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69-93-2 Usage

Introduction

Uric acid is a breakdown substance of purines which exist in body tissues and some food and drinks. Purines are a type of chemical compound in nature consisted in nucleic acids (DNA and RNA). Uric acid is created in the body via purine metabolism and circulated within the bloodstream, and it will be excreted in urine as waste. As a result, there is a certain balanced amount of uric acid in the bloodstream, which is of great importance to the functions of body[1]. Uric acid is composed in the form of urate of ammonia, and it is the primary constituent of the urine of birds and reptiles. Uric acid helps to keep the birds' weight down which is crucial for their flight. Due to its acidic properties, uric acid from birds does damage paints on cars. Insects produce uric acid during protein catabolism. In addition, uric acid helps to make butterflies iridescent. Its crystals also reflect the light produced in fireflies by bioluminescence[2].

Properties and Preparation

Uric acid is a colorless, odorless and tasteless solid with molecular formula C5H4N4O3. It is largely insoluble in water (60 mg/L, at 20 °C)[2]. It is soluble in 1 M NaOH (50 mg/ml)[3]. Rather than melt, it decomposes in air above 250°C. Uric acid is produced from purines by the enzyme xanthine oxidase via the purine metabolism pathway. In the majority of mammals, uric acid is further degraded to allantoin via the urate oxidase (uricase) enzyme. Allantoin is then freely excreted from the body in the urine. Humans, apes, and certain New World monkeys have higher uric acid levels compared with other mammals[4]. Commercially, uric acid has been prepared from guano, which is essentially the droppings of bats or seabirds. Large quantities of guano can be found on some islands. Uric acid can be produced via extracting guano with alkali and then precipitating with acid[5][6].

Chemical Properties

Uric acid, (C5H4O3N4) is a white solid, insoluble in cold water, alcohol or ether, sparingly soluble in hot water. Uric acid is a weak dibasic acid thus forming two series of salts, most of which are very slightly soluble in water (lithium urate soluble).

Occurrence

Uric acid is found in the urine, blood, and muscle juices of carnivorous animals (herbivorous animals secrete hippuric acid), in the excrement of birds, serpents and insects, and is an oxidation product of the complex nitrogenous compounds of the animal organism.

Uses

Uric Acid is a heterocyclcic compound that is created when purine nucleotides are broken down of by the human body. High blood concetration of Uric Acid is known as hyperuricemia and is often associated with a wide range of disorders and medical conditions such as gout, diabetes and metabolic syndrome. Uric acid may be a marker of oxidative stress and may have a potential therapeutic role as an antioxidant.

Definition

Different sources of media describe the Definition of 69-93-2 differently. You can refer to the following data:
1. A nitrogen compound produced from purines. In certain animals (e.g. birds and reptiles), it is the main excretory product resulting from breakdown of amino acids. In humans, uric acid crystals in the joints are the cause of gout.
2. uric acid: The end product of purinebreakdown in most primates, birds,terrestrial reptiles, and insects andalso (except in primates) the majorform in which metabolic nitrogen isexcreted. Being fairly insoluble, uricacid can be expelled in solid form,which conserves valuable water inarid environments. The accumulationof uric acid in the synovial ?uidof joints causes gout.

Biochem/physiol Actions

Uric acid is an insoluble catabolite produced by adenine and guanine metabolism. Accumulation of uric acid leads to gout, hyperuricemia, arthritis and renal failure. Elevated uric acid levels contributes to hypertension and pathogenesis of cardiovascular disease. Low uric acid levels associated with Parkinson′s disease and multiple sclerosis, may elicit protective functionality. High levels of uric acid in patients with chronic obstructive pulmonary disease (COPD) may serve as potential marker for diagnosis.

Safety Profile

Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise uric acid from hot distilled H2O (the solubility in H2O is 1part/39,000parts at 18o and 1part/2,000parts at 100o). It is best purified by dissolving in an alkaline solution and acidifying with dilute HCl and drying it at 100o in a vacuum. [Bergmann & Dikstein J Am Chem Soc 77 691 1955, Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp256-257 1971, ISBN 0-471-38205-1, Beilstein 26 H 513, 26 I 151, 26 II 293, 26 III/IV 2619.]

