5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran (CAS 13679-86-2) — Green Middle Note Fragrance Ingredient
5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran
CAS 13679-86-2
What Is 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran?
5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran is a synthetic fragrance ingredient primarily used in professional perfumery. It’s not commonly encountered in consumer products but may appear in niche fragrances. This molecule contributes unique woody-green nuances to fragrance compositions, valued for its ability to add structural complexity without dominating a scent profile.
Safety Profile
USE WITH AWARENESSWhat Does 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran Smell Like?
This molecule presents a fascinating olfactory profile – opening with crisp green facets reminiscent of crushed stems and freshly cut bamboo. The heart reveals a subtle woody character with faintly resinous undertones, like the sappy edge of pine bark. Dry-down brings surprising softness, evolving into a dry, paper-like texture with whispers of dried herbs. The vinyl group contributes a modern, slightly ozonic lift that prevents the base from becoming too heavy.
2D Molecular Structure
SMILES: CC(=C)C1CCC(C)(O1)C=C
Chemistry, Properties & Perfumer Guide
The Chemistry
5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran belongs to the furanoid class of oxygenated terpenes. While not found in nature, its structure mimics certain oxidative degradation products of terpenes. Synthesis typically involves acid-catalyzed cyclization of appropriate terpene precursors. The molecule’s stereochemistry influences its odor profile, with different isomers displaying varying intensity of green versus woody characteristics.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | Not established |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as green-woody modifier |
| Functional Fragrance | 0.1-1% | Up to 3% | Provides naturalistic green notes |
Classic Accords
Tip: Use sparingly in chypre bases to enhance mossy facets without adding heaviness.
Alternatives & Comparisons
Offers similar green-woody character with more pronounced citrus top notes, useful when brighter openings are desired.
Provides comparable green stem-like effects with greater diffusion and less woody base.
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
No formal RIFM evaluation published as of current data.
Sustainability
As a synthetic material, this ingredient doesn’t impact natural resources directly. Production typically involves petrochemical feedstocks, though some manufacturers may use bio-based precursors. The molecule’s potency allows for low usage levels, reducing environmental load compared to less powerful alternatives.
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Ingredient Data Sheet
CAS 13679-86-2Odor & Flavor
| 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran has a pungent, herbaceousgreen, bold-like camphoraceous, piney, terpene-like and slightly cineol-like odor.📖 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: DTXSID20864429
Physical Properties
| Molecular Weight | 152.237 g/mol🔬 EPA CompTox |
| Density | 0.881 g/cm^3📊 OPERA |
| Boiling Point | 173.116 °C📊 OPERA |
| Melting Point | -11.67 °C📊 OPERA |
| Flash Point | 47.626 °C📊 OPERA |
| Refractive Index | 1.505 Dimensionless📊 OPERA |
| Molar Volume | 164.572 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.59 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.59 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.59 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.43 Log10 unitless📊 OPERA |
| Water Solubility | 0.017 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 1.719 mmHg📊 OPERA |
| Viscosity | 1.6 cP📊 OPERA |
| Surface Tension | 30.004 dyn/cm📊 OPERA |
| Thermal Conductivity | 117.995 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 9.23 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 2 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 48.823 cm^3/mol📊 OPERA |
| Polarizability | 19.355 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.
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