5-(cis-3-Hexenyl)dihydro-5-methyl-2(3H)furanone (CAS 70851-61-5) — Green Top to Mid Note Fragrance Ingredient
5-(cis-3-Hexenyl)dihydro-5-methyl-2(3H)furanone
CAS 70851-61-5
What Is 5-(cis-3-Hexenyl)dihydro-5-methyl-2(3H)furanone?
5-(cis-3-Hexenyl)dihydro-5-methyl-2(3H)furanone is a synthetic fragrance ingredient used to add green, fresh nuances to perfumes. It’s found in modern floral and fougère compositions. This molecule matters because it helps recreate the crisp, dewy quality of freshly cut grass or crushed leaves without using natural extracts, making fragrances more consistent and sustainable.
Safety Profile
GENERALLY SAFEWhat Does 5-(cis-3-Hexenyl)dihydro-5-methyl-2(3H)furanone Smell Like?
A vibrant green burst reminiscent of torn galbanum leaves and young bamboo shoots. Opens with a sharp, almost metallic vegetal intensity that quickly softens into a lactonic, coconut-like undertone. The dry-down reveals a creamy woodiness with whispers of fresh hay. Unlike many green notes, it maintains remarkable persistence for a top-mid note, transitioning smoothly into heart accords without turning harsh or soapy.
2D Molecular Structure
SMILES: CC\C=C/CCC1(C)CCC(=O)O1
Chemistry, Properties & Perfumer Guide
The Chemistry
This synthetic lactone belongs to the furanone class, structurally featuring a gamma-lactone ring with a hexenyl side chain in cis configuration. While not found in nature, it mimics the behavior of leaf alcohol derivatives. Industrial synthesis typically involves the condensation of cis-3-hexenol with methylbutenolide precursors. The cis-configuration of the hexenyl group is crucial for odor quality, as the trans isomer exhibits markedly different sensory properties.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Green modifier for floral bouquets |
| Functional Fragrances | 0.1-0.5% | Up to 1% | Laundry fresheners |
Classic Accords
Tip: Stabilize with antioxidant to prevent discoloration in ethanol bases.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards.
RIFM Assessment
Not yet evaluated by RIFM as of 2023.
Sustainability
As a synthetic material, production avoids agricultural land use but depends on petrochemical feedstocks. The efficient synthesis route (typically 3-4 steps) gives it better carbon footprint than some natural green alternatives. Biodegradability studies indicate moderate environmental persistence.
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Physicochemical Properties
DTXSID: DTXSID1052454
Physical Properties
| Molecular Weight | 182.263 g/mol🔬 EPA CompTox |
| Density | 0.954 g/cm^3📊 OPERA |
| Boiling Point | 271.2 °C📊 OPERA |
| Melting Point | 7.812 °C📊 OPERA |
| Flash Point | 112.661 °C📊 OPERA |
| Refractive Index | 1.462 Dimensionless📊 OPERA |
| Molar Volume | 191.893 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.834 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.834 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.834 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.33 Log10 unitless📊 OPERA |
| Water Solubility | 0.003 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.02 mmHg📊 OPERA |
| Viscosity | 2.631 cP📊 OPERA |
| Surface Tension | 30.361 dyn/cm📊 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 | 4 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 52.712 cm^3/mol📊 OPERA |
| Polarizability | 20.897 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.
