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.
