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Send EmailMenthone, L-Menthone, D-Menthone, M-Menthone, 89-80-5
MENTHONE – MENTON
CAS Number: 89-80-5
EC Number (EINECS): 201-941-1
Molecular Formula: C₁₀H₁₈O
Molecular Weight: 154.25 g/mol
Chemical Class: Monoterpenoid ketone
SECTION 1: CHEMICAL IDENTITY AND DEFINITION
| Parameter | Information |
|---|---|
| Chemical Name (IUPAC) | (2S,5R)-2-Isopropyl-5-methylcyclohexanone |
| Other Names | Menthone, p-Menthan-3-one, d-Menthone, l-Menthone, M-Menthone |
| Chemical Formula | C₁₀H₁₈O |
| Molecular Weight | 154.25 g/mol |
| CAS Number | 89-80-5 |
| EC Number (EINECS) | 201-941-1 |
| Chemical Class | Monoterpenoid ketone |
| Appearance | Colorless to pale yellow, clear liquid |
| Odor | Fresh, minty, aromatic, characteristic |
| Taste | Minty, cooling |
| Physical State (20°C) | Liquid |
| Optical Activity | L-Menthone and D-Menthone enantiomers available |
| Source | Peppermint, corn mint, pennyroyal, geranium |
| E Number | Not assigned |
SECTION 2: PHYSICAL PROPERTIES
| Property | Value |
|---|---|
| Appearance | Colorless to pale yellow, clear liquid |
| Odor | Fresh, minty, aromatic, characteristic |
| Taste | Minty, cooling |
| Molecular Weight | 154.25 g/mol |
| Melting Point | -6 °C |
| Boiling Point | 207 °C |
| Density (20°C) | 0.895 g/cm³ |
| Refractive Index (nD²⁰) | 1.450 – 1.453 |
| Specific Rotation [α]D²⁰ | -28° to -32° (L-form), +28° to +32° (D-form) |
| Solubility in Water | Slightly soluble |
| Solubility in Ethanol | Miscible |
| Solubility in Oils | Miscible |
| Solubility in Organic Solvents | Miscible (ether, chloroform, hexane) |
| Flash Point | 72 °C (closed cup) |
| Vapor Pressure (20°C) | ~0.5 mmHg |
| Log P (octanol/water) | 2.85 |
SECTION 3: CHEMICAL PROPERTIES
| Property | Information |
|---|---|
| Chemical Formula | C₁₀H₁₈O |
| Molecular Weight | 154.25 g/mol |
| Chemical Class | Monoterpenoid ketone |
| Functional Groups | Ketone (C=O) |
| Structure | Cyclohexanone ring with isopropyl and methyl substituents |
| SMILES | CC1CCC(C(=O)C1)C(C)C |
| InChI Key | NFLGAXVYCFJBMK-UHFFFAOYSA-N |
| Optical Isomers | L-Menthone (natural, peppermint), D-Menthone (natural, geranium) |
| Stability | Stable under normal storage conditions |
| Reduction | Can be reduced to menthol |
| Oxidation | Slowly oxidizes in air |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
Chemical Structure:
O
||
C
/ \
/ \
C C
| |
C C
\ /
\ /
C
/ \
CH₃ CH(CH₃)₂
2-Isopropyl-5-methylcyclohexanone
(Menthone)
SECTION 4: ENANTIOMERS
| Isomer | CAS Number | Source | Odor Profile |
|---|---|---|---|
| L-Menthone | 14073-97-3 | Peppermint, corn mint | Fresh, minty, cooling |
| D-Menthone | 3391-87-5 | Geranium, pennyroyal | Minty, earthy |
| Racemic (R/S) | 89-80-5 | Synthetic mixture | Mixed minty profile |
SECTION 5: NATURAL SOURCES
| Source | Content (%) | Main Isomer |
|---|---|---|
| Peppermint (Mentha piperita) | 15-30% | L-Menthone |
| Corn Mint (Mentha arvensis) | 15-35% | L-Menthone |
| Pennyroyal (Mentha pulegium) | 10-25% | L-Menthone |
| Geranium (Pelargonium graveolens) | 5-15% | D-Menthone |
| Bergamot Mint (Mentha citrata) | 10-20% | L-Menthone |
SECTION 6: APPLICATION AREAS
6.1. Perfume and Cosmetic Industry
| Application | Function |
|---|---|
| Perfumes | Fragrance component; fresh, minty note |
| Cosmetic Products | Fragrance component |
