L-Menthol

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Names

[ Name ]:
L-Menthol

[Synonym ]:
(-)-(1R,3R,4S)-Menthol
(−)-menthol
(-)-trans-p-Methan-cis-3-ol
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
L-Menthol
(-)-(1R,2S,5R)-Menthol
(1R)-(-)-Menthol
Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-
DL-Menthol
(-)-p-Menthan-3-ol
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (5-Methyl-2-(1-methylethyl)cyclohexanol
MFCD00062979
UNII:YS08XHA860
Menthol, l-
(−)-Menthol,(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol,5-Methyl-2-(1-methylethyl)cyclohexanol
Menthol
Minclea
(1R,2S,5R)-(−)-Menthol
levo-menthol
uspmenthol
Levomenthol
(-)-MENTHYL ALCOHOL
(R)-(-)-Menthol
(1R,2S,5R)-5-methyl-2-propan-2-yl-cyclohexan-1-ol
[1R-(1a,2b,5a)]-5-Methyl-2-(1-methylethyl)cyclohexanol
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-
(-)-Menthol
(−)-Menthol,(1R,2S,5R)-(−)-Menthol,(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
L(-)-Menthol
L-MentholuM
EINECS 218-690-9
(1R,2S,5R)-(-)-Menthol

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
215.4±8.0 °C at 760 mmHg

[ Melting Point ]:
41-43ºC

[ Molecular Formula ]:
C₁₀H₂₀O

[ Molecular Weight ]:
156.265

[ Flash Point ]:
93.3±0.0 °C

[ Exact Mass ]:
156.151413

[ PSA ]:
20.23000

[ LogP ]:
3.20

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.457

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OT0700000

CHEMICAL NAME :: l-Menthol

CAS REGISTRY NUMBER :: 2216-51-5

LAST UPDATED :: 199701

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C10-H20-O

MOLECULAR WEIGHT :: 156.30

WISWESSER LINE NOTATION :: L6TJ AY1&1 DQ D1 -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Behavioral - general anesthetic Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - respiratory depression

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA repair

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 10 mg/disc

REFERENCE :: OIGZDE Osaka-shi Igakkai Zasshi. Journal of Osaka City Medical Association. (Osaka-shi Igakkai, c/o Osaka-shiritsu Daigaku Igakubu, 1-4-54 Asahi-cho, Abeno-ku, Osaka, 545, Japan) V.24- 1975- Volume(issue)/page/year: 34,267,1985 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6896 No. of Facilities: 499 (estimated) No. of Industries: 5 No. of Occupations: 27 No. of Employees: 43996 (estimated) No. of Female Employees: 34625 (estimated)

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38;R41

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
OT0700000

[ HS Code ]:
29061100

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane
1-((((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)methyl)-4-methoxybenzene
tetrahydro-2-[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclo-hexyl]oxy]-2H-pyran
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl picolinate
(1S,2R,4R)-(-)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane
ISOPULEGOL
Isopulegol
Menthyl acetate

DownStream

1-Menthoxy-1-butyne
(1S,2S,5R)-Neomenthyl azide
(+)-TRANS-P-MENTH-2-ENE
Δ3-p-mentene
DPO-1
Isopropylcyclopentane
1-methyl-3-(2-Cyclopentane)
(1-PYRROLIDIN-3-YL-PIPERIDIN-4-YL)-CARBAMICACIDTERT-BUTYLESTER
Mononmethyl succinate
bis(5-methyl-2-propan-2-ylcyclohexyl) but-2-enedioate

Customs

[ HS Code ]: 2906199090

[ Summary ]:
2906199090. cyclanic, cyclenic or cyclotherpenic alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.

Antimicrob. Agents Chemother. 53 , 1898-906, (2009)

Menstrual toxic shock syndrome is a rare but potentially life-threatening illness manifest through the actions of Staphylococcus aureus toxic shock syndrome toxin 1 (TSST-1). Previous studies have sho...

Effects of Menthol on Nicotine Pharmacokinetic, Pharmacology and Dependence in Mice.

PLoS ONE 10 , e0137070, (2015)

Although menthol, a common flavoring additive to cigarettes, has been found to impact the addictive properties of nicotine cigarettes in smokers little is known about its pharmacological and molecular...