5627-00-9

Basic information

• Product Name: 5,6-DIHYDROTHYMIDINE
• Synonyms: 5,6-DIHYDROTHYMIDINE;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione;1-[(2R,4S,5R)-4-hydroxy-5-methylol-tetrahydrofuran-2-yl]-5-methyl-5,6-dihydrouracil;5,6-Dihydro-2'-deoxy-5-methyluridine;(5S)-5,6-Dihydrothymidine
• CAS NO: 5627-00-9
• Molecular Formula: C₁₀H₁₆N₂O₅
• Molecular Weight: 244.24
• Mol File: 5627-00-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.391 g/cm³
• Refractive Index: 1.553
• Storage Temp.: −20°C
• CAS DataBase Reference: 5,6-DIHYDROTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDROTHYMIDINE(5627-00-9)
• EPA Substance Registry System: 5,6-DIHYDROTHYMIDINE(5627-00-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5627-00-9(Hazardous Substances Data)

Usage

Uses

5,6-Dihydrothymine is one of the most important products of base damage by gamma irradiation of DNA in anoxic conditions.

Definition

ChEBI: A pyrimidine 2'-deoxyribonucleoside having dihydrothymine as the nucleobase.

InChI:InChI=1/C10H16N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h5-8,13-14H,2-4H2,1H3,(H,11,15,16)/t5?,6-,7+,8+/m0/s1

Upstream product

• 50-89-5 thymidine 
• 208466-62-0 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-5-phenylselanyl-dihydro-pyrimidine-2,4-dione 
• 132576-68-2 5S-(α-thymidyl)-5,6-dihydrothymidine 

Downstream Products

• 187979-94-8 5-Benzoyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-dihydro-pyrimidine-2,4-dione 
• 187979-93-7 5-Benzoyl-1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-dihydro-pyrimidine-2,4-dione 
• 187979-95-9 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(hydroxy-phenyl-methyl)-5-methyl-dihydro-pyrimidine-2,4-dione 
• 187979-88-0 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(4-methoxy-benzoyl)-5-methyl-dihydro-pyrimidine-2,4-dione 
• 187980-00-3 (R)-1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-isobutyryl-5-methyl-dihydro-pyrimidine-2,4-dione 
• 187979-99-3 (S)-1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-isobutyryl-5-methyl-dihydro-pyrimidine-2,4-dione 
• 1072452-75-5 5'-O-tert-butyldiphenylsilyl-5,6-dihydrothymidine 
• 1334176-57-6 C₆₀H₈₀N₄O₁₂SSi₂ 
• 1334176-58-7 C₅₉H₇₆N₄O₁₂Si₂ 
• 1334176-59-8 C₄₃H₆₀N₄O₁₀Si₂ 
• 1334176-53-2 N⁽³⁾-benzyloxymethyl-3',5'-O-di(triethylsilyl)-5,6-dihydrothymidine 
• 1334176-62-3 C₆₀H₁₀₀N₄O₁₂Si₄ 
• 1334176-61-2 C₆₀H₁₀₀N₄O₁₂Si₄ 
• 1334176-54-3 C₄₈H₇₂N₄O₁₂Si₂ 

Relevant articles and documents

Sonochemical transformation of thymidine: A mass spectrometric study

Abstract Ultrasound is extensively used in medical field for a number of applications including targeted killing of cancer cells. DNA is one of the most susceptible entities in any kind of free radical induced reactions in living systems. In the present work, the transformation of thymidine (dT) induced by ultrasound (US) was investigated using high resolution mass spectrometry (LC-Q-ToF-MS). dT was subjected to sonolysis under four different frequencies (200, 350, 620 and 1000 kHz) and at three power densities (10.5, 24.5 and 42 W/mL) in aerated as well as argon saturated conditions. A total of twenty modified nucleosides including non-fully characterized dT dimeric compounds were detected by LC-Q-ToF-MS. Out of these products, seven were obtained only in the argon atmosphere and two only in the aerated conditions. Among the identified products, there were base modified products and sugar modified products. The products were formed by the reaction of hydroxyl radical and hydrogen atom. Under aerated conditions, the reactions proceed via the formation of hydroperoxides, while in argon atmosphere disproportionation and radical recombinations predominate. The study provides a complete picture of sonochemical transformation pathways of dT which has relevance in DNA damage under ultrasound exposure.

Release of superoxide from nucleoside peroxyl radicals, a double-edged sword?

5,6-Dihydrothymidin-5-yl (1) and 2'-deoxyuridin-1'-yl (3) were independently generated in solution under aerobic conditions. The release of superoxide (O2.-) from the respective peroxyl radicals derived from 1 and 3 was determined spectrophotometrically. Competition studies enable one to estimate that the rate constant for elimination of O2.- from the peroxyl radical (4) derived from 3 is ~1 s-1. This process is competitive with the anticipated rate of trapping of 4 in DNA by glutathione. Relative rate studies indicate that O2.- generation reslting from the formation of 1 under aerobic conditions competes effectively with trapping of the peroxyl radical by Bu3SnH. Superoxide elmination from the peroxyl radical of 1 (2) restores the damaged nucleoside to its unaltered form, implying that this reactive intermediate has a naturally occurring detoxification pathway available to it. However, the freely diffusible superoxide can react further to generate other reactive species capable of damaging nucleic acids, suggesting that the eliminations of O2.- from 2 is a potential double- edged sword.