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65-86-1

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65-86-1 Usage

General Description

Different sources of media describe the General Description of 65-86-1 differently. You can refer to the following data:
1. Orotic acid (also known as pyrimidinecarboxylic acid) is a heterocyclic acid; it is also known as. Historically it was believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin. It is well known as a precursor in biosynthesis of pyrimidines; in mammals it is released from the mitochondrial dihydroorotate dehydrogenase (DHODH) for conversion to UMP by the cytoplasmic UMP synthase enzyme[1]. OA is also a normal part of the diet, being found in milk and dairy products[5], and it is converted to uridine for use in the pyrimidine salvage pathway predominantly in liver, kidney and erythrocytes. Before its essential role as an intermediate of pyrimidine biosynthesis was established in the 1950s[3], the compound OA was discovered in whey (Greek oros) by Biscaro and Belloni (1905)[4]. Since then it has received attention from several different aspects. For example, it is proposed that the dietary orotate is beneficial for animals and humans obviously arose from its considerable natural amounts in milk and dairy products[5]. In addition, it also draw great attention from its medical potentials such as improvement of learning behavior of adult rats, neuro-protective effect for gerbils and cats under transient cerebral ischemia, and optimization of functions in normal and ischemic rat hearts[6-9].
2. White crystals or crystalline powder.

Metabolism

Orotate [orotic acid, OA] is the product of dihydroorotate dehydrogenase [DHODH], the fourth enzyme of pyrimidine [UMP] de novo synthesis [Fig. 1]. It is abundant in the serum and particularly urine of patients suffering from hereditary orotic academia or from enzyme defects in the urea cycle[10]. The sequence of six chemical reactions of UMP de novo synthesis is conserved from microorganisms to humans [Figure 1], although the organization of enzymes involved is different in eukaryotes[11-13]. In mammals, the six enzymes are coded by only three genes. The tri-functional CAD enzyme and the bifunctional UMP synthase each contain their appropriate catalytic activities on one polypeptide chain. The product of the third gene, dihydroorotate dehydrogenase [DHODH] holds a mitochondrial targeting sequence and a transmembrane domain at the N-terminus, which enable the enzyme to find its place in the inner mitochondrial membrane[14]. Through its electron acceptor, ubiquinone, DHODH is functionally united with the respiratory chain and can contribute to energy conservation in mitochondria. In turn, the formation of orotic acid [OA] by mitochondria, and hence the de novo synthesis of UMP, is strictly aerobic. In growth processes OA can be considered as a metabolic link between environmental oxygen tension and the proliferative capacity of cells[15].

Applications

Overview Orotic Acid is used in the preparation of therapeutic agents for chronic obstructive pulmonary disease [COPD] treatment[16]. As it is an intermediate in de novo pyrimidine biosynthesis, it may be used to study the specificity and kinetics of orotate phosphoribosyltransferase [OPRT] which catalyzes the reversible phosphoribosyl transfer from 5′-phospho-α-d-ribose 1′-diphosphate [PRPP] to orotic acid [OA], forming pyrophosphate and orotidine 5′-monophosphate [OMP][17]. Orotic acid can also be used as a starting material for the potential commercial bio-production of uridine 5′-monophosphate [UMP] by microbes such as Corynebacterium ammoniagenes [ATCC 6872] or Saccharomyces cerevisiae. Moreover, it may be used to study the AMPK/SREBP-1 dependent cell-signaling pathway and transcription regulation mechanisms associated with the induction hepatic lipogenesis[17]. Medical aspects OA has strong pharmacological potentials. The improvement of learning behavior of adult rats, neuro-protective effect for gerbils and cats under transient cerebral ischemia, and optimization of functions in normal and ischemic rat hearts were generally assigned to the precursor role of OA in cells for pyrimidine nucleotides and RNA[6-9]. The development of complexes and salts with metal ions [Mg2+, Zn2+, Ca2+, K+] and organic cations [e.g. choline, carnitine] exploited the favorable carrier function of OA for transportation and delivery of these ligands in living organisms to compensate deficiency syndromes[5]. Likewise, the construction of platinum, palladium and tin coordination compounds with OA for administration in cancer chemotherapy followed this principle[18]. The positive impact of OA preparations claimed for humans are highlighted by promises given in the public domain, such as beneficial cardiovascular effects, energy provision, improvement of body composition, and enhanced athletic performance. Study has also shown that OA may lower the serum cholesterol and lipid[19-21]. Orotic acid also has strong uricosuric effect, originating from its role as a true transport substrate for the anion exchangerURAT1 [encoded by human SLC22A12 gene] located at the luminal site of the tubule cells[22]. Dietary aspects The assumption that dietary orotate is beneficial for animals and humans obviously arose from its considerable natural amounts in milk and dairy products[5]. In the 1970s OA was proposed to increase the UDP-glucuronate pool for hepatic detoxification of bilirubin in the treatment of neonatal jaundice[5]. Another, underestimated, benefit of OA in the diet of newborns may be the establishment of the anaerobic OA-degrading intestinal microflora. Overall, it has strong potential to become a growth-enhancer for livestock. Central Nervous systems OA’s benefit for the brain, mentioned earlier, deserves closer attention. It can be assumed that a continuous supply of pyrimidine nucleotides is essential not only for the developing central nervous system[23], but equally for its plasticity, regeneration and neurotransmission: for example, some metabotropic P2Y receptor subtypes are sensitive to uridine nucleotides[24]. OA has putative protective and improvement effects of pyrimidine nucleotide pools, RNA synthesis, receptor saturation, repairing of ischeamia-induced membrane damage, which is explained by the function of OA as an intermediate in de novo UMP synthesis[25, 26]. Research field OA had became a compound of considerable interest as a tool for studying pyrimidine metabolism in cells, tissues and animals: monitoring precursors, nucleotide pools and the rate of RNA synthesis, differentiating between de novo and salvage/recycling pathways, searching for antimetabolites and anticancer drugs[27, 29]. Concurrently, the growth-promoting features of OA were still of interest, and OA was used on animals and humans, with various biochemical rationales, assumptions and expectations[28, 30]. When OA was an additive to pharmaceutical preparations, its benefits were attributed to its being an intermediate of pyrimidine biosynthesis and therefore augmenting uridine nucleotide pools which are required for nucleic acid synthesis and for all pyrimidine nucleotide dependent biosynthetic processes[31, 32].

