5238-86-8

Basic information

• Product Name: 5-hydroxymethyldeoxyuridylate
• Synonyms: 5-hydroxymethyldeoxyuridylate
• CAS NO: 5238-86-8
• Molecular Formula: C₁₀H₁₅N₂O₉P
• Molecular Weight: 338.21
• Mol File: 5238-86-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.748±0.06 g/cm3(Predicted)
• PKA: 1.86±0.10(Predicted)
• CAS DataBase Reference: 5-hydroxymethyldeoxyuridylate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxymethyldeoxyuridylate(5238-86-8)
• EPA Substance Registry System: 5-hydroxymethyldeoxyuridylate(5238-86-8)

Safety Data

• Hazardous Substances Data: 5238-86-8(Hazardous Substances Data)

Upstream product

• 964-26-1 2'-deoxyuridine-5'-monophosphate 
• 3432-99-3 N⁵,N¹⁰-methylene-5,6,7,8-tetrahydrofolate 
• 2236-60-4 2-aminopteridin-4(3H)-one 
• 365-07-1 thymidine 5'-phosphate 

Downstream Products

• 4433-40-3 5-hydroxymethyl uracil 
• 137941-20-9 deoxyribose 5-monophosphate 

Relevant articles and documents

Thymidine radical formation via one-electron transfer oxidation photoinduced by pterin: Mechanism and products characterization

UV-A radiation (320-400 nm), recognized as a class I carcinogen, induces damage to the DNA molecule and its components through different mechanisms. Pterin derivatives are involved in various biological functions, including enzymatic processes, and it has been demonstrated that oxidized pterins may act as photosensitizers. In particular, they accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. We have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the degradation of the pyrimidine nucleotide thymidine 5′-monophosphate (dTMP) in aqueous solutions under UV-A irradiation. Although thymine is less reactive than purine nucleobases, our results showed that Ptr is able to photoinduce the degradation of dTMP and that the process is initiated by an electron transfer from the nucleotide to the triplet excited state of Ptr. In the presence of molecular oxygen, the photochemical process leads to the oxidation of dTMP, whereas Ptr is not consumed. In the absence of oxygen, both compounds are consumed to yield a product in which the pterin moiety is covalently linked to the thymine. This compound retains some of the spectroscopic properties of Ptr, such as absorbance in the UV-A region and fluorescence properties.

Oxidation of nucleic acid related compounds by the peroxodisulfate ion

The treatment of nucleic acid bases, nucleosides, and nucleotides with peroxodisulfate ion in a phosphate buffer solution at pH 7.0 or water at 70-75°C was investigated. The reaction of thymine and 5-methylcytosine nucleosides and nucleotides resulted in the oxidation of the 5-methyl groups. The oxidation products from 1,3-dimethyluracils and the time-course of the reaction of uracils led to two plausible reaction mechanisms for the oxidation of uracils.