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| CAS No.: | 2216-51-5 |
|---|---|
| Name: | L-Menthol |
| Molecular Structure: | |
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|
|
| Formula: | C10H20O |
| Molecular Weight: | 156.268 |
| Synonyms: | Cyclohexanol,5-methyl-2-(1-methylethyl)-, [1R-(1a,2b,5a)]-;Menthol, (1R,3R,4S)-(-)- (8CI);(-)-Menthol;(-)-Menthylalcohol;(-)-trans-p-Methan-cis-3-ol;(1R)-(-)-Menthol;(1R,2S,5R)-(-)-Menthol;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexan-1-ol;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol;(R)-(-)-Menthol;L-Menthol;Levomenthol;NSC 62788; |
| EINECS: | 218-690-9 |
| Density: | 0.89 g/cm3 |
| Melting Point: | 41-44 °C(lit.) |
| Boiling Point: | 215.383 °C at 760 mmHg |
| Flash Point: | 93.333 °C |
| Solubility: | insoluble in water |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 37/38-41-36/37/38 |
| Safety: | 26-39-37/39-36 |
| PSA: | 20.23000 |
| LogP: | 2.43950 |
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- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 76648-56-1
menthyl allyl carbonate
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water for 0.5h; Ambient temperature; | 100% |
- 34350-47-5
(1S,2R,4R)-(-)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With sodium iodide; cerium(III) chloride In acetonitrile at 70℃; for 2h; | 100% |
| With cerium(III) chloride; sodium iodide In acetonitrile at 70℃; for 17h; |
- 76648-56-1
menthyl allyl carbonate
- 75-33-2
2-propanethiol
A
- 50996-72-0
allylisopropyl sulfide
B
- 124-38-9
carbon dioxide
C
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With Roussin's red salt ester; tetrabutylammomium bromide; potassium hydride In tetrahydrofuran; ethanol at 40℃; for 14h; | A n/a B n/a C 100% |
| Conditions | Yield |
|---|---|
| With hydrogen In water at 80℃; under 7500.75 Torr; for 48h; Inert atmosphere; Autoclave; | 100% |
| With 20percent 12-tungstophosphoric acid supported on MCM-41 In dichloromethane at 20℃; for 3h; Inert atmosphere; | |
| Multi-step reaction with 2 steps 1: 0 - 5 °C 2: Raney nickel / 10 h / 70 °C / 18751.9 Torr / Inert atmosphere View Scheme | |
| With hydrogen In water at 60℃; under 7500.75 Torr; for 23h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; | 99 %Chromat. |
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With hydrogen In toluene at 100℃; under 22502.3 Torr; for 0.25h; Catalytic behavior; Pressure; Temperature; Reagent/catalyst; Flow reactor; | 99.9% |
| With hydrogen; nickel; 4-methoxy-aniline In hexane at 80℃; under 30003 Torr; for 10h; Temperature; Pressure; Solvent; Autoclave; | 99.9% |
| With ethanol; palladium on activated charcoal; sodium hydroxide; silicon at 20℃; for 72h; Schlenk technique; | 94% |
- 10458-14-7, 14073-97-3
(2R,5S)-menthone
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With iron(II) chloride tetrahydrate; lithium In tetrahydrofuran; mineral oil at 20℃; for 4h; Reagent/catalyst; Inert atmosphere; stereoselective reaction; | 99% |
| With tris(pentafluorophenyl)borate; hydrogen In diethyl ether at 70℃; under 45603.1 Torr; for 12h; Solvent; Glovebox; | 88% |
| With sulfuric acid bei der elektrolytischen Reduktion; |
| Conditions | Yield |
|---|---|
| With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen In toluene at 80℃; under 30003 Torr; for 3h; | 99% |
| With ytterbium(III) triflate In isopropyl alcohol for 74h; Deacetylation; Heating; | 95% |
| With sodium hydroxide In methanol; dichloromethane at 20℃; for 0.75h; Solvent; | 95% |
- 72020-06-5, 80924-03-4, 97526-56-2, 123121-06-2, 128946-28-1, 128946-29-2, 128946-30-5, 128946-31-6, 134052-28-1
2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)tetrahydro-2H-pyran
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 45h; Hydrolysis; | 98% |
| With trichloroisocyanuric acid In methanol at 20℃; for 4h; | 94% |
| With tris-(4-bromophenyl)aminium hexachloroantimonate In methanol at 20℃; for 2.5h; | 93% |
- 548464-35-3
4-methoxybenzyl (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ether
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With trifluorormethanesulfonic acid; 1,3-Dimethoxybenzene In dichloromethane at 21℃; for 0.166667h; | 98% |
| With trifluorormethanesulfonic acid; toluene-4-sulfonamide In diethyl ether | 95% |
| With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 2.5h; | 93% |
