22126-44-9

Basic information

• Product Name: 6-(HYDROXYMETHYL)URACIL
• Synonyms: 6-(HYDROXYMETHYL)URACIL;RARECHEM AH CK 0116;2,4(1H,3H)-Pyrimidinedione, 6-(hydroxymethyl)- (9CI);6-(Hydroxymethyl)uracil 98%;NSC 104987;NSC 253551;6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 22126-44-9
• Molecular Formula: C₅H₆N₂O₃
• Molecular Weight: 142.11
• Product Categories: PYRIMIDINE
• Mol File: 22126-44-9.mol

Chemical Properties

• Appearance: /
• Density: 1.401 g/cm³
• Refractive Index: 1.528
• PKA: 8.38±0.10(Predicted)
• CAS DataBase Reference: 6-(HYDROXYMETHYL)URACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(HYDROXYMETHYL)URACIL(22126-44-9)
• EPA Substance Registry System: 6-(HYDROXYMETHYL)URACIL(22126-44-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 22126-44-9(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
6-(HYDROXYMETHYL)URACIL is used as an antiviral agent for its ability to inhibit viral DNA synthesis, making it a potential treatment for various viral infections such as herpes and HIV.
Used in Cancer Therapy:
In the field of oncology, 6-(HYDROXYMETHYL)URACIL is used as an antitumor agent due to its potential to inactivate DNA methyltransferases, which can contribute to the suppression of tumor growth and progression.
Used in Immunomodulation:
6-(HYDROXYMETHYL)URACIL is utilized as an immunomodulatory agent for its capacity to modulate the immune response, which can be beneficial in the treatment of certain diseases and conditions.
Used in Gene Therapy:
6-(HYDROXYMETHYL)URACIL is employed as a component in gene therapy approaches, leveraging its properties to potentially influence gene expression and contribute to therapeutic outcomes.
Overall, 6-(HYDROXYMETHYL)URACIL's diverse applications reflect its potential as a versatile compound in the development of new pharmaceuticals and therapies across different medical fields.

InChI:InChI=1/C5H6N2O3/c8-2-3-1-4(9)7-5(10)6-3/h1,8H,2H2,(H2,6,7,9,10)

Upstream product

• 6153-44-2 methyl orotate 
• 65-86-1 orotic acid 
• 16953-46-1 6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde 
• 626-48-2 6-Methyluracil 
• 36327-91-0 orotoaldehyde 
• 76222-53-2 1-β-D-ribofuranosyl-6-(hydroxymethyl)uracil 
• 31555-11-0 6-hydroxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 

Downstream Products

• 73742-45-7 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione 
• 18592-13-7 6-chloromethyluracil 
• 626-48-2 6-Methyluracil 

Relevant articles and documents

UV and visible light activated TiO2 photocatalysis of 6-hydroxymethyl uracil, a model compound for the potent cyanotoxin cylindrospermopsin

TiO2 photocatalyses of 6-hydroxymethyl uracil (6-HOMU) a model compound for the potent cyanotoxin, cylindrospermopsin (CYN), were carried out employing visible and UV irradiation using different non-metal doped TiO 2 materials, nitrogen and fluorine-TiO2 (NF-TiO 2), phosphorus and fluorine-TiO2 (PF-TiO2) and sulfur-TiO2 (S-TiO2). The model compound was readily degraded under UV TiO2 photocatalysis with pseudo-first-order rate constants (k) of 2.1, 1.0, and 0.44 h-1 for NF-TiO2, PF-TiO2 and S-TiO2, respectively. Under visible light activated (VLA), NF-TiO2 was the most active photocatalyst, PF-TiO2 was marginally active and S-TiO2 inactive. VLA NF-TiO2 was effective and increased the k with increasing pH from 3 to 9. The presence of humic acid (HA), Fe3+ and Cu2+ can enhance the degradation. However, at 20 ppm HA significant inhibition was observed, likely due to shadowing of the catalyst, quenching of ROS or blocking active sites of TiO2. We probed the roles of different reactive oxygen species (ROS) using specific scavengers and the results indicate that O2- plays an important role in VLA TiO2 photocatalysis. Our results demonstrate that NF-TiO2 photocatalysis is effective under UV and visible irradiation and over a range of water qualities. VLA NF-TiO2 photocatalysis is an attractive alternative technology for the CYN contaminated water treatment.

