Methyl anthranilate (CAS 134-20-3) — Floral Heart Note Fragrance Ingredient
Methyl anthranilate
CAS 134-20-3
What Is Methyl anthranilate?
Methyl anthranilate is a sweet, grape-like fragrance ingredient commonly found in perfumes and flavored products. It’s what gives many fruity body sprays and candies their distinctive grape scent. This versatile molecule bridges the worlds of flavor and fragrance, prized for its ability to add both fruity and floral nuances to compositions.
Safety Profile
GENERALLY SAFEWhat Does Methyl anthranilate Smell Like?
Methyl anthranilate bursts forth with an intensely sweet, grape-like top note reminiscent of Concord grapes and orange blossoms. As it evolves, the floral character becomes more pronounced, revealing a neroli-like heart with hints of jasmine. The dry-down is softly powdery, leaving a delicate trail that blends beautifully with woody and musky bases. Its character is simultaneously fruity and floral, making it a chameleon in compositions.
Scent Profile
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a key floral modifier, adding grape-like sweetness that bridges the citrus top notes to the mossy base.
Enhances the orange blossom theme with its grape-like floralcy, adding depth to the citrus-neroli accord.
2D Molecular Structure
SMILES: COC(=O)C1=C(N)C=CC=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
Methyl anthranilate is an ester formed from anthranilic acid and methanol. While it occurs naturally in grapes and some flowers, most commercial material is synthesized. The synthetic route typically involves esterification of anthranilic acid under acidic conditions. Its molecular structure features both an ester group and an aromatic amine, giving it unique dual functionality in fragrance chemistry.
Physical & Chemical Properties
| Boiling Point | 256 °C |
|---|---|
| Density | 1.168 g/cm³ |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 1-3% | Up to 5% | Floral-fruity modifier |
| Functional Fragrance | 0.5-1% | Up to 2% | Grape theme enhancer |
Classic Accords
Tip: Use to add fruity-floral complexity to orange blossom themes without overwhelming the composition.
Alternatives & Comparisons
Similar grape character but softer and more floral, useful when a less intense effect is desired.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. IFRA, REACH, EU Cosmetics Regulation standards update periodically. Consult current IFRA Standards Library before formulating. Not legal or regulatory advice.
IFRA Status
No IFRA restrictions currently apply to methyl anthranilate.
RIFM Assessment
RIFM has evaluated methyl anthranilate and found it safe for current use levels in fragrance.
Sustainability
As primarily a synthetic material, methyl anthranilate production doesn’t impact natural resources. Modern synthesis routes have improved atom economy and reduced waste compared to traditional methods.
Explore Methyl anthranilate
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References
- Bauer et al. (2001). Common Fragrance and Flavor Materials. Wiley-VCH.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Mar 2026.
Report a data errorIngredient Data Sheet
CAS 134-20-3Physical Properties
| Molecular Weight | 151.16 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 1.9🔬 PubChem |
| Boiling Point | 256.1 °C🔬 EPA CompTox |
| Vapor Pressure | 0.02 mmHg @ 25°C📊 OPERA |
| Flash Point | 104.4 °C🔬 EPA CompTox |
| Involatility Index | 0.0018💻 Calculated |
| log Kp (skin permeability) | -2.273💻 Calculated |
| SMILES | COC(=O)C1=CC=CC=C1N🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.5 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | grape• leffingwell |
| Functional Groups | esteretheraromaticamine💻 RDKit |
| “Musty-fruity and somewhat dry-floral odor reminiscent of Concord grapes, Orangeblossom, and having good tenacity. The odor appears much sweeter in high dilution.”📖 Arctander | |
| Methyl anthranilate has a characteristic orange-flower odor and slightly bitter, pungent taste.📖 Fenaroli | |
Flavor Notes (Arctander)
| “Sweet fruity, Grape-like taste with a distinct-ly floral-perfumey character. The ester finds also extensive use in flavor compositions, not only in Grape (to imitate the Concord Grape in which it is a natural component), but also in various berry flavors, Melon, Honey, Citrusfruit, floral types (Ros”📖 Arctander |
Sensory Thresholds
| Odor Detection Threshold | 0.1982 ppm (n=11)📖 van Gemert |
Regulatory Status
| FEMA Number | FEMA 2682⚖️ FEMA GRAS |
| GRAS Status | Generally Recognized as Safe⚖️ FEMA GRAS |
| IOFI Classification | Nature Identical📖 Fenaroli |
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: DTXSID6025567
Physical Properties
| Molecular Weight | 151.165 g/mol🔬 EPA CompTox |
| Density | 1.173 g/cm^3🔬 EPA CTX |
| Boiling Point | 254.516 °C🔬 EPA CTX |
| Melting Point | 24.274 °C🔬 EPA CTX |
| Flash Point | 108.636 °C🔬 EPA CTX |
| Refractive Index | 1.566 Dimensionless📊 OPERA |
| Molar Volume | 129.606 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.909 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.028 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.029 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.71 Log10 unitless📊 OPERA |
| Water Solubility | 0.019 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 0.025 mmHg🔬 EPA CTX |
| Viscosity | 4.795 cP📊 OPERA |
| Surface Tension | 46.232 dyn/cm📊 OPERA |
| Thermal Conductivity | 161.921 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 52.32 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 | 42.262 cm^3/mol📊 OPERA |
| Polarizability | 16.754 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.