References

https://www.springer.com/us/book/9780852002940 L?ffler, M.; Carrey E.; Zameitat, E. Orotic acid, more than just an intermediate of pyrimidine de novo synthesis, J. Genet. Genomics 2015, 42, 207–219. Reichard P.; Lagerkvist, U. The biogenesis of orotic acid in liver slices, Acta Chem. Scand. 1953, 7, 1207–1217. Biscaro, G.; Belloni E. About a new compound of the milk, Annuario della Soc. Chimica di Milano 1905, 11, 15. L?ffler, M.; Carrey E.; Zameitat, E. Orotic acid,more than just an intermediate of pyrimidine de novo synthesis, J. Genet. Genomics 2015, 42, 207–219. Ru?thrich, H.; Wetzel, W.; Matthies, H. Postnatal orotate treatment: effects on learning and memory in adult rats, Psychopharmacology 1979, 63, 25–28. Krug, M.; Koch, M.; Schoof, E.; Wagner, M.; Matthies, H. Methylglucamine orotate, a memory-improving drug, prolongs hippocampal long-term potentiation, Eur. J. Pharmacol. 1989, 173, 223–226. Akiho, H.; Iwai, A.; Katoh-Sudoh,M.; Tsukamoto, S.; Koshiya, K.; Yamaguchi, T. Neuroprotective effect of Y-39558, orotic acid ethylester, in gerbil forebrain ischemia, Jpn. J. Pharmacol. 1998, 76, 441–444. Vilskersts, R.; Liepinsh, E.; Kuka, J.; Cirule, H.; Veveris, M.; Kalvinsh, I.; Dambrova, M. Myocardial infarct size-limiting and anti-arrhythmic effects of mildronate orotate in the rat heart, Cardiovasc. Drug Ther. 2009, 21, 281–288. Webster, D.R., Becroft, D.M., van Gennip, A.H., van Kuilenburg, A.B.P., 2001. Hereditary orotic aciduria and other disorders of pyrimidine metabolism. In: Scriver, C.R., Beaudet, A.L., Sly,W.S., Valle, D. [Eds.], The Metabolic and Molecular Bases of Inherited Disease, Vol. II. Medical Publishing Division, McGraw-Hill, New York, USA, pp. 2663e2702. Jones, M.E. Pyrimidine nucleotide biosynthesis in animals: genes, enzymes, and regulation of UMP biosynthesis, Ann. Rev. Biochem. 1980, 49, 253–279. Evans, D.R.; Guy, H.I. Mammalian pyrimidine biosynthesis: fresh insights into an ancient pathway, J. Biol. Chem. 2004, 279, 33035–33038. L?fflerM.; Zameitat, E.. Pyrimidine biosynthesis and degradation [catabolism] in The Encyclopedia of Biological Chemistry, eds. W.J. Lennarz; M.D. Lane, Academic Press, Waltham, 2013, Vol III, pp. 712–718. Rawls, J.; Knecht, W.; Diekert, K.; Lill, R.; L?ffler, M. Requirements for the mitochondrial import and localization of dihydroorotate dehydrogenase, Eur. J. Biochem. 2000, 267, 2079– 2087. L?ffler, M.; Carrey, E.A.; Zameitat, E. Essential role of mitochondria in pyrimidine metabolism, in Tumor Cell Metabolism: Pathways, Regulation and Biology, eds. S. Mazurek; S. Shoshan, Springer,Wien, Austria, 2015, pp. 287–312 https://www.trc-canada.com/product-detail/?CatNum=O691500&CAS=50887-69-9%20&Chemical_Name=Orotic%20Acid%20Monohydrate&Mol_Formula=C?H?N?O??H?O https://www.sigmaaldrich.com/catalog/product/sigma/o2750?lang=en®ion=US Nath, M.; Vats, M.; Roy, P. Tri- and diorganotin[IV] complexes of biologically important orotic acid: synthesis, spectroscopic studies, in vitro anti-cancer, DNA fragmentation, enzyme assays and in vivo anti-inflammatory