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

Description

5,6-Dihydrothymidine, also known as thymidine, is a pyrimidine 2'-deoxyribonucleoside with dihydrothymine as the nucleobase. It is one of the most important products of base damage by gamma irradiation of DNA in anoxic conditions. This molecule plays a crucial role in DNA repair and has potential applications in various fields due to its unique properties.

Uses

Used in Medical Research:
5,6-Dihydrothymidine is used as a biomarker for [detecting DNA damage caused by gamma irradiation in anoxic conditions] because it is one of the most important products of base damage in such scenarios. This application is significant for understanding the effects of radiation on DNA and developing strategies for radiation protection and DNA repair.
Used in Cancer Therapy:
5,6-Dihydrothymidine is used as a therapeutic agent for [targeting cancer cells with damaged DNA] as it can potentially interfere with the DNA repair mechanisms in cancer cells, making them more susceptible to the effects of radiation therapy. This application aims to enhance the efficacy of cancer treatments and improve patient outcomes.
Used in Pharmaceutical Industry:
5,6-Dihydrothymidine is used as a key component in [developing new drugs targeting DNA repair pathways] due to its involvement in DNA repair processes. This application can lead to the development of novel therapeutic strategies for various diseases, including cancer, by exploiting the vulnerabilities of cells with compromised DNA repair mechanisms.
Used in Radiation Protection:
5,6-Dihydrothymidine is used as a protective agent for [reducing the harmful effects of radiation exposure] by potentially modulating the DNA repair process and mitigating the damage caused by gamma irradiation in anoxic conditions. This application is important for the development of radiation countermeasures and protective measures for individuals exposed to high levels of radiation, such as medical professionals, astronauts, and military personnel.
Used in Diagnostics:
5,6-Dihydrothymidine is used as a diagnostic tool for [assessing the extent of DNA damage in various conditions], including radiation exposure, oxidative stress, and other genotoxic agents. This application can help in the early detection of DNA damage and the development of personalized treatment strategies based on the individual's DNA repair capacity and susceptibility to damage.

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

Downstream Products

• 1072452-75-5 5'-O-tert-butyldiphenylsilyl-5,6-dihydrothymidine 
• 1334214-53-7 C₃₈H₆₂N₂O₆Si₃ 
• 1334214-60-6 C₃₂H₄₈N₂O₅Si₂ 
• 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 
• 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 
• 187979-88-0 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 
• 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 
• 187979-93-7 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 
• 187979-94-8 5-Benzoyl-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-dihydro-pyrimidine-2,4-dione 
• 1334176-56-5 C₆₆H₉₄N₄O₁₂SSi₃ 
• 1334176-55-4 C₆₄H₉₀N₄O₁₂Si₃ 
• 1334176-54-3 C₄₈H₇₂N₄O₁₂Si₂ 
• 1334176-62-3 C₆₀H₁₀₀N₄O₁₂Si₄ 
• 1334176-61-2 C₆₀H₁₀₀N₄O₁₂Si₄ 

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.