| Soaps | Fragrance component |
| Toothpaste | Flavoring and fragrance component |
| Mouthwash | Flavoring and fragrance component |
| Shampoos | Fragrance component |
| After-Shave Lotions | Cooling and fragrance component |
6.2. Food Industry
| Application | Function |
|---|---|
| Flavoring Agent | Natural mint flavor component (FEMA 2667) |
| Chewing Gum | Flavoring component |
| Confectionery | Flavoring component |
| Beverages | Mint flavoring |
| Dental Products | Flavoring component |
6.3. Pharmaceutical Applications
| Application | Function |
|---|---|
| Cough Drops | Flavoring and cooling component |
| Chest Rubs | Flavoring and cooling component |
| Topical Analgesics | Cooling and counterirritant |
6.4. Chemical Synthesis
| Application | Function |
|---|---|
| Intermediate | Precursor for menthol synthesis |
| Chemical Synthesis | Reagent in organic synthesis |
SECTION 7: BIOLOGICAL ACTIVITIES
| Activity | Description |
|---|---|
| Cooling Effect | Activates TRPM8 receptors; provides cooling sensation |
| Antimicrobial | Effective against bacteria and fungi |
| Anti-inflammatory | Reduces inflammation |
| Cough Suppressant | Mild antitussive activity |
| Insect Repellent | Natural insect repellent |
SECTION 8: COMPARISON WITH MENTHOL
| Property | Menthone | Menthol |
|---|---|---|
| Chemical Class | Ketone | Alcohol |
| Cooling Effect | Moderate | Strong |
| Odor | Fresh, minty | Intense minty |
| Solubility | Moderate | Moderate |
| Application | Flavoring, fragrance | Flavoring, topical analgesic |
| Bioactivity | Moderate | Strong |
SECTION 9: SAFETY AND HEALTH INFORMATION
GHS Classification
| Hazard Class | Category |
|---|---|
| Skin Irritation | Category 2 (H315) |
| Eye Irritation | Category 2A (H319) |
| Signal Word | Warning |
Hazard Statements (H-Codes)
| Code | Statement |
|---|---|
| H315 | Causes skin irritation |
| H319 | Causes serious eye irritation |
Precautionary Statements (P-Codes)
| Code | Statement |
|---|---|
| P261 | Avoid breathing vapors |
| P280 | Wear protective gloves/eye protection |
| P302+P352 | IF ON SKIN: Wash with plenty of soap and water |
| P305+P351+P338 | IF IN EYES: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing |
SECTION 10: TOXICOLOGICAL INFORMATION
| Parameter | Value |
|---|---|
| Oral LD50 (Rat) | 2,500-3,500 mg/kg |
| Dermal LD50 (Rabbit) | > 5,000 mg/kg |
| Skin Irritation | Mild irritant |
| Eye Irritation | Mild irritant |
| Skin Sensitization | Non-sensitizer |
| Carcinogenicity | Not classified |
| Mutagenicity | Negative in standard tests |
SECTION 11: FIRST AID MEASURES
| Exposure Route | Action |
|---|---|
| Inhalation | Move to fresh air. If respiratory irritation persists, seek medical attention. |
| Skin Contact | Wash with plenty of soap and water. Remove contaminated clothing. |
| Eye Contact | Rinse immediately with plenty of water for at least 15 minutes. Seek medical attention. |
| Ingestion | Rinse mouth. Do not induce vomiting. Seek medical attention. |
SECTION 12: STORAGE AND SHELF LIFE
| Parameter | Information |
|---|---|
| Storage Conditions | Cool (15-25°C), dry, well-ventilated area |
| Container Requirements | Tightly closed, light-resistant containers |
| Protect From | Light, air (oxidation), heat, strong oxidizing agents |
| Shelf Life | 24-48 months (unopened original packaging) |