activities, Eur. J. Med. Chem. 2013, 9, 310–321. Kelley,W.N.; Greene,M.L.; Fox, I.H.; Rosenbloom, F.M.; Levy R.I.; Seegmiller, J.E. Effects of orotic acid on purine and lipoprotein metabolism in man, Metabolism 1979, 19, 1025–1035. Robinson, J.L.; Dombrowski, D.B. Effects of orotic acid ingestion on urinary and blood parameters in humans, Nutr. Res. 1983, 3, 407–415. Robinson, J.K.;Dombrowski,D.B.; Tauss, L.R.; Jones, L.R.Assessment in humans of hypolipidemia induced by orotic acid, Am. J. Clin.Nutr. 1985, 41, 605–608. Miura,D.;Anzai,N.; Jutabha, P.; Chanluang, S.;He, X.; Toshiyuki, F.; Endou,H.Human urate transporter 1 [hURAT1] mediates the transport of orotate, J. Physiol. Sci. 2011, 61, 253–257. Connolly, G.P., Duley, J.A., 1999. Uridine and its nucleotides: biological actions, therapeutic potentials. Trends Pharmacol. Sci. 20, 218e225. Von Ku¨gelen, I., 2006. Pharmacological profiles of cloned mammalian P2Yreceptor subtypes. Pharmacol. Therapeut. 110, 414e432. Akiho, H., Iwai, A., Katoh-Sudoh, M., Tsukamoto, S., Koshiya, K., Yamaguchi, T., 1997. Post-ischaemic treatment with orotic acid prevented neuronal injury in gerbil brain ischaemia. Neuroreport 8, 607e610. Akiho, H., Iwai, A., Katoh-Sudoh, M., Tsukamoto, S., Koshiya, K., Yamaguchi, T., 1998a. Neuroprotective effect of Y-39558, orotic acid ethylester, in gerbil forebrain ischemia. Jpn. J. Pharmacol. 76, 441e444. Heidelberger, C., 1965. Fluorinated pyrimidines. Prog. Nucleic Acid Res. Mol. Biol. 4, 1e50. O’Sullivan, W.J., 1973. Orotic acid. Aust. N. Z. J. Med. 3, 417e423. Kaneti, J.J., Golovinsky, E.V., 1971. Quantitative relationships between the electronic structure and biological activity of some analogues of orotic acid. Chem. Biol. Interact. 3, 421e428. Falk, M., 1985. Orotsa¨ure. Die Pharmazie 40, 377e383 Grisham, C.M., Garrett, R.H., Garrett, R., 2008. Biochemistry. Brooks Cole Publishing, Pacific Grove, USA. Voet, D., Voet, J.G., 2011. Biochemistry. John Wiley and Sons, New York, USA.

Chemical Properties

white crystalline powder

Originator

Lactinium, Roland

Uses

Different sources of media describe the Uses of 65-86-1 differently. You can refer to the following data:
1. Orotic acid is an intermediate in de novo pyrimidine biosynthesis that may be used to study the specificity and kinetics of orotate phosphoribosyltransferase (OPRT) which catalyzes the reversible phosphoribosyl transfer from 5?-phospho-α-d-ribose 1?-diphosphate (PRPP) to orotic acid (OA), forming pyrophosphate and orotidine 5?-monophosphate (OMP). It is used as a starting material for the potential commercial bioproduction of uridine 5?-monophosphate (UMP) by microbes such as Corynebacterium ammoniagenes (ATCC 6872) or Saccharomyces cerevisiae. It may be used to study the AMPK/SREBP-1 dependent cell signaling pathway and transcription regulation mechanisms that induce hepatic lipogenesis.
2. hepatoprotectant, uricosuric agent
3. An intermediate in de novo pyrimidine biosynthesis.

Definition

ChEBI: A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.

