L-Menthol

Modify Date: 2024-01-02 11:44:20

L-Menthol Structure
L-Menthol structure
 Common Name L-Menthol
CAS Number 2216-51-5 Molecular Weight 156.265
Density 0.9±0.1 g/cm3 Boiling Point 215.4±8.0 °C at 760 mmHg
Molecular Formula C10H20O Melting Point 41-43ºC
MSDS Chinese USA Flash Point 93.3±0.0 °C
Symbol GHS05 GHS07
GHS05, GHS07		 Signal Word Danger

 Use of L-Menthol


(-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1].

 Names

Name (-)-menthol
Synonym More Synonyms

 L-Menthol Biological Activity

Description (-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1].
Related Catalog
Target

TRPM8[1]

In Vitro (-)-Menthol (Menthol ) per se does not exhibit antiproliferative activity, but it is able to enhance 1α,25(OH)2D3-mediated growth inhibition in LNCaP cells. At high (-)-Menthol concentrations above 1.6 mM, the cells begin to detach from the culture dish[1]. (-)-Menthol (0.8 mM) can increase [Ca2+]i via transmembrane influx or store release pathways. Peak increase in [Ca2+]i was 102.3±39 nM (n=3) in (-)-Menthol alone and 124.5±51 nM (n=3) in combination of 1α,25(OH)2D3 with (-)-Menthol, respectively[1]. Combination of 1α,25(OH)2D3 with (-)-Menthol (0.8 mM) cooperatively modulates bcl-2 and p21 expression[1].
References

[1]. Park EJ, et al. Menthol Enhances an Antiproliferative Activity of 1alpha,25-Dihydroxyvitamin D(3) in LNCaP Cells. J Clin Biochem Nutr. 2009 Mar;44(2):125-30.

 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

 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
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

 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%

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 Synonyms

(-)-(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
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