144-16-1

Basic information

• Product Name: 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)
• Synonyms: 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid);5-Oxo-1,3-dioxolane-4,4-diacetic acid;3-Dioxolane-4,4-diaceticacid, 5-oxo-;PXPMCAKTYKAROX-UHFFFAOYSA-N
• CAS NO: 144-16-1
• Molecular Formula: C₇H₈O₇
• Molecular Weight: 204.1342
• EINECS: 205-618-6
• Mol File: 144-16-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 302.61°C (rough estimate)
• Flash Point: 226.7 °C
• Appearance: /
• Density: 1.5542 (rough estimate)
• Vapor Pressure: 5.63E-13mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: 47.7g/L(20 oC)
• CAS DataBase Reference: 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)(144-16-1)
• EPA Substance Registry System: 5-oxo-1,3-dioxolan-4-ylidenedi(acetic acid)(144-16-1)

Safety Data

• Hazardous Substances Data: 144-16-1(Hazardous Substances Data)

Usage

Uses

5-Oxo-1,3-dioxolane-4,4-diacetic Acid is used as a reagent to synthesize vibrioferrin, a siderophore. It can also be used as a building block of lipophilic isosteres of nucleoside triphosphates which are potential inhibitors of HIV reverse transcriptase.

InChI:InChI=1/C7H8O7/c8-4(9)1-7(2-5(10)11)6(12)13-3-14-7/h1-3H2,(H,8,9)(H,10,11)

Upstream product

• 77-92-9 citric acid 
• 17140-33-9 2-acetoxy-propane-1,2,3-tricarboxylic acid 
• 20757-83-9 [1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide 
• 628-51-3 diacetoxymethane 
• 625-56-9 Chloromethyl acetate 
• 15454-33-8 chloromethanol 
• 50-00-0 formaldehyd 

Downstream Products

• 108872-58-8 {4-[(methyl-phenyl-carbamoyl)-methyl]-5-oxo-[1,3]dioxolan-4-yl}-acetic acid 
• 108872-07-7 [4-(benzylcarbamoyl-methyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid 
• 83948-79-2 Sodium; 3-[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-2-{[5-(acetyl-benzyloxy-amino)-pentylcarbamoyl]-methyl}-2-hydroxy-propionate 
• 83948-78-1 Sodium; 3-[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-2-{[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-propionate 
• 83948-75-8 Tribenzylarthrobactin 
• 83948-71-4 N-[3-(Acetyl-benzyloxy-amino)-propyl]-2-{[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinamic acid benzyl ester 
• 83948-74-7 2-{[3-(Acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinic acid 1-benzyl ester 4-(4-nitro-phenyl) ester 
• 83948-73-6 N-[3-(Acetyl-benzyloxy-amino)-propyl]-2-{[3-(acetyl-benzyloxy-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinamic acid isopropyl ester 
• 83948-69-0 3-Benzyloxycarbonyl-3-hydroxy-pentanedioic acid bis-(4-nitro-phenyl) ester 
• 83966-25-0 2-isopropyl citrate 
• 39007-57-3 Arthrobactin 
• 83948-70-3 3-Hydroxy-3-methoxycarbonyl-pentanedioic acid bis-(4-nitro-phenyl) ester 
• 35418-52-1 schizokinen 
• 110333-20-5 2-<4-<(allyloxycarbonyl)methyl>-5-oxo-1,3-dioxolan-4-yl>acetic acid 

Relevant articles and documents

An improved synthesis of trisodium (U)-homocitrate from citric acid

A method of synthesis of trisodium (R)-homocitrate starting from citric acid is reported. The procedure affords the final product of high optical purity with satisfactory yield.

Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase

We describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophile derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5'-amino-d4T is included. Intramolecular rearrangement of several amide-linked isosteres are also reported, along with an alternative synthetic strategy to the desired amide-linked isosteres.