L-Menthol supplier | CasNO.2216-51-5

Name
L-Menthol
EINECS 218-690-9
CAS No. 2216-51-5
Article Data352
CAS DataBase
Density 0.89 g/cm³
Solubility insoluble in water
Melting Point 41-44 °C(lit.)
Formula C₁₀H₂₀O
Boiling Point 215.383 °C at 760 mmHg
Molecular Weight 156.268
Flash Point 93.333 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-39-37/39-36
Risk Codes 37/38-41-36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 20.23000
LogP 2.43950

Synthetic route

: 76648-56-1
menthyl allyl carbonate

: 2216-51-5
(-)-menthol

Conditions

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

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

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%

...Expand

: 2385-77-5
(R)-Citronellal

: 2216-51-5
(-)-menthol

Conditions

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.

: 7786-67-6, 18674-65-2, 20549-46-6, 21290-09-5, 29141-10-4, 50373-36-9, 59905-53-2, 59905-54-3, 96612-21-4, 104870-56-6, 121468-66-4, 122517-60-6, 122517-61-7, 144541-38-8, 89-79-2
isopulegol

: 2216-51-5
(-)-menthol

Conditions

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

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;

: 2623-23-6
L-menthyl acetate

: 2216-51-5
(-)-menthol

Conditions

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

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

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

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%

: 76358-81-1
tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With iodine In methanol for 4h; Ambient temperature;	97%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 6h;	96%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 6h;	96%

: 163015-24-5
(1S,2S,6R,7R,8R)-9-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]decane-8-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

A: 2216-51-5
(-)-menthol

B: 163015-25-6
2-[(1R,2R,6S,7S,9R)-9-Hydroxymethyl-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.02,6]dec-(8E)-ylidene]-ethanol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -78 - 0℃;	A 96% B 93%

: 129368-71-4
2-{[(tert-butyl)dimethylsilyl]oxy}-4-methyl-1-(1-methylethyl)cyclohexane

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Microwave irradiation;	96%

: 33744-74-0
menthyl hydrogen phthalate

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With hydroxide solution at 15℃; for 5h;	96%

: 118166-31-7
(1R,3R,4S)-p-menth-3-yl (R)-6,7-dichloro-2,3-dibenzofuran-2-carboxylate

A: 2216-51-5
(-)-menthol

B: 118206-00-1
(R)-6,7-Dichloro-2,3-dihydro-benzofuran-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In acetonitrile for 17h; Ambient temperature;	A 95% B 515 mg

: 363603-37-6
acetaldehyde ethyl menthyl acetal

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.25h;	95%
With CuCl2*H2O In water; acetone for 1h; Hydrolysis; Heating;	91%

: 10458-14-7, 14073-97-3
(2R,5S)-menthone

A: 2216-51-5
(-)-menthol

B: 2216-52-6
Neomenthol

Conditions

Conditions	Yield
With sodium tetrahydroborate; cerium(III) chloride In methanol for 0.0833333h; Yields of byproduct given;	A 94% B n/a
With methanol; sodium tetrahydroborate at 20℃;	A 50% B 31%
With sodium tetrahydroborate In isopropyl alcohol Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 123482-46-2
methoxyethoxymethyl ether of menthol

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With cerium(III) chloride In acetonitrile for 1.5h; Heating;	94%

: 775356-24-6
4-(2-isopropyl-5-methyl-cyclohexyloxymethyl)-phenol

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With iron(III) chloride In diethyl ether; dichloromethane	94%

: 38470-12-1
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl picolinate

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With zinc diacetate In methanol; dichloromethane at 38℃; for 3.8h;	94%
With methanol; copper diacetate In chloroform at 20℃; for 6h; Inert atmosphere;	91%

: 5564-44-3
O-(-)-menthyl S-methyl carbonodithioate

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With 3-azapentane-1,5-diamine at 160℃; for 0.5h; Sealed tube; Microwave irradiation;	94%

: 67-56-1
methanol

: 118166-31-7
(1R,3R,4S)-p-menth-3-yl (R)-6,7-dichloro-2,3-dibenzofuran-2-carboxylate

A: 2216-51-5
(-)-menthol

B: 118166-28-2
methyl (R)-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 20h; Heating;	A 81% B 93%

