CAS: 538-75-0
MF: C13H22N2
Appearance: colorless solid
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Dicyclohexylcarbodiimide (DCC) is a waxy, white solid with a faintly sweet odor, commonly used in organic chemistry as a coupling agent, especially in peptide synthesis. DCC presents significant health risks and should be handled with extreme care. It is a strong skin sensitizer and allergenic substance, often causing skin irritation, allergic reactions, and even dermatitis or conjunctivitis upon contact. Inhalation of DCC fumes can lead to bronchial irritation and pneumoconiosis, while ingestion or prolonged exposure may cause gastrointestinal distress, jaw necrosis, and inflammatory changes in the mouth. To minimize these risks, proper personal protective equipment (PPE), such as chemical safety goggles and gloves, should be worn, and contaminated clothing should not leave the workplace. Additionally, DCC should be stored in tightly closed containers under an inert atmosphere and refrigerated to maintain its stability.
The CAS number of Dicyclohexylcarbodiimide is 538-75-0.
Synonyms for Dicyclohexylcarbodiimide 538-75-0:Carbodiimide,dicyclohexyl- (6CI,7CI,8CI);1,3-Dicyclohexylcarbodiimide;Bis(cyclohexyl)carbodiimide;DCC;DCCD;DCCI;Cyclohexanamine,N,N'-methanetetraylbis-;N,N'-Dicyclohexylcarbodiimide;NSC30022;NSC 53373;NSC 57182;N, N’-Dicyclohexylcarbodiimide (DCC);
Dicyclohexylcarbodiimide (DCCD) is identified as an inhibitor of oxidative phosphorylation by blocking ADP-stimulated respiration in tightly coupled mitochondria. At concentrations around 2 μmoles/mg of protein, it specifically inhibits electron transport and ATP-driven partial reactions, but does not affect substrate-linked phosphorylation, such as with α-oxoglutarate oxidation. The action of DCCD is believed to involve covalent binding to a phosphorylated intermediate within oxidative phosphorylation, affecting ATP synthase and associated reactions in submitochondrial particles. The inhibition varies with experimental conditions like time, temperature, and pH. Additionally, DCCD has shown potential as a biochemical tool to study energy-linked reactions, as it stimulates certain aerobic enzymatic activities under specific conditions.
Relevant articles related to Dicyclohexylcarbodiimide:
Article |
Source |
The Properties of Dicyclohexylcarbodiimide as an Inhibitor of Oxidative Phosphorylation* |
R. B. BeecheyA. M. RobertonCaroline T. HollowayI. G. Knight , Biochemistry 1967, 6, 12, 3867–3879 |
Dicyclohexylcarbodiimide binds specifically and covalently to cytochrome c oxidase while inhibiting its H+-translocating activity. |
R.P. Casey ∙ M. Thelen ∙ A. Azzi , Journal of Biological Chemistry, Volume 255, Issue 9, 3994 - 4000 |
Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide |
- Paragraph 0032-0051, (2021/04/17) |
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