387334-40-9

Basic information

• Product Name: 5-Pyrimidinecarboxaldehyde, 4-amino-1,2-dihydro-1-methyl-2-oxo- (9CI)
• Synonyms: 5-Pyrimidinecarboxaldehyde, 4-amino-1,2-dihydro-1-methyl-2-oxo- (9CI)
• CAS NO: 387334-40-9
• Molecular Formula: C6H7N3O2
• Molecular Weight: 153.13868
• Product Categories: ALDEHYDE;ALCOHOL
• Mol File: 387334-40-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Pyrimidinecarboxaldehyde, 4-amino-1,2-dihydro-1-methyl-2-oxo- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarboxaldehyde, 4-amino-1,2-dihydro-1-methyl-2-oxo- (9CI)(387334-40-9)
• EPA Substance Registry System: 5-Pyrimidinecarboxaldehyde, 4-amino-1,2-dihydro-1-methyl-2-oxo- (9CI)(387334-40-9)

Safety Data

• Hazardous Substances Data: 387334-40-9(Hazardous Substances Data)

Upstream product

• 17634-60-5 1,5-dimethylcytosine 
• 1146966-36-0 1-methyl-5-hydroxymethylcytosine 

Relevant articles and documents

The pH-Dependence of the Hydration of 5-Formylcytosine: an Experimental and Theoretical Study

5-Formylcytosine is an important nucleobase in epigenetic regulation, whose hydrate form has been implicated in the formation of 5-carboxycytosine as well as oligonucleotide binding events. The hydrate content of 5-formylcytosine and its uracil derivative has now been quantified using a combination of NMR and mass spectroscopic measurements as well as theoretical studies. Small amounts of hydrate can be identified for the protonated form of 5-formylcytosine and for neutral 5-formyluracil. For neutral 5-formylcytosine, however, direct detection of the hydrate was not possible due to its very low abundance. This is in full agreement with theoretical estimates.

The (α-4) photoconjugates of 5-methylcytosine, 1,5-dimethylcytosine, 1-methylthymine and thymidine

The pyrimidine nucleobases contained in DNA undergo a variety of photoinduced reactions in which two moieties become joined to form a product (e.g. formation of cyclobutane dimers and [6-4] adducts). Herein, we describe a new type of photoconjugation reaction that has been shown to occur for 5-methylcytosine (5-MeC), 1,5-dimethylcytosine (1,5-diMeC), 1-methylthymine and thymidine; in this reaction the 5-methyl group of one nucleobase (or nucleoside) becomes attached to the 4-position of the second moiety. For example, 5-MeC forms α-4′-(5′-methylpyrimidin-2′-one)-5-methylcytosine. The various (α-4) conjugates are produced upon irradiation of the parent compound in frozen aqueous solution at -78.5°C. The UV spectra of these compounds display a characteristic double humped profile, similar to that expected from overlaying the spectrum of parent nucleobase with that of a 2′-pyrimidone moiety. Preliminary results suggest that thymine and 5-methyl-2′-deoxycytidine (5-MedCyd) form analogous photoproducts. A variety of other previously unreported photoproducts are described as well for the 5-MeC, 1,5-diMeC and 5-MedCyd systems.