Check Digit Verification of cas no

The CAS Registry Mumber 69-93-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 69-93:
(4*6)+(3*9)+(2*9)+(1*3)=72
72 % 10 = 2
So 69-93-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)

69-93-2 Well-known Company Product Price

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  • TCI America

  • (U0018)  Uric Acid  >98.0%(T)

  • 69-93-2

  • 25g

  • 295.00CNY

  • Detail
  • TCI America

  • (U0018)  Uric Acid  >98.0%(T)

  • 69-93-2

  • 100g

  • 995.00CNY

  • Detail
  • TCI America

  • (U0018)  Uric Acid  >98.0%(T)

  • 69-93-2

  • 500g

  • 3,450.00CNY

  • Detail
  • Alfa Aesar

  • (A13346)  Uric acid, 99%   

  • 69-93-2

  • 25g

  • 276.0CNY

  • Detail
  • Alfa Aesar

  • (A13346)  Uric acid, 99%   

  • 69-93-2

  • 100g

  • 878.0CNY

  • Detail
  • Alfa Aesar

  • (A13346)  Uric acid, 99%   

  • 69-93-2

  • 500g

  • 3901.0CNY

  • Detail

69-93-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 7,9-dihydro-1H-purine-2,6,8(3H)-trione

1.2 Other means of identification

Product number -
Other names 2,6,8-trioxypurine

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:69-93-2 SDS

69-93-2Synthetic route

5,6-diaminouracil
3240-72-0

5,6-diaminouracil

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 170 - 180℃;
5-hydroxybarbituric acid
444-15-5

5-hydroxybarbituric acid

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
im kuenstlichen Kreislaufversuch;
(6-amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-urea
84455-48-1

(6-amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 230℃; laesst sich auch durch trockenes Erhitzen;
(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-urea
487-63-8

(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-urea

oxalic acid
144-62-7

oxalic acid

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 185℃;
5-sulfaminouracil
5435-16-5

5-sulfaminouracil

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 200℃;
cyanoacetic acid
372-09-8

cyanoacetic acid

urea
57-13-6

urea

A

uric Acid
69-93-2

uric Acid

B

N-(aminocarbonyl)-2-cyano-acetamide
1448-98-2

N-(aminocarbonyl)-2-cyano-acetamide

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With bovine spleen-extract; oxygen
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With oxygen In various solvent(s) Kinetics; Km, Ki,slope, Vmax; xanthine oxidase;
With bovine spleen-extract; oxygen
With oxygen
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

A

uric Acid
69-93-2

uric Acid

B

xanthin
69-89-6

xanthin

Conditions
ConditionsYield
bei enzymatischen Oxydation;
LACTIC ACID
849585-22-4

LACTIC ACID

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With goose liver extract; oxygen at 38℃; bei pH 7.4 bis 7.6;
With chicken liverextract; oxygen at 38℃; bei pH 7.4 bis 7.6;
at 38℃; unter aeroben Bedingungen;
3,3,3-trichloro-2-hydroxy-propionic acid
599-01-9

3,3,3-trichloro-2-hydroxy-propionic acid

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

3,3,3-trichloro-2-hydroxy-propionamide
74592-79-3

3,3,3-trichloro-2-hydroxy-propionamide

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

5,6-diaminouracil sulfate
42965-55-9

5,6-diaminouracil sulfate

urea
57-13-6

urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 180℃;
urea
57-13-6

urea

glycine
56-40-6

glycine

uric Acid
69-93-2

uric Acid

xanthin
69-89-6

xanthin

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With sodium azide; phosphate buffer; McIlvaine buffer; (E)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazine;hydrochloride; N,N-dimethyl-aniline; citric acid; xanthine oxidase; peroxidase 1.) pH=8.5; 2.) pH=3.5; 3.) standard assay of XO activity in serum;
With several organs of the rat; tissuesuspensionene different; methylene blue
With oxygen
guanine
73-40-5

guanine

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With bovine spleen-extract; oxygen
guanine
73-40-5

guanine

A

uric Acid
69-93-2

uric Acid

B

xanthin
69-89-6

xanthin

Conditions
ConditionsYield
Verfuetterung an Enten;
N-(guanin-C8-yl)-1-naphthylamine
80156-61-2

