3391-90-0

Basic information

• Product Name: S-(-)-PULEGONE
• Synonyms: (-)-PULEGONE;PULEGONE, S-(-)-;S-(-)-PULEGONE;(S)-P-MENTH-4(8)-EN-3-ONE;(S)-2-ISOPROPYLIDENE-5-METHYLCYCLOHEXANONE;S-(-)-2-ISOPROPYLIDENE-5-METHYLCYCLOHEXANONE;S-(-)-PULEGONE WITH GC;(S)-2-Isopropylidene-5-methylcyclohexanone, (S)-p-Menth-4(8)-en-3-one
• CAS NO: 3391-90-0
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• Mol File: 3391-90-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 244°C
• Boiling Point: 223-224 °C
• Flash Point: 185 °F
• Appearance: /
• Density: 0.937 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0934mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Storage Temp.: 2-8°C
• BRN: 2040703
• CAS DataBase Reference: S-(-)-PULEGONE(CAS DataBase Reference)
• NIST Chemistry Reference: S-(-)-PULEGONE(3391-90-0)
• EPA Substance Registry System: S-(-)-PULEGONE(3391-90-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 16-26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 3391-90-0(Hazardous Substances Data)

Usage

Description

S-(-)-PULEGONE, also known as (S)-Pulegone, is a monoterpene that is commonly found in the essential oils of Nepeta cataria, commonly known as catnip. It is a stereoisomer of (R)-Pulegone (P840140) and has distinct properties and applications.

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 
• 13368-65-5 (3R)-3-methylcyclohexanone 
• 67-64-1 acetone 
• 56764-09-1 2-isopropylidene-1,5-dimethyl-cyclohexanol 
• 3058-01-3 3-methyladipic acid 
• 56763-63-4 (-)-6-isopropylidene-1,3-dimethyl-cyclohexene; (-)-methylpulegene 
• 56763-63-4 6-isopropylidene-1,3-dimethyl-cyclohexene 
• 18369-31-8 1-ethyl-2-isopropylidene-5-methyl-cyclohexanol 
• 16206-43-2 (-)-2-methyl-2-((1Ξ,4R)-4-methyl-2-oxo-cyclohexyl)-propionic acid 
• 626-51-7 3-methyl glutaric acid 
• 597-43-3 2,2-dimethylsuccinic acid 
• 99-82-1 Menthane 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 

Relevant articles and documents

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

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.

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.