2,2′-(Dithiodimethylene)-difuran (CAS 4437-20-1) — Spicy Top to Middle Note Fragrance Ingredient
2,2'-(Dithiodimethylene)-difuran
CAS 4437-20-1
What Is 2,2'-(Dithiodimethylene)-difuran?
2,2′-(Dithiodimethylene)-difuran is a synthetic fragrance ingredient used in advanced perfumery. It creates unique sulfurous notes reminiscent of roasted coffee or toasted bread. People encounter it in niche fragrances where unconventional notes are desired. This ingredient matters because it allows perfumers to create complex, savory accords that stand out in modern compositions.
Safety Profile
USE WITH AWARENESSWhat Does 2,2'-(Dithiodimethylene)-difuran Smell Like?
2,2′-(Dithiodimethylene)-difuran delivers a powerful, sulfurous character that evolves from an initial burnt matchstick sharpness to a deep, roasted coffee heart. The dry-down reveals surprising gourmand qualities – imagine the crust of freshly baked sourdough meeting dark molasses. Its tenacity allows it to act as both a top note with surprising diffusion and a base note that anchors more volatile materials.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to create the dark roasted coffee accord that defines this fragrance, adding depth to the rum and chocolate notes.
Provides the burnt coffee edge that makes this fragrance smell like a Turkish coffee shop at dawn.
2D Molecular Structure
SMILES: C(SSCC1=CC=CO1)C1=CC=CO1
Chemistry, Properties & Perfumer Guide
The Chemistry
This sulfur-containing heterocyclic compound belongs to the furan family. The dithiodimethylene bridge creates unique stability while contributing to its distinctive odor profile. Synthesis typically involves the reaction of furfuryl derivatives with sulfur-containing reagents. The compound’s planar structure allows for strong interaction with olfactory receptors, explaining its potent aroma at low concentrations.
Physical & Chemical Properties
| Molecular Weight | Not publicly available |
|---|---|
| Appearance | Likely colorless to pale yellow liquid |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used sparingly for effect |
| Functional Fragrance | 0.01-0.1% | Up to 0.2% | Masking agent for industrial odors |
Classic Accords
Tip: Balance with sweet materials to prevent overpowering sulfur character.
Alternatives & Comparisons
When a more intense roasted coffee note is needed, though with greater safety concerns.
For a meatier, more savory sulfur character in gourmand compositions.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA, but recommended usage levels should be carefully monitored due to limited safety data.
GHS Classification
RIFM Assessment
No formal RIFM assessment available. Recommended to follow precautionary principle.
Sustainability
As a synthetic material, production can be controlled to minimize environmental impact. However, sulfur-containing compounds require careful handling to prevent emissions. Future development may focus on more sustainable synthetic pathways.
Explore 2,2'-(Dithiodimethylene)-difuran
Browse essential oils and aroma compounds.
Browse on iHerb →Affiliate disclosure: we may earn a small commission at no extra cost to you.
References
- PubChem Compound Summary CID Not Available
- Sulfur Compounds in Fragrance Chemistry
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 4437-20-1Physical Properties
| Molecular Weight | 226.3 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.1🔬 PubChem |
| Boiling Point | 229 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.589💻 Calculated |
| SMILES | C1=COC(=C1)CSSCC2=CC=CO2🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
Odor & Flavor
| Primary Descriptors | roastedsulfurous• leffingwell |
| Functional Groups | aromatic💻 RDKit |
| “attractive, caramellic-burnt, "roasted" odor.”📖 Arctander | |
| 2,2'-(Dithiodimethylene)-difuran has a powerful, repulsive sulfide odor.📖 Fenaroli | |
Flavor Notes (Arctander)
| “It has found use in the flavor bases which are used to re-constitute the aroma of instant Coffee and other Coffee products. It is also used in imitation Coffee flavor. Another Coffee flavor component, Furfuryl mercaptan, is produced by reduction of the above disulfide.”📖 Arctander |
Sensory Thresholds
| Odor Detection Threshold | 0 ppm📖 van Gemert |
Regulatory Status
| 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: DTXSID3063463
Physical Properties
| Molecular Weight | 226.31 g/mol🔬 EPA CompTox |
| Density | 1.239 g/cm^3🔬 EPA CTX |
| Boiling Point | 229.5 °C🔬 EPA CTX |
| Melting Point | 10.25 °C🔬 EPA CTX |
| Flash Point | 128.129 °C📊 OPERA |
| Refractive Index | 1.606 Dimensionless📊 OPERA |
| Molar Volume | 176.48 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.03 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 3.928 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.923 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.45 Log10 unitless📊 OPERA |
| Water Solubility | 0.015 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.001 mmHg📊 OPERA |
| Surface Tension | 48.319 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 26.28 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 4 count💻 Computed |
| Rotatable Bonds | 5 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 60.883 cm^3/mol📊 OPERA |
| Polarizability | 24.136 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.
