2,2′,4,4′-Tetrahydroxybenzophenone (CAS 131-55-5) — Citrus N/A Note Fragrance Ingredient
2,2',4,4'-Tetrahydroxybenzophenone
CAS 131-55-5
What Is 2,2',4,4'-Tetrahydroxybenzophenone?
2,2′,4,4′-Tetrahydroxybenzophenone is a synthetic chemical primarily used in industrial applications such as UV stabilizers for plastics and coatings. While not commonly found in consumer fragrances, it may appear in some specialty formulations. This ingredient serves functional purposes rather than olfactory ones, acting as a protective agent against light degradation rather than contributing to scent profiles.
Safety Profile
PROFESSIONAL USEWhat Does 2,2',4,4'-Tetrahydroxybenzophenone Smell Like?
2,2′,4,4′-Tetrahydroxybenzophenone is not typically used for its odor characteristics in perfumery. As an industrial UV stabilizer, it lacks the complex scent profile of traditional fragrance ingredients. In pure form, it may present faint phenolic or chemical notes, but these are not considered desirable in fragrance compositions.
2D Molecular Structure
SMILES: OC1=CC(O)=C(C=C1)C(=O)C1=CC=C(O)C=C1O
Chemistry, Properties & Perfumer Guide
The Chemistry
2,2′,4,4′-Tetrahydroxybenzophenone belongs to the benzophenone class of compounds, characterized by two benzene rings connected by a carbonyl group. The four hydroxyl groups make it highly polar and water-soluble compared to other benzophenone derivatives. It is synthesized through Friedel-Crafts acylation of resorcinol followed by hydroxylation. The multiple phenolic groups allow for strong UV absorption, making it valuable as a photostabilizer rather than a fragrance component.
Physical & Chemical Properties
| Melting Point | 198-200 °C |
|---|
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Industrial Coatings | 0.1-0.5% | Up to 1% | UV stabilizer |
| Plastic Stabilization | 0.2-0.8% | Up to 2% | Light protection additive |
Classic Accords
Tip: Not recommended for use in perfumery due to functional rather than olfactory properties.
Alternatives & Comparisons
More commonly used UV filter with better safety profile for cosmetic applications.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not listed in IFRA standards due to non-fragrance applications.
GHS Classification
RIFM Assessment
Not evaluated by RIFM for fragrance use.
Sustainability
As an industrial chemical, 2,2′,4,4′-Tetrahydroxybenzophenone is produced through synthetic routes with standard petrochemical feedstocks. Its environmental impact is primarily associated with manufacturing processes rather than end-use applications. Proper disposal procedures should be followed to prevent aquatic contamination due to phenolic structure.
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Ingredient Data Sheet
CAS 131-55-5Physical Properties
| Molecular Weight | 246.21 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.4🔬 PubChem |
| Boiling Point | 491 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.498💻 Calculated |
| SMILES | C1=CC(=C(C=C1O)O)C(=O)C2=C(C=C(C=C2)O)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Functional Groups | ketonephenolaromatic💻 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: DTXSID5041306
Physical Properties
| Molecular Weight | 246.218 g/mol🔬 EPA CompTox |
| Density | 1.21 g/cm^3🔬 EPA CTX |
| Boiling Point | 491 °C🔬 EPA CTX |
| Melting Point | 200.965 °C🔬 EPA CTX |
| Flash Point | 289.3 °C🔬 EPA CTX |
| Refractive Index | 1.718 Dimensionless📊 OPERA |
| Molar Volume | 161.268 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.567 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.556 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.049 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.38 Log10 unitless📊 OPERA |
| Water Solubility | 0.036 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Viscosity | 26.301 cP📊 OPERA |
| Surface Tension | 83.135 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 97.99 Ų💻 Computed |
| H-Bond Donors | 4 count💻 Computed |
| H-Bond Acceptors | 5 count💻 Computed |
| Rotatable Bonds | 2 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 63.572 cm^3/mol📊 OPERA |
| Polarizability | 25.202 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.
