146502-80-9

Basic information

• Product Name: (-)-(1R,2R,5S)-NEOMENTHYL ACETATE
• Synonyms: (-)-(1R,2R,5S)-NEOMENTHYL ACETATE;(1R)-(-)-NEOMENTHYL ACETATE;NEOMENTHYLACETATE, (1R)-(-)-;(-)-(1R,2R,5S)-NEOMENTHYL ACETATE, TERPE NE STANDARD;NEOMENTHYLACETATE, (1R)-(-)-(RG)
• CAS NO: 146502-80-9
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• Mol File: 146502-80-9.mol

Chemical Properties

• Melting Point: 36-38 °C(lit.)
• Boiling Point: 81 °C3 mm Hg(lit.)
• Flash Point: 90 °F
• Appearance: /
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0707mmHg at 25°C
• Refractive Index: 1.4306 (estimate)
• CAS DataBase Reference: (-)-(1R,2R,5S)-NEOMENTHYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,2R,5S)-NEOMENTHYL ACETATE(146502-80-9)
• EPA Substance Registry System: (-)-(1R,2R,5S)-NEOMENTHYL ACETATE(146502-80-9)

Safety Data

• Hazard Codes: F
• Statements: 11
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 146502-80-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
(-)-(1R,2R,5S)-NEOMENTHYL ACETATE is used as a key component in the production of menthol, a widely used compound in the flavor and fragrance industry. Its unique properties provide a cooling sensation and a minty aroma, making it an essential ingredient in various products such as chewing gum, toothpaste, and perfumes.
Used in Pharmaceutical Industry:
(-)-(1R,2R,5S)-NEOMENTHYL ACETATE is also utilized in the pharmaceutical industry for its potential therapeutic applications. Its cooling effect can be beneficial in the development of medications for respiratory conditions, such as cough suppressants and nasal decongestants.
Used in Cosmetics Industry:
In the cosmetics industry, (-)-(1R,2R,5S)-NEOMENTHYL ACETATE is employed for its refreshing and soothing properties. It is often incorporated into skincare products, hair care products, and makeup to provide a pleasant sensory experience and enhance the overall effectiveness of the products.
Used in Food and Beverage Industry:
(-)-(1R,2R,5S)-NEOMENTHYL ACETATE is used as a flavoring agent in the food and beverage industry, particularly in products that require a minty taste or cooling sensation. It can be found in candies, beverages, and even alcoholic drinks, adding a unique flavor profile and enhancing the overall consumer experience.

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 
• 20747-49-3 (-)-neomenthol 
• 490-99-3 DL-neomenthol 
• 72-89-9 acetylcoenzyme A 
• 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 

Downstream Products

• 20747-49-3 (-)-neomenthol 
• 64-19-7 acetic acid 
• 1421312-52-8 C₁₂H₂₂O₃ 
• 1421312-53-9 (+)-neomenthyl acetate 
• 89-78-1 menthol 
• 2216-51-5 (-)-menthol 
• 5157-89-1 D-menthyl acetate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 491-07-6 (+/-)-menthone 
• 2623-23-6 L-menthyl acetate 
• 64240-81-9 3-iodo-p-menthane 
• 663218-93-7 3ξ-bromo-1r-methyl-4t-isopropyl-cyclohexane 
• 99-82-1 Menthane 

Relevant articles and documents

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.].

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.

Continuous-Flow Chemo and Enzymatic Synthesis of Monoterpenic Esters with Integrated Purification

Monoterpenic esters are very important flavor and fragrance compounds due to their organoleptic properties. Despite their importance, many drawbacks are found for the production of monoterpenic esters. Here in we report two different approach's (chemo and enzymatic) for the continuous production of monoterpenic esters with integrated purification arriving on the desired molecules with high yields (>95%) and short reaction times.

Proton-gradient-transfer acid complexes and their catalytic performance for the synthesis of geranyl acetate

Special proton-gradient-transfer acid complexes (PGTACs) in which the bonded protons are not equivalent and have gradients in transfer ability, acidity, and reactivity were reported. The acidity gradient of the protons gave the PGTACs excellent catalytic activity and selectivity in the esterification of terpenols. These PGTACs are “reaction-induced self-separation catalysts” and can be easily reused. The kinetics with PGTACs as catalyst in the esterification of geraniol were also studied for use in engineering design.

