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703-95-7 Usage

Chemical Properties

White to Off-White Crystalline Solid

Uses

Different sources of media describe the Uses of 703-95-7 differently. You can refer to the following data:
1. 5-FOA(5-Fluoroorotic acid ) has become a valuable tool for research in the field of molecular genetics. It has been employed in the selection of resistant strains of Saccharomyces cerevisiae that possess a mutant URA3 gene which renders them orotidine-5'-phosphate decarboxylase deficient. 5-FOA is coverted to 5-fluorouridine monophosphate (5-FUMP) in yeast cells, which can become incorporated into RNA or metabolized to the highly toxic 5-fluoro-2’-deoxyuridine monophosphate (5-FdUMP). 5-FdUMP is a potent inhibitor of thymidylate synthase (TS), causing the cessation of DNA synthesis. More recently, 5-FOA has been shown to possess potent antimalarial activity against both chloroquine-susceptible and chloroquine-resistant clones of Plasmodium falciparum. Studies indicate that TS is the primary target of 5-FOA in malarial parasites. The combination of 5-FOA and uracil has been effective in treating mice infected with Plasmodium yoelli. 5-FOA may also have potential in the treatment of human malarial infections when used in combination with other agents.
2. Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.

Check Digit Verification of cas no

The CAS Registry Mumber 703-95-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 3 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 703-95:
(5*7)+(4*0)+(3*3)+(2*9)+(1*5)=67
67 % 10 = 7
So 703-95-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)

703-95-7 Well-known Company Product Price

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  • TCI America

  • (F0382)  5-Fluoroorotic Acid Monohydrate  >95.0%(HPLC)(T)

  • 703-95-7

  • 100mg

  • 450.00CNY

  • Detail
  • TCI America

  • (F0382)  5-Fluoroorotic Acid Monohydrate  >95.0%(HPLC)(T)

  • 703-95-7

  • 1g

  • 1,490.00CNY

  • Detail

703-95-7SDS

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 5-Fluoroorotic Acid

1.2 Other means of identification

Product number -
Other names 4-Pyrimidinecarboxylic acid, 5-fluoro-1,2,3,6-tetrahydro-2,6-dioxo-

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 -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:703-95-7 SDS

703-95-7Synthetic route

C7H7FN2O4

C7H7FN2O4

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 3h;83%
C8H9FN2O4

C8H9FN2O4

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 60℃; for 4h;79%
ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate
717-48-6

ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;48.4%
2-ethylsulfanyl-5-fluoro-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester
721-33-5

2-ethylsulfanyl-5-fluoro-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

methyl iodide
74-88-4

methyl iodide

methyl 5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
1996-54-9

methyl 5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Conditions
ConditionsYield
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-d6-formamide at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 4h;
70%
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

ethyl iodide
75-03-6

ethyl iodide

ethyl 5-fluoroorotic acid
132214-26-7

ethyl 5-fluoroorotic acid

Conditions
ConditionsYield
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.5h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide at 60℃; for 2h;
66%
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.5h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide at 60℃; for 2h;
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.5h;
Stage #2: ethyl iodide at 60℃; for 2h;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

benzylglycylglycinate hydrochloride
7797-34-4

benzylglycylglycinate hydrochloride

5-FOrt-Gly-Gly-O-Bzl

5-FOrt-Gly-Gly-O-Bzl

Conditions
ConditionsYield
With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 50 - 55℃;53%
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

Boc-Dap(Fmoc)-OH
131570-56-4, 122235-70-5

Boc-Dap(Fmoc)-OH

N-Fmoc-3-aminobenzoic acid(2R,3S)-N-Fmoc-3-amino-2-hydroxy-4-phenylbutyric acid

N-Fmoc-3-aminobenzoic acid(2R,3S)-N-Fmoc-3-amino-2-hydroxy-4-phenylbutyric acid

KMI-446

KMI-446

Conditions
ConditionsYield
Multistep reaction;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

5-fluoroorotyl-L-leucyl-L-leucine

5-fluoroorotyl-L-leucyl-L-leucine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline, N-methylmorpholine / dimethylformamide / 36 h / 50 - 55 °C
2: 95 percent / 1N HCl in acetic acid / 2 h / Ambient temperature
View Scheme
{(S)-2-Amino-1-[(S)-1-((S)-1-{(1S,2R)-1-benzyl-2-hydroxy-2-[3-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

{(S)-2-Amino-1-[(S)-1-((S)-1-{(1S,2R)-1-benzyl-2-hydroxy-2-[3-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C42H53FN10O12

C42H53FN10O12

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
{(S)-2-Amino-1-[(S)-1-((S)-1-{(1S,2R)-1-benzyl-2-hydroxy-2-[3-(5-thioxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

{(S)-2-Amino-1-[(S)-1-((S)-1-{(1S,2R)-1-benzyl-2-hydroxy-2-[3-(5-thioxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C42H53FN10O11S

C42H53FN10O11S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C36H52N10O7

C36H52N10O7

C41H53FN12O10

C41H53FN12O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C37H52N8O8S

C37H52N8O8S

C42H53FN10O11S

C42H53FN10O11S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C37H52N8O8S

C37H52N8O8S

C42H53FN10O11S

C42H53FN10O11S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C38H55N9O7S

C38H55N9O7S

C43H56FN11O10S

C43H56FN11O10S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

5-phospho-α-D-ribosyl 1-pyrophosphate

5-phospho-α-D-ribosyl 1-pyrophosphate

5-fluoroorotidine 5′-monophosphate
70629-37-7

5-fluoroorotidine 5′-monophosphate

Conditions
ConditionsYield
With orotate phosphoribosyl transferase Enzymatic reaction;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C36H53N5O8
1258505-53-1

C36H53N5O8

C41H54FN7O11

C41H54FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C36H53N5O8
1258505-53-1

C36H53N5O8

C35H50FN7O11

C35H50FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C39H57N5O8

C39H57N5O8

C44H58FN7O11

C44H58FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C33H53N5O8

C33H53N5O8

C38H54FN7O11

C38H54FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C29H48N6O7

C29H48N6O7

C34H49FN8O10

C34H49FN8O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C32H52N6O7

C32H52N6O7

C37H53FN8O10

C37H53FN8O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide

703-95-7Relevant articles and documents

Anticandidal activity of pyrimidine-peptide conjugates

Ti,Steinfeld,Naider,Gulumoglu,Lewis,Becker

, p. 913 - 918 (1980)

The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoro-ortic acid to enter 'Candida albicans' was investigated. A number of conjugates of 5-fluoro-orotic acid and peptides were synthesized using 1-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoro-orotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into 'C. albicans' WD 18-4. Inhibition by 5-fluoro-orotyl-L-leucine was competitive, as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide - 5 - fluorocytosine conjugates suggest that these conjugates enter 'C. albicans' in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.

An improved synthesis and mass fragmentometry of 5 fluoroorotic acid

Alam,Shires,Aboul Enein

, p. 375 - 378 (2007/10/06)

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