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
• Article Data: 3

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

• 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 
• 95087-48-2 (Z)-4-chloro-3-nonenoic acid 
• 103927-49-7 (E)-4-chloro-3-nonenoic acid 
• 67-56-1 methanol 

Downstream Products

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

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.

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.