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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:
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| Odor and/or flavor descriptions from others (if found). |
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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: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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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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