- 40940-58-7, 144266-44-4, 67528-21-6
(1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane
- 2216-51-5
(-)-menthol
| Conditions | Yield |
|---|---|
| With diisobutylaluminium hydride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether; toluene at 0 - 20℃; for 3h; | 97% |
| Stage #1: (1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane; Grubbs catalyst first generation In dichloromethane at 20℃; for 12h; Stage #2: With hydrogenchloride | 95% |
| With triisopropoxytitanium(IV) chloride; n-butyl magnesium bromide In tetrahydrofuran; diethyl ether; hexane for 2h; Ambient temperature; | 94% |
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Consensus Reports
Specification
The L-Menthol is an organic compound with the formula C10H20O. The IUPAC name of this chemical is (1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol. With the CAS registry number 2216-51-5, it is also named as (±)-Menthol. The product's categories are Organics; Chiral; Biochemistry; Terpenes; Terpenes (Others); For Resolution of Acids; Monocyclic Monoterpenes; Optical Resolution; Synthetic Organic Chemistry. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place. It can be used flavoring agent in toothpaste, perfume, drinks and candy. It is used as stimulate drug in medicine.
Physical properties about L-Menthol are: (1)ACD/LogP: 3.22; (2)ACD/LogD (pH 5.5): 3.216; (3)ACD/LogD (pH 7.4): 3.216; (4)ACD/BCF (pH 5.5): 163.88; (5)ACD/BCF (pH 7.4): 163.88; (6)ACD/KOC (pH 5.5): 1338.956; (7)ACD/KOC (pH 7.4): 1338.956; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 20.23 Å2; (12)Index of Refraction: 1.457; (13)Molar Refractivity: 47.833 cm3; (14)Molar Volume: 175.542 cm3; (15)Polarizability: 18.963×10-24cm3; (16)Surface Tension: 29.706 dyne/cm; (17)Density: 0.89 g/cm3; (18)Flash Point: 93.333 °C; (19)Enthalpy of Vaporization: 52.536 kJ/mol; (20)Boiling Point: 215.383 °C at 760 mmHg; (21)Vapour Pressure: 0.032 mmHg at 25°C.
Preparation: this chemical can be prepared by acetic acid menthyl ester. This reaction will need reagent sodium and solvent diethyl ether, 2-methyl-propan-2-ol, hexamethylphosphoric acid triamide. The yield is about 57%.
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Uses of L-Menthol: it can be used to produce p-menthan-3-one at temperature of 20 °C. It will need reagent o-iodoxy benzoic acid and 1-butyl-3-methyl-imidazolium chloride with reaction time of 8 hours. The yield is about 80%.
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When you are using this chemical, please be cautious about it as the following:
It is risk of serious damage to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: CC1CCC(C(C1)O)C(C)C
(2)InChI: InChI=1/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3
(3)InChIKey: NOOLISFMXDJSKH-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3
(5)Std. InChIKey: NOOLISFMXDJSKH-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LD50 | intraperitoneal | 800mg/kg (800mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 58, 1967. | |
| cat | LD50 | oral | 800mg/kg (800mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 58, 1967. | |
| cat | LDLo | intravenous | 34mg/kg (34mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 63, Pg. 43, 1939. |
| guinea pig | LDLo | intraperitoneal | 4gm/kg (4000mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 63, Pg. 43, 1939. | |
| mouse | LD50 | intraperitoneal | 6600mg/kg (6600mg/kg) | Farmatsevtichnii Zhurnal Vol. 17(3), Pg. 53, 1962. | |
| mouse | LD50 | oral | 3400mg/kg (3400mg/kg) | Quarterly Journal of Pharmacy & Pharmacology. Vol. 5, Pg. 233, 1932. | |
| mouse | LD50 | subcutaneous | 5gm/kg (5000mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 58, 1967. | |
| rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 14, Pg. 471, 1976. | |
| rabbit | LDLo | intraperitoneal | 2gm/kg (2000mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 58, 1967. | |
| rat | LD50 | intraperitoneal | 700mg/kg (700mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Pharmacy and Pharmacology. Vol. 35, Pg. 110, 1983. |
| rat | LD50 | oral | 3300mg/kg (3300mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 58, 1967. | |
| rat | LD50 | subcutaneous | 1gm/kg (1000mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 58, 1967. |
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