Methyl linoleate (CAS 112-63-0) — Woody Base Note Fragrance Ingredient
Methyl linoleate
CAS 112-63-0
What Is Methyl linoleate?
Methyl linoleate is a synthetic compound derived from linoleic acid, commonly found in vegetable oils like sunflower and safflower. You’ll encounter it in food flavorings, cosmetic emollients, and some industrial applications. While not a star perfume ingredient, it plays supporting roles in fragrance formulations where its mild, fatty character can round out sharper notes.
Safety Profile
GENERALLY SAFEWhat Does Methyl linoleate Smell Like?
Methyl linoleate presents a faint, fatty-waxy odor reminiscent of sunflower seeds and vegetable oils. The scent profile lacks top note vibrancy, instead offering a soft, slightly nutty base that can lend subtle richness to fragrance compositions. In dilution, it may recall the mild aroma of crushed linseeds or fresh cooking oil, with a clean but nondescript dry-down that primarily functions as a fixative for more volatile materials.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
2D Molecular Structure
SMILES: CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC
Chemistry, Properties & Perfumer Guide
The Chemistry
Methyl linoleate is the methyl ester of linoleic acid, an omega-6 fatty acid. As a straight-chain unsaturated ester, it’s typically synthesized via methanolysis of vegetable oils or through esterification of purified linoleic acid. The cis,cis-9,12 configuration of the double bonds makes it susceptible to oxidation, requiring stabilization in formulations. Industrially, it’s often produced as part of biodiesel manufacturing processes.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | ~215 °C at 10 mmHg |
| Density | ~0.89 g/cm³ |
| Solubility | Insoluble in water, miscible with oils |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Functional Fragrances | 0.5-2% | Up to 5% | Background fixative |
| Cosmetic Bases | 1-3% | Up to 8% | Skin-compatible emollient |
Classic Accords
Tip: Stabilize with antioxidants like tocopherol to prevent rancidity in formulations.
Alternatives & Comparisons
Similar fatty character with slightly higher volatility, useful when more diffusion is desired.
More stable monounsaturated alternative with comparable emollient properties.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions apply to methyl linoleate.
RIFM Assessment
Not currently assessed by RIFM due to low fragrance use.
Sustainability
While often synthesized, methyl linoleate can be derived from renewable plant sources. Production from waste vegetable oils offers potential sustainability benefits. Synthetic routes may involve petrochemical inputs, making sourcing transparency important for eco-conscious formulations.
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Ingredient Data Sheet
CAS 112-63-0Physical Properties
| Molecular Weight | 294.5 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 6.9🔬 PubChem |
| Boiling Point | 373 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 97 °C🔬 EPA CompTox |
| log Kp (skin permeability) | 0.403💻 Calculated |
| SMILES | CCCCCC=CCC=CCCCCCCCC(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 17.2 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | fatty• leffingwell |
| Functional Groups | esteretheralkene💻 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: DTXSID7020843
Physical Properties
| Molecular Weight | 294.479 g/mol🔬 EPA CompTox |
| Density | 0.873 g/cm^3📊 OPERA |
| Boiling Point | 373.5 °C🔬 EPA CTX |
| Melting Point | -35 °C🔬 EPA CTX |
| Flash Point | 105.063 °C🔬 EPA CTX |
| Refractive Index | 1.465 Dimensionless📊 OPERA |
| Molar Volume | 332.875 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 6.82 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 6.99 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 6.99 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.85 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Viscosity | 5.006 cP📊 OPERA |
| Surface Tension | 29.505 dyn/cm📊 OPERA |
| Thermal Conductivity | 150.764 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 26.3 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 14 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 91.964 cm^3/mol📊 OPERA |
| Polarizability | 36.457 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.