A 6 - chloromethyl uracil synthetic method (by machine translation)

The invention discloses a 6 - chloromethyl uracil synthetic method, comprises the following steps: (1) esterification reaction: the orotic adding anhydrous in methanol, adds by drops two chlorine Asia sulphone, reaction 6 hours, to evaporate the solvent, the organic solvent is added, stirring at the room temperature, filtered, and dried to get the orotic acid methyl ester; (2) reduction reaction: the methyl orotic dissolved in methanol, added to the Lewis acid, adding sodium borohydride, stirring at room temperature for 12 - 16 hours, ice for acetic acid neutralization, to evaporate the solvent, the organic solvent is added, stirring at the room temperature, filtering, drying, be 6 - hydroxy methyl uracil; (3) chlorinated reaction: the 6 - hydroxy methyl uracil in the added to the organic solvent, by adding thionyl chloride and a catalytic amount of N, N - dimethyl formamide, reaction 2 hours, cooled to the room temperature, filtering, drying, be 6 - chloro methyl uracil. Synthesis method of the invention, avoids the use of toxic reagents, mild reaction conditions, cheap, high yield, and is favorable for industrial production. (by machine translation)

Tipiracil hydrochloride and synthesis method of intermediate 6-(chloromethyl)uracil

The invention provides a synthesis method of 6-(chloromethyl)uracil. The synthesis method comprises the steps that 6-(methyl)uracil and copper oxide perform oxidizing reaction in a solvent to obtain 6-(formyl)uracil; the 6-(formyl)uracil is reduced to obtain 6-(hydroxymethyl)uracil; the 6-(hydroxymethyl)uracil is subjected to chlorination to obtain the 6-(chloromethyl)uracil, wherein the purity of the 6-(chloromethyl)uracil is high than 99.0%. The synthesis method of the 6-(chloromethyl)uracil is optimized, selenium dioxide is replaced by low-toxicity metal oxide to achieve a 6-(formyl)uracil oxidation process, environmental friendliness is improved, and meanwhile the yield and purity of the 6-(chloromethyl)uracil are improved. The invention further provides a synthesis method of tipiracil hydrochloride. The obtained 6-(chloromethyl)uracil obtained by adopting the process is an intermediate, the tipiracil hydrochloride is directly prepared through three steps of chloro, condensing and salifying reaction, the obtained raw material drug does not need any purifying process, and the purity ishigher than 99.0%.

Fragment-based approach to the design of 5-chlorouracil-linked-pyrazolo[1, 5-a][1,3,5]triazines as thymidine phosphorylase inhibitors

5-Chlorouracil-linked-pyrazolo[1,5-a][1,3,5]triazines were designed as new thymidine phosphorylase inhibitors based on the fragment based drug design approach. Multiple-step convergent synthetic schemes were devised to generate the target compounds. The intermediate 5-chloro-6-chloromethyluracil was synthesized by a 4-step reaction. A series of the second bicyclic intermediates, namely pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-one, was obtained from various substituted 3-aminopyrazoles. These two intermediates were coupled finally in the presence of sodium ethoxide and methanol to yield the desirable target compounds. The methylthio coupling spacer was found to be suitable in enabling the interaction of the two fragments at the active site and allosteric site of the enzyme. The best coupled compound (9q) inhibited the thymidine phosphorylase with an IC50 value as low as 0.36 ± 0.1 μM. In addition, 9q demonstrated a mixed-type of enzyme inhibition kinetics, thus suggesting that it might indeed potentially bind at two different sites on the enzyme. Georg Thieme Verlag KG Stuttgart New York ISSN 0935-8943.

6-Substituted 5-fluorouracil derivatives as transition state analogue inhibitors of thymidine phosphorylase

A combination of mechanism-based and structure-based design strategies led to the synthesis of a series of 5- and 6-substituted uracil derivatives as potential inhibitors of thymidine phosphorlase/platelet derived endothelial cell growth factor (TP/PD-ECGF). Among those tested, 6-imidazolylmethyl-5- fluorouracil was found to be the most potent inhibitor with a K i-value of 51 nM, representing a new class of 5-fluoropyrimidines with a novel mechanism of action. Copyright Taylor & Francis, Inc.

SYNTHESIS OF 6-SUBSTITUTED URIDINES. SYNTHESIS OF (R OR S)-6-(3-AMINO-2-CARBOXYPROPYL)URIDINE

Addition of 5-bromo-2',3'-O-isopropylidene-5'-O-trityluridine (2) in pyridine to an excess of 2-lithio-1,3-dithiane (3) in oxolane at -78 degC gave (6R)-5,6-dihydro-(1,3-dithian-2-yl)-2',3'-O-isopropylidene-5'-O-trityluridine (4), (5S,6S)-5-bromo-5,6-dihy