Category:information only not used for fragrances or flavors
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Assay: | 95.00 to 100.00
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Food Chemicals Codex Listed: | No |
Soluble in: |
| water, 1.86e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
Not determined
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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Safety in Use Information:
Category: | information only not used for fragrances or flavors |
Recommendation for 5,6-dihydrouracil usage levels up to: | | not for fragrance use.
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Recommendation for 5,6-dihydrouracil flavor usage levels up to: |
| not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
1,3- | diazinane-2,4-dione | | hexahydropyrimidine-2,4-dione | 2,4(1H,3H)- | pyrimidinedione, dihydro- |
Articles:
PubMed:Development, validation and application of a novel liquid chromatography tandem mass spectrometry assay measuring uracil, 5,6-dihydrouracil, 5-fluorouracil, 5,6-dihydro-5-fluorouracil, α-fluoro-β-ureidopropionic acid and α-fluoro-β-alanine in human plasma. |
PubMed:Probing the activity of NTHL1 orthologs by targeting conserved amino acid residues. |
PubMed:Solvation of Uracil and Its Derivatives by DMSO: A DFT-Supported (1)H NMR and (13)C NMR Study. |
PubMed:Base Release and Modification in Solid-Phase DNA Exposed to Low-Energy Electrons. |
PubMed:Conformational Dynamics of DNA Repair by Escherichia coli Endonuclease III. |
PubMed:Metabolomic markers of altered nucleotide metabolism in early stage adenocarcinoma. |
PubMed:Effect of agronomical practices on carpology, fruit and oil composition, and oil sensory properties, in olive (Olea europaea L.). |
PubMed:Communication: Electronic UV-Vis transient spectra of the ∙OH reaction products of uracil, thymine, cytosine, and 5,6-dihydrouracil by using the complete active space self-consistent field second-order perturbation (CASPT2//CASSCF) theory. |
PubMed:Is uracil aromatic? The enthalpies of hydrogenation in the gaseous and crystalline phases, and in aqueous solution, as tools to obtain an answer. |
PubMed:Gender-specific elimination of continuous-infusional 5-fluorouracil in patients with gastrointestinal malignancies: results from a prospective population pharmacokinetic study. |
PubMed:Novel amidases of two Aminobacter sp. strains: Biotransformation experiments and elucidation of gene sequences. |
PubMed:Profiling cytosine oxidation in DNA by LC-MS/MS. |
PubMed:Validation of an ultra-high performance liquid chromatography tandem mass spectrometric method for quantifying uracil and 5,6-dihydrouracil in human plasma. |
PubMed:Yields of damage to C4' deoxyribose and to pyrimidines in pUC18 by the direct effect of ionizing radiation. |
PubMed:LC-MS/MS method for simultaneous analysis of uracil, 5,6-dihydrouracil, 5-fluorouracil and 5-fluoro-5,6-dihydrouracil in human plasma for therapeutic drug monitoring and toxicity prediction in cancer patients. |
PubMed:Stereoselective hydrolysis of aryl-substituted dihydropyrimidines by hydantoinases. |
PubMed:Opened-ring adducts of 5-methylcytosine and 1,5-dimethylcytosine with amines and water and evidence for an opened-ring hydrate of 2'-deoxycytidine. |
PubMed:Time-dependent pharmacokinetics of 5-fluorouracil and association with treatment tolerability in the adjuvant setting of colorectal cancer. |
PubMed:Escherichia coli dihydropyrimidine dehydrogenase is a novel NAD-dependent heterotetramer essential for the production of 5,6-dihydrouracil. |
PubMed:The photochemistry of uracil: a reinvestigation. |
PubMed:A (6-4) photoproduct of 5-bromouracil. |
PubMed:Crystallization and preliminary X-ray analysis of human endonuclease 1 (APE1) in complex with an oligonucleotide containing a 5,6-dihydrouracil (DHU) or an alpha-anomeric 2'-deoxyadenosine (alphadA) modified base. |
PubMed:Dihydropyrimidinase deficiency: Phenotype, genotype and structural consequences in 17 patients. |
