504-17-6 Usage
Description
4,6-Dihydroxy-2-mercaptopyrimidine is an organic compound characterized by the presence of two hydroxyl groups and a thiol group attached to a pyrimidine ring. It is known for its versatile chemical properties and potential applications in various fields.
Uses
Used in Biochemical Analysis:
4,6-Dihydroxy-2-mercaptopyrimidine is used as a quantification agent for various biomolecules, including lipopolysaccharides, carrageenan, and sialic acids. Its unique chemical structure allows it to selectively react with these compounds, enabling accurate measurement and analysis.
Additionally, 4,6-Dihydroxy-2-mercaptopyrimidine is used as a detection agent for lipid hydroperoxides and lipid oxidation. Its reactivity with oxidized lipids makes it a valuable tool in studying oxidative stress and related processes in biological systems.
Used in Lipid Peroxidation Assays:
In the field of lipid peroxidation assays, 4,6-Dihydroxy-2-mercaptopyrimidine is used in conjunction with 2-thiobarbituric acid to measure malondialdehyde (MDA), a biomarker of lipid peroxidation. The reaction between MDA and these compounds results in a colored complex, allowing for the quantification of MDA levels and assessment of oxidative stress in biological samples.
Overall, 4,6-Dihydroxy-2-mercaptopyrimidine is a versatile compound with applications in biochemical analysis and lipid peroxidation assays, making it a valuable tool for researchers in various scientific disciplines.
Preparation
2-thiobarbituric acid was synthesized by the reaction of diethyl malonate with thiourea. Dissolve thiourea in methanol, add sodium methoxide and diethyl malonate, heat under reflux for 4-5h, then distill under reduced pressure to recover methanol to the end, and add hydrochloric acid to acidify to pH 1-2 after cooling. After standing overnight, thiobarbituric acid crystals were precipitated, filtered, and recrystallized with water to obtain the pure product.
Biochem/physiol Actions
2-Thiobarbituric acid (TBA) is useful to quantitate lipopolysaccharides, carrageenan, and sialic acids. It is also used to detect lipid hydroperoxides and lipid oxidation. It has applications in the field of medicine and biochemistry. TBA may possess the ability to prevent metal corrosion.
Purification Methods
Crystallise it from water. [Beilstein 24 H 476, 24 I 414, 24 II 275, 24 III/IV 1884.]
Check Digit Verification of cas no
The CAS Registry Mumber 504-17-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 4 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 504-17:
(5*5)+(4*0)+(3*4)+(2*1)+(1*7)=46
46 % 10 = 6
So 504-17-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H4N2O2S/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
504-17-6Relevant articles and documents
Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives
Bayramo?lu, Duygu,Kurtay, Gülbin,Güllü, Mustafa
, p. 649 - 658 (2020/02/11)
Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (~30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies.
Synthesis, spectroscopic characterization, computational exploration of 6-(2-(2, 4-dinitrophenylhydrazano)-tetrahydro-2-thioxopyrimidin-4(1h)-one
Kalaiarasi,Manivarman
, p. 304 - 317 (2017/03/17)
The structural and vibrational properties of 6-(2-(2,4-dinitrophenylhydrazano)-tetrahydro-2-thioxopyrimidin-4(1H)-one (3) prepared by condensation of synthesized thiobarbituric acid (1) with 2,4-dinitrophenylhydrazine (2) were studied using experimental F
Synthesis, characterization, solvatochromic properties, and antimicrobial evaluation of 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione-based chalcones
Dhorajiya, Bhaveshkumar D.,Bhakhar, Bhimji S.,Dholakiya, Bharatkumar Z.
, p. 4075 - 4086 (2013/09/02)
A new series of chalcone analogs namely 5-(3-phenyl-acryloyl)-2-thioxo- dihydro-pyrimidine-4,6-dione have been synthesized from the key intermediate 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione 4′ with different aldehyde derivatives were performed to get the target compounds as thiobarbituric acid-based chalcones 5(a′-k′) and they were obtained in excellent yields. The newly synthesized compounds were characterized by spectral analysis (FT-IR, 1H NMR, 13C NMR, and UV spectroscopy) and elemental analysis. The synthesized compounds were evaluated for their antimicrobial activity against five bacterial strains (S. aureus, S. pyogenes, E. coli, K. pneumoniae, and P. aeruginosa) and four fungal strains (C. albicans, A. clavatus, T. rubrum, and Penicillium wild strain). Among the screened compounds, 5e′ and f′ showed comparable activity (minimum inhibitory concentration = 500 μg/mL) nearly to that of standard antibiotics griseofulvin.