| Stability Note | Slowly oxidizes in air; color may darken |
SECTION 13: PACKAGING OPTIONS
| Packaging Type | Quantity | Material |
|---|---|---|
| Glass bottle | 1-5 L | Amber glass |
| Plastic drum | 200-250 kg | HDPE |
| Plastic pail | 20-25 kg | HDPE |
| Aluminum foil bag | 1-5 kg | Laminated aluminum |
SECTION 14: TRANSPORT INFORMATION
| Parameter | Information |
|---|---|
| UN Number | Not regulated (not dangerous goods) |
| Hazard Class | Not applicable |
| Packing Group | Not applicable |
| ADR/RID | Not regulated |
| IMDG Code | Not regulated |
| IATA (Air) | Not regulated |
| Marine Pollutant | No |
SECTION 15: FIRE-FIGHTING MEASURES
| Parameter | Information |
|---|---|
| Fire Hazard | Combustible liquid |
| Flash Point | 72 °C |
| Suitable Extinguishing Media | CO₂, dry chemical powder, alcohol-resistant foam, water spray |
| Specific Hazards | When heated, emits CO, CO₂ |
| Decomposition Products | CO, CO₂ |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
SECTION 16: ACCIDENTAL SPILLAGE AND CLEANUP
| Parameter | Information |
|---|---|
| Personal Protection | Nitrile gloves, protective goggles, chemical-resistant clothing |
| Cleaning Methods | Absorb with inert material (sand, vermiculite); dispose in sealed containers |
| Environmental Precautions | Prevent entry into drains, soil, and surface waters |
| Waste Disposal | According to local regulations; incineration at licensed facilities |
SECTION 17: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| Turkish Names | Menton, Nane Yağı Bileşiği |
| English Names | Menthone, p-Menthan-3-one, d-Menthone, l-Menthone, M-Menthone |
| Chemical Names | 2-Isopropyl-5-methylcyclohexanone |
| CAS Number | 89-80-5 |
| EC Number | 201-941-1 |
| FEMA Number | 2667 |
| PubChem CID | 26447 |
SECTION 18: SUMMARY AND CRITICAL NOTES
Product Summary
| Parameter | Value |
|---|---|
| Product | Menthone |
| CAS Number | 89-80-5 |
| Appearance | Colorless to pale yellow liquid |
| Odor | Fresh, minty |
| Boiling Point | 207 °C |
| Primary Function | Flavoring, fragrance component |
Critical Notes
-
Natural Source: Menthone is naturally found in peppermint, corn mint, pennyroyal, and geranium oils.
-
Enantiomers: L-Menthone (peppermint) and D-Menthone (geranium) are the two optical isomers.
-
Mint Flavor: Menthone is a key component of natural mint flavor and fragrance.
-
Fragrance Component: Widely used in perfumes, cosmetics, soaps, and detergents.
-
Flavoring Agent: Used as a natural flavoring agent in the food industry (FEMA 2667).
-
Cooling Effect: Provides a cooling sensation through TRPM8 receptor activation (less potent than menthol).
-
Precursor: Used as a precursor for menthol synthesis.
-
Bioactivity: Exhibits antimicrobial and anti-inflammatory properties.
-
Oxidation: Slowly oxidizes in air; store in airtight, light-resistant containers.
-
Regulatory Status: Approved in food, cosmetic, and fragrance industries; no E number assigned.
IMPORTANT DECLARATION: This Technical Data Sheet (TDS) is for informational purposes only and has been prepared based on available technical data. The user is responsible for determining the product's suitability for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, use, transport, waste, and regulatory compliance information, refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier.
