Menthol, L-
L(-)-Menthol
CAS: 2216-51-5
Molecular Formula: C10H20O
Menthol, L- - Names and Identifiers
| Name | L(-)-Menthol |
| Synonyms | L-Menthol levomenthol Menthol, L- L(-)-Menthol (R)-(-)-Menthol hexahydrothymol L-p-Menthan-3-ol (-)-paramenthol-3 L-Menthol natural (1r,3r,4s)-(-)-mentho (1R,2S,5R)-(-)-Menthol (1R,3R,4S)-(-)-MENTHOL Natural Menthol Crystal Emtricitabine Impurity 31 methylhydroxyisopropylcyclohexane DL-Menthol menthol crystal extract L-Meng alcohol Natural menthol Menthol (L) (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexanol (1R-(1-alpha,2-beta,5-alpha))-5-Methyl-2-(1-methylethyl)cyclohexanol |
| CAS | 2216-51-5 |
| EINECS | 218-690-9 |
| InChI | InChI=1/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9?,10?/m1/s1 |
| InChIKey | NOOLISFMXDJSKH-KXUCPTDWSA-N |
Menthol, L- - Physico-chemical Properties
| Molecular Formula | C10H20O |
| Molar Mass | 156.27 |
| Density | 0.89 g/mL at 25 °C (lit.) |
| Melting Point | 41-45 °C (lit.) |
| Boling Point | 212 °C (lit.) |
| Specific Rotation(α) | -51 º (589nm, c=10, EtOH) |
| Flash Point | 200°F |
| Water Solubility | insoluble |
| Solubility | Soluble in organic solvents such as ethanol, acetone, ether, chloroform and benzene, slightly soluble in water. |
| Vapor Presure | 0.8 mm Hg ( 20 °C) |
| Appearance | Colorless needle crystal |
| Specific Gravity | 0.89 |
| Color | Colorless to white |
| Merck | 14,5837 |
| BRN | 1902293 |
| pKa | 15.30±0.60(Predicted) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. |
| Refractive Index | 1.46 |
| MDL | MFCD00062979 |
| Physical and Chemical Properties | Colorless needle-like crystals with a cool aroma of mint. Relative density d1515 = 0.890, melting point 41~43 ℃, boiling point 216 ℃,111 ℃(2.67kPa), specific optical rotation αD20 =-49.3 °, refractive index nD20 = 1.4609. Soluble in ethanol, acetone, ether, chloroform and benzene and other organic solvents, water-soluble. The chemical properties are relatively stable, and can be volatilized with steam. Rat oral LD503.3g/kg,ADI0 ~ 0.2 mg/kg(FAO/WHO,1994). |
Menthol, L- - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | OT0700000 |
| TSCA | Yes |
| HS Code | 29061100 |
| Toxicity | LD50 orally in Rabbit: 3300 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
Menthol, L- - Reference
| Reference Show more | 1. [IF=7.561] Liu Songqi et al."Menthol Targeting AMPK Alleviates the Inflammatory Response of Bovine Mammary Epithelial Cells and Restores the Synthesis of Milk Fat and Milk Protein."Front Immunol. 2021 Dec;0:5523 |
Menthol, L- - Reference Information
| FEMA | 2665 | MENTHOL RACEMIC |
| LogP | 3.15 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | menthol is a edible spice allowed in our country, mainly used for flavoring toothpaste, candy and beverage. The dosage is 1100 mg/kg in chewing gum according to normal production requirements. 400 mg/kg in candy; 130 mg/kg in baked food; 68 mg/kg in ice cream; 35 mg/kg in soft drinks. GB 2760-1996 stipulates that natural thin brains are allowed to be used as edible spices. GB 2760-2001 stipulates that dl-type thin-film brain is also a permitted food spice. For the preparation of mint spices (can account for 10% ~ 18%), can also be used for candy (mint candy, gum candy), beverages, ice cream, etc. (dosage 0.054% ~ 0.1%). Menthol and racemic menthol can be used as flavoring agents for toothpaste, perfume, beverage and candy. It is used as a irritant in medicine, acting on the skin or mucous membranes, and has a cooling and antipruritic effect; oral administration can be used as a wind repellent for headaches and nasal, pharyngeal, and laryngeal inflammation. Its esters are used in spices and medicines. In the world, China and Brazil are the main natural mint producers, and the annual output of peppermint oil reaches 2000-3000t. The main component of peppermint oil. Due to its unique mint flavor and cooling effect, it is widely used in candy, cosmetics and toothpaste. |
| production method | menthol can be purified from natural mint crude oil or can be prepared by synthesis. The essential oil obtained by steam distillation of the above-ground parts (stems, branches, leaves and inflorescences) of the Lamiaceae plant mint is called mint crude oil, and the oil yield is 0.5-0.6. There are many ways to synthesize thin synencephalon. 1. Manufactured from citronellal, using the nature of citronellal that is easily cyclized into isophanthenol, the dextral is cyclized into L-isophanthol with an acid catalyst (such as silica gel), and the L-isophanthol is separated, Hydrogenated to produce L-mint. The three-dimensional tutor structure can be partially converted into dextral and recycled after thermal cracking. 2. Produced from thymol in the presence of m-cresol aluminum, and alkylation of m-cresol to produce thymol. After catalytic hydrogenation, all four pairs of menthol stereoisomers (ie, racemic menthol, racemic new menthol, racemic isomenthol and racemic new menthol) are obtained. It is distilled, the spin menthol fraction is canceled, the ester is produced and recrystallized repeatedly, and the isomer is separated and optically resolved. The isolated L-menthol ester is saponified to obtain menthol. l-type is obtained by cooling, crystallization and separation of natural mint crude oil. Peppermint oil contains brain 50% ~ 60%, cooled to 15 ℃, menthol will crystallize and precipitate, centrifuge, oil will be cooled to 5 ℃, menthol will be obtained, then cooled to -10 ℃, menthol will be obtained, and 50% menthol can be removed three times (there is still about 50% menthol remaining). L-menthol can be made from l-menthone. The residual oil obtained by the above method is steamed to remove terpenoids (about 20% ~ 25%) under reduced pressure, the rest is dissolved with 96% ethanol, and then reduced to menthol with metallic sodium. The synthetic product (dl-) is made from aromatic aldehyde. menthol naturally exists in peppermint oil with a content of up to 80%. menthol can be separated from peppermint oil in industry. The mint crude oil is frozen to a 20 DEG C, and the crystalline crude menthol is separated; the mother liquor is further frozen to -40 DEG C, and a part of the crude menthol can be separated. Coarse menthol is heated and melted, dehydrated by decompression, and filtered while hot. Cool to about 0 ℃, let stand for 7~9 days, separate crystals, dry at 42 ℃ for 24 hours, and dry to room temperature to be the finished product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:48
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