...Expand

: L-O-(4-Nitrobenzyl)menthol

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With indium; ammonium chloride In methanol for 18h; Heating;	93%

: menthyl β-(trimethylsilyl)ethoxymethyl ether

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With carbon tetrabromide In methanol Irradiation;	93%

: C54H45F51N2O4

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With sodium methylate In methanol; diethyl ether at 20℃;	93%

: 136375-73-0
[[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]benzene

A: 2216-51-5
(-)-menthol

B: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With bis(acetylacetonate)oxovanadium; methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate at 120℃; for 48h;	A 90% B 93%

: 180477-54-7
(1S,2R,4R)-1-isopropyl-4-methyl-2-(3-methylbut-2-en-1-yloxy)cyclohexane

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With iodine In dichloromethane at 20℃; for 1h;	92%
With 3 A molecular sieve; iodine In dichloromethane at 0 - 20℃; for 1h;	92%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 1.5h;	86%
With sodium iodide; zirconium(IV) chloride In acetonitrile for 1.5h; Heating;	86%

: 312493-45-1
(1S,2R,4S)-1-isopropyl-4-methyl-2-trityloxy-cyclohexane

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
With bismuth(III) chloride In acetonitrile at 20℃; for 0.0833333h;	92%

: 958883-15-3
(1R,2S,5R)-menthyl 2-(prenyloxymethyl)benzoate

: 2216-51-5
(-)-menthol

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-menthyl 2-(prenyloxymethyl)benzoate With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 6h; Stage #2: With ytterbium(III) triflate In dichloromethane at 20℃; for 3h;	92%

: 2216-51-5
(-)-menthol

: 10458-14-7, 14073-97-3
(2R,5S)-menthone

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 4h;	100%
With 1,3,5,7-tetrakis-(4-(diacetoxyiodo)phenyl)adamantane; potassium bromide In water at 20℃; for 4h;	100%
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 0.5h;	100%

: 2216-51-5
(-)-menthol

: 26510-92-9
dimenthyl sulfite

Conditions

Conditions	Yield
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution;	100%
With thionyl chloride; triethylamine In dichloromethane at -60℃;	95%
With pyridine; diethyl ether; chlorosulfurous acid

: 2216-51-5
(-)-menthol

: 94-02-0
ethyl 3-oxo-3-phenylpropionate

: 217473-70-6
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-oxo-3-phenylpropanoate

Conditions

Conditions	Yield
at 100℃; for 8h;	100%
With N-Bromosuccinimide In toluene at 90 - 100℃; for 4h;	77%
at 120℃;
at 160℃;
With dmap Dean-Stark; Reflux;

: 2216-51-5
(-)-menthol

: 103-71-9
phenyl isocyanate

: 637336-84-6
phenylcarbamic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

Conditions

Conditions	Yield
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h;	100%
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h; Reagent/catalyst; Inert atmosphere; Sealed tube;	100%

: 2216-51-5
(-)-menthol

: 93-97-0
benzoic acid anhydride

: 612-33-9, 31481-49-9, 38649-18-2, 50465-37-7, 58641-29-5, 71617-14-6, 87038-98-0, 88764-74-3, 88764-75-4, 91840-42-5, 6284-35-1
L-menthyl benzoate

Conditions

Conditions	Yield
With 1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene	100%
With 4-(1H,1H-perfluorotetradecyl)-C6F4-CH(SO2CF3)2 In toluene at 70℃; for 14h;	99%
With 4-(dimethylamino)pyridine hydrochloride In toluene at 60℃; for 6h;	98%

: 2216-51-5
(-)-menthol

: 79-04-9
chloroacetyl chloride

: 7377-98-2, 27994-88-3, 88644-14-8, 106916-72-7, 111957-92-7, 21758-29-2
(-)-menthyl chloroacetate

Conditions

Conditions	Yield
In benzene Heating;	100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Temperature;	98.8%
for 5.5h; Reflux;	95%

: 2216-51-5
(-)-menthol

: 598-21-0
2-Bromoacetyl bromide

: 16832-20-5, 32815-12-6, 55284-67-8
(1R,2S,5R)-menthol bromoacetate

Conditions

Conditions	Yield
With pyridine In dichloromethane at -78℃; Inert atmosphere;	100%
With potassium carbonate In dichloromethane at 0 - 20℃; Inert atmosphere;	95%
With N,N-dimethyl-aniline In diethyl ether 1.) 0 deg C, 3 h, 2.) reflux, 3 h;	77%