PubMed:Hydrolytic deamination of 5,6-dihydrocytosine in a protic medium: a theoretical study. |
PubMed:The oxidative DNA glycosylases of Mycobacterium tuberculosis exhibit different substrate preferences from their Escherichia coli counterparts. |
PubMed:Heavy metal ions affect the activity of DNA glycosylases of the fpg family. |
PubMed:Coupling of the nucleotide incision and 3'-->5' exonuclease activities in Escherichia coli endonuclease IV: Structural and genetic evidences. |
PubMed:Reaction of cytosine with bisulfite and hydroxylamine. |
PubMed:Metal-triggered changes in the stability and secondary structure of a tetrameric dihydropyrimidinase: a biophysical characterization. |
PubMed:X-ray crystallographic identification of bisulfite-uracil adduct as sodium 5,6-dihydrouracil 6-sulfonate. |
PubMed:[Interactions of human ribosomal protein S3 with undamaged and damaged DNA]. |
PubMed:5-fluorouracil pharmacokinetics predicts disease-free survival in patients administered adjuvant chemotherapy for colorectal cancer. |
PubMed:[Pro or con the phenotyping/genotyping of patients treated by 5-Fluorouracil to prevent adverse drug reactions?]. |
PubMed:Clinical, biochemical and genetic findings in two siblings with a dihydropyrimidinase deficiency. |
PubMed:Crystallization and preliminary crystallographic studies of the recombinant dihydropyrimidinase from Sinorhizobium meliloti CECT4114. |
PubMed:A pharmacokinetic-based test to prevent severe 5-fluorouracil toxicity. |
PubMed:Catalytic mechanism of Escherichia coli endonuclease VIII: roles of the intercalation loop and the zinc finger. |
PubMed:Liquid chromatography-tandem mass spectrometric assay for the analysis of uracil, 5,6-dihydrouracil and beta-ureidopropionic acid in urine for the measurement of the activities of the pyrimidine catabolic enzymes. |
PubMed:Purification, crystallization and X-ray diffraction analysis of dihydropyrimidinase from Dictyostelium discoideum. |
PubMed:Crystallization and X-ray diffraction analysis of dihydropyrimidinase from Saccharomyces kluyveri. |
PubMed:Physiologically based pharmacokinetic modelling of the three-step metabolism of pyrimidine using C-uracil as an in vivo probe. |
PubMed:Feasibility of measuring 5-fluorouracil catabolic potential by oral loading. |
PubMed:A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. |
PubMed:Improved analysis of 5-Fluorouracil and 5,6-dihydro-5-Fluorouracil by HPLC with diode array detection for determination of cellular dihydropyrimidine dehydrogenase activity and pharmacokinetic profiling. |
PubMed:5-Fluorouracil catabolism to 5-fluoro-5,6-dihydrouracil is reduced by acute liver impairment in mice. |
PubMed:Mouse NEIL1 protein is specific for excision of 2,6-diamino-4-hydroxy-5-formamidopyrimidine and 4,6-diamino-5-formamidopyrimidine from oxidatively damaged DNA. |
PubMed:Plasma concentrations of 5-fluorouracil and its metabolites in colon cancer patients. |
PubMed:[Assay method for uracil, dihydrouracil, 5-fluorouracil and 5-fluoro-5, 6-dihydrouracil by high-performance liquid chromatography]. |
PubMed:Quantification of 5,6-dihydrouracil by HPLC-electrospray tandem mass spectrometry. |
PubMed:Orchestration of base excision repair by controlling the rates of enzymatic activities. |
PubMed:Synthesis and anti-HIV-1 activity of novel 10-thiaisoalloxazines, a structural analog of C-5 and/or C-6 substituted pyrimidine acyclonucleoside. |
PubMed:Crystallization and preliminary X-ray diffraction analysis of thermophilic imidase from pig liver. |
PubMed:The novel DNA glycosylase, NEIL1, protects mammalian cells from radiation-mediated cell death. |
PubMed:Severe 5-fluorouracil toxicity associated with a marked alteration of pharmacokinetics of 5-fluorouracil and its catabolite 5-fluoro-5,6-dihydrouracil: a case report. |
PubMed:Chalcone isomerase gene from rice (Oryza sativa) and barley (Hordeum vulgare): physical, genetic and mutation mapping. |
