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T0376

Sigma-Aldrich

Thymine

≥99%

Synonym(s):

2,4-Dihydroxy-5-methylpyrimidine, 5-Methyluracil

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O2
CAS Number:
65-71-4
Molecular Weight:
126.11
Beilstein/REAXYS Number:
117880
EC Number:
200-616-1
MDL number:
MFCD00006026
UNSPSC Code:
41106305
PubChem Substance ID:
24899883
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥99%

form

powder

mp

~320 °C (dec.) (lit.)

SMILES string

CC1=CNC(=O)NC1=O

InChI

1S/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)

InChI key

RWQNBRDOKXIBIV-UHFFFAOYSA-N

Gene Information

mouse ... Tymp(72962)

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General description

Thymine is one of the four nucleobases, along with adenine, guanine and cytosine found in deoxyribonucleic acids (DNA).

Application

Thymine has been used as a standard nitrogenous base in high-performance liquid chromatography-ultraviolet (HPLC-UV) for the quantification of bone DNA samples, Raman scattering experiments. It has also been used as supplement in C2C12 myoblast cells. Thymine may be used to study chemical processes that affect DNA structure, such a radiation induced radical production leading to base cross-linking reactions and derivitizations. It may be used to study the parameters of hydrogen bonding kinetics and energies with other nucleobases such as adenine.Thymine is used to develop sensitive heavy metal (mercury) detectors based on coordination chemistry and nanoparticle structures.

Biochem/physiol Actions

Thymine used in studying DNA structure byirradtaion methods leading to cross-linking reactions and derivitizations. Thymine dimers are indicative of DNA damage. Thymine is used with metal (mercury) to form thymine−HgII−thymine (T−HgII−T) duplexes. Thymine starvation in bacteria leads to halt in DNA synthesis and is referred as thymine-less death.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Methods for detection of cytosine and thymine modifications in DNA
Berney M and McGouran JF
Nature Reviews Chemistry, 1-1 (2018)
On How Watson and Crick Discovered what Watson and Crick had Suggested: The" Folk" Concept of Discovery Rediscovered
Charpa U
History and philosophy of the life sciences, 7-30 (2008)
Andrej Dementjev et al.
Scientific reports, 10(1), 17097-17097 (2020-10-15)
Identification of chemically homologous microcrystals in a polycrystal sample is a big challenge and requires developing specific highly sensitive tools. Second harmonic (SHG) and coherent anti-Stokes Raman scattering (CARS) spectroscopy can be used to reveal arrangement of thymine molecules, one
MercuryII-mediated formation of thymine- HgII- thymine base pairs in DNA duplexes
Miyake Y, et al.
Journal of the American Chemical Society, 128(7), 2172-2173 (2006)
Yang-Wei Lin et al.
The Analyst, 136(5), 863-871 (2010-12-16)
Monitoring the levels of potentially toxic metal (PTM) ions (e.g., Hg(2+), Pb(2+), Cu(2+)) in aquatic ecosystems is important because these ions can have severe effects on human health and the environment. Gold (Au) nanomaterials are attractive sensing materials because of
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