2623-23-6

Basic information

• Product Name: (1R)-(-)-Menthyl acetate
• Synonyms: 2-isopropyl-5-methyl-,acetate,l-cyclohexan-1-o;5-methyl-2-(1-methylethyl)-,acetate,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol;acetate,(1r,3r,4s)-(-)-mentho;aceticacid(1R)-menthylester;cyclohexanol,5-methyl-2-(1-methylethyl)-,acetate,(1r-(1alpha,2beta,5alpha);cyclohexanol,5-methyl-2-(1-methylethyl)-,acetate,[1theta-(1alpha,2beta,5;l-p-menth-3-ylacetate;p-menth-3-ylester,l-aceticaci
• CAS NO: 2623-23-6
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• EINECS: 220-076-0
• Product Categories: Pharmaceutical Raw Materials;Monocyclic Monoterpenes;Biochemistry;Terpenes;Esters;Chiral Building Blocks;EstersAlphabetic;M;MEA - MES;Organic Building Blocks
• Mol File: 2623-23-6.mol
• Article Data: 174

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.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: 23.2mg/L at 20℃
• Merck: 14,5839
• BRN: 2208505
• CAS DataBase Reference: (1R)-(-)-Menthyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-Menthyl acetate(2623-23-6)
• EPA Substance Registry System: (1R)-(-)-Menthyl acetate(2623-23-6)

Safety Data

• Safety Statements: 24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: AI5900000
• TSCA: Yes
• Hazardous Substances Data: 2623-23-6(Hazardous Substances Data)

Usage

Chemical Properties

(1R)-(-)-Menthyl acetate occurs in peppermint oils. It is a colorless liquid with a fresh, fruity, peppermint odor. (?)-Menthyl acetate is prepared by acetylation of (?)-menthol (e.g., with acetic anhydride). It is used mainly in peppermint flavors and reconstituted peppermint oils, but also to a small extent in perfumery.

Uses

L-Menthyl Acetate, and its derivatives, is used as a penetration enhancers, to enhance the skin permeation of various drugs with differing lipophilicities, such as 5-aminolevulinic acid (ALA), 5-fluorouracil (5-FU), isosorbide dinitrate (ISDN), lidocaine (LD), etc.

Flammability and Explosibility

Notclassified

Safety Profile

Low toxicity by ingestion and skin contact. A skin irritant. 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

• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 3623-53-8 neoisomenthol 
• 75-36-5 acetyl chloride 
• 3623-52-7 isomenthol 
• 15356-70-4 menthol 
• 490-99-3 DL-neomenthol 
• 108-22-5 Isopropenyl acetate 
• 2216-51-5 (-)-menthol 
• 2889-74-9 perchlorate d'acetyle 
• 57576-09-7 (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate 
• 61548-81-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate 
• 64-19-7 acetic acid 

Downstream Products

• 112297-88-8 l-menthyl (trimethylsilyl)acetate 
• 139336-54-2 (E)-3-Oxo-hex-4-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 89-78-1 menthol 
• 2216-51-5 (-)-menthol 
• 5157-89-1 D-menthyl acetate 
• 190185-41-2 3-Oxo-3-(2-pent-4-inylcarboxy)phenylpropansaeure(-)menthylester 
• 190185-27-4 3-Oxo-3-(pent-4-enylcarboxy)phenylpropansaeure(-)menthylester 
• 2216-52-6 Neomenthol 
• 61949-23-3 menthyl formate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 491-07-6 (+/-)-menthone 
• 270087-73-5 [(1S,4S)-1-Hydroxy-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enyl]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 710293-16-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-(4-methoxyphenylamino)-3-phenylpropanoate 

Relevant articles and documents

The role of the reaction medium in lipase-catalyzed esterifications and transesterifications

The nature of the reaction medium (different organic solvents and supercritical fluids) markedly influenced the microbial lipase activity in esterification and transesterification reactions employing as substrates natural and synthetic compounds in terms of reaction rates and lipase enantioselectivity. The experimental data obtained show that while there are no substantial correlations between enantioselectivity and some physicochemical characteristics of the solvent as hydrophobicity and dielectric constant, the solvent polarity and hydrophobicity is able to modulate greatly lipase activity. The possible effects of the solvent characteristics on the catalytic performance of the enzymes are discussed and a rationale is proposed to explain the results obtained.

Preparation and characterization of SO4 2-/Fe 2O3-TiO2-Nd2O3 catalyst

This paper reports on the preparation of SO4 2-/Fe2O3-TiO2-Nd2O 3 (SFTN) by combustion method. The effect of Nd content on catalytic activity was investigated. The prepared materials doped and undoped by Nd were compared by means of TG-DTG, XRD, FT-IR, NH3-TPD and TEM techniques. Results indicated that the introduction of Nd improved the catalytic activities of the catalysts. Catalytic activity of SFTN was the highest with 98.3 % menthol conversion when Nd content was at 2 wt%. The introduction of Nd stabilized the coordination bond between the sulfate irons and the metallic oxides, helping in the formation of solid acid sites, enhancing the dispersion of catalyst particles, and inhibiting the growth of catalyst particles under heating.

Solvent-free Acetylation Procedure

-

Ring-Closing Metathesis of Aliphatic Ethers and Esterification of Terpene Alcohols Catalyzed by Functionalized Biochar

Functionalized biochars, renewable carbon materials prepared from waste biomass, can catalyze transformations of a range of oxygen-containing substrates via hydrogen-bonding interactions. Good conversions (up to 75.2 %) to different O-heterocycles are obtained from ring-closing C?O/C?O metathesis reactions of different aliphatic ethers under optimized conditions using this heterogeneous, metal-free, and easy separable catalyst. The diversity in the sorts of O-containing feedstocks is further demonstrated by the utilization of functionalized biochar to promote the esterification of terpene alcohols, an important reaction in food and flavor industries. Under the optimized conditions, full conversions to various terpene esters are obtained. Moreover, both of the reactions studied herein are performed under neat conditions, thus increasing the overall sustainability of the process described.

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.