5157-89-1

Basic information

• Product Name: (1S)-(+)-MENTHYL ACETATE
• Synonyms: (+)-(1S)-MENTHYL ACETATE;(1S)-(+)-MENTHYL ACETATE;(+)-(1S)-MENTHYL ACETATE, TERPENE STANDA RD;(1S)-(+)-Menthyl acetate 99%;(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl acetate
• CAS NO: 5157-89-1
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3
• Product Categories: EstersAlphabetic;MEA - MESChromatography;Natural CompoundsChemical Class;Natural Terpene Standards;Analytical Standards;Chemical Class;Life Sciences Standards;M;Natural Compounds;Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 5157-89-1.mol

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 228-229 °C(lit.)
• Flash Point: 198 °F
• Appearance: /
• Density: 0.925 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 1909419
• CAS DataBase Reference: (1S)-(+)-MENTHYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(+)-MENTHYL ACETATE(5157-89-1)
• EPA Substance Registry System: (1S)-(+)-MENTHYL ACETATE(5157-89-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5157-89-1(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
(1S)-(+)-Menthyl acetate is used as a fragrance ingredient for its fresh and minty scent, adding a pleasant aroma to a variety of products.
Used in Flavor Industry:
(1S)-(+)-Menthyl acetate is used as a flavoring agent to impart a cooling and refreshing taste to food and beverages, enhancing the overall sensory experience.
Used in Pharmaceutical Industry:
(1S)-(+)-Menthyl acetate is used as an active ingredient or additive in pharmaceuticals, potentially contributing to the development of medications with a fresh and cooling sensation.
Used in Cosmetics Industry:
(1S)-(+)-Menthyl acetate is used in cosmetics to provide a refreshing and soothing effect, often included in products like creams, lotions, and other skincare formulations.
Used in Personal Care Products:
(1S)-(+)-Menthyl acetate is used in personal care products to add a cooling and invigorating sensation, making it a popular component in items such as deodorants, toothpaste, and mouthwashes.

Upstream product

• 108-24-7 acetic anhydride 
• 1181819-05-5 menthol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 89-48-5 rac-2-isopropyl-5-methylcyclohexyl acetate 
• 108-22-5 Isopropenyl acetate 
• 15356-70-4 menthol 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 108-05-4 vinyl acetate 
• 1254745-37-3 C₁₃H₂₆O₂ 
• 102-76-1 triacetylglycerol 
• 89-78-1 [1-α]-5-methyl-2-[1-methylethyl]-cyclohexanol 
• 20752-34-5 neoisomenthol 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 

Downstream Products

• 36567-70-1 (3R)-3-phenyl-3-hydroxybutanoic acid 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 64-19-7 acetic acid 
• 1421312-44-8 C₁₂H₂₂O₃ 
• 1421312-45-9 C₁₂H₂₀O₃ 
• 326894-43-3 (-)-(S)-N-(cyclopentylphenylmethyl)acetamide 
• 89-78-1 menthol 
• 2216-51-5 (-)-menthol 
• 491-07-6 (+/-)-menthone 

Relevant articles and documents

Synthesis, Characterisation, and Determination of Physical Properties of New Two-Protonic Acid Ionic Liquid and its Catalytic Application in the Esterification

A new ionic liquid was synthesised, and its chemical structure was elucidated by FT-IR, 1D NMR, 2D NMR, and mass analyses. Some physical properties, thermal behaviour, and thermal stability of this ionic liquid were investigated. The formation of a two-protonic acid salt namely 4,4′-trimethylene-N,N′-dipiperidinium sulfate instead of 4,4′-trimethylene-N,N′-dipiperidinium hydrogensulfate was evidenced by NMR analyses. The catalytic activity of this ionic liquid was demonstrated in the esterification reaction of n-butanol and glacial acetic acid under different conditions. The desired acetate was obtained in 62-88 % yield without using a Dean-Stark apparatus under optimal conditions of 10 mol-% of the ionic liquid, an alcohol to glacial acetic acid mole ratio of 1.3: 1.0, a temperature of 75-100°C, and a reaction time of 4 h. α-Tocopherol (α-TCP), a highly efficient form of vitamin E, was also treated with glacial acetic acid in the presence of the ionic liquid, and O-acetyl-α-tocopherol (Ac-TCP) was obtained in 88.4 % yield. The separation of esters was conducted during workup without the utilisation of high-cost column chromatography. The residue and ionic liquid were used in subsequent runs after the extraction of desired products. The ionic liquid exhibited high catalytic activity even after five runs with no significant change in its chemical structure and catalytic efficiency.

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.

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.].

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.

DMAP-based flexible polymer networks formed via Heck coupling as efficient heterogeneous organocatalysts

Two DMAP-based flexible polymer networks TPB-DMAP and TPA-DMAP have been successfully synthesized via palladium catalyzed Heck cross-coupling. The structures of these polymers were confirmed by solid state 13C CP/MAS and Fourier transform infrared spectroscopy (FTIR). Although both polymers have negligible surface areas, they exhibit excellent catalytic efficiency for the acylation of 1-phenylethanol with acetic anhydride due to their good swelling capacities. Utilized as a typical catalyst, the polymer TPA-DMAP shows high activities for acylation of a variety of alcohols to the corresponding esters. Moreover, the catalyst can be recycled at least ten times without obvious loss of catalytic activity.

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.

Microwave-Assisted Catalytic Acetylation of Alcohols by Gold-Nanoparticle-Supported Gadolinium Complex

A gold nanoparticle (AuNP)-supported gadolinium complex (RS-Au-L-Gd) catalyst was prepared through simple chelation of GdCl3 to the surface-bound spacer, 1,4,7-tris(carboxymethyl)-10-(11-mercaptoundecyl)-1,4,7,10-tetraazacyclododecane (HSDO3A). This AuNP-supported Gd complex was found to be a highly effective catalyst for the acetylation of various alcohols and phenol in the presence of acetic anhydride. With a loading of 0.4 mol% of RS-Au-L-Gd, the almost complete transformation can be achieved in 60 s under microwave irradiation conditions. This hybrid catalyst was air stable, water soluble, dissolvable in many organic media, and precipitable. It can be readily recycled more than eight times without any significant loss of its catalytic activity. GRAPHICAL ABSTRACT.