2,5-Dimethyl-4-methoxy-3(2H)-furanone (CAS 4077-47-8) — Sweet Middle Note Fragrance Ingredient
2,5-Dimethyl-4-methoxy-3(2H)-furanone
CAS 4077-47-8
What Is 2,5-Dimethyl-4-methoxy-3(2H)-furanone?
2,5-Dimethyl-4-methoxy-3(2H)-furanone is a synthetic aroma chemical used to create caramel-like, sweet, and fruity notes in fragrances. You’ll encounter it in gourmand perfumes, flavored products, and some fruity body care items. This molecule matters because it adds depth to sweet accords, mimicking natural caramelization processes without the calories. Its unique structure allows perfumers to build realistic dessert-like fragrances that last.
Safety Profile
USE WITH AWARENESSWhat Does 2,5-Dimethyl-4-methoxy-3(2H)-furanone Smell Like?
A warm, enveloping aroma that unfolds like caramelizing sugar in a copper pot – first the sharp sweetness of burnt sugar, then rounding into maple syrup depth with a whisper of dried pineapple. The methoxy group lends a jammy fruitiness that prevents cloying sweetness, while the furanone skeleton provides remarkable tenacity for a top-mid note. In drydown, it leaves a comforting trace like the memory of molasses cookies cooling on a kitchen rack.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a caramelic modifier in the revolutionary gourmand accord, blending with ethyl maltol to create the scent’s signature edible quality without becoming cloying.
Provides fruity-caramel depth to the praline accord, bridging the gap between the top citrus and base patchouli notes.
2D Molecular Structure
SMILES: COC1=C(C)OC(C)C1=O
Chemistry, Properties & Perfumer Guide
The Chemistry
This furanone derivative belongs to the class of oxygenated heterocycles, specifically methoxy-substituted γ-lactones. While not found in nature, it structurally resembles Maillard reaction products. Industrial synthesis typically involves cyclization of appropriate dihydroxy or keto-acid precursors with methanol under acidic conditions. The methoxy group at position 4 creates steric hindrance that influences its odor profile and stability compared to simpler furanones.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | ~230 °C (estimated) |
| Density | ~1.05 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Gourmand accent |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Sweetness enhancer |
Classic Accords
Tip: Use with citrus top notes to prevent gourmand compositions from becoming overly heavy.
Alternatives & Comparisons
More natural strawberry-caramel character but less stable; choose when naturalness is prioritized over longevity.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions currently apply (as of Amendment 49).
GHS Classification
RIFM Assessment
RIFM evaluation complete; safe at current usage levels with recommended limits.
Sustainability
As a synthetic material, production avoids agricultural land use but requires petrochemical feedstocks. Recent advances allow production from bio-based methanol, improving its environmental profile. Being highly potent reduces the quantity needed per formulation.
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 4077-47-8Physical Properties
| Molecular Weight | 142.15 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 1🔬 PubChem |
| Boiling Point | 221 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.857💻 Calculated |
| SMILES | CC1C(=O)C(=C(O1)C)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
Odor & Flavor
| Primary Descriptors | caramelfruitysweet• leffingwell |
| Functional Groups | ketoneetheralkene💻 RDKit |
| 2,5-Dimethyl-4-methoxy-3(2H)-furanone has a sweet, cooked caramellic, burnt sugar odor.📖 Fenaroli | |
Sensory Thresholds
| Odor Detection Threshold | 0.016 ppm (n=11)📖 van Gemert |
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: DTXSID20863316
Physical Properties
| Molecular Weight | 142.154 g/mol🔬 EPA CompTox |
| Density | 1.118 g/cm^3📊 OPERA |
| Boiling Point | 206.011 °C📊 OPERA |
| Melting Point | 8.176 °C📊 OPERA |
| Flash Point | 83.979 °C📊 OPERA |
| Refractive Index | 1.461 Dimensionless📊 OPERA |
| Molar Volume | 129.187 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 0.441 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 0.441 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 0.441 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.43 Log10 unitless📊 OPERA |
| Water Solubility | 0.44 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.184 mmHg📊 OPERA |
| Surface Tension | 32.574 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 35.53 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 35.436 cm^3/mol📊 OPERA |
| Polarizability | 14.048 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.