N-(guanin-C8-yl)-1-naphthylamine

A

uric Acid
69-93-2

uric Acid

B

1-amino-naphthalene
134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With alkali
uric acid radical
69-93-2

uric acid radical

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With Chr-O(1-) In water at 20℃; Rate constant; Equilibrium constant; Irradiation; various substrate concentration, further reagent; pH 13.0;
xanthine
69-89-6

xanthine

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With sodium dihydrogenphosphate; oxygen; palladium dichloride Rate constant; xanthine oxidase; var. conc. PdCl2;
With hydroxide In water Product distribution; Mechanism; Irradiation; pH = 6 10 11; OH(1-) radical was generated by photolysis of sulfate radical anion or photolysis of H2O2; add of 4-mercaptopyridine-N-oxide; intermedier radicals were determined by ESR;
With oxygen; xanthine oxidase In water at 283℃; Enzyme kinetics; Activation energy; Kinetics; Further Variations:; Temperatures; Oxidation;
xanthin
69-89-6

xanthin

A

pyrimidine-2,4,5,6(1H,3H)-tetraone
61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

pyrimidine-2,4,5,6(1H,3H)-tetraone

B

uric Acid
69-93-2

uric Acid

C

urea
57-13-6

urea

Conditions
ConditionsYield
at 25℃; Product distribution; Mechanism; Rate constant; electrochemical oxidation; buffer (pH=2-6); various times, potentials and electrodes;
hydrogenchloride
7647-01-0

hydrogenchloride

2,6-dichloro-7,9-dihydro-purin-8-one
98027-86-2

2,6-dichloro-7,9-dihydro-purin-8-one

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 120℃;
hydrogenchloride
7647-01-0

hydrogenchloride

8-amino-2-methylsulfanyl-1,7-dihydro-purin-6-one

8-amino-2-methylsulfanyl-1,7-dihydro-purin-6-one

uric Acid
69-93-2

uric Acid

hydrogenchloride
7647-01-0

hydrogenchloride

(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-carbamonitrile

(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-carbamonitrile

uric Acid
69-93-2

uric Acid

hydrogenchloride
7647-01-0

hydrogenchloride

2-methylsulfanyl-7,9-dihydro-1H-purine-6,8-dione
14443-37-9

2-methylsulfanyl-7,9-dihydro-1H-purine-6,8-dione

uric Acid
69-93-2

uric Acid

hydrogenchloride
7647-01-0

hydrogenchloride

(6-amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-urea
84455-48-1

(6-amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-urea

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
at 120℃;
hydrogenchloride
7647-01-0

hydrogenchloride

(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-urea
487-63-8

(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-urea

uric Acid
69-93-2

uric Acid

hydrogenchloride
7647-01-0

hydrogenchloride

(6,8-dioxo-6,7,8,9-tetrahydro-1H-purin-2-ylmercapto)-acetic acid

(6,8-dioxo-6,7,8,9-tetrahydro-1H-purin-2-ylmercapto)-acetic acid

uric Acid
69-93-2

uric Acid

6.8-dioxy-2-carboxymethylsulfanyl-purine

6.8-dioxy-2-carboxymethylsulfanyl-purine

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With hydrogenchloride
uric Acid
69-93-2

uric Acid

5-aminouracil-6-thiol

5-aminouracil-6-thiol

Conditions
ConditionsYield
With ammonium sulfide; potassium hydroxide In water at 180℃; for 6h; Microwave irradiation;89%
uric Acid
69-93-2

uric Acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 185℃; under 3750.38 Torr; for 5h; Inert atmosphere; Autoclave;85.9%
In water at 160℃; under 760.051 Torr;82.4%
formaldehyd
50-00-0

formaldehyd

uric Acid
69-93-2

uric Acid

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 100℃; under 3750.38 Torr; for 24h; Inert atmosphere; Autoclave;82.3%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