P4VPy–CuO nanoparticles as a novel and reusable catalyst: application at the protection of alcohols, phenols and amines

P4VPy–CuO nanoparticles were synthesized using ultrasound irradiations. Relevant properties of the synthesized nanoparticles were investigated by X-ray diffraction, scanning electron microscopy, transmission electron microscopy and Fourier transform infrared spectroscopy. After identification, the prepared reagent was used for the promotion of different types of protection reactions of alcohols, phenols and amines. Easy workup, short reaction times, excellent yields, relatively low cost and reusability of the catalyst are the striking features of the reported methods.

Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: Acetylation of nopol and terpenic alcohols

The cesium salt of tungstophosphoric heteropoly acid, Cs2.5H0.5PW12O40, is an active and environmentally friendly heterogeneous catalyst for the liquid-phase acetylation of nopol and several biomass-derived terpenic alcohols (i.e., α-terpineol, nerol, geraniol, linalool, menthol, isoborneol, perillyl alcohol, carveol, isopulegol, carvacrol and nerolidol) with acetic anhydride. The resulting flavor and fragrance acetic esters, which are widely used in perfumery, household and food products, are obtained in good to excellent yields. The reactions occur at room temperature with low catalyst loadings without substantial catalyst leaching and can be performed with stoichiometric amounts of an acetylating agent in solvent free systems.

Efficient approach for the chemoselective acetylation of alcohols catalyzed by a novel metal oxide nanocatalyst CuO-ZnO

A new method has been developed for the chemoselective acetylation of alcohols with acetic anhydride in the presence of phenols using a novel, recyclable CuO-ZnO nanocatalyst. The catalyst was synthesized using the co-precipitation method and characterized by N2 adsorption-desorption, X-ray diffraction, scanning electron microscopy, transmission electron microscopy and energy dispersion scanning analyses. Furthermore, this catalyst could be recycled up to six times without significant loss in its activity.

Synthesis of lipase nano-bio-conjugates as an efficient biocatalyst: Characterization and activity-stability studies with potential biocatalytic applications

In the present study, we have synthesized lipase-nano-bio-conjugates via immobilization of various lipases on multiwall carbon nano-tubes (MCNT), in order to construct an efficient and recyclable biocatalytic system. In a screening study lipase Pseudomonas fluorescens (PFL) acted as an efficient biocatalyst (lipase-nano-bio-conjugates) which showed higher retention of lipase activity and protein loading. Consequently the immobilization support : lipase (MCNT : PFL) composition was screened in which MCNT : PFL (2 : 1) was calculated as a robust biocatalyst composition which showed higher activity retention and protein loading. This nano-bio-conjugate was then characterized in detail with physical and biochemical techniques using SEM, TEM, FTIR, Km, Vmax, catalytic efficiency and (%) water content analysis. This developed biocatalyst was further used for practical biocatalytic applications such as O-acylation reactions. Various reaction parameters were optimized in detail like reactant molar ratio (2 : 3.5), solvent, MCNT : PFL biocatalyst amount (36 mg), temperature (50°C) etc. The developed biocatalytic protocol was then extended to synthesize several (twenty-two) industrially important acylated moieties with an excellent yield, these products are well characterized by 1HNMR, 13CNMR and GCMS analysis. Moreover in the present study, we have reviewed the potential industrial applications of various synthesized compounds. Also, we have studied the thermodynamic aspect which demonstrated more feasibility of use of immobilized MCNT : PFL lipase over free lipase. Interestingly, immobilized MCNT : PFL lipase showed 2.3 fold higher catalytic activity than free PFL. Besides this, the biocatalyst was efficiently recycled for up to five cycles. Thus the present protocol demonstrated, (i) synthesis of nano-bio-conjugates as a bio-catalyst, (ii) detailed physical-biochemical characterization of nano-bio-conjugates, (iii) optimization of the biocatalytic protocol (iv) practical biocatalytic applications along with a mechanistic study (v) a thermodynamic feasibility study and (vi) recyclability study. 2015

Tribromoisocyanuric acid (TBCA) as a mild and metal free catalyst for the acetylation and formylation of hydroxyl groups under solvent free conditions

A convenient approach for acetylation and formylation of various types of alcohols and phenols with acetic anhydride and formic acid in the presence of Tribromoisocyanuric acid (TBCA) as catalyst is reported. The reactions were carried out under solvent-free condition and in good to high yields at room temperature. This present method is featured with relatively mild reaction conditions, simple operation, broad substrate scope, clean work-up, short reaction times, good to high yields, excellent selectivity and also avoids tedious purifications and the use of toxic reagents.