(+/-)-Pulegone (CAS 15932-80-6) — Green Top to middle Note Fragrance Ingredient
(+/-)-Pulegone
CAS 15932-80-6
What Is (+/-)-Pulegone?
Pulegone is a minty, cooling compound found naturally in pennyroyal and peppermint oils, though most commercial versions are synthetic. It’s used in flavorings and some traditional herbal products. This ingredient requires careful handling due to potential toxicity concerns at higher concentrations, making its use in consumer products highly regulated.
Safety Profile
PROFESSIONAL USEWhat Does (+/-)-Pulegone Smell Like?
Pulegone delivers an intense, piercing mint character with cooling menthol-like top notes that border on medicinal. The initial burst evolves into a greener, herbaceous heart with slight camphoraceous undertones. In drydown, it leaves a faintly sweet, earthy residue reminiscent of dried mint leaves, though the overall profile remains dominated by its sharp, penetrating freshness.
2D Molecular Structure
SMILES: CC1CCC(=C(C)C)C(=O)C1
Chemistry, Properties & Perfumer Guide
The Chemistry
Pulegone is a monoterpene ketone that exists as two enantiomers, with the (+)-form being more common in nature. It’s biosynthesized in plants via the methylerythritol phosphate pathway. Industrial production typically involves chemical synthesis from piperitone or other terpene precursors. The ketone group at position 1 makes it more reactive than simple terpenes, contributing to both its odor characteristics and toxicity concerns.
Physical & Chemical Properties
| Boiling Point | Not available |
|---|---|
| Density | Not available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Flavorings | 0.1-1% | Up to 2% | Highly restricted in food applications |
| Fragrance | Not used | N/A | Banned in cosmetic applications |
Classic Accords
Tip: Not recommended for perfumery due to safety restrictions – use isomenthone or menthone as safer alternatives.
Alternatives & Comparisons
Provides similar minty freshness without toxicity concerns, though less intense.
Structural isomer with comparable cooling effects but better safety profile.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Banned under IFRA standards (Amendment 49) due to hepatotoxicity concerns.
GHS Classification
RIFM Assessment
RIFM assessment confirms significant toxicity risk, recommending complete avoidance in fragrance applications.
Sustainability
While naturally occurring in some plants, commercial pulegone is almost exclusively synthetic due to safety concerns with extraction. Production requires careful waste management due to potential environmental toxicity. The fragrance industry has largely phased out its use in favor of safer alternatives.
Explore (+/-)-Pulegone
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References
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID3051757
Physical Properties
| Molecular Weight | 152.237 g/mol🔬 EPA CompTox |
| Density | 0.932 g/cm^3🔬 EPA CTX |
| Boiling Point | 222.5 °C🔬 EPA CTX |
| Melting Point | 26.054 °C📊 OPERA |
| Flash Point | 84.06 °C📊 OPERA |
| Refractive Index | 1.47 Dimensionless📊 OPERA |
| Molar Volume | 164.828 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.08 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 3.099 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.099 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.08 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 46.084 mmHg🔬 EPA CTX |
| Surface Tension | 31.624 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 | 0 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 45.987 cm^3/mol📊 OPERA |
| Polarizability | 18.231 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.
