59259-38-0

Basic information

• Product Name: (-)-Menthyl lactate
• Synonyms: Propanoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, [1R-[1alpha(R*),2beta,5alpha]]-;(-)-Menthyl D-lactate;(R)-2-Hydroxypropanoic acid (1R)-5β-methyl-2β-(1-methylethyl)cyclohexyl ester;(-)-Menthyl lactate,98%;(R)-2-Hydroxypropionic Acid (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl Ester L-Menthyl D-Lactate;2-isopropyl-5-Methylcyclohexyl 2-hydroxypropanoate;(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 2-hydroxypropanoate;(R)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 2-hydroxypropanoate
• CAS NO: 59259-38-0
• Molecular Formula: C₁₃H₂₄O₃
• Molecular Weight: 228.33
• EINECS: 261-678-3
• Product Categories: chiral;Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 59259-38-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 40 °C
• Boiling Point: 310.14°C (rough estimate)
• Flash Point: 128 °C
• Appearance: white to light yellow crystal powder
• Density: -80
• Vapor Pressure: 8.58E-05mmHg at 25°C
• Refractive Index: -80 ° (C=5, MeOH)
• Storage Temp.: 2-8°C
• PKA: 13.01±0.20(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• CAS DataBase Reference: (-)-Menthyl lactate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Menthyl lactate(59259-38-0)
• EPA Substance Registry System: (-)-Menthyl lactate(59259-38-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 24/25-45
• Hazardous Substances Data: 59259-38-0(Hazardous Substances Data)

Usage

Description

(-)-Menthyl lactate, also known as L-Menthyl Lactate, is a white, crystalline substance with a weak odor reminiscent of tobacco and chamomile. It is almost tasteless, with a lasting gentle cooling effect on the skin and mucosa. (-)-Menthyl lactate is prepared by esterification of menthol with lactic acid and is known for its physiological cooling sensation.

Uses

Used in Flavor and Fragrance Industry:
(-)-Menthyl lactate is used as a flavoring agent for its cooling effect and sweet salicylate nuance, providing a menthol-like aroma at 1.0% concentration.
Used in Cosmetics and Oral Care:
(-)-Menthyl lactate is used as an ingredient in cosmetic and oral care preparations for its neutral cooling effects, enhancing the sensory experience of the products.
Used in the Preparation of Amides:
(-)-Menthyl lactate is used in the preparation of amides to generate a trigeminal sensory effect, which can be beneficial in various applications where a cooling sensation is desired.

Trade name

Frescolat ML (Symrise)

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

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 

Downstream Products

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

Relevant articles and documents

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).