5116-24-5

Basic information

• Product Name: 5-HYDROXYMETHYL-2'-DEOXYURIDINE
• Synonyms: 2’-deoxy-5-(hydroxymethyl)-uridin;2’-deoxy-5-(hydroxymethyl)uridine;5-hydroxymethyldeoxyuridine;alpha-hydroxythymidine;5-HYDROXYMETHYL-2'-DEOXYURIDINE;α-Hydroxythymidine;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)pyrimidine-2,4-dione;1-[(2R,4S,5R)-4-hydroxy-5-methylol-tetrahydrofuran-2-yl]-5-methylol-pyrimidine-2,4-quinone
• CAS NO: 5116-24-5
• Molecular Formula: C₁₀H₁₄N₂O₆
• Molecular Weight: 258.23
• EINECS: 225-848-0
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 5116-24-5.mol
• Article Data: 36

Chemical Properties

• Melting Point: 176-179 °C
• Boiling Point: 401.48°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.3598 (rough estimate)
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated), Water (Slightly)
• PKA: 9.01±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 5-HYDROXYMETHYL-2'-DEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXYMETHYL-2'-DEOXYURIDINE(5116-24-5)
• EPA Substance Registry System: 5-HYDROXYMETHYL-2'-DEOXYURIDINE(5116-24-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: YU7600000
• Hazardous Substances Data: 5116-24-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless solid

Uses

5-Hydroxymethyl-2’-deoxyuridine acts as a biomarker for the diagnosis for oxidative stress in humans. Used as a diagnostic to for propensitiy for the development of breast cancer.

Definition

ChEBI: A pyrimidine 2'-deoxyribonucleoside composed of 2'-deoxyuridine having a 5-hydroxymethyl substituent.

Upstream product

• 4494-26-2 5-formyl-2'-deoxyuridine 
• 50-89-5 thymidine 
• 6979-97-1 3',5'-diacetylthymidine 
• 58589-18-7 3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine 
• 1404513-24-1 3',5'-bis-O-acetyl-5-(4-nitro-1H-imidazol-1-ylmethyl)-2'-deoxythymidine 
• 1404513-35-4 5-(2-nitro-1H-imidazol-1-ylmethyl)-2'-deoxythymidine 
• 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 
• 148134-86-5 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine 
• 838-07-3 5-methyldeoxycytidine 
• 7226-77-9 5-hydroxymethyl-2'-deoxycytidine 
• 354581-59-2 3',5'-bis(O-tert-butyldimethylsilyl)-5-hydroxymethyl-2'-deoxyuridine 
• 4433-40-3 5-hydroxymethyl uracil 
• 75-66-1 2-methylpropan-2-thiol 

Downstream Products

• 72274-19-2 5-(azidomethyl)-5'-azido-2',5'-dideoxyuridine 
• 59090-48-1 5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 148380-57-8 C₄₂H₅₁N₄O₁₀P 
• 4494-26-2 5-formyl-2'-deoxyuridine 
• 1292210-15-1 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-2'-deoxyuridine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 
• 150491-85-3 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-2'-deoxyuridine 
• 1292210-18-4 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 
• 1292210-14-0 5'-O-(4,4'-dimethoxytrityl)-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 
• 1292210-13-9 5-tert-butyldimethylsiloxymethyl-N₄-benzoyl-2'-deoxycytidine 
• 1292210-12-8 3',5'-O-di-tert-butylsilyl-5-tert-butyldimethylsiloxymethyl-N⁽⁴⁾-benzoyl-2'-deoxycytidine 
• 188411-06-5 N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite 
• 1277097-10-5 N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine 
• 1277097-09-2 5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine 

Relevant articles and documents

Catalytic Space Engineering as a Strategy to Activate C-H Oxidation on 5-Methylcytosine in Mammalian Genome

Conditional remodeling of enzyme catalysis is a formidable challenge in protein engineering. Herein, we have undertaken a unique active site engineering tactic to command catalytic outcomes. With ten-eleven translocation (TET) enzyme as a paradigm, we show that variants with an expanded active site significantly enhance multistep C-H oxidation in 5-methylcytosine (5mC), whereas a crowded cavity leads to a single-step catalytic apparatus. We further identify an evolutionarily conserved residue in the TET family with a remarkable catalysis-directing ability. The activating variant demonstrated its prowess to oxidize 5mC in chromosomal DNA for potentiating expression of genes including tumor suppressors.

Fluorescent Wittig reagent as a novel ratiometric probe for the quantification of 5-formyluracil and its application in cell imaging

The chemically selective detection of natural nucleobase modifications has been regarded as the key step in understanding their important roles in epigenetics. Herein, for the first time, we introduce a Wittig reaction into the design of reaction-based fluorescent probes for ratiometrically detecting 5fU, selectively labelling 5fU-modified DNA and imaging intracellular 5fU produced by γ-irradiation.

5-Hydroxymethylcytosine and 5-formylcytosine containing deoxyoligonucleotides: Facile syntheses and melting temperature studies

An oxidation-based synthetic approach was developed for facile preparation of 5-formyl-2′-deoxycytidine and 5-hydroxymethyl-2′-deoxycytidine phosphoramidites. Upon introducing organic solvent components and copper catalysts, C5-methyl groups of 5-methyl-2′-deoxycytidine and thymidine were readily oxidized to formyl and hydroxyl functionality, respectively. Standard solid phase DNA synthesis and conventional deprotection methods were applicable to synthesize 5-formyl- or 5-hydroxymethyl-cytosine containing DNA oligonucleotides, which were used to study the effect of epigenetic modifications on DNA thermal dynamic stability.