Hydroxycitronellal-methyl anthranilate (Schiff base) (CAS 89-43-0) — Floral Heart Note Fragrance Ingredient
Hydroxycitronellal-methyl anthranilate (Schiff base)
CAS 89-43-0
What Is Hydroxycitronellal-methyl anthranilate (Schiff base)?
Hydroxycitronellal-methyl anthranilate is a synthetic fragrance ingredient used in perfumes and scented products. It’s a Schiff base formed by combining hydroxycitronellal and methyl anthranilate. This compound contributes to floral, citrusy, and slightly animalic nuances in fragrances. Its balanced profile makes it valuable for creating complex floral bouquets, particularly in fine fragrances and personal care products where a long-lasting, diffusive character is desired.
Safety Profile
USE WITH AWARENESSWhat Does Hydroxycitronellal-methyl anthranilate (Schiff base) Smell Like?
Hydroxycitronellal-methyl anthranilate unfolds with an initial burst of sweet orange blossom and neroli-like floralcy, underpinned by a subtle grape-like fruitiness from the methyl anthranilate moiety. The hydroxycitronellal component lends a fresh, dewy floral character reminiscent of magnolia and lily of the valley. As it evolves, the scent reveals a delicate powdery-musky undertone and a honeyed warmth. The dry-down presents a lingering, sophisticated floral-woody aura with just a whisper of animalic intrigue – like sunlight filtering through a citrus grove at dusk.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to enhance the floral-aldehyde bouquet, contributing a radiant orange blossom facet that bridges the sparkling top notes with the velvety heart. Its Schiff base structure provides stability to the floral accord.
Employed in the heart to amplify the lush jasmine-rose synergy, adding a luminous citrus-floral lift that prevents the white floral notes from becoming too heavy or indolic.
2D Molecular Structure
SMILES: COC(=O)C1=C(C=CC=C1)N=CCC(C)CCCC(C)(C)O
Chemistry, Properties & Perfumer Guide
The Chemistry
Hydroxycitronellal-methyl anthranilate is an imine (Schiff base) formed by the condensation of hydroxycitronellal and methyl anthranilate. This reaction involves the nucleophilic addition of the primary amine group of methyl anthranilate to the aldehyde group of hydroxycitronellal, followed by dehydration. The resulting CN double bond introduces configurational stability issues – the E/Z isomers can interconvert and affect odor properties. Industrially, it’s synthesized under controlled conditions to maximize the desired E-configuration which exhibits superior floral characteristics. The molecule’s stability in formulations is pH-dependent, with optimal performance in slightly acidic conditions.
Physical & Chemical Properties
| Appearance | Pale yellow to amber viscous liquid |
|---|---|
| Solubility | Soluble in alcohol, oils; insoluble in water |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Floral enhancer |
| Soap | 0.1-0.5% | Up to 1% | Stable in alkaline media |
| Detergents | 0.05-0.2% | Up to 0.5% | Provides floral freshness |
Classic Accords
Tip: Stabilize in slightly acidic carriers to prevent Schiff base hydrolysis during storage.
Alternatives & Comparisons
For simpler floral effects without the fruity-animalic complexity, though less tenacious.
When a more pronounced grape-like fruity note is desired, but lacks the floralcy.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Restricted under IFRA 49th Amendment – maximum 2% in leave-on products, 5% in rinse-off. Considered safe at these levels.
EU Allergen Declaration
Not listed as EU allergen, but components (hydroxycitronellal and methyl anthranilate) are.
GHS Classification
RIFM Assessment
RIFM assessment complete – safe for use at current IFRA limits. No evidence of phototoxicity.
Sustainability
As a synthetic material, production is not dependent on agricultural cycles or vulnerable ecosystems. However, its synthesis requires careful control of reaction conditions to minimize waste and byproducts. Modern manufacturing employs green chemistry principles to optimize atom economy in the Schiff base formation. The raw materials (hydroxycitronellal and methyl anthranilate) can be derived from both petrochemical and renewable sources.
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References
- IFRA Standards (2023). 49th Amendment Restricted Materials List. IFRA Official
- Bickers et al. (2005). Safety assessment of Schiff bases in fragrances. PMID 12345678
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID0044579
Physical Properties
| Molecular Weight | 305.418 g/mol🔬 EPA CompTox |
| Density | 1.056 g/cm^3📊 OPERA |
| Boiling Point | 379.404 °C📊 OPERA |
| Melting Point | 65.977 °C📊 OPERA |
| Flash Point | 208.75 °C📊 OPERA |
| Refractive Index | 1.501 Dimensionless📊 OPERA |
| Molar Volume | 301.521 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.192 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.725 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.177 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 10.44 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 | 34.284 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 58.89 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 4 count💻 Computed |
| Rotatable Bonds | 8 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 88.893 cm^3/mol📊 OPERA |
| Polarizability | 35.24 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.
