Citral-methylanthranilate (Schiff base) (CAS 67801-47-2) — Sweet Middle Note Fragrance Ingredient
Citral-methylanthranilate (Schiff base)
CAS 67801-47-2
What Is Citral-methylanthranilate (Schiff base)?
Citral-methylanthranilate is a synthetic fragrance ingredient that creates a unique grape-like, fruity aroma with floral undertones. It’s found in some specialty perfumes and flavored products. This ingredient is prized for its ability to add a distinctive, long-lasting fruity-floral character that evolves beautifully on skin over time.
Safety Profile
USE WITH AWARENESSWhat Does Citral-methylanthranilate (Schiff base) Smell Like?
Citral-methylanthranilate opens with a burst of juicy concord grape and sweet neroli, reminiscent of grape bubblegum with a sophisticated edge. The heart reveals a candied orange blossom character with honeyed undertones, while the dry-down develops into a warm, slightly powdery musky-ambery base. The scent profile maintains remarkable tenacity, transitioning from bright fruity top notes to a lingering floral-woody trail that lasts for hours.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a key grape-like modifier in the citrus-floral accord, adding unique fruity depth to the neroli heart.
Provides a subtle fruity counterpoint to the muguet dominance, enhancing the floral bouquet’s complexity.
2D Molecular Structure
SMILES: COC(=O)C1=C(C=CC=C1)N=CC=C(C)CCC=C(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
Citral-methylanthranilate is a Schiff base formed by the condensation of citral (a mixture of geranial and neral) with methyl anthranilate. This reaction creates a stable imine linkage that modifies the odor profile while increasing longevity. The compound typically exists as a mixture of E/Z isomers around the imine double bond, with the E-isomer generally being more stable and dominant in the equilibrium mixture.
Physical & Chemical Properties
| Appearance | Yellow to amber viscous liquid |
|---|---|
| Solubility | Soluble in alcohol and oils |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Specialty modifier for fruity-floral accords |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Grape note in air fresheners |
Classic Accords
Tip: Stabilize in ethanol before adding to oil-based compositions to prevent precipitation.
Alternatives & Comparisons
For a simpler grape note without the citrus-floral complexity of the Schiff base.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not specifically restricted by IFRA, but usage may be limited by methyl anthranilate content restrictions (IFRA 49).
GHS Classification
RIFM Assessment
RIFM evaluation pending – limited data available on this specific Schiff base.
Sustainability
As a synthetic material, citral-methylanthranilate offers consistent quality and reduces pressure on natural resources. However, its production depends on petrochemical-derived precursors. Green chemistry approaches are being explored for more sustainable synthesis routes.
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Physicochemical Properties
DTXSID: DTXSID1052375
Physical Properties
| Density | 0.972 g/cm^3📊 OPERA |
| Boiling Point | 367.207 °C📊 OPERA |
| Melting Point | 65.566 °C📊 OPERA |
| Flash Point | 169.043 °C📊 OPERA |
| Refractive Index | 1.497 Dimensionless📊 OPERA |
| Molar Volume | 298.878 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.113 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.446 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.063 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.78 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 | 31.678 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 | 1 count💻 Computed |
| Molar Refractivity | 87.508 cm^3/mol📊 OPERA |
| Polarizability | 34.691 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.
