3-Propylidenephthalide (CAS 17369-59-4) — Green Top to Middle Note Fragrance Ingredient
3-Propylidenephthalide
CAS 17369-59-4
What Is 3-Propylidenephthalide?
3-Propylidenephthalide is a synthetic fragrance compound used in perfumery to create unique, herbaceous-green nuances. You might encounter it in niche fragrances or as a component in sophisticated floral-green accords. This ingredient matters because it offers perfumers a tool to craft crisp, celery-like top notes with exceptional diffusion, helping bridge green and floral elements in modern compositions.
Safety Profile
GENERALLY SAFEWhat Does 3-Propylidenephthalide Smell Like?
3-Propylidenephthalide bursts with an intensely green, celery seed-like aroma that evolves into a crisp herbal heart. Imagine snapping fresh celery stalks with earthy undertones of lovage root. The dry-down reveals subtle woody-powdery facets, like dried herbs in an apothecary jar. Its sharp initial impact softens to a sophisticated green veil that lingers close to the skin.
2D Molecular Structure
SMILES: CCC=C1OC(=O)C2=CC=CC=C12
Chemistry, Properties & Perfumer Guide
The Chemistry
3-Propylidenephthalide belongs to the phthalide class of benzofuranoids, structurally related to natural compounds found in celery and lovage. It’s synthesized through the condensation of phthalic anhydride derivatives with propionaldehyde. The double bond at the 3-position creates geometric isomers that influence odor character. While not found in significant quantities in nature, it mimics the green notes of its natural phthalide cousins.
Physical & Chemical Properties
| Molecular Weight | 188.22 g/mol |
|---|
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used as green modifier |
| Functional Fragrance | 0.01-0.1% | Trace amounts | For fresh herbal effects |
Classic Accords
Tip: Use in trace amounts to prevent dominance in the composition.
Alternatives & Comparisons
Longer-lasting green note with similar celery character but greater tenacity.
Naturally occurring phthalide from lovage, offering more complex earthy-green nuances.
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 RIFM safety assessment publicly available.
Sustainability
As a synthetic material, 3-Propylidenephthalide avoids agricultural impacts but requires petrochemical feedstocks. Its production is energy-intensive but allows precise control without natural variability. The molecule’s potency means small quantities achieve desired effects, reducing overall environmental load compared to natural extracts with similar odor profiles.
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Ingredient Data Sheet
CAS 17369-59-4Physical Properties
| Molecular Weight | 174.2 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.6🔬 PubChem |
| Boiling Point | 172.8 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0003 mmHg @ 25°C📊 OPERA |
| Flash Point | 93.3 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.917💻 Calculated |
| SMILES | CCC=C1C2=CC=CC=C2C(=O)O1🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 6 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | esteretheralkenearomatic💻 RDKit |
| 3-Propylidenephthalide has a very powerful and warm, spicy odor with a warm, spicy, herbaceous flavor.📖 Fenaroli | |
Regulatory Status
| IFRA Listed | Yes — see IFRA Standards for category limits⚖️ IFRA 51 |
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: DTXSID7025972
Physical Properties
| Molecular Weight | 174.199 g/mol🔬 EPA CompTox |
| Density | 1.132 g/cm^3🔬 EPA CTX |
| Boiling Point | 318.2 °C🔬 EPA CTX |
| Melting Point | 66.8 °C🔬 EPA CTX |
| Flash Point | 123.802 °C📊 OPERA |
| Refractive Index | 1.651 Dimensionless📊 OPERA |
| Molar Volume | 139.783 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.169 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.169 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.169 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.88 Log10 unitless📊 OPERA |
| Water Solubility | 0.006 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Viscosity | 3.581 cP📊 OPERA |
| Surface Tension | 55.8 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 | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 51.066 cm^3/mol📊 OPERA |
| Polarizability | 20.244 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.
