2-Thiobarbituric acid
Synonym(s):4,6-Dihydroxy-2-mercaptopyrimidine;4,6-Dihydroxypyrimidine-2-thiol;TBA
- CAS NO.:504-17-6
- Empirical Formula: C4H4N2O2S
- Molecular Weight: 144.15
- MDL number: MFCD00006674
- EINECS: 207-985-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2025-01-27 09:38:02
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What is 2-Thiobarbituric acid?
Chemical properties
Off-White to Yellow Powder. soluble in hot water, alcohol, ether, alkali and sodium carbonate solution, slightly soluble in water.
The Uses of 2-Thiobarbituric acid
2-Thiobarbituric acid has been used to measure malondialdehyde (MDA) in lipid peroxidation assay.
The Uses of 2-Thiobarbituric acid
4,6-Dihydroxy-2-mercaptopyrimidine can be used to quantitate lipopolysaccharides, carrageenan, and sialic acids, and to detect lipid hydroperoxides and lipid oxidation.
Definition
ChEBI: 2-thiobarbituric acid is a barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur. It has a role as a reagent and an allergen.
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.
General Description
2-Thiobarbituric acid is a molecule made up of heteroatoms: nitrogen, sulphur and oxygen.
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.]
Properties of 2-Thiobarbituric acid
Melting point: | 245 °C (dec.)(lit.) |
Density | 1.451 (estimate) |
refractive index | 1.7690 (estimate) |
storage temp. | Inert atmosphere,2-8°C |
solubility | 50g/l slightly soluble |
form | Liquid |
pka | 3.96±0.20(Predicted) |
color | Clear colorless |
PH | 1.7-1.9 (10g/l, H2O, 20℃) |
Water Solubility | <6 g/L (20 ºC) |
BRN | 120663 |
Stability: | Stable. Incompatible with strong oxidizing agents. |
CAS DataBase Reference | 504-17-6(CAS DataBase Reference) |
NIST Chemistry Reference | 4,6(1H,5h)-pyrimidinedione, dihydro-2-thioxo-(504-17-6) |
EPA Substance Registry System | 4,6(1H,5H)-Pyrimidinedione, dihydro-2-thioxo- (504-17-6) |
Safety information for 2-Thiobarbituric acid
Signal word | Warning |
Pictogram(s) |
![]() Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for 2-Thiobarbituric acid
InChIKey | RVBUGGBMJDPOST-UHFFFAOYSA-N |
2-Thiobarbituric acid manufacturer
Chemco Innovative Chemie Pvt Ltd (Chemco International)
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