16409-45-3

Basic information

• Product Name: L-MENTHYL ACETATE
• Synonyms: (R)-(-)-MENTHYL ACETATE;2-Isopropyl-5-methylcyclohexyl acetate;5-methyl-2-(1-methylethyl)-cyclohexanoacetate;5-methyl-2-(1-methylethyl)cyclohexanolacetate;Acetic acid, p-menth-3-yl ester, dl-;aceticacidmenthylester;Cyclohexanol,5-methyl-2-(1-methylethyl)-,acetate;femanumber:2668
• CAS NO: 16409-45-3
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• EINECS: 220-076-0
• Mol File: 16409-45-3.mol
• Article Data: 55

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 229-230 °C(lit.)
• Flash Point: 171 °F
• Appearance: /
• Density: 0.92 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0707mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• CAS DataBase Reference: L-MENTHYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: L-MENTHYL ACETATE(16409-45-3)
• EPA Substance Registry System: L-MENTHYL ACETATE(16409-45-3)

Safety Data

• WGK Germany: 3
• RTECS: AI5900000
• Hazardous Substances Data: 16409-45-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 16409-45-3 differently. You can refer to the following data:
1. Colorless liquid; menthol-like odor.Slightly soluble in water; miscible with alcohol and ether. Combustible.
2. l-Menthyl acetate has a fresh odor similar to mint and rose (on dilution). It has a characteristic, fresh, pungent flavor, different from menthol (being much milder). It has a cool mouthfeel with only a trace of mint flavor.

Occurrence

Reported as a normal constituent of peppermint oil in varying amounts, depending on the source; the synthetic product is optically levorotatory; the commercial product is optically inactive.

Uses

Different sources of media describe the Uses of 16409-45-3 differently. You can refer to the following data:
1. L-Menthyl Acetate is a component of essential oils extracted from natural sources.
2. Perfumery, flavoring.

Preparation

By reacting acetic anhydride with menthol in the presence of anhydrous sodium acetate.

Taste threshold values

Taste characteristics at 10 ppm: tea-like, cooling and fruity

Biochem/physiol Actions

Taste at 25 ppm

Safety Profile

Mildly toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m0/s1

Upstream product

• 3623-53-8 neoisomenthol 
• 64-19-7 acetic acid 
• 3623-52-7 isomenthol 
• 57706-87-3 (1S,2R,4R)-2-(1-Ethyl-1,5-dimethyl-hexyloxy)-1-isopropyl-4-methyl-cyclohexane 
• 2216-51-5 (-)-menthol 
• 1445-45-0 Trimethyl orthoacetate 
• 89-78-1 menthol 
• 108-05-4 vinyl acetate 
• 75-05-8 acetonitrile 
• 15356-70-4 menthol 
• 79-10-7 acrylic acid 
• 108-24-7 acetic anhydride 
• 91898-14-5 1-Isopropyl-2-methoxymethoxy-4-methyl-cyclohexane 
• 91898-16-7 2-Ethoxymethoxy-1-isopropyl-4-methyl-cyclohexane 

Downstream Products

• 89-78-1 menthol 
• 2216-51-5 (-)-menthol 
• 5157-89-1 D-menthyl acetate 
• 2623-23-6 L-menthyl acetate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 491-07-6 (+/-)-menthone 
• 99-82-1 Menthane 
• 663218-93-7 3ξ-bromo-1r-methyl-4t-isopropyl-cyclohexane 
• 64240-81-9 3-iodo-p-menthane 

Relevant articles and documents

Solvent-free Acetylation Procedure

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IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway

An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.

Production of l-menthyl acetate through kinetic resolution by?Candida cylindracea lipase: effects of alkaloids as additives

Abstract: Enzymatic transesterification of dl-menthol with vinyl acetate in tert-Butyl methyl ether (TBME) catalyzed by Candida cylindracea lipase (CCL) was carried out in the presence of cinchona alkaloid as additive. The effects of various reaction parameters, such as lipase nature and loading, acylating agent, molecular sieves, solvents and various additives, on the reactivity as well as on the enantioselectivity were investigated. A significant improvement of CCL reactivity has been recorded after using cinchona alkaloid as additive in TBME. A high enantiomeric ratio (E = 80) was achieved when 30?mol% of quinidine was added, and l-(-)-menthyl acetate was obtained with 93% optical purity and 49% conversion. This process was easily applied to gram-scale quantities, using commercially inexpensive lipase, providing high yield optically active menthol under mild experimental conditions. Graphical abstract: [Figure not available: see fulltext.].