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

• 108-05-4 vinyl acetate 
• 89-78-1 [1-α]-5-methyl-2-[1-methylethyl]-cyclohexanol 
• 20752-34-5 neoisomenthol 
• 108-24-7 acetic anhydride 
• 3623-53-8 neoisomenthol 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 3623-52-7 isomenthol 
• 15356-70-4 menthol 
• 490-99-3 DL-neomenthol 
• 2216-51-5 (-)-menthol 
• 61548-81-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate 
• 89036-22-6 L-menthyl chloromethanesulphonate 
• 141-78-6 ethyl acetate 

Downstream Products

• 139336-53-1 (E)-4-Methyl-3-oxo-hex-4-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 99-82-1 Menthane 
• 89-78-1 menthol 
• 2216-51-5 (-)-menthol 
• 87776-14-5 L(-)menthyl (diphenylmethylsilyl)acetate 
• 116173-75-2 (S)-3-Methoxycarbonylamino-4-methyl-pentanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 116173-75-2 (R)-3-Methoxycarbonylamino-4-methyl-pentanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 55284-67-8 C₁₂H₂₁BrMgO₂ 
• 91667-08-2 [(1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methylcyclohexyl] acetate 
• 151963-62-1 (-)-menthyl (S)-3-hydroxy-3-phenylpropanoate 
• 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 
• 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 

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.

Method for producing ester based on eco-friendly and high efficiency esterification by using base exchange of salt and the compound thereof

The present invention relates to an esterification reaction-based eco-friendly and high efficiency ester compound using ion exchange and an ester compound thereof. The esterification generally proceeds by reverse reaction with water, resulting in poor yield of the ester. In order to avoid hydrolysis, the esterification reaction was environmentally or non-limited due to the continuous supply of hydrochloric acid gas or the use of chlorinated thionyl chloride as a noxious substance. To the present invention, a continuous hydrochloric acid gas is provided by ion exchange of a salt, and magnesium sulfate acts as a dehydrating agent to remove water generated in esterification. In addition, the reactants are cheap and the product is also low in harmfulness and easier to handle and thus more efficient reaction is possible.

Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives

Insight into the mechanism of a safe, simple, and inexpensive phosphoric acid (H3PO4)-catalyzed acylation of alcohols with acid anhydrides is described. The corresponding in situ-generated diacylated mixed anhydrides, unlike traditionally proposed monoacylated mixed anhydrides, are proposed as the active species. In particular, the diacylated mixed anhydrides act as efficient catalytic acyl transfer reagents rather than as Br?nsted acid catalysts simply activating acid anhydrides. Remarkably, highly efficient phosphoric acid (1-3 mol %)-catalyzed acylation of alcohols with acid anhydrides was achieved and a 23 g scale synthesis of an ester was demonstrated. Also, phosphoric acid catalyst was effective for synthetically useful esterification from carboxylic acids, alcohols, and acid anhydride. Moreover, with regard to recent developments in chiral 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid diester catalysts toward asymmetric kinetic resolution of alcohols by acylation, some phosphate diesters were examined. As a result, a 31P NMR study and a kinetics study strongly supported not only the acid-base cooperative mechanism as previously proposed by other researchers but also the mixed anhydride mechanism as presently proposed by us.

Solvent-free Acetylation Procedure

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