uric Acid
69-93-2

uric Acid

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 115℃; under 3750.38 Torr; for 18h; Inert atmosphere; Autoclave;82%
uric Acid
69-93-2

uric Acid

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 190℃; under 3750.38 Torr; for 8h; Inert atmosphere; Autoclave;81.5%
uric Acid
69-93-2

uric Acid

trimethyl orthoformate
149-73-5

trimethyl orthoformate

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 220℃; under 3750.38 Torr; for 48h; Inert atmosphere; Autoclave;80%
uric Acid
69-93-2

uric Acid

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 190℃; under 3750.38 Torr; for 2.5h; Inert atmosphere; Autoclave;79.2%
uric Acid
69-93-2

uric Acid

A

parabanic acid
120-89-8

parabanic acid

B

Oxalyldiurea
5676-27-7

Oxalyldiurea

C

dehydro-allantoin
105245-87-2

dehydro-allantoin

D

Allantoin
97-59-6

Allantoin

Conditions
ConditionsYield
With lithium hydroxide; iodine In water for 0.0833333h; excess of I2;A n/a
B n/a
C 75%
D n/a
With lithium hydroxide; iodine In water for 0.0833333h; Mechanism; also with substituted uric acid; effect of amount of I2; 2H and 13C labelling experiment;
uric Acid
69-93-2

uric Acid

tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 200℃; under 3750.38 Torr; for 2h; Inert atmosphere; Autoclave;75%
uric Acid
69-93-2

uric Acid

dihydroxyuric acid
67708-22-9

dihydroxyuric acid

Conditions
ConditionsYield
With rose bengal In glycerol for 23h; Irradiation;74.71%
With chlorine; acetic acid
pH=7; Electrochemical reaction; aq. phosphate buffer;
With Fe exchanged nanocrystalline ZSM-5 In aq. phosphate buffer pH=3.5; Kinetics; Electrochemical reaction;
With titanium dioxide nanorods with multi-walled carbon nanotubes pH=4; Electrochemical reaction;
uric Acid
69-93-2

uric Acid

A

pyrimidine-2,4,5,6(1H,3H)-tetraone
61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

pyrimidine-2,4,5,6(1H,3H)-tetraone

B

urea
57-13-6

urea

Conditions
ConditionsYield
With rose bengal; sodium hydroxide In glycerol for 36h; Irradiation;A 72.18%
B n/a
uric Acid
69-93-2

uric Acid

dimethyl sulfate
77-78-1

dimethyl sulfate

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 84℃; under 3750.38 Torr; for 2.5h; Inert atmosphere; Autoclave;71.4%
uric Acid
69-93-2

uric Acid

Allantoin
97-59-6

Allantoin

Conditions
ConditionsYield
With lithium hydroxide; iodine In water at 4℃; equimolar amount of I2;70%
With sodium hydroxide; oxygen; pyrographite
With water; ozone
uric Acid
69-93-2

uric Acid

methyl iodide
74-88-4

methyl iodide

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 84℃; under 3750.38 Torr; for 2h; Inert atmosphere; Autoclave;69.2%
With alkaline solution at 100 - 110℃;
uric Acid
69-93-2

uric Acid

1,5-diamino-3,7-dioxo-2,4,6,8-tetraazabicyclo-[3.3.0]octane
133364-43-9

1,5-diamino-3,7-dioxo-2,4,6,8-tetraazabicyclo-[3.3.0]octane

Conditions
ConditionsYield
With sodium persulfate; ammonia; water; sodium chloride at -8 - -5℃; for 2h;69%
Stage #1: uric Acid With ammonium hydroxide; sodium persulfate; sodium chloride In water at -10℃; for 2h;
Stage #2: With ammonium hydroxide In water at -10 - 20℃; for 1h;
64%
uric Acid
69-93-2

uric Acid

6-thiouramil ammonium salt

6-thiouramil ammonium salt

Conditions
ConditionsYield
With diammonium sulfide; water; potassium hydroxide at 0 - 180℃; for 8h; Sealed tube;63%
uric Acid
69-93-2

