Benzoic acid, 2-hydroxy-5-methyl-, methyl ester (CAS 22717-57-3) — Woody Middle Note Fragrance Ingredient
Benzoic acid, 2-hydroxy-5-methyl-, methyl ester
CAS 22717-57-3
What Is Benzoic acid, 2-hydroxy-5-methyl-, methyl ester?
This synthetic fragrance ingredient is a methyl ester derived from benzoic acid. It’s used in perfumery to add subtle aromatic nuances. While not commonly recognized by name, it may appear in various cosmetic and personal care products. Its controlled release makes it valuable for creating lasting scent profiles in fine fragrances and functional products alike.
Safety Profile
USE WITH AWARENESSWhat Does Benzoic acid, 2-hydroxy-5-methyl-, methyl ester Smell Like?
This methyl ester presents a complex aromatic character with subtle phenolic undertones. Initially, it offers a crisp, slightly medicinal top note that evolves into a warmer, balsamic heart. The dry-down reveals a faintly sweet, woody-resinous quality that lingers close to the skin. Its restrained potency makes it an excellent blender, adding depth without overpowering compositions.
2D Molecular Structure
SMILES: COC(=O)C1=C(O)C=CC(C)=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
This compound belongs to the class of aromatic esters derived from substituted benzoic acids. The methyl ester group enhances volatility while the hydroxyl and methyl substituents on the benzene ring influence both scent profile and chemical reactivity. Synthesized through esterification of the corresponding benzoic acid derivative, its structure offers stability in various formulation matrices. The specific substitution pattern creates unique interactions with olfactory receptors.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Background modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Fixative component |
Classic Accords
Tip: Use as a bridge between citrus top notes and woody base materials.
Alternatives & Comparisons
More pronounced wintergreen character, useful when stronger top notes are desired.
Less phenolic, with cleaner aromatic profile for delicate compositions.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions under current guidelines (Amendment 51).
RIFM Assessment
Currently under RIFM evaluation for comprehensive safety assessment.
Sustainability
As a synthetic material, production involves controlled chemical processes with minimal environmental impact compared to natural extraction. The synthetic route allows for consistent quality and reduces agricultural land use. However, like all synthetic aromatics, petroleum-derived precursors raise sustainability questions that manufacturers are addressing through green chemistry initiatives.
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Ingredient Data Sheet
CAS 22717-57-3Physical Properties
| Molecular Weight | 166.17 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.1🔬 PubChem |
| Boiling Point | 244.5 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0091 mmHg @ 25°C📊 OPERA |
| Flash Point | 98.5 °C🔬 EPA CompTox |
| Involatility Index | 0.0008💻 Calculated |
| log Kp (skin permeability) | -1.513💻 Calculated |
| SMILES | CC1=CC(=C(C=C1)O)C(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 3.7 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | balsamicwoody• leffingwell |
| Functional Groups | esterphenoletheraromatic💻 RDKit |
| “Faint, warm-herbaceous odor with some NOTE: Do no? NOTE: Do not confuse with: Methyl-para- methylsalicylate (see monograph). etc., mostly in variations of Pine or Fir or Very slightly soluble in water, soluble in Cedarwood fragrances and often for technical alcohol and oils. Sweet-herbaceous, Wintergreen-Anise-Fen- It carries the usual drawbacks of a phenol nel type odor of moderate tenacity.”📖 Arctander | |
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: DTXSID0066822
Physical Properties
| Molecular Weight | 166.176 g/mol🔬 EPA CompTox |
| Density | 1.169 g/cm^3📊 OPERA |
| Boiling Point | 244.5 °C🔬 EPA CTX |
| Melting Point | -1 °C🔬 EPA CTX |
| Flash Point | 100.212 °C📊 OPERA |
| Refractive Index | 1.542 Dimensionless📊 OPERA |
| Molar Volume | 142.031 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.541 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.536 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.395 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.58 Log10 unitless📊 OPERA |
| Water Solubility | 0.014 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.013 mmHg📊 OPERA |
| Viscosity | 7.639 cP📊 OPERA |
| Surface Tension | 40.755 dyn/cm📊 OPERA |
| Thermal Conductivity | 144.275 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 46.53 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 44.733 cm^3/mol📊 OPERA |
| Polarizability | 17.733 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.
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