Manufacturing Process

91.7 g (0.5 mol) of trichloroacetyl chloride was cooled to -35°C in a glass vessel by means of a cooling brine. In the course of 3 h, 27.0 g (0.06 mol) of pure ketene was introduced through a tube. After completion of the reaction, the vessel was immediately put under dry nitrogen to prevent penetration of moisture. So γ,γ,γ-trichloroacetoacetylchloride was produced. The reaction mixture containing the γ,γ,γ-trichloroacetoacetyl chloride was transfered under nitrogen to a dropping funnel and in the course of 15 min was added with vigorous agitation to a suspension of 69.0 g (1.15 mole) of urea in 90.0 g of anhydrous acetic acid. Water cooling was used so that the reaction temperature would not exceed 40°C. After completion of the addition, the reaction mixture was heated as rapidly as possible to 115°C, and held at this temperature for 30 min. Subsequently there was cooling and one more 99.0 g of glacial acetic acid and 180.0 g of water were added. The precipitated 6-trichloromethyluracil was filtered off and dried at 60°C in a vacuum drying cabinet. The yield was 91.0 g or 80%. In a glass vessel equipped with an agitator, thermometer and pH electrode, 500 ml of water was placed and heated to 80°C. 50 g of 6trichloromethyluracil was then added. By means of the pH electrode, the addition of sodium hydroxide was automatically controlled so that the pH value throughout the whole hydrolysis was 6.5. Into, 165 ml of 5 N NaOH was consumed. Finally, the hydrolysis solution was cooled and the precipitated sodium orotate filtered off. The crude sodium orotate was again suspended at 80°C in water and brought into solution (pH 10.5) by addition of 30 ml of 5 N NaOH. After treatment with active charcoal, the solution was acidified with 30.0 g of 50% sulfuric acid. The solution was then cooled. The orotic acid was filtered off and carefully washed with water. After drying, 20.5 g of orotic acid, having a purity of 99.3% (titration) was obtained. This corresponds to a 60% yield.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 1382, 1947 DOI: 10.1021/ja01198a042

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Carboxylic acids, such as Orotic acid, donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Orotic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Fire Hazard

Flash point data for Orotic acid are not available; however, Orotic acid is probably combustible.

Safety Profile

Moderately toxic by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 65-86-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 65-86:
(4*6)+(3*5)+(2*8)+(1*6)=61
61 % 10 = 1
So 65-86-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)

65-86-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B25349)  Orotic acid, anhydrous, 97%   

  • 65-86-1

  • 100g

  • 975.0CNY

  • Detail
  • Alfa Aesar

  • (B25349)  Orotic acid, anhydrous, 97%   

  • 65-86-1

  • 500g

  • 2732.0CNY

  • Detail

65-86-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name orotic acid

1.2 Other means of identification

Product number -
Other names Orotonsan

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
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More Details:65-86-1 SDS

65-86-1Synthetic route

6-Methyluracil
626-48-2

6-Methyluracil

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); oxygen; cobalt(II) acetate; acetic acid at 80℃; for 15h;92%
With potassium hydroxide; potassium hexacyanoferrate(III)
2,4-imidazolidinedione
461-72-3

2,4-imidazolidinedione

Glyoxilic acid
298-12-4

Glyoxilic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 115 - 120℃; for 2h; Temperature; Large scale;91.9%
(2Z)-(2,5-dioxoimidazolidin-4-ylidene)acetic acid
153816-00-3

(2Z)-(2,5-dioxoimidazolidin-4-ylidene)acetic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide at 64℃; for 3h;85%
With potassium hydroxide at 64℃; for 3h; Mechanism; Kinetics; var. conc. of KOH;85%
C5H6N2O4

C5H6N2O4

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With oxygen; palladium dichloride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 36h; Reagent/catalyst; Solvent; Pressure; Temperature;85%
glycoluril
496-46-8

glycoluril

Glyoxal
131543-46-9

Glyoxal

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
Stage #1: glycoluril; Glyoxal With sodium hydroxide In water for 8h; Autoclave; Reflux; Large scale;
Stage #2: With chlorine at 20℃; Time; Large scale;
33%
orotoaldehyde
36327-91-0

orotoaldehyde

A

6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione
22126-44-9

6-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione

B

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide
orotoaldehyde
36327-91-0

orotoaldehyde

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde
16953-46-1

6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
Multi-step reaction with 2 steps
1: aqueous KOH
2: aqueous alkali .H2O2
View Scheme
2-thioorotic acid
6953-78-2

2-thioorotic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With alkali .H2O2
6-carboxymethyluracil
4628-39-1

6-carboxymethyluracil

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium hexacyanoferrate(III) 22 d;
2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid
6314-14-3