uric Acid

cis-1,5-diamino-2,4,6,8-tetraazabicyclo-<3.3.0>octane-3,7-dione
133364-43-9

cis-1,5-diamino-2,4,6,8-tetraazabicyclo-<3.3.0>octane-3,7-dione

Conditions
ConditionsYield
With ammonium hydroxide; potassium hexacyanoferrate(III) In water60%
uric Acid
69-93-2

uric Acid

cyanuric acid
108-80-5

cyanuric acid

Conditions
ConditionsYield
With dihydrogen peroxide In not given oxidation of uric acid by alk. H2O2-soln.;50%
uric Acid
69-93-2

uric Acid

A

5,6-dihydroxypyrimidine-2,4(1H,3H)-dione
102636-37-3

5,6-dihydroxypyrimidine-2,4(1H,3H)-dione

B

urea
57-13-6

urea

Conditions
ConditionsYield
With rose bengal In acetic acid; glycerol for 38h; Irradiation;A 45.11%
B n/a
uric Acid
69-93-2

uric Acid

A

5-Amino-4-iminoallantoin
133364-42-8

5-Amino-4-iminoallantoin

B

cis-1,5-diamino-2,4,6,8-tetraazabicyclo-<3.3.0>octane-3,7-dione
133364-43-9

cis-1,5-diamino-2,4,6,8-tetraazabicyclo-<3.3.0>octane-3,7-dione

Conditions
ConditionsYield
With ammonium hydroxide; potassium hexacyanoferrate(III) In water 1) r.t., 30 min, 2) 0 deg C, 1 h;A 45%
B 30%
uric Acid
69-93-2

uric Acid

1H,4H-3a,6a-(epiminomethanoimino)imidazo[4,5-d]imidazole-2,5,8(3H,6H)-trione
1431648-72-4

1H,4H-3a,6a-(epiminomethanoimino)imidazo[4,5-d]imidazole-2,5,8(3H,6H)-trione

Conditions
ConditionsYield
Stage #1: uric Acid With ammonium hydroxide; potassium hexacyanoferrate(III) In water at 0 - 20℃; for 6h;
Stage #2: With 1,1'-carbonyldiimidazole In dimethyl sulfoxide at 20℃; for 72h;
44%
uric Acid
69-93-2

uric Acid

1-O-acetyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose
112841-30-2

1-O-acetyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose

A

C39H30N4O12

C39H30N4O12

B

C39H30N4O12

C39H30N4O12

C

C39H30N4O12

C39H30N4O12

Conditions
ConditionsYield
Stage #1: uric Acid With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Reflux; Inert atmosphere;
Stage #2: 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 48h; Reflux; Inert atmosphere;
A 39%
B 9%
C 4%
uric Acid
69-93-2

uric Acid

[Na2(H2O)4(2H-imidazo-[4,5-e]-as-1,2,4-triazine-2,7-dihydro-3,6-dione)2]n

[Na2(H2O)4(2H-imidazo-[4,5-e]-as-1,2,4-triazine-2,7-dihydro-3,6-dione)2]n

Conditions
ConditionsYield
With sodium persulfate; ammonia; water; sodium chloride at 2 - 10℃;36%
uric Acid
69-93-2

uric Acid

A

potassium salt of uroxanate
121669-46-3

potassium salt of uroxanate

B

Allantoin
97-59-6

Allantoin

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate In water for 4h; Product distribution; Mechanism; Ambient temperature; labelled 14C in position of 5;A 26%
B 14%
uric Acid
69-93-2

uric Acid

A

uroxanate
508-37-2

uroxanate

B

Allantoin
97-59-6

Allantoin

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate In water for 4h; Ambient temperature; Yield given;A n/a
B 14%
uric Acid
69-93-2

uric Acid

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
With diethyl ether
uric Acid
69-93-2

uric Acid

8-methoxycaffeine
569-34-6

8-methoxycaffeine

Conditions
ConditionsYield
With diethyl ether
pyridine
110-86-1

pyridine

uric Acid
69-93-2

uric Acid

acetic anhydride
108-24-7

acetic anhydride

8-methylxanthine
17338-96-4

8-methylxanthine

Conditions
ConditionsYield
mehrtaegigem Kochen;
O-methylcaprolactim
2525-16-8

O-methylcaprolactim

uric Acid
69-93-2

uric Acid

theacrine
2309-49-1

theacrine

Conditions
ConditionsYield
at 155℃;

