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

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

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

• 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).

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.