10397-75-8

Basic information

• Product Name: iocarmic acid
• Synonyms: iocarmic acid;Iocarmic;3,3'-[(1,6-Dioxohexane-1,6-diyl)diimino]bis[2,4,6-triiodo-5-[(methylamino)carbonyl]benzoic acid];3,3'-[Tetramethylenebis(carbonylimino)]bis(2,4,6-triiodo-5-methylcarbamoylbenzoic acid);5,5'-[Tetramethylenebis(carbonylimino)]bis[3-(methylcarbamoyl)-2,4,6-triiodobenzoic acid];MP 2032
• CAS NO: 10397-75-8
• Molecular Formula: C₂₄H₂₀I₆N₄O₈
• Molecular Weight: 1253.85
• EINECS: 233-861-8
• Mol File: 10397-75-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 302° (dec)
• Boiling Point: 868.1°Cat760mmHg
• Flash Point: 478.8°C
• Appearance: /
• Density: 2.4238 (estimate)
• Vapor Pressure: 3.52E-32mmHg at 25°C
• Refractive Index: 1.791
• CAS DataBase Reference: iocarmic acid(CAS DataBase Reference)
• NIST Chemistry Reference: iocarmic acid(10397-75-8)
• EPA Substance Registry System: iocarmic acid(10397-75-8)

Safety Data

• Hazardous Substances Data: 10397-75-8(Hazardous Substances Data)

Usage

Originator

Myelotrast,Winthrop

Uses

Diagnostic aid (radiopaque medium, cholecystographic).

Manufacturing Process

5-Amino-2,4,6-triiodo-N-methylisophthalamic acid (228.0 g, 4 mole) was added to stirred, heated dimethylacetamide (400 ml). When the temperature reached 95°C, adipoyl chloride (27.5 g, 0.15 mole) was added all at once, followed by an equal amount added slowly over a period of 15 min (a total of 55.0 g). After addition of the adipoyl chloride the solution was stirred at about 95°C for another 15 min, then poured into 2 L of hot water. As the above mixture cooled to room temperature a gum separated. The mother liquor was discarded and the gum was dissolved in water (2 L) with sufficient sodium hydroxide to complete solution. The solution was acidified with hydrochloric and acetic acids, treated with decolorizing charcoal and filtered. The filtrate was then strongly acidified with hydrochloric acid, which caused the separation of an apparently amorphous granular solid. This was filtered off, digested 0.5 h with hot ethanol (500 ml) collected, washed with ethanol and dried at 110°C. Yield of crude 5,5-(adipoyldiimino)-bis[2,4,6-triiodo-Nmethylisophthalamic acid].The 5,5-(adipoyldiimino)-bis[2,4,6-triiodo-N-methylisophthalamic acid] was precipitated a second and third time from its sodium salt solution. The third precipitate was then dissolved in hot dimethylformamide (400 ml), and water (1.5 L) was slowly added. The mixture was digested and the hot mixture filtered, yielding a crystalline product which, after drying at 110°C, weighed 126.0 g (neutral equivalent, 724). This product was dissolved in dilute sodium hydroxide solution (1 L) and the solution was acidified (pH 5) and filtered into a hot stirred solution of hydrochloric acid (25 ml of concentrated acid in 75 ml water). The mixture was chilled and the solid collected, washed with water and dried at 110°C. Yield of 5,5-(adipoyldiimino)-bis[2,4,6-triiodo-Nmethylisophthalamic acid] 114.0 g (45%). Melting point, 302°C (corrected), with decomposition.

Brand name

Dimeray (Mallinckrodt).

Therapeutic Function

Diagnostic aid

InChI:InChI=1/C24H20I6N4O8/c1-31-21(37)9-13(25)11(23(39)40)17(29)19(15(9)27)33-7(35)5-3-4-6-8(36)34-20-16(28)10(22(38)32-2)14(26)12(18(20)30)24(41)42/h3-6H2,1-2H3,(H,31,37)(H,32,38)(H,33,35)(H,34,36)(H,39,40)(H,41,42)

Relevant articles and documents

Polyiodinated aroyloxy esters

Compounds having the structure STR1 wherein Z--COO)m is the residue of a polyiodinated aromatic acid; m is 1, 2, 3 or 4; n is an integer from 1 to 20; R1 and R2 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy or aryloxy; R3 and R4 are independently H, alkyl, fluoroalkyl, cycloalkyl, aryl, aralkyl, alkoxy, aryloxy, halogen, hydroxy or acylamino; and R5 is H, alkyl, cycloalkyl, aryl, aralkyl, alkoxyalkyl or acetamidoalkyl; are useful as contrast agents in x-ray imaging compositions and methods.