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

Description

(1R)-(-)-Menthyl acetate is a chiral monoterpene ester that occurs naturally in peppermint oils. It is a colorless liquid with a fresh, fruity, and characteristic peppermint odor. (1R)-(-)-Menthyl acetate is prepared by the acetylation of (-)-menthol, typically using acetic anhydride, and is known for its ability to enhance the permeation of various drugs through the skin.

Uses

Used in Pharmaceutical Industry:
(1R)-(-)-Menthyl acetate is used as a penetration enhancer for improving the skin permeation of various drugs with differing lipophilicities. This application is particularly beneficial for drugs such as 5-aminolevulinic acid (ALA), 5-fluorouracil (5-FU), isosorbide dinitrate (ISDN), and lidocaine (LD), allowing for more effective transdermal drug delivery.
Used in Flavor and Fragrance Industry:
(1R)-(-)-Menthyl acetate is primarily used in the creation of peppermint flavors and reconstituted peppermint oils, providing a fresh and cooling sensation to food products, oral care items, and beverages. Its unique aroma also makes it a valuable component in perfumery, where it contributes to the overall scent profile of various fragrances.

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

• 108-24-7 acetic anhydride 
• 1181819-05-5 menthol 
• 89-78-1 [1-α]-5-methyl-2-[1-methylethyl]-cyclohexanol 
• 108-05-4 vinyl acetate 
• 20752-34-5 neoisomenthol 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 127-09-3 sodium 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 

Downstream Products

• 64240-81-9 3-iodo-p-menthane 
• 663218-93-7 3ξ-bromo-1r-methyl-4t-isopropyl-cyclohexane 
• 880-65-9 (-)S β-hydroxy β-phenyl n-butanoate de methyle 
• 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 
• 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 

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.

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.

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.

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.