Cyclamen aldehyde-methyl anthranilate (Schiff base) (CAS 91-50-9) — Floral Heart to base Note Fragrance Ingredient
Cyclamen aldehyde-methyl anthranilate (Schiff base)
CAS 91-50-9
What Is Cyclamen aldehyde-methyl anthranilate (Schiff base)?
Cyclamen aldehyde-methyl anthranilate Schiff base is a synthetic fragrance ingredient created by combining cyclamen aldehyde with methyl anthranilate. It’s found in fine perfumes, especially floral and citrus compositions. This molecule offers perfumers a unique way to blend floralcy with fruity nuances in a single ingredient. The Schiff base formation creates a more stable and longer-lasting scent profile than its individual components, making it valuable for modern fragrance design where both tenacity and complexity are desired.
Safety Profile
USE WITH AWARENESSWhat Does Cyclamen aldehyde-methyl anthranilate (Schiff base) Smell Like?
This Schiff base delivers a sophisticated interplay of floral and citrus character. Initially, it presents a bright, almost effervescent quality reminiscent of orange blossoms dipped in honey. The heart reveals a powdery cyclamen softness wrapped in a gauzy, transparent sweetness. As it dries down, a delicate muskiness emerges alongside subtle grape-like undertones from the methyl anthranilate moiety. The overall effect is like sunlight filtering through sheer floral curtains – radiant yet diffused, with excellent diffusion that lingers close to the skin.
2D Molecular Structure
SMILES: COC(=O)C1=CC=CC=C1N=CC(C)CC1=CC=C(C=C1)C(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This Schiff base forms through the condensation reaction between cyclamen aldehyde (2-methyl-3-(4-isopropylphenyl)propanal) and methyl anthranilate. The resulting imine structure (R₂C=NR’) exhibits increased stability compared to its parent aldehydes while maintaining the aromatic character of both precursors. Unlike simple mixtures, this covalent bonding creates new olfactory properties distinct from either component. The electron-rich nitrogen in the Schiff base linkage may participate in additional molecular interactions that modify volatility and substantivity.
Physical & Chemical Properties
| Appearance | Pale yellow to amber viscous liquid |
|---|---|
| Solubility | Soluble in ethanol, propylene glycol; insoluble in water |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as floral-fruity bridge |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Limited by potential allergenicity |
Classic Accords
Tip: Use to create seamless transitions between citrus top notes and floral heart notes.
Alternatives & Comparisons
Similar Schiff base of hydroxycitronellal and methyl anthranilate, offering more pronounced orange blossom character with less powderiness.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA, but components may be limited under separate regulations.
EU Allergen Declaration
Contains methyl anthranilate derivative – may require declaration above 0.01% in leave-on products.
RIFM Assessment
No specific RIFM assessment available for this Schiff base; evaluated as component mixture.
Sustainability
As a synthetic material, production avoids agricultural impacts but requires careful solvent management. Schiff bases generally have better atom economy than many fragrance synthetics since they form through simple condensation reactions with water as the only byproduct. Future green chemistry approaches could optimize the synthesis further.
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Physicochemical Properties
DTXSID: DTXSID70861685
Physical Properties
| Molecular Weight | 323.436 g/mol🔬 EPA CompTox |
| Density | 1.057 g/cm^3📊 OPERA |
| Boiling Point | 401.399 °C📊 OPERA |
| Melting Point | 73.669 °C📊 OPERA |
| Flash Point | 175.677 °C📊 OPERA |
| Refractive Index | 1.532 Dimensionless📊 OPERA |
| Molar Volume | 318.587 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.469 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 5.177 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.463 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.26 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 | 34.141 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 38.66 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 6 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 98.785 cm^3/mol📊 OPERA |
| Polarizability | 39.162 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.
