Lilial-methyl anthranilate (Schiff base) (CAS 91-51-0) — Sweet Heart to base Note Fragrance Ingredient
Lilial-methyl anthranilate (Schiff base)
CAS 91-51-0
What Is Lilial-methyl anthranilate (Schiff base)?
Lilial-methyl anthranilate Schiff base is a synthetic fragrance ingredient used in modern perfumery to create long-lasting floral-oriental accords. Consumers encounter it in fabric softeners, body washes, and prestige perfumes where it contributes a warm, powdery nuance with exceptional tenacity. This molecule matters because it bridges natural floralcy with contemporary chemical longevity, allowing perfumers to achieve effects that would otherwise require multiple ingredients.
Safety Profile
USE WITH AWARENESSWhat Does Lilial-methyl anthranilate (Schiff base) Smell Like?
Opens with a surprising burst of orange blossom absolute drizzled over warm plastic, like sunlight on vinyl car seats. The heart reveals itself as a plush union of methyl anthranilate’s grape bubblegum and lilial’s lily-of-the-valley cleanliness. Dry-down is where the magic happens – the Schiff base formation creates a velvety muskiness reminiscent of vintage face powder settling into skin, with a faint metallic shimmer that keeps it modern.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a futuristic floralizer, creating a hyper-realistic gardenia effect when paired with stemone and florhydral. The Schiff base’s tenacity allows the green notes to persist unusually long.
Forms a luminous bridge between lavender and vanilla in this oriental fougère. The molecule’s powdery facet enhances the cosmetic elegance while its warmth supports the tonka bean base.
2D Molecular Structure
SMILES: COC(=O)C1=CC=CC=C1N=NC(C)CC1=CC=C(C=C1)C(C)(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This Schiff base forms through condensation of methyl anthranilate and lilial (butylphenyl methylpropional), creating a molecule with unique properties. Unlike its precursors, it exhibits remarkable stability against hydrolysis in cosmetic matrices. The conjugated system formed by the C=N double bond shifts absorption into the UV range, contributing to photostability. Industrial synthesis typically proceeds via azeotropic removal of water in toluene with p-toluenesulfonic acid catalysis.
Physical & Chemical Properties
| Appearance | Pale yellow viscous liquid |
|---|---|
| Boiling Point | Decomposes before boiling |
| Flash Point | >100°C |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 3% | Provides radiance to white florals |
| Functional Products | 0.1-0.5% | Up to 1% | Used for fabric substantivity |
Classic Accords
Tip: Combine with ionones to create a ‘magnetic powder’ effect that clings to skin.
Alternatives & Comparisons
The parent amine component, offering more grape-like top notes but lacking the tenacity and powderiness of the Schiff base.
Provides similar lily character but without the warm, powdery dry-down. Being restricted by IFRA, the Schiff base offers regulatory advantages.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA. The Schiff base formation reduces amine availability compared to methyl anthranilate.
EU Allergen Declaration
None under current EU regulations as the Schiff base is not hydrolyzed back to amine precursors under normal conditions.
RIFM Assessment
Under review by RIFM as part of the methyl anthranilate derivatives assessment program.
Sustainability
As a fully synthetic material, production is not constrained by agricultural limitations. The condensation reaction is atom-efficient, generating only water as byproduct. However, the petroleum-derived starting materials impact its environmental footprint. Future green chemistry routes may employ bio-based lilial analogs.
Explore Lilial-methyl anthranilate (Schiff base)
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References
- Sell, C. (2019). A Fragrant Introduction to Terpenoid Chemistry. Royal Society of Chemistry. ISBN 978-1-78801-335-1
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 91-51-0Physical Properties
| Molecular Weight | 338.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 5.9🔬 PubChem |
| Boiling Point | 366 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 259.6 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -0.575💻 Calculated |
| SMILES | CC(CC1=CC=C(C=C1)C(C)(C)C)N=NC2=CC=CC=C2C(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Primary Descriptors | floralsweet• leffingwell |
| Functional Groups | esteretheraromatic💻 RDKit |
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: DTXSID2052609
Physical Properties
| Molecular Weight | 338.451 g/mol🔬 EPA CompTox |
| Density | 1.038 g/cm^3📊 OPERA |
| Boiling Point | 404.121 °C📊 OPERA |
| Melting Point | 86.068 °C📊 OPERA |
| Flash Point | 246.553 °C📊 OPERA |
| Refractive Index | 1.536 Dimensionless📊 OPERA |
| Molar Volume | 327.776 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.305 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 5.291 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.305 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.37 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 34.996 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 51.02 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 | 102.187 cm^3/mol📊 OPERA |
| Polarizability | 40.51 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.