2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With hydrogenchloride
6-diethoxymethyl-1H-pyrimidine-2,4-dione
16953-48-3

6-diethoxymethyl-1H-pyrimidine-2,4-dione

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
Multi-step reaction with 2 steps
1: Hydrolysis
2: Na2Cr2O7/H2SO4
View Scheme
6-diethoxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
16953-49-4

6-diethoxymethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
Multi-step reaction with 3 steps
1: aqueous H2O2; aqueous NaOH
2: Hydrolysis
3: Na2Cr2O7/H2SO4
View Scheme
Multi-step reaction with 2 steps
1: aqueous H2O2; aqueous NaOH
2: Na2Cr2O7/H2SO4
View Scheme
(2,5-dioxo-imidazolidin-4-yliden)-acetic acid
58668-24-9

(2,5-dioxo-imidazolidin-4-yliden)-acetic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide
2,6-Dioxo-3,6-dihydro-2H-[1,3]oxazine-4-carboxylic acid
119767-58-7

2,6-Dioxo-3,6-dihydro-2H-[1,3]oxazine-4-carboxylic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With ammonia In various solvent(s)
methyl N1,N3-dibenzyloxymethyl-orotate
80140-18-7

methyl N1,N3-dibenzyloxymethyl-orotate

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With trimethylsilyl iodide; water 1.) chloroform, reflux, 6 h, 2.) reflux, 30 min; 160-180 deg C, 15 min; reflux; Yield given. Multistep reaction;
uracil
66-22-8

uracil

A

orotic acid
65-86-1

orotic acid

B

isoorotidine
489-36-1

isoorotidine

Conditions
ConditionsYield
at 37℃; for 72h; Product distribution; strain 556F from Bacillus subtilis, pH 7.2; effect of different amounts of uracil, other mutants of Bacillus subtilis;
L-dihydroorotic acid
5988-19-2

L-dihydroorotic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With dihydroorotate dehydrogenase; bis(1-chloro-2-propyl) ether; All-Trans Coenzyme Q6; Triton X-100 In water at 37℃; pH=7.8;
With dihydroorotate dehydrogenase In phosphate buffer at 22℃; pH=7; Enzyme kinetics; Further Variations:; also in the presence of detergent;
With human dihydroorotate dehydrogenase; 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone Enzyme kinetics;
With 2,3-Dimethoxy-5-methyl-1,4-benzoquinone; 2,6-Dichlorophenolindophenol; glycerol; sodium chloride; Triton X-100 In water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid Microbiological reaction; Enzymatic reaction;
With decylubiquinone; pfDHODH at 25℃; Enzyme kinetics; buffer C;
4.5-dichloro-2.6-dioxo-hexahydropyrimidine-carboxylic acid-(4)

4.5-dichloro-2.6-dioxo-hexahydropyrimidine-carboxylic acid-(4)

orotic acid
65-86-1

orotic acid

(2,5-dioxo-imidazolidin-4-yliden)-acetic acid
58668-24-9

(2,5-dioxo-imidazolidin-4-yliden)-acetic acid

aqueous KOH

aqueous KOH

orotic acid
65-86-1

orotic acid

uracil-carboxylic acid-(4)-amide

uracil-carboxylic acid-(4)-amide

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide
uracil-carboxylic acid-(4)-ethyl ester

uracil-carboxylic acid-(4)-ethyl ester

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With potassium hydroxide
dialuryldiazoacetic acid ethyl ester

dialuryldiazoacetic acid ethyl ester

A

orotic acid
65-86-1

orotic acid

B

5-ethoxycarbonylmethylene-hydantoin

5-ethoxycarbonylmethylene-hydantoin

Conditions
ConditionsYield
With sodium hydroxide
ureidosuccinic acid
923-37-5, 173298-46-9

ureidosuccinic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 77 percent / 20percent aq. HCl
2: 71 percent / Br2 / acetic acid / 4 h / 100 °C
3: 85 percent / aq. KOH / 3 h / 64 °C / var. conc. of KOH
View Scheme
5-hydantoinacetic acid
5427-26-9

5-hydantoinacetic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / Br2 / acetic acid / 4 h / 100 °C
2: 85 percent / aq. KOH / 3 h / 64 °C / var. conc. of KOH
View Scheme
Multi-step reaction with 2 steps
1: bromine; acetic acid / Beim Erhitzen des Reaktionsprodukts mit H2O
2: aqueous KOH
View Scheme
5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
7164-43-4