: 2216-51-5
(-)-menthol

: 79-08-3
bromoacetic acid

: 16832-20-5, 32815-12-6, 55284-67-8
(1R,2S,5R)-menthol bromoacetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 3h;	100%
With dmap; dicyclohexyl-carbodiimide at 100℃; for 3h;	96%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	91%

: 2216-51-5
(-)-menthol

: 471-25-0
Propiolic acid

: 65018-52-2
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propiolate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark;	100%
With sulfuric acid
With sulfuric acid for 216h; Ambient temperature;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 6h;

: 674-82-8
4-methyleneoxetan-2-one

: 2216-51-5
(-)-menthol

: 59557-05-0
(L)-menthyl 3-oxobutyrate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	100%
With sodium acetate In acetonitrile for 2h; Heating;	96%
With triethylamine In acetone for 2h; Heating;	92%

: 25726-04-9
phenylglyoxylyl chloride

: 2216-51-5
(-)-menthol

: 20229-41-8
l-menthyl phenylglyoxylate

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane at 0℃;	100%
With pyridine In toluene for 14h; Ambient temperature;	89%

: 3095-95-2
diethylphosphonoacetic acid

: 2216-51-5
(-)-menthol

: 141540-20-7
(diethoxy-phosphoryl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; Inert atmosphere;	100%
With triethylamine; 2-chloropyridinium iodide

: 79-37-8
oxalyl dichloride

: 2216-51-5
(-)-menthol

: 70894-19-8
2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoacetic acid

Conditions

Conditions	Yield
Stage #1: oxalyl dichloride; (-)-menthol In diethyl ether at 0 - 23℃; for 1.5h; Inert atmosphere; Stage #2: With water In diethyl ether at 0 - 23℃; Inert atmosphere;	100%
1) CH2Cl2, room temperature, 2) hydrolysis; Multistep reaction;
In diethyl ether; dichloromethane at 0 - 20℃; for 18h;

: 625-35-4, 3488-22-0, 10487-71-5
trans-chrotonyl chloride

: 2216-51-5
(-)-menthol

: 109977-81-3
l-menthyl 3-butenoate

Conditions

Conditions	Yield
With triethylamine at 0℃;	100%

: 18187-31-0
3-(trimethylsilyl)propanoyl chloride

: 2216-51-5
(-)-menthol

: 133124-91-1
3-trimethylsilanyl-propionic acid-((1R)-menthyl ester)

Conditions

Conditions	Yield
With pyridine	100%

: 32315-10-9
bis(trichloromethyl) carbonate

: 2216-51-5
(-)-menthol

: 14602-86-9
(1R,2S,5R)-menthyl chloroformate

Conditions

Conditions	Yield
With pyridine In tetrachloromethane at 55 - 60℃; for 6h;	100%
Stage #1: bis(trichloromethyl) carbonate With pyridine In toluene at 0℃; for 0.25h; Inert atmosphere; Stage #2: (-)-menthol In toluene at 20℃; for 15h; Inert atmosphere;	100%
Stage #1: bis(trichloromethyl) carbonate With pyridine In toluene at 0℃; Inert atmosphere; Stage #2: (-)-menthol In toluene at 0 - 20℃; Inert atmosphere;	100%

: 2216-51-5
(-)-menthol

: 1914-59-6
(E)-2-oxo-4-phenyl-3-butenoic acid

: 110143-65-2
2-oxo-4-phenylbut-3-enoic acid 2-isopropyl-5-methylcyclohexyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 5h; Heating;	100%
With toluene-4-sulfonic acid In toluene for 3h; Heating;	79%
With toluene-4-sulfonic acid In toluene Heating;	79%

