6064-52-4

Basic information

• Product Name: 4-OXONONANOIC ACID
• Synonyms: 4-OXONONANOIC ACID;4-Ketopelargonic acid
• CAS NO: 6064-52-4
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.22
• Mol File: 6064-52-4.mol

Chemical Properties

• Boiling Point: 298.2°Cat760mmHg
• Flash Point: 148.4°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 0.000307mmHg at 25°C
• Refractive Index: 1.449
• CAS DataBase Reference: 4-OXONONANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-OXONONANOIC ACID(6064-52-4)
• EPA Substance Registry System: 4-OXONONANOIC ACID(6064-52-4)

Safety Data

• Hazardous Substances Data: 6064-52-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2039, 1986 DOI: 10.1021/jo00361a019

InChI:InChI=1/C9H16O3/c1-2-3-4-5-8(10)6-7-9(11)12/h2-7H2,1H3,(H,11,12)

Upstream product

• 67-56-1 methanol 
• 103927-49-7 (E)-4-chloro-3-nonenoic acid 
• 95087-48-2 (Z)-4-chloro-3-nonenoic acid 
• 860582-83-8 2-acetyl-2-butyl-3-oxo-adipic acid diethyl ester 
• 7732-18-5 water 
• 37174-92-8 4-oxo-nonanoic acid ethyl ester 

Downstream Products

• 33566-57-3 methyl 4-oxononanoate 
• 21963-26-8 2-nonen-4-olide 
• 51352-68-2 5-n-pentyl-2,3-dihydro-2-furanone 
• 7779-53-5 (R)-4-Hydroxy-nonanoic acid 
• 409060-26-0 5-pentyl-1,3-dihydro-pyrrol-2-one 
• 63357-96-0 (R)-(+)-γ-nonalactone 
• 112-05-0 nonanoic acid 

Relevant articles and documents

Microbial bioreductions of γ- and δ-ketoacids and their esters

A series of yeasts were used in the bioreductions of aliphatic and aromatic γ- and δ-ketoacids and esters to investigate the preparation of enantiomerically pure γ- and δ-lactones through the intermediacy of their corresponding γ- and δ-hydroxyacids and esters. Bioreduction of ethyl 4-oxononanoate 2a with Pichia etchellsii afforded the γ-nonanolide (+)-5a with 99% e.e., while Pichia minuta proved to be the best choice for the bioreduction of ethyl 2-oxocyclohexylacetate 2e, which afforded cis-(-)-5e and trans-(-)-5e with 98 and 99% e.e., respectively. Reduction of 3-(2-oxocyclohexyl)propionic acid 3e with Pichia glucozyma gave predominantly the corresponding δ-lactone trans-(-)-6e with 94% e.e., whose absolute configuration was determined by means of CD spectroscopy.

Regio- and Stereoselective Ring Opening of ω-Alkenyllactones Using Organocopper Reagents

New synthetic methods are described for the preparation of (E)-3, (E)-4, and (E)-5-alkenoic acids by the regio- and stereoselective ring opening of β, γ, and δ-lactones with unsaturated substituents at the ω-position using organocopper reagents such as halomagnesium diorganocuprates or Grignard reagents in the presence of copper(I) iodide.Both the organocopper reagents with primary, secondary, tertiary alkyl, and phenyl groups gave the corresponding carbon homologated alkenoic acids in good yields.Alkadienoic acids were also obtained in good yields by the reactions of ω-alkenyllactones with divinyl- and diallylcuprates.Utilizing the ring opening of β-isopropenyl-β-propiolactone, homoterpenoid carboxylic acids were easly obtained in good yields.The ring opening of β-(1-chlorovinyl)-β-propiolactone afforded 4-chloro-3-alkenoic acids which were easly transformed to 4-oxoalkanoic acids and 4-oxo-2-alkenoic acids.

A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-CHLORO-3-ALKENOIC ACID, A NEW USEFUL SYNTHETIC BLOCK FOR 4-OXOALKANOIC AND 4-OXO-2-ALKENOIC ACIDS

Easily available material, β-(1-chlorovinyl)-β-propiolactone reacted with organocopper reagents to afford 4-chloro-3-alkenoic acids in high yields.The acids were easily transformed into two kinds of useful carboxylic acids such as 4-oxoalkanoic and 4-oxo-(E)-2-alkenoic acids leading to various natural products.