5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
1.1 g (73%)
cyanomethylurea
5962-07-2

cyanomethylurea

Glyoxilic acid
298-12-4

Glyoxilic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water
With sodium hydroxide for 2h; Reflux; Large scale;
orotidine 5'-monophosphate
2149-82-8

orotidine 5'-monophosphate

A

orotic acid
65-86-1

orotic acid

B

5-phosphoribosyl-1-pyrophosphate
97-55-2, 7540-64-9, 99945-37-6, 130384-52-0

5-phosphoribosyl-1-pyrophosphate

Conditions
ConditionsYield
With Salmonella typhimurium OMP synthase wild type; magnesium chloride at 30℃; pH=8; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction;
4,5-dihydroorotic acid
155-54-4

4,5-dihydroorotic acid

orotic acid
65-86-1

orotic acid

Conditions
ConditionsYield
With dihydroorotate dehydrogenase Enzymatic reaction;
With dihydroorotate dehydrogenase; coenzyme Q0 pH=8; Enzymatic reaction;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

orotic acid
65-86-1

orotic acid

2,6-Bis-trimethylsilanyloxy-pyrimidine-4-carboxylic acid
32865-94-4

2,6-Bis-trimethylsilanyloxy-pyrimidine-4-carboxylic acid

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane Ambient temperature;99%
orotic acid
65-86-1

orotic acid

sitagliptin
486460-32-6

sitagliptin

sitagliptin orotate
1246343-77-0

sitagliptin orotate

Conditions
ConditionsYield
In acetonitrile at 25 - 75℃; Product distribution / selectivity;99%
In water at 35 - 37℃; for 0.166667h;
orotic acid
65-86-1

orotic acid

acetyl 2,3-O-isopropylidene-α,β-ribofuranose

acetyl 2,3-O-isopropylidene-α,β-ribofuranose

1'-O-acetyl-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside

1'-O-acetyl-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside

Conditions
ConditionsYield
Stage #1: orotic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 16h;
Stage #2: acetyl 2,3-O-isopropylidene-α,β-ribofuranose With pyridine hydrochloride In acetonitrile at 20℃;
98%
1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine

1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine

orotic acid
65-86-1

orotic acid

1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine orotate

1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine orotate

Conditions
ConditionsYield
In acetone for 0.5h; Solvent; Reflux;98%
4-[ethyl(dimethyl)ammonio]butanoate
1293923-09-7

4-[ethyl(dimethyl)ammonio]butanoate

orotic acid
65-86-1

orotic acid

3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
1404369-24-9

3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Conditions
ConditionsYield
In isopropyl alcohol97.4%
orotic acid
65-86-1

orotic acid

tenofovir disoproxil

tenofovir disoproxil

9-[2-[(R)[[bis[[isopropoxycarbonyl]oxy]methoxy]phosphinyl]methoxy]propyl]adenine orotate

9-[2-[(R)[[bis[[isopropoxycarbonyl]oxy]methoxy]phosphinyl]methoxy]propyl]adenine orotate

Conditions
ConditionsYield
With triethylamine In water; dimethyl sulfoxide at 20 - 30℃; Temperature; Solvent; Reagent/catalyst;97%
In methanol; water at 20 - 70℃; Solvent;85%
orotic acid
65-86-1

orotic acid

L-carnitine
541-15-1

L-carnitine

L-carnitine oroate

L-carnitine oroate

Conditions
ConditionsYield
In water; acetone for 5h; Solvent; Reflux;96%
edoxaban

edoxaban

orotic acid
65-86-1

orotic acid

N1-(5-chloropyridin-2-yl)-N2-((1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-{[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino}cyclohexyl)ethanediamide orotinate

N1-(5-chloropyridin-2-yl)-N2-((1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-{[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino}cyclohexyl)ethanediamide orotinate

Conditions
ConditionsYield
In acetonitrile at 60℃; for 5h;96%
In ethanol at 65℃;5.5 g
orotic acid
65-86-1

orotic acid

1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-6-carbonsaeuremethylester
4116-39-6

1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-6-carbonsaeuremethylester

Conditions
ConditionsYield
In methanol; diethyl ether at 0℃;95%
In methanol Ambient temperature;93%
AMD070
558447-26-0

AMD070

orotic acid
65-86-1

orotic acid

(S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine orotate
880549-28-0

(S)-(N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl))-1,4-butanediamine orotate

Conditions
ConditionsYield
In methanol; water at 20℃; for 1h;95%
orotic acid
65-86-1

orotic acid

5-nitroorotic acid
17687-24-0

5-nitroorotic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 15 - 48℃; for 6h; Temperature; Cooling with ice;95%
With sulfuric acid; nitric acid In water at 50 - 55℃; for 3h;90%
Stage #1: orotic acid With sodium hydroxide In water for 3h;
Stage #2: With sulfuric acid; nitric acid In water at 25 - 45℃; Inert atmosphere;
88.6%
With sulfuric acid; nitric acid In water at 50 - 55℃;
orotic acid
65-86-1

orotic acid

5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylic acid
37832-55-6

5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylic acid

Conditions
ConditionsYield
With hydrazine hydrate In water at 90℃; for 5h; Temperature;95%
1-O-benzoyl-2,3-O-isopropylidene-D-ribofuranoside

