57576-09-7

Basic information

• Product Name: ISOPULEGOL ACETATE
• Synonyms: P-MENTH-8-EN-3-OL ACETATE;P-MENTH-8-EN-3-YL-ACETATE;1-METHYL-4-ISOPROPENYLCYCLOHEXAN-3-OL ACETATE;FEMA 2965;ISOPULEGYL ACETATE;ISOPULEGOL ACETATE;5-methyl-2-(1-methylethenyl)-,acetate,[1R-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol;aceticacid(L)-p-menth-8-en-3-ylester
• CAS NO: 57576-09-7
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 260-820-1
• Mol File: 57576-09-7.mol

Chemical Properties

• Melting Point: 85°C
• Boiling Point: 232 °C
• Flash Point: 85.6°C
• Appearance: /
• Density: 0.92
• Vapor Pressure: 0.0248mmHg at 25°C
• Refractive Index: 1.4566 (estimate)
• CAS DataBase Reference: ISOPULEGOL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPULEGOL ACETATE(57576-09-7)
• EPA Substance Registry System: ISOPULEGOL ACETATE(57576-09-7)

Safety Data

• Hazardous Substances Data: 57576-09-7(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
ISOPULEGOL ACETATE is used as a flavoring agent for its woody, berry, green, and camphoraceous taste with a fruity nuance. Its unique taste profile makes it suitable for enhancing the flavor of various food and beverage products.
ISOPULEGOL ACETATE is also used as a fragrance ingredient for its sweet, mint-like odor. It can be incorporated into perfumes, colognes, and other scented products to provide a refreshing and invigorating scent.
Used in Essential Oils:
ISOPULEGOL ACETATE is used as a component in the formulation of essential oils, particularly those derived from buchu and peppermint plants. Its presence in these oils contributes to their characteristic aroma and potential therapeutic properties.

Preparation

By prolonged heating of citronellal with acetic anhydride (with or without sodium acetate)

InChI:InChI=1/C12H20O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3

Upstream product

• 89-79-2 isopulegol 
• 72-89-9 acetylcoenzyme A 
• 463-51-4 Ketene 
• 7786-67-6 isopulegol 
• 108-24-7 acetic anhydride 
• 91739-72-9 Trans-p-Menthane-3,8-diol 
• 108-05-4 vinyl acetate 
• 89-79-2 Isopulegol 
• 91667-08-2 [(1R,2R,5R)-2-(1-hydroxy-1-methyl-ethyl)-5-methylcyclohexyl] acetate 
• 89-79-2 isopulegol 
• 29606-79-9 p-menth-8-en-3-one 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 89-79-2 (rac)-neo-isopulegol 

Downstream Products

• 7786-67-6 isopulegol 
• 13834-14-5 2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propen-1-ol 
• 38049-01-3 2-<(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl>-2-propenal 
• 2623-23-6 L-menthyl acetate 
• 38049-01-3 2-((1R,2S,4S)-2-Hydroxy-4-methyl-cyclohexyl)-propenal 
• 13834-14-5 (+/-)-(1RS,3SR,4SR)-p-menth-8⁽¹⁰⁾-ene-3,9-diol 
• 38049-01-3 2-((1R,2R,4S)-2-Hydroxy-4-methyl-cyclohexyl)-propenal 
• 13834-14-5 (+/-)-(1RS,3SR,4SR)-p-menth-8⁽¹⁰⁾-ene-ane-3,9-diol 

Relevant articles and documents

PREPARATION OF ACETATE COMPOUNDS VIA A KETENE COMPOUND

The present invention relates to a method for preparing acetate compounds using ketene.

Reductive Alkylation of 2-Bromoazoles via Photoinduced Electron Transfer: A Versatile Strategy to Csp2-Csp3 Coupled Products

Access to Csp2-Csp3-coupled products is a challenging goal at the forefront of catalysis. The photocatalytic reductive coupling of aryl bromides with unactivated alkenes is introduced as a convenient method that circumvents any need for synthesis of sp3-hybridized coupling partners. The reaction takes place via photoinduced electron transfer from a tertiary amine to an aryl bromide that fragments to provide an aryl radical and subsequently reacts with an alkene to form a C-C bond. Conveniently, the amine also serves as the final reductant. The method is operationally simple, functional group tolerant, and takes place with selectivities that will allow it to be used in the context of complex molecule synthesis.

Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species

Selected plants within the Origanum, Mentha and Salvia genera, that contain significant amounts of chiral volatile alcohols and their related acetates, exhibit remarkable enantioselectivity of alcohol acetyl transferase (AAT) activity and particularly can discriminate between linalool enantiomers. Origanum dayi AAT produced almost enantiomerically pure (R)-linalyl acetate by enzymatic acetylation of racemic linalool, whereas the closely related O. majorana AAT produced a mixture of (R)- and (S)-linalyl acetate with a ratio of 6:4. Vmax of O. dayi acetylation activity was 30-fold higher for (R)-linalool, whereas in O. majorana no such differences were found.

Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol

A study on the enzymic resolution of the most common p-menthan-3-ol monoterpene isomers is described. Enantioenriched alcohols 1, 5, 10, 11 and 12 are obtained by means of the lipase-mediated kinetic acetylation of the corresponding racemic materials. The stereochemical aspects of the enzymic process have been investigated. We found that the structural features of the starting p-menthan-3-ol as well as the kind of lipase used, impacted strongly on the enantioselectivity of the resolution. The potentialities of this approach for preparative purposes are discussed.

Chiral hydride complexes

Novel chiral boron and aluminum hydride complexes, compositions comprising the chiral hydride complexes, and methods for their synthesis and use are described. The novel chiral hydride complexes are of the formulas: PA1 MBH4-n-a (R*)n (R')a ; PA1 MBH2-b (R**) (R')b ; PA1 MBH(R***); PA1 MBH(R*) (R"); PA1 MAlH4-n-a (R*)n (R')a ; PA1 MAlH2-b (R**)(R')b ; PA1 MAlH(R***); and PA1 MAlH(R*) (R"), PAL wherein PA1 M is Na+, Li+ or K+ ; PA1 each R* is independently a monodentate chiral ligand; PA1 R** is a bidentate chiral ligand; PA1 R*** is a tridentate chiral ligand; PA1 R' is a monodentate achiral ligand; PA1 R" is a bidentate achiral ligand; PA1 n is 1-3; PA1 a is 0-2; and PA1 b is 0-1, PAL with the proviso that n+a3, and with the further proviso that when R** is S-BINOL, M is not Li+.

TOTAL SYNTHESIS OF VARIOUS ELEMANOLIDES

Starting with a suitable substituted divinyl cyclohexanone, eleven naturally occurring 12.8-elemanolides bearing exo-methylene or methyl groups at C-11 and differing in substitution as well as in relative configuration, have been synthesized in racemic form.An approach to elemanolides with additional oxygen functionalities is principally possible by modification of the basic concept.Methods for the oxidative generation of terpenoid exo-methylene lactone and furan units are exemplified by synthesis of menthofuran and the p-menthenolides from isopulegols.