9,10-Anthracenedione, 1-hydroxy-4-[(4-methylphenyl)amino]- (CAS 81-48-1) — Citrus N/A Note Fragrance Ingredient
9,10-Anthracenedione, 1-hydroxy-4-[(4-methylphenyl)amino]-
CAS 81-48-1
What Is 9,10-Anthracenedione, 1-hydroxy-4-[(4-methylphenyl)amino]-?
1-Hydroxy-4-[(4-methylphenyl)amino]-9,10-anthracenedione is a synthetic dye molecule primarily used in industrial applications. It’s not commonly encountered in consumer products due to its specialized nature. This compound belongs to the anthraquinone family, which includes many important dyes and pigments. While not used in fragrances, anthraquinone derivatives have significance in textile, paper, and cosmetic coloration.
Safety Profile
PROFESSIONAL USEWhat Does 9,10-Anthracenedione, 1-hydroxy-4-[(4-methylphenyl)amino]- Smell Like?
This compound is not used in perfumery and has no significant odor profile. Anthraquinone derivatives are primarily valued for their color properties rather than olfactory characteristics. The molecule’s complex structure suggests it would have minimal volatility and therefore no detectable scent at room temperature.
2D Molecular Structure
SMILES: CC1=CC=C(NC2=C3C(=O)C4=C(C=CC=C4)C(=O)C3=C(O)C=C2)C=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
1-Hydroxy-4-[(4-methylphenyl)amino]-9,10-anthracenedione is a substituted anthraquinone derivative. Anthraquinones are characterized by a central 9,10-dioxoanthracene structure. This particular derivative features a hydroxyl group at position 1 and a 4-methylanilino substituent at position 4. The compound is synthesized through nucleophilic aromatic substitution reactions on halogenated anthraquinone precursors. The electron-withdrawing carbonyl groups activate the anthraquinone core for substitution reactions.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|
Classic Accords
Tip: This compound is not suitable for perfumery applications.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not evaluated by IFRA as it’s not used in fragrance applications.
RIFM Assessment
Not assessed by RIFM due to non-perfumery use.
Sustainability
As an industrial dye chemical, environmental considerations focus on manufacturing waste streams and potential aquatic toxicity. Synthetic anthraquinones are petroleum-derived and require careful handling in production facilities. There are no known natural sources of this specific compound, making sustainable alternatives challenging.
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Ingredient Data Sheet
CAS 81-48-1Physical Properties
| Molecular Weight | 329.3 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 5.5🔬 PubChem |
| Boiling Point | 432 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 268.7 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -0.804💻 Calculated |
| SMILES | CC1=CC=C(C=C1)NC2=C3C(=C(C=C2)O)C(=O)C4=CC=CC=C4C3=O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Functional Groups | ketonephenolaromaticamine💻 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: DTXSID1026293
Physical Properties
| Molecular Weight | 329.355 g/mol🔬 EPA CompTox |
| Density | 1.365 g/cm^3📊 OPERA |
| Boiling Point | 474.694 °C📊 OPERA |
| Melting Point | 188.75 °C🔬 EPA CTX |
| Flash Point | 262.672 °C📊 OPERA |
| Refractive Index | 1.72 Dimensionless📊 OPERA |
| Molar Volume | 239.812 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.26 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 4.497 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.383 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.56 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 67.998 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 66.4 Ų💻 Computed |
| H-Bond Donors | 2 count💻 Computed |
| H-Bond Acceptors | 4 count💻 Computed |
| Rotatable Bonds | 2 count💻 Computed |
| Aromatic Rings | 3 count💻 Computed |
| Molar Refractivity | 94.749 cm^3/mol📊 OPERA |
| Polarizability | 37.562 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.
