| Identification | More | [Name]
L-Menthol | [CAS]
2216-51-5 | [Synonyms]
(1alpha,2beta,5alpha)-5-methyl-2-(1-methylethyl)-cyclohexanol
1-P-MENTHAN-3-OL
(1R,2S,5R)-(-)-2-ISOPROPYL-5-METHYLCYCLOHEXANOL
(1R,2S,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANOL
(1R,2S,5R)-(-)-MENTHOL
(1R,2S,5R)-MENTHOL
3-P-METHANOL
5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANOL
FEMA 2665
L-2-ISOPROPYL-5-METHYLCYCLOHEXANOL
L-4-MENTHAN-3-OL
LEVO-MENTHOL
LEVOMENTHOLUM
L-MENTHAN-3-OL
(-)-L-MENTHOL
L(-)-MENTHOL
L-MENTHOL
L-MENTHOL (NATURAL)
L-P-MENTHAN-3-OL
(-)-MENTHOL | [EINECS(EC#)]
218-690-9 | [Molecular Formula]
C10H20O | [MDL Number]
MFCD00062979 | [Molecular Weight]
156.27 | [MOL File]
2216-51-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
41-45 °C (lit.) | [alpha ]
-51 º (589nm, c=10, EtOH) | [Boiling point ]
212 °C (lit.) | [bulk density]
450kg/m3 | [density ]
0.89 g/mL at 25 °C(lit.)
| [vapor pressure ]
0.8 mm Hg ( 20 °C)
| [FEMA ]
2665 | [refractive index ]
1.46
| [Fp ]
200 °F
| [storage temp. ]
−20°C
| [solubility ]
490mg/l | [form ]
Crystals or Crystalline Needles | [pka]
15.30±0.60(Predicted) | [color ]
Colorless to white | [Specific Gravity]
0.89 | [Odor]
at 10.00 % in dipropylene glycol. peppermint cooling mentholic minty | [Stability:]
Stable. | [biological source]
synthetic (organic) | [Odor Type]
mentholic | [optical activity]
[α]22/D 49°, c = 10 in 95% ethanol | [Water Solubility ]
insoluble | [Detection Methods]
GC,NMR,Rotation | [Merck ]
14,5837 | [BRN ]
1902293 | [Dielectric constant]
3.2（Ambient） | [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]
2216-51-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
OT0700000
| [TSCA ]
Yes | [HS Code ]
29061100 | [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. | [Hazardous Substances Data]
2216-51-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 3300 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [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. | [Uses]
analgesic (topical), antipruritic agent | [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]
Nonflammable | [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 | [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.
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