Carvone (CAS 99-49-0) — Green Top to Middle Note Fragrance Ingredient
Carvone
CAS 99-49-0
What Is Carvone?
Carvone is a naturally occurring organic compound that gives caraway and spearmint their characteristic aromas. You’ll encounter it in chewing gums, toothpaste, and some herbal liqueurs. This molecule is nature’s perfect example of chirality – its two forms smell completely different (spearmint vs caraway) despite being chemically identical mirror images.
Safety Profile
GENERALLY SAFEWhat Does Carvone Smell Like?
Carvone’s (R)-form bursts with the crisp, herbaceous sweetness of fresh spearmint leaves crushed between fingers, carrying a cooling menthol-like edge without the icy bite. The (S)-form swaps this freshness for warm, earthy caraway seed richness with anise-like depth. Both variants share a bright, slightly fruity opening that settles into a clean herbal heart. In dilution, the minty version develops a surprising floral nuance, while the caraway form grows more savory and bread-like during drydown.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Uses (R)-carvone’s spearmint character as the focal point, paired with rose and patchouli to create a modern herbal chypre with exceptional cooling freshness.
Showcases carvone’s minty facet in a transparent citrus-musk structure, achieving photorealistic crushed mint leaves effect.
2D Molecular Structure
SMILES: CC(=C)C1CC=C(C)C(=O)C1
Chemistry, Properties & Perfumer Guide
The Chemistry
Carvone is a monoterpenoid ketone existing as two enantiomers: (R)-(−)-carvone (spearmint) and (S)-(+)-carvone (caraway). Industrially produced via oxidation of limonene or from essential oil fractions. The chiral center at C1 dictates olfactory differences – a rare case where mirror-image molecules have distinct smells. Both forms readily undergo reduction to carveols or hydrogenation to dihydrocarvone, important intermediates in fragrance chemistry.
Physical & Chemical Properties
| Boiling Point | 230-231 °C |
|---|---|
| Density | 0.96 g/cm³ |
| Refractive Index | 1.499 |
| Flash Point | 92 °C |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Herbal freshnes |
| Oral Care | 0.1-0.5% | Up to 1% | Minty freshness |
| Flavorings | 10-50 ppm | Up to 100 ppm | Caraway/spearmint character |
Classic Accords
Tip: Use (R)-carvone for cooling effects, (S)-carvone for warm spice blends – test chiral purity before committing to large batches.
Alternatives & Comparisons
For deeper mint character without the herbal facets, though lacks carvone’s chiral versatility.
Hydrogenated derivative with softer, more floral mint character and better stability in alkaline formulations.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions. Listed as safe when used at industry standard levels (IFRA 49th Amendment).
GHS Classification
RIFM Assessment
RIFM evaluation confirms safety at current use levels, with margin of safety >100 for all exposure scenarios.
Sustainability
Synthetic production from renewable turpentine sources (α-pinene → limonene → carvone) offers consistent quality and reduces agricultural land use compared to spearmint oil extraction. Biocatalytic routes using immobilized enzymes show promise for greener synthesis with higher enantiomeric purity.
Explore Carvone
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. Book reference
- PubChem Compound Summary for Carvone CID 7439
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID8047426
Physical Properties
| Molecular Weight | 150.221 g/mol🔬 EPA CompTox |
| Density | 0.947 g/cm^3📊 OPERA |
| Boiling Point | 230.333 °C🔬 EPA CTX |
| Melting Point | 22.179 °C📊 OPERA |
| Flash Point | 88.9 °C🔬 EPA CTX |
| Refractive Index | 1.481 Dimensionless📊 OPERA |
| Molar Volume | 159.761 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.29 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.581 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.581 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.06 Log10 unitless📊 OPERA |
| Water Solubility | 0.009 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.108 mmHg📊 OPERA |
| Surface Tension | 32.018 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 | 45.485 cm^3/mol📊 OPERA |
| Polarizability | 18.032 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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