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

L-Menthyl lactate has a weak odor somewhat reminiscent of tobacco and chamomile. It is almost tasteless, with a lasting gentle cooling effect.

Chemical Properties

Different sources of media describe the Chemical Properties of 59259-38-0 differently. You can refer to the following data:
1. l-Menthyl lactate has a weak odor somewhat reminiscent of tobacco and chamomile. It is almost tasteless, with a last ing, gentle cooling effect.
2. white to light yellow crystal powde
3. (-)-Menthyl lactate is a white, crystalline substance giving a physiological cooling sensation on the skin and mucosa. It is used to create neutral cooling effects in cosmetic or oral care preparations. The material is prepared by esterification of menthol with lactic acid.

Uses

L-Menthyl Lactate is used in preparation of amides for generating a trigeminal sensory effect.

Aroma threshold values

Aroma characteristics at 1.0%: menthol-like, cooling with a sweet salicylate nuance.

Taste threshold values

Taste characteristics at 25 ppm: a mouthwash-like effect with an aromatic mentholic coolness.

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

• 29066-36-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propionate 
• 951-98-4 2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

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).