Piperitone (CAS 89-81-6) — Green Top to middle Note Fragrance Ingredient
Piperitone
CAS 89-81-6
What Is Piperitone?
Piperitone is a minty, slightly camphoraceous fragrance molecule found in some essential oils like peppermint and eucalyptus. You might encounter it in herbal cough drops, mentholated products, or fresh masculine fragrances. This synthetic ingredient provides a cooling, crisp character that perfumers use to create invigorating top notes and aromatic fougère bases.
Safety Profile
GENERALLY SAFEWhat Does Piperitone Smell Like?
Piperitone greets the nose with a brisk, minty-camphoraceous punch reminiscent of crushed peppermint leaves and eucalyptus bark. The initial sharpness gradually softens into a herbal heart with subtle woody undertones, like walking through a sun-warmed pine forest after rain. In drydown, it leaves a clean, slightly medicinal aura that blends beautifully with citrus and spice notes. The cooling effect is less intense than menthol but more complex, with a dry texture that prevents it from feeling cloying.
2D Molecular Structure
SMILES: CC(C)C1CCC(C)=CC1=O
Chemistry, Properties & Perfumer Guide
The Chemistry
Piperitone is a monoterpene ketone with two stereoisomers – the more common (-)-piperitone found in Mentha oils and the rarer (+)-form from Eucalyptus species. Industrially, it’s synthesized via oxidation of d-limonene or isolated from mint oil fractions. The molecule’s rigid cyclohexanone structure with an isopropyl group gives it both volatility and tenacity. Its ketone group makes it more polar than typical terpenes, contributing to the cooling sensation through TRPM8 receptor activation like menthol but with less intensity.
Physical & Chemical Properties
| Boiling Point | 232-233 °C |
|---|---|
| Density | 0.933 g/cm³ |
| Refractive Index | 1.484 |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Fougère and chypre accents |
| Functional Fragrance | 1-3% | Up to 8% | Oral care products |
| Aromatherapy | 0.1-0.5% | Up to 1% | Respiratory blends |
Classic Accords
Tip: Use with citrus oils to brighten minty effects without toothpaste associations.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions under current 51st Amendment standards.
RIFM Assessment
RIFM evaluation confirms safe use at current industry levels with minimal sensitization risk.
Sustainability
Most commercial piperitone is synthesized from renewable turpentine or citrus oil feedstocks, avoiding wild mint oil extraction. The synthesis route has moderate energy requirements but produces minimal hazardous waste. Biodegradation studies show rapid breakdown in aquatic environments (90% in 28 days).
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References
- PubChem Compound Summary for Piperitone CID 6987
- Bauer et al. (2001). Common Fragrance and Flavor Materials.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 89-81-6Physical Properties
| Molecular Weight | 152.23 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.2🔬 PubChem |
| Boiling Point | 233 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0398 mmHg @ 25°C📊 OPERA |
| Flash Point | 83.5 °C🔬 EPA CompTox |
| Involatility Index | 0.0035💻 Calculated |
| log Kp (skin permeability) | -2.067💻 Calculated |
| SMILES | CC1=CC(=O)C(CC1)C(C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.2 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | freshherbalminty• leffingwell |
| Functional Groups | ketonealkene💻 RDKit |
| “Powerful, fresh-minty-camphoraceous odor. The material may turn darker yellow and its odor become more tobacco-herbaceous upon aging.”📖 Arctander | |
Flavor Notes (Arctander)
| “The cyclic ketone is more commonly used in flavor compositions, particularly in spice complexes with Caraway, Estragon, etc., and in fruit complexes, mint flavors, etc. Now and then it becomes "fashionable" in dentifrice”📖 Arctander |
Sensory Thresholds
| Odor Detection Threshold | 1.8774 ppm (n=10)📖 van Gemert |
Regulatory Status
| FEMA Number | FEMA 2910⚖️ FEMA GRAS |
| GRAS Status | Generally Recognized as Safe⚖️ FEMA GRAS |
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: DTXSID7052604
Physical Properties
| Molecular Weight | 152.237 g/mol🔬 EPA CompTox |
| Density | 0.932 g/cm^3🔬 EPA CTX |
| Boiling Point | 229 °C🔬 EPA CTX |
| Melting Point | 10.58 °C📊 OPERA |
| Flash Point | 88.483 °C🔬 EPA CTX |
| Refractive Index | 1.465 Dimensionless📊 OPERA |
| Molar Volume | 166.339 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.794 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.788 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.788 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5 Log10 unitless📊 OPERA |
| Water Solubility | 0.008 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.04 mmHg🔬 EPA CTX |
| Surface Tension | 30.914 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 17.07 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.973 cm^3/mol📊 OPERA |
| Polarizability | 18.225 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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