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DL-Menthol

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DL-Menthol

EINECS 201-939-0
CAS No. 89-78-1 Density 0.89 g/cm3
PSA 20.23000 LogP 2.43950
Solubility insoluble in water Melting Point 32-36 °C
Formula C10H20O Boiling Point 215.383 °C at 760 mmHg
Molecular Weight 156.268 Flash Point 93.333 °C
Transport Information UN 1888 6.1/PG 3 Appearance colorless need-like crystals
Safety 36/37/39-24/25-36-26 Risk Codes 37/38-41-36/37/38
Molecular Structure Molecular Structure of 89-78-1 (DL-Menthol) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1a,2b,5a)-;Menthol, cis-1,3,trans-1,4- (8CI);Menthol, dl- (6CI);(1R,2S,5R)-rel-5-Methyl-2-(1-methylethyl)cyclohexanol;(?à)-Menthol;DL-Menthol;Fisherman's Friend Lozenges;Hexahydrothymol;Menthacamphor;Menthol;Menthomenthol;NSC 2603;Peppermint camphor;Racementhol;Therapeutic MineralIce;Thymomenthol;

Article Data 186

DL-Menthol Synthetic route

82003-87-0

2-(2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-furan

89-78-1

menthol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;100%
129368-71-4

2-{[(tert-butyl)dimethylsilyl]oxy}-4-methyl-1-(1-methylethyl)cyclohexane

89-78-1

menthol

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
With dimethylbromosulphonium bromide In methanol at 20℃; for 9h;99%
With copper(ll) sulfate pentahydrate In methanol at 100℃; for 0.25h; Microwave irradiation;98%
62338-23-2, 66808-39-7, 88390-70-9, 122999-13-7, 18419-38-0

(2-isopropyl-5-methylcyclohexyloxy)trimethylsilane

89-78-1

menthol

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry;99%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.333333h;94%
164352-04-9

benzyl-menthyl ether

89-78-1

menthol

Conditions
ConditionsYield
With 18-crown-6 ether; tert-butylamine; tert-butyl alcohol; potassium In tetrahydrofuran at 20℃; for 1h;99%
Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In methanol for 0.116667h; Heating;98%
With dimethylbromosulphonium bromide In methanol; dichloromethane at 20℃; for 0.25h;95%
With water; lithium chloride In dimethyl sulfoxide at 90℃; for 6h; Hydrolysis;92%
10458-14-7

Menthone

89-78-1

menthol

Conditions
ConditionsYield
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 24h; Glovebox;93%
With hydrogen at 80℃; under 150015 Torr;78%
With tri-tert-butoxyaluminum hydride In tetrahydrofuran at 9.9℃; Rate constant; Thermodynamic data; var. temp., ΔG(excit.), ΔH(excit.), ΔS(excit.);
89-83-8

thymol

89-78-1

menthol

Conditions
ConditionsYield
With hydrogen In tert-butyl alcohol at 150℃; for 48h; Autoclave;92%
91898-15-6

1-Isopropyl-2-(2-methoxy-ethoxymethoxy)-4-methyl-cyclohexane

89-78-1

menthol

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h; wet ZnBr2, CH2Cl2, 17 h, room temperature;91%
With dimethylboron bromide; water; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 1) Me2BBr, 2) NEt3 / 1) CH2Cl2, 1,2-dichloroethane, -78 deg C, 1h, 2) RT, 1h
2: 1) Me2BBr, 2) satd. aq. NaHCO3/H2O / 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min
View Scheme
Multi-step reaction with 2 steps
1: 1.) Me2BBr, 2.) Et3N / multistep reaction
2: 90 percent / dimethylboron bromide / CH2Cl2; 1,2-dichloro-ethane / 1 h / -78 °C
View Scheme
91898-14-5

1-Isopropyl-2-methoxymethoxy-4-methyl-cyclohexane

89-78-1

menthol

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;90%
With magnesium bromide In diethyl ether for 36h; Ambient temperature;85%
With dimethylboron bromide; water; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
144266-44-4

Menthol allyl ether

89-78-1

menthol

Conditions
ConditionsYield
With polymethylhydrosiloxane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;89%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 0 - 35℃; Hydrolysis;80%
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 0 - 35℃;75%

DL-Menthol History

There is evidence that Menthol (CAS NO.89-78-1) has been known in Japan for more than 2000 years, but in the West it was not isolated until 1771, by Hieronymous David Gaubius. Early characterizations were done by Oppenheim, Beckett, Moriya, and Atkinson.

DL-Menthol Consensus Reports

Reported in EPA TSCA Inventory.

DL-Menthol Specification

The IUPAC name of Menthol is (1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol. With theCAS registry number 89-78-1, it is also named as Racementhol. The classification codes are Agricultural Chemical; Insecticide; Mutation data; Natural Product; Skin / Eye Irritant; Tumor data. It is colorless need-like crystals with cool, refreshing and pleasant mint aroma. Additionally, this chemical should be sealed in the container and stored in the cool place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.216; (4)ACD/LogD (pH 7.4): 3.216; (5)ACD/BCF (pH 5.5): 163.88; (6)ACD/BCF (pH 7.4): 163.88; (7)ACD/KOC (pH 5.5): 1338.956; (8)ACD/KOC (pH 7.4): 1338.956; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.457; (13)Molar Refractivity: 47.833 cm3; (14)Molar Volume: 175.542 cm3; (15)Polarizability: 18.963×10-24 cm3; (16)Surface Tension: 29.706 dyne/cm; (17)Enthalpy of Vaporization: 52.536 kJ/mol; (18)Vapour Pressure: 0.032 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 156.151415; (21)MonoIsotopic Mass: 156.151415; (22)Topological Polar Surface Area: 20.2; (23)Heavy Atom Count: 11; (24)Complexity: 120; (25)Defined Atom StereoCenter Count: 3.

Preparation of Menthol: It can be obtained from peppermint or other mint oils. It also can be produced by the following method:

Uses of Menthol: It is widely used to relieve minor throat irritation. It is not only used to produce cooling oil and pain killer, but also used in making toothpaste, tooth powder, candy, beverages, spices, etc. In addition, it also react with acetic acid anhydride to get Isomentholacetat. This reaction needs reagent TaCl5-SiO2 and solvent CH2Cl2 at ambient temperature. The yield is 79%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. And it has risk of serious damage to the eyes. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. 

People can use the following data to convert to the molecule 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

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 37mg/kg (37mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 63, Pg. 43, 1939.
cat LDLo oral 1500mg/kg (1500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LDLo intraperitoneal 1800mg/kg (1800mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 63, Pg. 43, 1939.
rat LD50 intramuscular 10gm/kg (10000mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 244, 1954.
rat LD50 oral 3180mg/kg (3180mg/kg) BEHAVIORAL: ATAXIA Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LDLo intraperitoneal 1500mg/kg (1500mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: MUSCLE WEAKNESS
Annales Pharmaceutiques Francaises. Vol. 10, Pg. 481, 1952.
 

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