1-O-benzoyl-2,3-O-isopropylidene-D-ribofuranoside

orotic acid
65-86-1

orotic acid

1'-O-benzoyl-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside

1'-O-benzoyl-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside

Conditions
ConditionsYield
Stage #1: orotic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 16h;
Stage #2: 1-O-benzoyl-2,3-O-isopropylidene-D-ribofuranoside With pyridine hydrochloride In acetonitrile at 20℃; for 4h;
94%
methanol
67-56-1

methanol

orotic acid
65-86-1

orotic acid

methyl orotate
6153-44-2

methyl orotate

Conditions
ConditionsYield
With thionyl chloride at 0 - 5℃; for 6h; Reflux;92.9%
With hydrogenchloride for 24h; Fischer esterification; Heating;91%
With hydrogenchloride90%
orotic acid
65-86-1

orotic acid

α-chloroorotic acid
36313-98-1

α-chloroorotic acid

Conditions
ConditionsYield
Stage #1: orotic acid With iron(III) chloride; acetic anhydride; acetic acid at 90 - 95℃;
Stage #2: With sulfuryl dichloride Reagent/catalyst; Temperature; Reflux;
92%
With hydrogenchloride; dihydrogen peroxide
(2S,4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine
252870-53-4

(2S,4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine

orotic acid
65-86-1

orotic acid

orotic acid salt of (2S)-(4E)-N-methyl-5-[5-isopropoxypyridin-3-yl]-4-penten-2-amine

orotic acid salt of (2S)-(4E)-N-methyl-5-[5-isopropoxypyridin-3-yl]-4-penten-2-amine

Conditions
ConditionsYield
In ethanol Heating / reflux;91.4%
1-O-pivaloyl-2,3-O-isopropylidene-D-ribofuranoside

1-O-pivaloyl-2,3-O-isopropylidene-D-ribofuranoside

orotic acid
65-86-1

orotic acid

1'-O-pivaloyl-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside

1'-O-pivaloyl-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside

Conditions
ConditionsYield
Stage #1: orotic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 16h;
Stage #2: 1-O-pivaloyl-2,3-O-isopropylidene-D-ribofuranoside With pyridine hydrochloride In acetonitrile at 20℃;
90%
N-hydroxy-2-(4-(4-phenylbutyl)phenyl)acetamide
342373-13-1

N-hydroxy-2-(4-(4-phenylbutyl)phenyl)acetamide

orotic acid
65-86-1

orotic acid

N-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide

N-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyloxy)-2-(4-(4-phenylbutyl)phenyl)acetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;90%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide90%
orotic acid
65-86-1

orotic acid

bis(tri-n-butyltin)oxide
56-35-9

bis(tri-n-butyltin)oxide

C34H62N4O9Sn2

C34H62N4O9Sn2

Conditions
ConditionsYield
In toluene for 6h; Reflux; Inert atmosphere; Dean-Stark;90%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate

bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate

orotic acid
65-86-1

orotic acid

bis(2,2’-bipyridine) orotate ruthenium(II)

bis(2,2’-bipyridine) orotate ruthenium(II)

Conditions
ConditionsYield
Stage #1: bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate; orotic acid In ethanol at 125℃; for 2h; Sealed tube; Microwave irradiation;
Stage #2: ammonium hexafluorophosphate In ethanol; water at 20℃;
89%
orotic acid
65-86-1

orotic acid

ethyl iodide
75-03-6

ethyl iodide

ethyl orotate
1747-53-1

ethyl orotate

Conditions
ConditionsYield
Stage #1: orotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; N,N-dimethyl-formamide for 0.0833333h;
Stage #2: ethyl iodide In water; N,N-dimethyl-formamide at 60℃; for 5h;
88%
Stage #1: orotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0833333h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide at 60℃; for 5h;
88%
10-ethoxy-6-(methoxymethyl)-8-(morpholinomethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one

10-ethoxy-6-(methoxymethyl)-8-(morpholinomethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one

orotic acid
65-86-1

orotic acid

10-ethoxy-8-(morpholinomethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

10-ethoxy-8-(morpholinomethyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

