38709-52-3

Basic information

• Product Name: Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-
• CAS NO: 38709-52-3
• Molecular Formula: C10H16N2O7
• Molecular Weight: 276.246
• Mol File: 38709-52-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-(38709-52-3)
• EPA Substance Registry System: Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-(38709-52-3)

Safety Data

• Hazardous Substances Data: 38709-52-3(Hazardous Substances Data)

Upstream product

• 50-89-5 thymidine 
• 96221-62-4 trans-(5R,6R)-6-hydroxy-5-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl-N-oxide)-5,6-dihydrothymidine 
• 96221-62-4 trans-(5S,6S)-6-hydroxy-5-(2,2,6,6-tetramethyl-4-oxo-1-piperidinyl-N-oxide)-5,6-dihydrothymidine 
• 43179-29-9 (5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine 

Relevant articles and documents

Selective one-electron oxidation of duplex DNA oligomers: Reaction at thymines

The one-electron oxidation of duplex DNA generates a nucleobase radical cation (electron hole ) that migrates long distances by a hopping mechanism. The radical cation reacts irreversibly with H2O or O 2 to form oxidation products (damaged bases). In normal DNA (containing the four common DNA bases), reaction occurs most frequently at guanine. However, in DNA duplexes that do not contain guanine (i.e., those comprised exclusively of A/T base pairs), we discovered that reaction occurs primarily at thymine and gives products resulting from oxidation of the T-C5 methyl group and from addition to its C5-C6 double bond. This surprising result shows that it is the relative reactivity, not the stability, of a nucleobase radical cation that determines the nature of the products formed from oxidation of DNA. A mechanism for reaction is proposed whereby a thymine radical cation may either lose a proton from its methyl group or H2O/O2 may add across its double bond. In the latter case, addition may initiate a tandem reaction that converts both thymines of a TT step to oxidation products. The Royal Society of Chemistry.

Oxidation of Thymidine by Peroxymono- and Peroxodisulfate Ions

Oxidation of thymidine by KHSO5 gave thymidine glycols, while a similar treatment with Na2S2O8 gave 5-hydroxymethyl-2'-deoxyuridine.

Radiation-Induced Degradation of Purine and Pyrimidine 2'-Deoxyribonucleosides in Aqueous KBr Solutions

Steady-state γ-radiolysis of 5E-4 M pyrimidine and purine 2'-deoxyribonucleosides in aqueous solutions saturated with N2, N2O and O2, respectively, have been carried out in the presence of 0.1 M KBr.The main final degradation products have been isolated and characterised by various spectroscopic measurements including 1H and 13C NMR, UV, C.D. and mass spectrometry.The radiation-induced decomposition of thymidine is mostly accounted for by an ionic mechanism involving Br2, the decay product of Br2, as the reactive oxidising specie.On the other hand the degradation of the purine ring of 2'-deoxyadenosine and 2'-deoxyguanosine may be accounted for by the action of Br2 or Br3. - Keywords: 2'-Deoxyribonucleosides, Inorganic Radical, γ-Irradiation, Radical Reactions, Thymidine Oxidation