112193-75-6

Basic information

• Product Name: 1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid
• Synonyms: 1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid;SPSJFVXUOKRIGT-UHFFFAOYSA-N
• CAS NO: 112193-75-6
• Molecular Formula: C12H24N4O4
• Molecular Weight: 288.34336
• Mol File: 112193-75-6.mol

Chemical Properties

• Boiling Point: 526.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: 1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid(112193-75-6)
• EPA Substance Registry System: 1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid(112193-75-6)

Safety Data

• Hazardous Substances Data: 112193-75-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid is used as a chelating agent for metal ions, particularly in the context of Gadoteridol (G125900), an MRI contrast agent. Its role in this application is crucial for enhancing the imaging capabilities of MRI scans by improving the contrast between different tissues.
Used in Medical Imaging:
1,4,7,10-Tetraazacyclododecane-1,7-diacetic acid is used as a component in MRI contrast agents for medical imaging. Its presence in Gadoteridol (G125900) contributes to the effectiveness of the contrast agent, allowing for clearer visualization of internal structures and aiding in the diagnosis of various medical conditions.

Upstream product

• 162148-48-3 (7-tert-butoxycarbonylmethyl-1,4,7,10-tetraaza-cyclododec-1-yl)-acetic acid tert-butyl ester 
• 162148-45-0 1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester 
• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 187240-78-4 dibenzyl 4,10-bis(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate 

Relevant articles and documents

COMPOSITIONS FOR TARGETED IMAGING AND THERAPY

The present invention relates to the field of radiochemistry, nuclear imaging, radionuclide therapy and chemical synthesis. More particularly, it concerns a strategy for radiolabeling target ligands. It further concerns methods of using those radiolabeled ligands for imaging, radionuclide therapy and tissue-specific disease imaging.

1,4,7,10-tetraazabicyclo[8.2.2]tetradecan-2-one, a process for the preparation thereof and the use thereof for the preparation of tetraazamacrocycles

The present invention relates to the novel compound, 1,4,7,10-tetraazabicyclo[8.2.2]tetradecan-2-one of formula (I), its preparation and the use thereof for the preparation of tetraazamacrocycles. STR1

Process for the preparation of tetraazamacrocycles

A process for the preparation of the compounds of formula (I), and (II) comprising the steps represented in the following Scheme, in which the substituents are as defined in the specification. STR1

Formation constants for complexes of 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid and the crystal structure of its nickel(II) complex

The crystal structure of the nickel(II) complex of 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid (H2doda) has been determined. The ligand binds in a cis-octahedral fashion through the four nitrogen atoms and two carboxylate groups and dimerizes via an apparently symmetrical hydrogen bond from the non-bonding oxygen of a carboxylate group to a lone hydrogen ion originating from a perchloric acid molecule of crystallization. Carbon-13 NMR studies of the corresponding zinc(II) complex indicated that it has a similar structure. pKa Measurements for doda, at 298.2 K in 0.1 mol dm-3 NEt4ClO4, suggested that the two secondary amines are the first to protonate followed by the two carboxylates and then the two tertiary nitrogen atoms. A marked disparity in the magnitude of the pKa values for the two carboxylic groups [4.00(1) and 2.36(3)] suggests that internal hydrogen bonding between the two stabilizes one of the protons. Formation constants for some divalent metal complexes (Co, Ni, Cu, Zn, Cd or Pb) of H2doda have been determined. The results from this work are compared to data for analogous macrocycles having three or four carboxymethyl groups.

A General Synthesis of 1,7-Disubstituted 1,4,7,10-Tetraazacyclododecanes

1,4,7,10-Tetraazacyclododecane reacts regioselectively in acid solution with several chloroformates to give 1,7-diprotected derivatives which could be alkylated and deprotected to afford 1,7-disubstituted 1,4,7,10-tetraazacyclododecanes.