2-Methylpropyl 3-methylbutyrate (CAS 589-59-3) — Sweet Top to mid Note Fragrance Ingredient
2-Methylpropyl 3-methylbutyrate
CAS 589-59-3
What Is 2-Methylpropyl 3-methylbutyrate?
2-Methylpropyl 3-methylbutyrate is a synthetic fragrance compound used to add fruity, apple-like notes in perfumes and flavored products. You’ll encounter it in body sprays, fruity perfumes, and some food flavorings. This ester matters because it creates natural-smelling fruit accords without using actual fruit extracts, making fragrances more stable and consistent across batches.
Safety Profile
GENERALLY SAFEWhat Does 2-Methylpropyl 3-methylbutyrate Smell Like?
This ester bursts with crisp, juicy apple peel freshness – think biting into a just-picked Granny Smith with subtle banana undertones. The top note has a sparkling, slightly green character that smooths into a ripe pear heart. Dry-down reveals a clean, woody-musky base that prevents the fruitiness from becoming cloying. Unlike simpler fruit esters, it maintains dimensional character for 2-3 hours, making it valuable in modern fruity-floral compositions where naturalness is key.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Provides the signature crisp apple top note that makes this fragrance instantly recognizable, blending seamlessly with grapefruit and cucumber for a refreshing urban fruit cocktail.
Used sparingly to enhance the citrus opening with fruity depth, creating the illusion of sun-warmed apples in a Mediterranean orchard.
2D Molecular Structure
SMILES: CC(C)COC(=O)CC(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Methylpropyl 3-methylbutyrate belongs to the ester class, formed through Fischer esterification of isobutanol with isovaleric acid. Unlike many fruit esters, its branched structure (both on the alcohol and acid portions) creates unique steric hindrance that slows evaporation and modifies odor character. Industrial synthesis typically uses acid catalysis under reflux conditions. While not found in nature, its components mimic those occurring in apple and banana volatiles, explaining its natural-smelling profile despite being purely synthetic.
Physical & Chemical Properties
| Boiling Point | ~170-175°C (estimated) |
|---|---|
| Density | ~0.86 g/cm³ (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-3% | Up to 5% | Fruity top note modifier |
| Body Care | 0.1-1% | Up to 2% | Fresh fruit accent |
Classic Accords
Tip: Use with bergamot and hedione to create photorealistic fruit effects that avoid candy-like sweetness.
Alternatives & Comparisons
For brighter, greener apple notes but less tenacity. Prefer when blending with citrus-heavy tops.
More banana-dominant character. Use when warmer tropical fruit effects are desired.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not restricted under any IFRA standards. No usage limits apply.
RIFM Assessment
RIFM evaluation found no significant safety concerns at current usage levels in fragrances.
Sustainability
As a synthetic material, production doesn’t depend on agricultural cycles but does require petrochemical feedstocks. Modern manufacturing typically achieves >90% atom efficiency in esterification. Unlike natural extracts, it requires no water-intensive crop cultivation and shows excellent batch-to-batch consistency, reducing wastage in fragrance production.
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. ISBN 9781439847503
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 589-59-3Physical Properties
| Molecular Weight | 158.24 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.7🔬 PubChem |
| Boiling Point | 168.5 °C🔬 EPA CompTox |
| Vapor Pressure | 1.8429 mmHg @ 25°C📊 OPERA |
| Flash Point | 50.5 °C🔬 EPA CompTox |
| Involatility Index | 0.1579💻 Calculated |
| log Kp (skin permeability) | -1.748💻 Calculated |
| SMILES | CC(C)CC(=O)OCC(C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Top💻 Calculated |
| Volatility Class | Moderate💻 Calculated |
| Persistence Score | 0.5 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | applefruity• leffingwell |
| Functional Groups | esterether💻 RDKit |
| “Fruity-ethereal Apple-Raspberry-like odor. Fruitier than all other Butylvalerates. Probably the most interesting of the four isomers. Not as pungent-chemical as the other esters.”📖 Arctander | |
| 2-Methylpropyl-3-methylbutyrate has an aroma reminiscent of apple and raspberry.📖 Fenaroli | |
Flavor Notes (Arctander)
| “Widely used in flavor compositions for imitation Apple, Raspberry, Wine ("Champagne"), Strawberry, Tutti-frutti, etc. Although iso-Butyl-iso-butyrate is specifically mentioned in the G.R.A.S.-list of the Federal Register (U.S.A.), the iso-Butyl-iso-valerate is NOT mentioned. This could be an omissio”📖 Arctander |
Sensory Thresholds
| Odor Detection Threshold | 0.036 ppm (n=2)📖 van Gemert |
Regulatory Status
| 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: DTXSID5060431
Physical Properties
| Molecular Weight | 158.241 g/mol🔬 EPA CompTox |
| Density | 0.852 g/cm^3🔬 EPA CTX |
| Boiling Point | 168.5 °C🔬 EPA CTX |
| Melting Point | -66.557 °C📊 OPERA |
| Flash Point | 50.575 °C🔬 EPA CTX |
| Refractive Index | 1.415 Dimensionless📊 OPERA |
| Molar Volume | 181.332 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.968 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.968 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.968 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.56 Log10 unitless📊 OPERA |
| Water Solubility | 0.004 mol/L📊 OPERA |
| Henry's Law Constant | 0.001 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 1.843 mmHg🔬 EPA CTX |
| Viscosity | 1.039 cP📊 OPERA |
| Surface Tension | 24.632 dyn/cm📊 OPERA |
| Thermal Conductivity | 125.638 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 | 4 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.437 cm^3/mol📊 OPERA |
| Polarizability | 18.013 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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