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

Description

L-MENTHYL ACETATE is a colorless liquid with a menthol-like odor and a fresh, pungent flavor that is different from menthol, being much milder. It has a cool mouthfeel with only a trace of mint flavor. It is a component of essential oils extracted from natural sources and is reported as a normal constituent of peppermint oil in varying amounts, depending on the source. The synthetic product is optically levorotatory, while the commercial product is optically inactive. It is slightly soluble in water and miscible with alcohol and ether, and is combustible.

Uses

Used in Perfumery:
L-MENTHYL ACETATE is used as a fragrance ingredient in perfumery due to its fresh, minty, and slightly fruity scent.
Used in Flavoring:
L-MENTHYL ACETATE is used as a flavoring agent in various food and beverage products, imparting a cooling and fruity taste with a tea-like characteristic at 10 ppm.
Used in Essential Oils:
L-MENTHYL ACETATE is used in essential oils extracted from natural sources, contributing to their unique aroma and flavor profiles.

Preparation

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

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

• 108-24-7 acetic anhydride 
• 1181819-05-5 menthol 
• 89-78-1 [1-α]-5-methyl-2-[1-methylethyl]-cyclohexanol 
• 108-05-4 vinyl acetate 
• 506-96-7 Acetyl bromide 
• 1106676-22-5 C₁₇H₂₆O 
• 3623-53-8 neoisomenthol 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 3623-52-7 isomenthol 
• 57706-87-3 (1S,2R,4R)-2-(1-Ethyl-1,5-dimethyl-hexyloxy)-1-isopropyl-4-methyl-cyclohexane 
• 15356-70-4 menthol 
• 57706-85-1 (3S,4S)-3-(1,5-Dimethyl-1-vinyl-hex-4-enyloxy)-4-isopropyl-1-methyl-cyclohexene 
• 490-99-3 DL-neomenthol 

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

A Method For Preparing (Meth)Acrylic Acid Ester Based Compound

The invention relates to a method for preparing a (meth)acrylic acid ester-based compound, and according to the preparation method, a (meth)acrylic acid ester-based compound can be prepared with high purity and high yield, by easily introducing an acrylic structure into alcohol using a diamine-based compound and acid anhydride.

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.].