primary Descriptors | greenwoody• leffingwell |
| Functional Groups | alcoholalkene💻 RDKit |
| “This alcohol, only recently brought into the market at a truly attractive price, has found use in artificial Lavender oils, Lavandin, Bergamot, Clary Sage, etc. As a perfume material, it has not yet found much use, perhaps because of its price was always too high for its odor type, except in the case of the specific application in artificial essential oils.”📖 Arctander | |
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: DTXSID70866690
Physical Properties
| Molecular Weight | 154.253 g/mol🔬 EPA CompTox |
| Density | 0.866 g/cm^3📊 OPERA |
| Boiling Point | 216.55 °C📊 OPERA |
| Melting Point | -13.199 °C📊 OPERA |
| Flash Point | 85.066 °C📊 OPERA |
| Refractive Index | 1.461 Dimensionless📊 OPERA |
| Molar Volume | 179.796 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.414 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.414 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.414 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.91 Log10 unitless📊 OPERA |
| Water Solubility | 0.008 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.146 mmHg📊 OPERA |
| Viscosity | 3.325 cP📊 OPERA |
| Surface Tension | 27.585 dyn/cm📊 OPERA |
| Thermal Conductivity | 137.62 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 | 4 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 49.34 cm^3/mol📊 OPERA |
| Polarizability | 19.56 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.
