L-Menthol Chemical Properties

Melting point:

41-45 °C (lit.)

alpha 

-51 º (589nm, c=10, EtOH)

Boiling point:

212 °C (lit.)

Density 

0.89 g/mL at 25 °C (lit.)

vapor pressure 

0.8 mm Hg ( 20 °C)

refractive index 

1.46

FEMA 

2665 | MENTHOL RACEMIC

Flash point:

200 °F

storage temp. 

Store below +30°C.

solubility 

490mg/l

form 

Crystals or Crystalline Needles

pka

15.30±0.60(Predicted)

Specific Gravity

0.89

color 

Colorless to white

Odor

at 10.00 % in dipropylene glycol. peppermint cooling mentholic minty

Odor Type

mentholic

optical activity

[α]22/D 49°, c = 10 in 95% ethanol

Water Solubility 

insoluble

Merck 

14,5837

BRN 

1902293

Dielectric constant

3.2（Ambient）

Stability:

Stable.

InChIKey

NOOLISFMXDJSKH-KXUCPTDWSA-N

LogP

3.15 at 25℃

CAS DataBase Reference

2216-51-5(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1«alpha»,2«beta»,5«alpha»)]-(2216-51-5)

EPA Substance Registry System

Levomenthol (2216-51-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-39-37/39-36

WGK Germany 

2

RTECS 

OT0700000

TSCA 

Yes

HS Code 

29061100

Hazardous Substances Data

2216-51-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 3300 mg/kg LD50 dermal Rabbit > 5000 mg/kg

MSDS

• Language:English Provider:(1R,2S,5R)-(-)-Menthol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L-Menthol Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

L-Menthol is used as a cooling agent that strongly activates TRPM8.(Transient Receptor Potential Cation Channel, Subfamily M, Member 8 is a Protein Coding gene). It is used as analgesic (topical), antipruritic agent. It is used as: refreshing agent, food flavor, cool and antipruritic drug, carminative drug. Menthol crystals is used for pers onal care and cosmetics.

Uses

(1R,2S,5R)-(-)-Menthol (L-Menthol) is the natural form of Menthol. L-Menthol is used as: refreshing agent, food flavor, cool and antipruritic drug, carminative drug. Menthol crystals is used for pers onal care and cosmetics.

Definition

ChEBI: A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.

Acquired resistance

(1R,2S,5R)-(-)-Menthol (L-Menthol) is the natural form of Menthol. L- and D-menthol are variants of the same molecule, but have a mirror-image structure in relation to each other, like the right and left hand.

General Description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Flammability and Explosibility

Non flammable

Biological Activity

l-Menthol inhibite the binding of 13 ligands (calcium channels, sodium channels, γ-aminobutyric acid type A (GABAA) receptor, GABA transporter, dopamine transporter, dopamine D4 receptor, adenosine A2a receptor, α2A-adrenergic receptor, histamine H2 receptor, bombesin receptor, angiotensin AT1 receptor, vasopressin V2 receptor, and leukotriene B4 receptor) with relatively high inhibition rates and acts on these ligands over a similar concentration range. It acts as a positive allosteric modulator of the GABAA receptor rather than an agonist. In periaqueductal grey neurons in rat midbrain slices, l-menthol was shown to prolong spontaneous GABAA receptor–mediated inhibitory current, most likely via a mechanism distinct from that of benzodiazepines. It acts on the dopamine D4 receptor and the dopamine transporter. l-menthol inhibits the [3H]-WIN35,428 binding, similar to GBR12909, suggesting that l-menthol inhibits the binding of dopamine to the dopamine transporter and leading to decreased dopamine uptake[1].

Biochem/physiol Actions

Taste at 25 ppm

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An eye irritant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise menthol from CHCl3,pet ether or EtOH/water. [Barrow & Atkinson J Chem Soc 638 1939, Beilstein 6 III 133, 6 IV 150.]

References

[1] Umezu T, et al. Identification of novel target molecules of l-menthol. Heliyon, 2021; 7: e07329.

L-Menthol(2216-51-5)Related Product Information

• ISOPROPYL LAURATE
• ISOPULEGOL, TECH.
• 2-Methylcyclohexanol
• METHYLCYCLOHEXANOL
• Cyclohexanone
• Cyclohexene
• (+)-ISOMENTHOL
• (1S)-(+)-mentho
• 1-Methylcyclohexanol
• Cyclohexanol
• Propylthiouracil
• Cyclohexylamine
• Molasses
• Isopropyl alcohol
• (+)-NEOMENTHOL
• Peppermint oil
• (2R,5S)-5-(5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• 5-fluoro-1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)cytosine
• Menthol Crystals