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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.

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  • 5627-00-9 Structure
  • Basic information

    1. Product Name: 5,6-DIHYDROTHYMIDINE
    2. 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
    3. CAS NO:5627-00-9
    4. Molecular Formula: C10H16N2O5
    5. Molecular Weight: 244.24
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 5627-00-9.mol
    9. Article Data: 4
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.391 g/cm3
    6. Refractive Index: 1.553
    7. Storage Temp.: −20°C
    8. Solubility: N/A
    9. CAS DataBase Reference: 5,6-DIHYDROTHYMIDINE(CAS DataBase Reference)
    10. NIST Chemistry Reference: 5,6-DIHYDROTHYMIDINE(5627-00-9)
    11. EPA Substance Registry System: 5,6-DIHYDROTHYMIDINE(5627-00-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5627-00-9(Hazardous Substances Data)

5627-00-9 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 5627-00-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,6,2 and 7 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5627-00:
(6*5)+(5*6)+(4*2)+(3*7)+(2*0)+(1*0)=89
89 % 10 = 9
So 5627-00-9 is a valid CAS Registry Number.
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

5627-00-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 5,6-DIHYDROTHYMIDINE

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5627-00-9 SDS

5627-00-9Relevant articles and documents

Sonochemical transformation of thymidine: A mass spectrometric study

Chandran, Jisha,Aravind, Usha K.,Aravindakumar

, p. 178 - 186 (2015/06/02)

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.

Synthesis and stereochemical assignment of DNA spore photoproduct analogues

Friedel, Marcus G.,Pieck, J. Carsten,Klages, Jochen,Dauth, Christina,Kessler, Horst,Carell, Thomas

, p. 6081 - 6094 (2007/10/03)

Investigation of the DNA repair process performed by the spore photoproduct (SP) lyase repair enzyme is strongly hampered by the lack of defined substrates needed for detailed enzymatic studies. The problem is particularly severe because the repair enzyme belongs to the class of strongly oxygen-sensitive radical (S)-adenosyl-methionine (SAM) enzymes, which are notoriously difficult to handle. We report the synthesis of the spore photoproduct analogues 1a and 1b, which have open backbones and are diastereoisomers. In order to solve the problem of stereochemical assignment, two further derivatives 2a and 2b with closed backbones were prepared. The key step of the synthesis of 2a/b is a metathesis-based macrocyclization that strongly increases the conformational rigidity of the synthetic spore photoproduct derivatives. NOESY experiments of the cyclic isomers furnished a clear cross-peak pattern that allowed the unequivocal assignment of the stereochemistry. The results were transfer red to the data for isomers 1a and 1b, which were subsequently used for enzymatic-repair studies. These studies were performed with the novel spore photoproduct lyase repair enzyme from Geobacillus stearothermophilus. The studies showed an accordance with a recent investigation performed by us with the spore photoproduct lyase from Bacillus subtilis,[1] in that only the 5 isomer la is recognized and repaired. The ability to prepare a defined functioning substrate now paves the way for detailed enzymatic studies of the SP-lyase lesion recognition and repair process.

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

Tallman, Keri A.,Tronche, Christopher,Yoo, Dong Jin,Greenberg, Marc M.

, p. 4903 - 4909 (2007/10/03)

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.

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

Cadet, J.,Voituriez, L.,Berger, M.,Myers, L. S., (Jr.)

, p. 1643 - 1651 (2007/10/02)

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

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