: 2216-51-5
(-)-menthol

: 75067-08-2
benzene

: 128328-14-3, 128328-15-4
<<(-)-menthyloxy>(tosyloxy)iodo>benzene

Conditions

Conditions	Yield
In dichloromethane	100%

: 2216-51-5
(-)-menthol

: 87161-57-7
(1S,2S,4R)-2-bromo-1-isopropyl-4-methylcyclohexane

Conditions

Conditions	Yield
With carbon tetrabromide; tris[4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctyloxy)phenyl]phosphane In toluene at 50℃; for 4h;	100%
With 1-bromo-N,N,2-trimethyl-1-propen-1-amine; methyloxirane In dichloromethane 1.) -78 deg C to r.t., 2.) r.t., overnight;	97%
With bromine; triethylamine; triphenylphosphine at 20℃; for 1.5h; Substitution;	86%
With chloro-trimethyl-silane; lithium bromide In acetonitrile for 20h; Heating;	72%
With 4-methylurazole; methyl bromide; triphenylphosphine 1) THF, 0 deg C, 2) room temperature, 6 h; Yield given. Multistep reaction;

: 2216-51-5
(-)-menthol

: 95456-31-8
(1R,2S,5R)-(-)-menthyl phosphorodichloridite

Conditions

Conditions	Yield
With phosphorus trichloride In tetrahydrofuran for 1h; Ambient temperature;	100%
With phosphorus trichloride Inert atmosphere;	98%
Stage #1: (-)-menthol With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With phosphorus trichloride In tetrahydrofuran Inert atmosphere;	64%

: 2216-51-5
(-)-menthol

: 124-63-0
methanesulfonyl chloride

: 61548-81-0
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	100%
With 1-methyl-1H-imidazole; triethylamine In toluene at 20 - 25℃; for 1h; Inert atmosphere;	99%

: 2216-51-5
(-)-menthol

: 644-97-3
Dichlorophenylphosphine

: (-)-(o-menthyl)chlorophenylphosphine

Conditions

Conditions	Yield
Stage #1: (-)-menthol With n-butyllithium In tetrahydrofuran; hexane at 0℃; Inert atmosphere; Stage #2: Dichlorophenylphosphine In tetrahydrofuran; hexane at -78 - 20℃; for 15h; Inert atmosphere;	100%
With R3N
With pyridine

: 2216-51-5
(-)-menthol

: 109-92-2
ethyl vinyl ether

: 363603-37-6
acetaldehyde ethyl menthyl acetal

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 96h;	100%
With acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 0.0833333h;	99%
With acetonyltriphenylphosphonium bromide In dichloromethane for 0.0833333h; Ambient temperature;	92%
With hydrogenchloride

: 2216-51-5
(-)-menthol

: 108-24-7
acetic anhydride

: 2623-23-6
L-menthyl acetate

Conditions

Conditions	Yield
zeolite HSZ-360 In neat (no solvent) at 60℃; for 1h; Product distribution; direct acetylation of phenols and alcohols, catalyst reusable without activity loss;	100%
zeolite HSZ-360 In neat (no solvent) at 60℃; for 1h;	100%
With polystyrene-bound tetrafluorophenylbis(triflyl)methane	100%

: 2216-51-5
(-)-menthol

: 64-19-7
acetic acid

: 2623-23-6
L-menthyl acetate

Conditions

Conditions	Yield
With methanesulfonic acid at 30 - 35℃; for 2h;	100%
With copper(II) nitrate for 3.5h; Heating;	98%
LaY zeolite at 116℃; for 10h; Acetylation;	98%

: 2216-51-5
(-)-menthol

: 109-94-4
formic acid ethyl ester

: 61949-23-3
menthyl formate

Conditions

Conditions	Yield
With copper(II) nitrate for 3.5h; Heating;	100%
With bismuth(III) chloride for 1h; Heating;	95%
With Silphos at 20℃; for 1h;	94%

: 62055-46-3
3-ethoxy-2-methylacrolein

: 2216-51-5
(-)-menthol

: 250267-09-5
3-[2-isopropyl-5-methylcyclohexyloxy-(1R,2S,5R)]-2-methyl-2E-propenal

Conditions

Conditions	Yield
With toluene-4-sulfonic acid under 23 Torr; for 24h; Substitution;	100%

: 2216-51-5
(-)-menthol

: 25197-75-5
(S)-chlorofluoroacetic acid

: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (2S)-2-chloro-2-fluoroacetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Esterification; Title compound not separated from byproducts;	100%

L-Menthol Consensus Reports

Reported in EPA TSCA Inventory.

L-Menthol 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%.

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%.

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.

Product Name

L-Menthol

Synthetic route

L-Menthol Consensus Reports

L-Menthol Specification

Related Products

Hot Products