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

Uses

(S)-Pulegone is the stereoisomer of (R)-Pulegone (P840140) which is a monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip).

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

• 64-17-5 ethanol 
• 29606-79-9 isopulegone 
• 7732-18-5 water 
• 141-52-6 sodium ethanolate 
• 67-56-1 methanol 
• 86613-13-0 8-bromo-p-menthan-3-one 
• 861590-26-3 8-isonitramino-p-menthan-3-one 
• 104870-56-6 (+)-isopulegol 
• 491-09-8 3-terpinolenone 
• 89-79-2 (S)-2-Isopropenyl-5-methyl-cyclohexanol 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 5949-05-3 (S)-Citronellal 
• 485818-76-6 6-[1-(trimethylsilyloxy)-1-methylethyl]cyclohex-2-en-1-one 
• 485818-75-5 6-(1-hydroxy-1-methylethyl)cyclohex-2-en-1-one 

Downstream Products

• 13368-65-5 (3R)-3-methylcyclohexanone 
• 67-64-1 acetone 
• 33557-42-5 1-allyl-2-isopropylidene-5-methyl-cyclohexanol 
• 22406-79-7 (3-hydroxy-p-menth-4⁽⁸⁾-en-3-yl)-acetic acid ethyl ester 
• 99-82-1 Menthane 
• 6711-26-8 methyl pulegone 
• 60296-05-1 6-isopropylidene-2,3-dimethyl-cyclohexanone 
• 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 
• 64-18-6 formic acid 
• 3058-01-3 3-methyladipic acid 
• 89-83-8 thymol 
• 89-78-1 menthol 

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.