2216-54-8

Basic information

• Product Name: L-MENTHYLAMINE
• Synonyms: [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexylamine;(1R)-2α-Isopropyl-5β-methylcyclohexane-1β-amine;(1R)-5β-Methyl-2α-(1-methylethyl)cyclohexan-1β-amine;(1R,3R,4S)-p-Menthane-3-amine;(1β)-2α-Isopropyl-5β-methylcyclohexanamine;Nsc7325;(1R)(-)-MENTHYLAMINE;L-MENTHYLAMINE
• CAS NO: 2216-54-8
• Molecular Formula: C₁₀H₂₁N
• Molecular Weight: 155.28
• EINECS: 218-693-5
• Mol File: 2216-54-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 192.8 °C at 760 mmHg
• Flash Point: 45.8 °C
• Appearance: /
• Density: 0.834 g/cm³
• PKA: 10.68±0.70(Predicted)
• CAS DataBase Reference: L-MENTHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-MENTHYLAMINE(2216-54-8)
• EPA Substance Registry System: L-MENTHYLAMINE(2216-54-8)

Safety Data

• Hazardous Substances Data: 2216-54-8(Hazardous Substances Data)

Usage

General Description

L-MENTHYLAMINE is a chemical compound that belongs to the class of amines and is derived from the menthol compound. It has a menthol-like odor and is used as a fragrance ingredient in various products. L-MENTHYLAMINE is also used in the synthesis of other organic compounds and as a building block in the production of pharmaceuticals and agrochemicals. It is considered to have low toxicity and is generally regarded as safe for use in consumer products. Additionally, it has potential applications in the field of medicinal chemistry due to its unique structure and properties.

Upstream product

• 2216-51-5 (-)-menthol 
• 540-69-2 ammonium formate 
• 10458-14-7 (2R,5S)-menthone 
• 65620-72-6 (1R,5S)-menthone oxime 
• 37886-68-3 (-)-(E)-(1R,4S)-menthyl oxime 
• 106637-04-1 (S)-N-(Benzyloxycarbonyl)proline (R)-menthylamide 
• 2385-77-5 (R)-Citronellal 
• 490-99-3 DL-neomenthol 
• 898543-45-8 2‐azido‐1‐isopropyl‐4‐methylcyclohexane 
• 2216-54-8 rac-menthylamine 
• 13398-40-8 (2R,3R)-threo-β-methylmalic acid 
• 21411-81-4 2-isopropyl-5-methyl-cyclohexylamine 
• 64-17-5 ethanol 
• 1198-91-0 (+/-)-isomenthone oxime 

Downstream Products

• 71054-02-9 N,N'-di-(-)menthylthiourea 
• 34048-58-3 N-((1R)-menthyl)-formamide 
• 114399-49-4 N.N'-di-((1R)-menthyl)-malonamide 
• 131374-09-9 N-((1R)-menthyl)-glycine ethyl ester 
• 20108-91-2 2-chloro-N-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]acetamide 
• 87007-64-5 N-((1R)-menthyl)-phthalimide 
• 71054-03-0 N-((1R)-menthyl)-N'-phenyl-thiourea; N-menthyl-N'-phenyl-thiourea derivative of l-menthylamine in aelterem sinn 
• 137465-68-0 (2S,3S)-2-Amino-3-methyl-pentanoic acid ((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide 
• 133287-32-8 (S)-2-Amino-4-methyl-pentanoic acid ((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide 
• 104787-96-4 N-(-)-menthyl-2-phenylpropionamide 
• 145621-91-6 2,3-Dichlor-N-(R)-menthylmaleinimid 
• 145621-90-5 3-Chlor-4-(R)-menthylamino-1-phenyl-pyrrolin-2,5-dion 
• 61585-35-1 p-menth-1-ene 

Relevant articles and documents

Structural and in Vitro Functional Characterization of a Menthyl TRPM8 Antagonist Indicates Species-Dependent Regulation

TRPM8 antagonists derived from its cognate ligand, (-)-menthol, are underrepresented. We determine the absolute stereochemistry of a well-known TRPM8 antagonist, (-)-menthyl 1, using VCD and 2D NMR. We explore 1 for its antagonist effects of the human TRPM8 (hTRPM8) orthologue to uncover species-dependent inhibition versus rat channels. (-)-Menthyl 1 inhibits menthol- and icilin-evoked Ca2+ responses at hTRPM8 with IC50 values of 805 ± 200 nM and 1.8 ± 0.6 μM, respectively, while more potently inhibiting agonist responses at the rat orthologue (rTRPM8 IC50 (menthol) = 117 ± 18 nM, IC50 (icilin) = 521 ± 20 nM). Whole-cell patch-clamp recordings of hTRPM8 confirm the 1 inhibition of menthol-stimulated currents, with an IC50 of 700 ± 200 nM. We demonstrate that 1 possesses ≥400-fold selectivity for hTRPM8 versus hTRPA1/hTRPV1. (-)-menthyl 1 can be used as a novel chemical tool to study hTRPM8 pharmacology and differences in species commonly used in drug discovery.

Efficient resolution of menthylamine with inexpensive (r,r)-tartaric acid by dielectrically controlled resolution (DCR)

A practical procedure for the resolution of menthylamine 2 with (R,R)-tartaric acid [(R,R)-3] as resolving agent is presented. Variation of the solvent system allows both enantiomers of 2 to be selectively crystallized. Performing the resolution in methanol containing 6 % water leads to (-)-2·(R,R)-3·MeOH. The other, less-soluble diastereomeric salt is obtained by applying a solvent system consisting of methanol with 19 % water with a yield of 14 %. Subsequent basic workup with aqueous sodium hydroxide gave the free menthylamine compounds. Further workup of the mother liquors and an additional recrystallization step allowed the (-)-2·(R,R)-3·MeOH salt to be obtained in an overall yield of 22 %; the other salt (+)-2·(R,R)-3·MeOH·H2O was obtained in 23 % yield. This is another important example of the dielectrically controlled resolution of an interesting amine by using inexpensive (R,R)-tartaric acid as resolving agent. With the same inexpensive resolving agent, (R,R)-tartaric acid, both antipodes of menthylamine can be selectively crystallized as diastereomeric salts. The concentration of water determines which salt is formed. In a few simple resolution steps, good yields and high enantiomeric excess can be achieved. Copyright

Efficient and stereodivergent electrochemical synthesis of optically pure menthylamines

The cathode directs the way to the epimeric menthylamines. The reduction of menthone oxime on a Hg cathode generates (-)-menthylamine as the major product, whereas a Pb cathode gives access to (+)-neomenthylamine (see scheme). Insitu decoration of the Pb cathode by small amounts of additives results in clean and quantitative conversions. Furthermore, Pb corrosion is completely prevented in this practical method. Copyright