Conditions
ConditionsYield
In ethanol at 90℃; for 3h;88%
orotic acid
65-86-1

orotic acid

glycine tert-butyl ester hydrochloride
27532-96-3

glycine tert-butyl ester hydrochloride

Ort-Gly-O-t-Bu

Ort-Gly-O-t-Bu

Conditions
ConditionsYield
With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 50 - 55℃;87%
orotic acid
65-86-1

orotic acid

1',5'-O-diorotyl-2',3'-O-isopropylidene-D-ribofuranoside

1',5'-O-diorotyl-2',3'-O-isopropylidene-D-ribofuranoside

Conditions
ConditionsYield
With pyridine hydrochloride; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃;87%
orotic acid
65-86-1

orotic acid

O-desmethylvenlafaxine
93413-62-8

O-desmethylvenlafaxine

O-desmethyl-venlafaxine orotate
1174652-08-4

O-desmethyl-venlafaxine orotate

Conditions
ConditionsYield
In diethyl ether; ethanol at 0 - 20℃; Reflux;85.4%
orotic acid
65-86-1

orotic acid

((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride
6491-83-4, 63889-48-5, 66190-38-3

((S)-2-amino-4-methylpentanoyl)-L-leucine methyl ester hydrochloride

orotyl-L-leucyl-L-leucine methyl ester
74019-79-7

orotyl-L-leucyl-L-leucine methyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 50 - 55℃;85%
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

orotic acid
65-86-1

orotic acid

N-(furan-2-ylmethyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxamide
302603-04-9

N-(furan-2-ylmethyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxamide

Conditions
ConditionsYield
for 0.166667h; microwave irradiation;85%

65-86-1Relevant articles and documents

Natural product piperine alleviates experimental allergic encephalomyelitis in mice by targeting dihydroorotate dehydrogenase

Chen, Wuyan,He, Jiacheng,Hu, Qian,Huang, Jin,Huang, Ying,Liu, Zehui,Lu, Sisi,Lu, Weiqiang,Wang, Wanyan,Wu, Dang,Xu, Yechun,Ze, Shuyin

, (2020/05/08)

Multiple sclerosis (MS) is the most popular chronic and debilitating inflammatory disease of the central nervous system (CNS) that remains incurable. Dihydroorotate dehydrogenase (DHODH) is critical to the activity of T lymphocytes and represents a potential therapeutic target for MS. Here we identify piperine, a bioactive constituent of black pepper, as a potent inhibitor of DHODH with an IC50 value of 0.88 μM. Isothermal titration calorimetry and thermofluor assay demonstrate the directly interaction between piperine and DHODH. The co-complex crystal structure of DHODH and piperine at 1.98 ? resolution further reveal that Tyr356 residue of DHODH is crucial for piperine binding. Importantly, we show that piperine can inhibit T cell overactivation in a DHODH-dependent manner in concanavalin A-triggered T-cell assay and mixed lymphocyte reaction assay. Finally, piperine exhibits strong preventive and therapeutic effect in the MOG-induced experimental allergic encephalomyelitis (EAE), a useful model for studying potential treatments for MS, by restricting inflammatory cells infiltration into the CNS and preventing myelin destruction and blood–brain barrier (BBB) disruption. Taken together, these findings highlight DHODH as a therapeutic target for autoimmune disease of the nervous system, and demonstrate a novel role for piperine in the treatment of MS.

Synthetic method of orotic acid

-

Paragraph 0062-0071, (2020/08/22)

The invention discloses a synthetic method of orotic acid, belonging to the technical field of chemical synthesis. The synthetic method of orotic acid comprises the following steps: reacting maleylurea with bromine, wherein the bromine is provided by a reaction of sodium bromide and hydrogen peroxide; and after a reaction of the hydrogen peroxide, the sodium bromide and the maleylurea is finished,adding strong alkali, and adding concentrated hydrochloric acid for acidification after the reaction is completed at 62-64 DEG C so as to obtain the orotic acid. According to the method, the hydrogenperoxide is used for oxidizing the sodium bromide, so elemental halogen used in an original process is replaced, and risks are greatly reduced; the method of applying intermediate bromine generated in situ to a reaction is adopted, so the reaction is uniform and mild, yield and product quality are improved, and the complexity of a production process is reduced; the sodium bromide can be recycled,so no hazardous waste is discharged; in the reaction of synthesizing the maleylurea, acetic acid can be distilled out through reduced-pressure distillation, so cyclic utilization of the acetic acid is achieved, and emission is reduced; and meanwhile, due to process improvement, the yield of the orotic acid is increased.

A orotic improved synthesis method

-

Paragraph 0032-0059, (2019/06/05)

The present invention discloses an improved synthesis of orotic method, which belongs to the field of organic chemical synthesis, Hein, chloroacetic acid and sodium hydroxide aqueous solution in particular in a microchannel reactor heating reaction to obtain a crude product of orotic, refining the crude product obtained after the pure orotic. The whole production process is carried out in a microchannel reactor, improves the reaction conversion and yield, the reaction yield of 90% or more.

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