Menthone Laevo Natural
l-Menthone
CAS: 14073-97-3
Molecular Formula: C10H18O
Menthone Laevo Natural - Names and Identifiers
Menthone Laevo Natural - Physico-chemical Properties
| Molecular Formula | C10H18O |
| Molar Mass | 154.25 |
| Density | 0.893g/mLat 20°C(lit.) |
| Melting Point | -6 °C |
| Boling Point | 207-210°C(lit.) |
| Specific Rotation(α) | D20 -24.8°; D27 -28.9° |
| Flash Point | 163°F |
| Water Solubility | 496.7mg/L(25 ºC) |
| Solubility | Soluble in organic solvent, slightly soluble in water |
| Vapor Presure | 0.5 mm Hg ( 20 °C) |
| Appearance | Oil |
| Color | Clear colorless to pale yellow |
| Merck | 14,5838 |
| BRN | 3648743 |
| Storage Condition | -20°C |
| Refractive Index | n20/D 1.45(lit.) |
| MDL | MFCD00062998 |
Menthone Laevo Natural - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 43 - May cause sensitization by skin contact |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. S23 - Do not breathe vapour. |
| UN IDs | NA 1993 / PGIII |
| WGK Germany | 3 |
| RTECS | OS9542200 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29142990 |
Menthone Laevo Natural - Reference
| Reference Show more | 1. [IF=4.27] Rui Ma et al."Molecular cloning and functional identification of a high-efficiency (+)-borneol dehydrogenase from Cinnamomum camphora (L.) Presl."Plant Physiol Bioch. 2021 Jan;158:363 |
Menthone Laevo Natural - Reference Information
| FEMA | 2667 | MENTHONE |
| LogP | 3.05 at 25℃ |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | levomenthone widely exists in mint volatile oil. studies have shown that levomenthone has cooling, analgesic and antipruritic effects. The experimental experimental model preliminarily confirmed that L-menthone may have antidepressant effect. The improvement effect of L-menthone on loss of interest in CUMS mice was observed by sugar water preference, and its effect on serum corticosterone, cortical GRmRNA and BDNF expression in CUMS mice was further detected. |
| application | natural levomenthone exists in nepeta, mint, scutellaria baicalensis and other traditional Chinese medicines. Nepeta is the dry aboveground part of Nepeta, a plant in the family Lamiaceae. The sex is slightly warm, the taste is pungent, and it belongs to the liver and lung meridian. It has the functions of relieving the surface and dispelling the wind, penetrating the rash, clearing the head, benefiting the throat, eliminating sores and relieving itching, stopping bleeding, and clearing the nose. Mint is the dry overground part of the perennial herb mint of the Lamiaceae Mint. Mint is pungent and cool, and belongs to the liver and lung meridian. Can dispel wind and heat, clear the boss, and penetrate the rash. Used for wind-heat cold, wind temperature, headache, red eyes, throat, aphthous sores, rubella, measles, chest and flank distension, etc. Levmenthone can also be used as an edible flavor and spice. |
| preparation | 1) preparation of catalyst [RuCl2(S)-XylBINAP(S)-DAIPEN] 1g(2mmol) [RuCl2(benzene)]2 and 2.940g(4mmol)(S)-XylBINAP are added to a 50mL dry round bottom flask, magnetic stirrer is added, and nitrogen protection system is passed. 15mL of deaerated N,N-dimethylformamide was added with a syringe, and the mixture was reacted at 100 ℃ for 15 minutes to form a reddish brown solution. After the system was cooled to room temperature, 1.258g(4mmol)(S)-DAIPEN was added and stirred for 12 hours. After the reaction, cool to room temperature, remove the solvent under reduced pressure, add 40mL of anhydrous ether to the residue to dissolve, filter to remove black insoluble matter, concentrate the solution to 3mL, add 3mL of degasified petroleum ether, precipitate brown solid, filter to discard the filtrate, precipitate under reduced pressure and dry to obtain 3.13g[RuCl2(S)-XylBINAP(S)-DAIPEN](yield 63%)m.p.178.5 ℃. 2) Selective hydrogenation reaction In a 100mL high-pressure reactor, 20mL of anhydrous tetrahydrofuran and 76.1g(0.5mol) of dexmothurone are added, nitrogen is introduced, the syringe is slowly added with the above catalyst solution [Rh((S)-p-Tol-BINAP)2]BF4(5mmol,0.1mol%) diluted with 10mL tetrahydrofuran, and the temperature after sealing the high-pressure reactor is 70 ℃, after replacing the system with H2 atmosphere for 3 times, the hydrogen pressure was raised to 100atm and the reaction was completed at 23h. After pouring out the reaction liquid, distilled at normal pressure to remove the solvent, the yield of levmenthone (70.13g,0.495mol) was 91%, and the purity of the product was 100% measured by meteorological chromatography. |
Last Update：2024-04-09 21:11:58
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