61597-98-6

Basic information

• Product Name: L-Menthyl lactate
• Synonyms: L-MENTHYL LACTATE 97+%;L-Menthyl lactate;L-(-)-Menthyl L-Lactate;(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl (S)-2-Hydroxypropionate;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (S)-2-Hydroxypropionate
• CAS NO: 61597-98-6
• Molecular Formula: C₁₃H₂₄O₃
• Molecular Weight: 228.33
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 61597-98-6.mol

Chemical Properties

• Melting Point: 42-47 °C(lit.)
• Boiling Point: 142 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.99 g/cm³
• Vapor Pressure: 8.58E-05mmHg at 25°C
• Refractive Index: 1.467
• PKA: 13.01±0.20(Predicted)
• CAS DataBase Reference: L-Menthyl lactate(CAS DataBase Reference)
• NIST Chemistry Reference: L-Menthyl lactate(61597-98-6)
• EPA Substance Registry System: L-Menthyl lactate(61597-98-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 61597-98-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystal powde

InChI:InChI=1/C13H24O3/c1-8(2)11-6-5-9(3)7-12(11)16-13(15)10(4)14/h8-12,14H,5-7H2,1-4H3/t9-,10+,11+,12-/m1/s1

Upstream product

• 951-98-4 2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 29066-36-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propionate 
• 79-33-4 L-Lactic acid 
• 2216-51-5 (-)-menthol 
• 923031-01-0 L-menthyl L-lactoyl L-lactate 
• 923031-02-1 L-menthyl L-lactoyl L-lactoyl L-lactate 

Downstream Products

• 1383468-49-2 (R)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] 2-(2-iodophenoxy)propanoate 

Relevant articles and documents

COMPOSITION OF MENTHOL AND MENTHYL LACTATE, ITS PREPARATION AND ITS USE AS A COOLING, FLAVOURING AND/OR FRAGRANCE AGENT

The present invention relates to a method of preparing liquid compositions essentially consisting of menthol and menthyl lactate and the use of such compositions as a cooling agent, flavouring agent and/or fragrance agent, products containing such compositions and methods of providing a physiological cooling effect by applying such compositions.

Menthyl lactate process

A simple, high-yield process for making menthyl lactate (ML) is disclosed. Menthol and lactic acid react to produce a mixture comprising menthyl lactate and one or more higher lactoyl esters of ML. Hydrolysis of the esterification mixture follows in the presence of aqueous base under conditions effective to convert the higher lactoyl esters to menthyl lactate. Coincidentally, the conditions minimize hydrolysis of menthyl lactate to menthol, thereby maximizing the overall yield of ML.

ON THE ASYMMETRIC INDUCTION INVOLVING LITHIUM ENOLATES OF 1-MENTHYLPROPIONATE

The stereoselectivities of the reaction between 1-menthylpropionate 1 with LDA under standard kinetic conditions depend on the solvent.The Z-enolate 2a predominates in LDA/THF (Z/E=7.5/2.5) while the E-enolate 3a is the main product in LDA/THF/hexane (E/Z=8/2).The mixture of these enolates (E/Z=8/2) was allowed to react with allylbromide, benzaldehyde and MoOPH respectively.The higher ?-facial diastereoselection was obtained from MoOPH (d.e.=60percent).

Highly diastereoselective reduction of (-) menthylphenylglyoxalate and (-) menthylpyruvate using new hindered lithiumtrialkoxyaluminohydrides

Reduction of the keto group of (-) menthylphenylglyoxalate and (-) menthyl pyruvate can be achieved with high diastereoisomeric excess (80-90percent) using newly synthesized hindered lithium trialkoxyaluminium hydrides in THF at -78 deg C.Hindered borohydrides such as lithium trisiamylborohydride reduce those ketoesters with a lower diastereoselectivity.