PubMed:Limited sampling model for the analysis of 5-fluorouracil pharmacokinetics in adjuvant chemotherapy for colorectal cancer. |
PubMed:Repair of dihydrouracil supported by base excision repair in mNTH1 knock-out cell extracts. |
PubMed:Relationship between plasma concentrations of 5-fluorouracil and 5-fluoro-5,6-dihydrouracil and toxicity of 5-fluorouracil infusions in cancer patients. |
PubMed:Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. |
PubMed:Identification and characterization of a novel human DNA glycosylase for repair of cytosine-derived lesions. |
PubMed:Porous graphitic carbon shows promise for the rapid screening partial DPD deficiency in lymphocyte dihydropyrimidine dehydrogenase in Chinese, Indian and Malay in Singapore by using semi-automated HPLC-radioassay. |
PubMed:Alternative nucleotide incision repair pathway for oxidative DNA damage. |
PubMed:DNA polymerase beta is the major dRP lyase involved in repair of oxidative base lesions in DNA by mammalian cell extracts. |
PubMed:Unique misinsertion specificity of poliota may decrease the mutagenic potential of deaminated cytosines. |
PubMed:Relationship between 5-fluorouracil disposition, toxicity and dihydropyrimidine dehydrogenase activity in cancer patients. |
PubMed:Determination of pH using water protons and chemical exchange dependent saturation transfer (CEST). |
PubMed:Comparative pharmacokinetic analysis of 5-fluorouracil and its major metabolite 5-fluoro-5,6-dihydrouracil after conventional and reduced test dose in cancer patients. |
PubMed:Mechanism-based inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil in the presence of NADPH. |
PubMed:alpha-fluoro-beta-alanine: effects on the antitumor activity and toxicity of 5-fluorouracil. |
PubMed:Radiochemical assay for determination of dihydropyrimidinase activity using reversed-phase high-performance liquid chromatography. |
PubMed:Purification, characterization, gene cloning, and expression of Saccharomyces cerevisiae redoxyendonuclease, a homolog of Escherichia coli endonuclease III. |
PubMed:Direct effects of gamma-radiation on 2'-deoxycytidine in frozen aqueous solution. |
PubMed:Properties of D-hydantoinase from Agrobacterium tumefaciens and its use for the preparation of N-carbamyl D-amino acids. |
PubMed:Reaction of bromotrichloromethane derived free radicals with uracil in a model system. Structures of products formed. |
PubMed:Formation of 5-hydroxy-5,6-dihydrouracil and release of undamaged uracil as a result of poly(U) irradiation in N2O-saturated aqueous solution. |
PubMed:Purification and cloning of Micrococcus luteus ultraviolet endonuclease, an N-glycosylase/abasic lyase that proceeds via an imino enzyme-DNA intermediate. |
PubMed:Attenuation of the antitumor activity of 5-fluorouracil by (R)-5-fluoro-5,6-dihydrouracil. |
PubMed:Dehalogenating and NADPH-modifying activities of dihydropyrimidine dehydrogenase. |
PubMed:(R)-5-fluoro-5,6-dihydrouracil: kinetics of oxidation by dihydropyrimidine dehydrogenase and hydrolysis by dihydropyrimidine aminohydrolase. |
PubMed:Determination of the concentrations of 5-fluorouracil and its metabolites in rabbit plasma and tissues by high-performance liquid chromatography. |
PubMed:Purification, characterization and inhibition of dihydropyrimidinase from rat liver. |
PubMed:Substrate specificity of the Escherichia coli endonuclease III: excision of thymine- and cytosine-derived lesions in DNA produced by radiation-generated free radicals. |
PubMed:Dihydropyrimidine dehydrogenase. Kinetic mechanism for reduction of uracil by NADPH. |
PubMed:Acid-base catalytic mechanism of dihydropyrimidinase from pH studies. |
PubMed:Detection of new metabolites of trifluridine (F3TdR) using 19F NMR spectroscopy. |
PubMed:Stereochemistry of NADPH oxidation by dihydropyrimidine dehydrogenase from pig liver. |
PubMed:Inactivation of dihydropyrimidine dehydrogenase by 5-iodouracil. |
PubMed:Formation and stability of repairable pyrimidine photohydrates in DNA. |
