CAS No.89-78-1,Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	89-78-1
Name:	Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel-
Article Data:	186
Cas Database

Formula:	C₁₀H₂₀O
Molecular Weight:	156.268
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;
EINECS:	201-939-0
Density:	0.89 g/cm³
Melting Point:	32-36 °C
Boiling Point:	215.383 °C at 760 mmHg
Flash Point:	93.333 °C
Solubility:	insoluble in water
Appearance:	colorless need-like crystals
Hazard Symbols:	Xn, Xi
Risk Codes:	37/38-41-36/37/38
Safety:	36/37/39-24/25-36-26
Transport Information:	UN 1888 6.1/PG 3
PSA:	20.23000
LogP:	2.43950

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Synthetic route

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

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menthol

Conditions

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

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

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Conditions

Conditions	Yield
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%

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(2-isopropyl-5-methylcyclohexyloxy)trimethylsilane

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Conditions

Conditions	Yield
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%

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benzyl-menthyl ether

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Conditions

Conditions	Yield
With 18-crown-6 ether; tert-butylamine; tert-butyl alcohol; potassium In tetrahydrofuran at 20℃; for 1h;	99%

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2-(2-isopropyl-5-methylcyclohexyloxy)tetrahydro-2H-pyran

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Conditions

Conditions	Yield
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%

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Menthone

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menthol

Conditions

Conditions	Yield
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.);

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thymol

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menthol

Conditions

Conditions	Yield
With hydrogen In tert-butyl alcohol at 150℃; for 48h; Autoclave;	92%

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

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Conditions

Conditions	Yield
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

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

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menthol

Conditions

Conditions	Yield
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;

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Menthol allyl ether

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Conditions

Conditions	Yield
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%

Raw Materials

64-19-7

109-79-5

7664-93-9

89-79-2

64-17-5

10458-14-7

36099-51-1

3391-87-5

Downstream Products

99-87-6

498-81-7

89-80-5

497-25-6

Total:231 Page 1 of 7 1 2 3 4 5 6 …7 Next>>

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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.

Consensus Reports

Reported in EPA TSCA Inventory.

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.