3391-90-0

Usage

Uses

Used in Flavor and Fragrance Industry:
S-(-)-PULEGONE is used as a key ingredient in the flavor and fragrance industry for its distinct aroma and flavor profile. It is often used in the production of perfumes, colognes, and other scented products due to its unique and appealing characteristics.
Used in Pharmaceutical Industry:
S-(-)-PULEGONE is used as an active compound in the pharmaceutical industry for its potential medicinal properties. It is being studied for its potential use in the development of new drugs and therapies, particularly in the areas of pain relief and anti-inflammatory treatments.
Used in Essential Oils:
S-(-)-PULEGONE is used as a component in essential oils, which are widely used in aromatherapy and alternative medicine. Its presence in catnip essential oil is particularly notable, as it is known to have a strong effect on cats, making it a popular ingredient in cat toys and other cat-related products.

InChI:InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m0/s1

Upstream product

• 91426-59-4 p-menth-8-en-3-one semicarbazone 
• 144-62-7 oxalic acid 
• 106-22-9 Citronellol 
• 36392-06-0 3,7-dimethyl-6-octenoyl chloride 
• 89-79-2 Isopulegol 
• 529-02-2 isopulegol 
• 57291-09-5 oxime E/Z de la methyl-5 (methyl-1 ethylidene)-2 cyclohexanone 
• 14252-45-0 2,2-bis(ethylthio)propane 
• 591-24-2 3-Methylcyclohexanone 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 29606-79-9 isopulegone 
• 7732-18-5 water 
• 141-52-6 sodium ethanolate 

Downstream Products

• 18368-85-9 1-butyl-2-isopropylidene-5-methyl-cyclohexanol 
• 78506-85-1 methylisopulegene 
• 6069-97-2 (+)-trans-Caran 
• 3101-50-6 1-methyl-3-methylene-cyclohexane 
• 2216-52-6 Neomenthol 
• 529-02-2 isopulegol 
• 1846-44-2 4,8-dibromo-p-menthan-3-one 
• 86613-13-0 8-bromo-p-menthan-3-one 
• 66448-75-7 8-chloro-p-menthan-3-one 
• 5342-56-3 8-hydroxyamino-p-menthan-3-one 
• 10458-14-7 Menthone 
• 591-24-2 3-Methylcyclohexanone 
• 864851-09-2 2-benzylidene-6-isopropylidene-3-methyl-cyclohexanone 
• 57279-11-5 2-(1-Methoxy-1-methyl-ethyl)-5-methyl-cyclohexanone 

Relevant academic research and scientific papers

Regioselective silver-mediated Kondakov-Darzens olefin acylation

Enone construction: A silver-mediated olefin acylation reaction is described, in which five-, six-, and -seven-membered rings, tetrasubstituted olefins, bridged bicycles, spirocycles, and benzoxepinones are prepared. Highly selective intermolecular reactions are coupled to a Nazarov cyclization for the effective preparation of cyclopentenones, including the core of modhephene (see scheme). Copyright

Flavor and fragrance compositions

The present invention provides a flavor and fragrance composition which comprises, as the active ingredient, an optically active (1S)-8-mercaptomenthone having an S-form/R-form mixing ratio for the configuration at the 4-position in the range of from 65:35 to 95:5 by weight, wherein the flavor and fragrance composition is for use in food and beverage, fragrances and cosmetics, pharmaceuticals or oral compositions and the like; a product which is scented with the flavor and fragrance composition; and a method for enhancing or modulating odor of the flavor and fragrance composition by adding the optically active (1S)-8-mercaptomenthone.

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.

An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3·7H2O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone

2-Alkylidenecycloalkanones are powerful synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective β-elimination reaction to (E)-2-alkylidenecycloalkanones in 2-(1-hydroxyalkyl)cycloalkanones. The synthetic value of the present procedure is demonstrated by the synthesis of monoterpene (S)-(-)-pulegone (8) in its optically active form.

A versatile cobalt(II)-Schiff base catalyzed oxidation of organic substrates with dioxygen: Scope and mechanism

Cobalt(II) complex 1a-f derived from Schiff bases act as efficient catalysts during the oxidation of wide range of organic substrates(e.g. alkenes, alcohols, benzylic compounds and aliphatic hydrocarbons) with dioxygen in the presence of aliphatic aldehydes or ketones or ketoesters. EPR studies on 1a-f complexes suggest that the aliphatic carbonyl compounds promote the formation of a cobalt(II)-superoxo species responsible for the oxidation of organic compounds. These studies also demonstrate the role of ligands on cobalt in controlling the chemoselectivity of these oxidations. A plausible mechanistic rational is also provided for these oxidations.

Regio- and enantio-selective enolisations of cyclic ketones using chiral lithium amide bases

Enolisations of 3-methylcyclohexanone 16, and of a trans-fused perhydroisoquinolone derivative 8, using several chiral lithium amide bases have been examined.In reactions involving a single enantiomer of the ketone 8, the use of a chiral base can result in enhancement or reversal of the normal regioselectivity of enolisation to give the enol silane derivatives 9 and 10, depending on the configuration of the base used.Similar matched and mismatched results are observed when (R)-3-methylcyclohexanone, (R)-16, is treated with either enantiomer of the chiral base 3.A new type of kinetic resolution, termed regiodivergent resolution, is observed when enolisation of the racemic ketones 8 or 16 is carried out using the chiral base 3.

Cobalt catalyzed oxidation of secondary alcohols with dioxygen in the presence of 2-methylpropanal

Cobalt schiff base complex 2 catalyses the oxidation of a wide range of secondary alcohols to the corresponding ketones in the presence of dioxygen and 2-methylpropanal.

Cobalt(II) Schiffs base complex catalysed oxidation of alcohols with dioxygen in the presence of ethyl 2-oxocyclopentanecarboxylate

Cobalt(II) Schiffs base complex 1 catalyses the oxidation of primary and secondary alcohols to aldehydes and ketones respectively, in the presence of dioxygen and ethyl 2-oxocyclopentanecarboxylate 2 at 60-70° C.

Tetramethyl-1-oxaspiro[2.5]octane

New 4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described. 4,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthetis of valuable fragrance ingredients.

Potassium Chlorochromate on a Solid Support: A Convenient and Mild Reagent for the Oxidation of Alcohols

The oxidation of primary and secondary alcohols by potassium chlorochromate supported on alumina or silica gel is reported.The results indicate that the yields in some cases depend on the support medium.Benzylic and secondary alcohols are oxidized in the best yields.The effect of solvent on the reaction is discussed and the conclusion is drawn that the best yields are obtained in non-polar solvents.