PubMed:Pulmonary elimination and metabolism of 5-fluoro-2'-deoxyuridine in isolated perfused rat lung and lung slices. |
PubMed:UV-induced pyrimidine hydrates in DNA are repaired by bacterial and mammalian DNA glycosylase activities. |
PubMed:Purification and properties of 5,6-dihydropyrimidine amidohydrolase from calf liver. |
PubMed:Nicotinamide and selenium stimulate the repair of DNA damage produced by N-nitrosobis (2-oxopropyl) amine. |
PubMed:Induction of hyperplastic liver nodules in Wistar and MRC-Wistar rats by phenobarbital and the liver carcinogens acetoxime, 1-nitroso-5,6-dihydrouracil and 3-nitroso-2-oxazolidinone. |
PubMed:Radiation chemistry of 2'-deoxycytidylyl-(3'-5')-2'-deoxyguanosine and its sequence isomer in N2O- and O2-saturated solutions. |
PubMed:Bovine liver dihydropyrimidine amidohydrolase: pH dependencies of the steady-state kinetic and proton relaxation rate properties of the Mn(II)-containing enzyme. |
PubMed:In vitro and in vivo formation of 7-(2'-carboxyethyl)guanine from the liver carcinogen 1-nitroso-5,6-dihydrouracil and its reactions with water and methanol. |
PubMed:Persistence of DNA single-strand breaks and other tests as indicators of the liver carcinogenicity of 1-nitroso-5,6-dihydrouracil and the noncarcinogenicity of 1-nitroso-5,6-dihydrothymine. |
PubMed:[Infrared spectra of uracil and thymine in an argon matrix]. |
PubMed:Isolation and characterization of two 5-fluorouracil-substituted Escherichia coli initiator methionine transfer ribonucleic acids. |
PubMed:Specific effects of 5-fluoropyrimidines and 5-azapyrimidines on modification of the 5 position of pyrimidines, in particular the synthesis of 5-methyluracil and 5-methylcytosine in nucleic acids. |
PubMed:N-Alkylated derivatives of 5-fluorouracil. |
PubMed:Carcinogenicity test of six nitrosamides and a nitrosocyanamide administered orally to rats. |
PubMed:GABA transaminase provides an alternative route of beta-alanine synthesis in Aspergillus nidulans. |
PubMed:Synthesis of uracil and thymine under simulated prebiotic conditions. |
PubMed:Role of enzymatically catalyzed 5-iodo-5,6-dihydrouracil ring hydrolysis on the dehalogenation of 5-iodouracil. |
PubMed:Histology of chemically induced mesotheliomas in MRC-Wistar rats. |
PubMed:Structure and stereochemistry of nucleic acid components and their reaction products. II. Crystal and molecular structure of a product obtained in the reaction of isocyanates with uracil (N1-(N-methylcarbamoyl)-N3-methyl-5,6-dihydrouracil). |
PubMed:Induction by an hepatic carcinogen, 1-nitroso-5,6-dihydrouracil, of single and double strand breaks of liver DNA with rapid repair. |
PubMed:6 Beta-hydroxylation of triamcinolone acetonide by a hepatic enzyme system. The effect of phenobarbital and 1-benzyl-2-thio-5,6-dihydrouracil. |
PubMed:5,6-dihydrouracil: its occurrence and metabolism in rat brain. |
PubMed:Effect of 1-benzyl-2-thio-5,6-dihydrouracil on hepatic metabolic activity in the rat. |
PubMed:The occurrence and source of beta-alanine in alkaline hydrolysates of sRNA: a sensitive method for the detection and assay of 5,6-dihydrouracil residues in RNA. |
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An intermediate breakdown product of uracil. Dihydropyrimidine dehydrogenase catalyzes the reduction of uracil to 5, 6-dihydrouracil then dihydropyrimidinase hydrolyzes 5, 6-dihydrouracil to N-carbamyl-b-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-b-alanine to beta-alanine. Patients with dihydropyrimidinase deficiency (DPYS; also called 5, 6-dihydropyrimidine amidohydrolase, or DHP; EC 3.5.2.2) exhibit highly increased concentrations of 5, 6-dihydrouracil in urine. The direct measurement of the activity of DHP in patients had been hampered by the fact that the enzyme is expressed almost exclusively in liver tissue. Various neurological abnormalities have been described in this group of patients. (OMIM 222748) [HMDB]
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