6299-61-2

Usage

Structure

A heterocyclic aromatic organic compound with a pyrimidine ring and two methyl groups attached to the first and fifth carbon atoms.

Functional Groups

Pyrimidine ring
Methyl groups
Carbonyl groups (C=O)

Aromaticity

Yes, due to the presence of the pyrimidine ring.

Genetic Code

A key component of the genetic code.

Applications

Used in the production of pharmaceuticals
Utilized in agrochemicals
Employed in materials science

Solubility

Generally soluble in water, slightly soluble in organic solvents like ethanol and methanol.

Stability

Relatively stable under normal conditions, but can undergo reactions such as hydrolysis and tautomerization.

Melting Point

Approximately 337°C

Boiling Point

Not well-defined due to decomposition at high temperatures.

Density

Not readily available, but expected to be similar to other small organic molecules.

Optical Properties

Exhibits UV absorbance due to the presence of the aromatic ring.

Reactivity

Can undergo reactions such as nucleophilic substitution, electrophilic substitution, and oxidation.

Hazards

Generally considered non-toxic, but should be handled with care due to its potential to cause irritation or allergic reactions.

Downstream Products

• 4160-72-9 1-methylthymine 

Relevant academic research and scientific papers

Radiation-induced and photosensitized splitting of c5-c5′-linked dihydrothymine dimers. 2. conformational effects on the reductive splitting mechanism

Radiation-induced and photosensitized reductive splitting of stereoisomeric C5-C5′-linked dihydrothymine dimers (1a,b[meso], meso compound of (5R,5′S)- and (5S,5′R)-bi-5,6-dihydrothymines; 1a,b[rac], racemic compound of (5R,5′R)- and (5S,5′S)-bi-5,6-dihydrothymines) in aqueous solution were studied to compare with the one-electron oxidative splitting mechanism and the photorepair reaction of cyclobutane pyrimidine photodimers. Reacting with radiation-chemically and photochemically generated hydrated electrons or with photoexcited reduced form of flavin adenine dinucleotide (*FADH-), the C5-C5′-linked dihydrothymine dimers 1a,b produced the corresponding 5,6-dihydrothymine derivatives (3a,b) along with the thyrnine monomers (2a,b) in minor yields. Both the product and laser flash photolysis studies indicated that oneelectron adducts of the C5-C5′-linked dimers 1a,b undergo C5-C5′-bond cleavage to generate the 5,6-dihydrothymin-5-yl radicals (5a,b) and the 5,6-dihydrothymine C5-anions (6a,b) resulting in the formation of 3a,b by facile protonation at C5. In the reduction by *FADH-, splitting of the 5,6-dihydro-1-methylthymine dimer 1a[meso] into the monomer 2a was more efficient than that of the racemic isomer 1a[rac]. Conformational analysis by NMR of 1a[meso] and 1a[rac] in solution suggested that 1a[meso] may favor a "closed-shell" conformation and undergo one-electron reduction to form 5a and 6a, whereas 1a[rac] may be in a "opened-shell" conformation and undergo successive two-electron reduction by *FADH- to produce 2 equiv of 6a as a precursor of 3a.

Radiation-induced and photosensitized splitting of C5-C5′-linked dihydrothymine dimers: Product and laser flash photolysis studies on the oxidative splitting mechanism

Radiation-induced and photosensitized one-electron oxidation of stereoisomeric C5-C5′-linked dihydrothymine dimers (1a,b[meso], meso compound of (5R,5′S)-bi-5,6-dihydrothymine; 1a,b[rac], racemic compound of (5R,5′R)-and (5S,5′S)-bi-5,6-dihydrothymines), which are the major products yielded by radiolytic reduction of 1-methylthymine (2a) and 1,3-dimethylthymine (2b) in aqueous solution, was studied to compare with the photoreactivating repair mechanism of cyclobutane pyrimidine photodimers. Reacting with sulfate radical anion (SO4.-), azide radical (N3.), or photoexcited anthraquinone-2-sulfonate (AQS) as oxidants, the C5-C5′-linked dihydrothymine dimers 1a,b split to regenerate the corresponding thymine monomers 2a,b along with 5,6-dihydrothymines (3a,b) in a pH dependent manner. The transient absorption spectra of 5,6-dihydrothymin-5-yl radicals (6a,b) were observed in the nanosecond laser flash photolysis of 1a,b in phosphate buffer under conditions of SO4.- generation. Both the product study and the laser flash photolysis study indicated an oxidative splitting mechanism by which one-electron oxidation of the C5-C5′-linked dimers 1a,b produces the radical cation intermediates (4a,b), which undergo facile fragmentation into 5,6-dihydrothymin-5-yl radicals 6a,b and C5-cations (5a,b), followed by deprotonation at C6 of 5a,b to regenerate the monomers 2a,b.