69-93-2Relevant articles and documents

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Horbaczewski

, p. 202,584 (1887)

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Xanthine dehydrogenase electrocatalysis: Autocatalysis and novel activity

Kalimuthu, Palraj,Leimkühler, Silke,Bernhardt, Paul V.

, p. 2655 - 2662 (2011)

The enzyme xanthine dehydrogenase (XDH) from the purple photosynthetic bacterium Rhodobacter capsulatus catalyzes the oxidation of hypoxanthine to xanthine and xanthine to uric acid as part of purine metabolism. The native electron acceptor is NAD+ but herein we show that uric acid in its 2-electron oxidized form is able to act as an artificial electron acceptor from XDH in an electrochemically driven catalytic system. Hypoxanthine oxidation is also observed with the novel production of uric acid in a series of two consecutive 2-electron oxidation reactions via xanthine. XDH exhibits native activity in terms of its pH optimum and inhibition by allopurinol.

Low-potential amperometric enzyme biosensor for xanthine and hypoxanthine

Kalimuthu, Palraj,Leimkühler, Silke,Bernhardt, Paul V.

, p. 10359 - 10365 (2012)

The bacterial xanthine dehydrogenase (XDH) from Rhodobacter capsulatus was immobilized on an edge-plane pyrolytic graphite (EPG) electrode to construct a hypoxanthine/xanthine biosensor that functions at physiological pH. Phenazine methosulfate (PMS) was used as a mediator which acts as an artificial electron-transfer partner for XDH. The enzyme catalyzes the oxidation of hypoxanthine to xanthine and also xanthine to uric acid by an oxidative hydroxylation mechanism. The present electrochemical biosensor was optimized in terms of applied potential and pH. The electrocatalytic oxidation response showed a linear dependence on the xanthine concentration ranging from 1.0 × 10-5 to 1.8 × 10-3 M with a correlation coefficient of 0.994. The modified electrode shows a very low detection limit for xanthine of 0.25 nM (signal-to-noise ratio = 3) using controlled potential amperometry.

Tetrathiatriarylmethyl radical with a single aromatic hydrogen as a highly sensitive and specific superoxide probe

Liu, Yangping,Song, Yuguang,De Pascali, Francesco,Liu, Xiaoping,Villamena, Frederick A.,Zweier, Jay L.

, p. 2081 - 2091 (2012)

Superoxide (O2?-) plays crucial roles in normal physiology and disease; however, its measurement remains challenging because of the limited sensitivity and/or specificity of prior detection methods. We demonstrate that a tetrathiatriarylmethyl (TAM) radical with a single aromatic hydrogen (CT02-H) can serve as a highly sensitive and specific O 2?- probe. CT02-H is an analogue of the fully substituted TAM radical CT-03 (Finland trityl) with an electron paramagnetic resonance (EPR) doublet signal due to its aromatic hydrogen. Owing to the neutral nature and negligible steric hindrance of the hydrogen, O 2?- preferentially reacts with CT02-H at this site with production of the diamagnetic quinone methide via oxidative dehydrogenation. Upon reaction with O2?-, CT02-H loses its EPR signal and this EPR signal decay can be used to quantitatively measure O2?-. This is accompanied by a change in color from green to purple, with the quinone methide product exhibiting a unique UV-Vis absorbance (ε =15,900 M-1 cm-1) at 540 nm, providing an additional O2?- detection method. More than five-fold higher reactivity of CT02-H for O2?- relative to CT-03 was demonstrated, with a second-order rate constant of 1.7×104 M-1 s-1 compared to 3.1×103 M-1 s-1 for CT-03. CT02-H exhibited high specificity for O2?- as evidenced by its inertness to other oxidoreductants. The O2?- generation rates detected by CT02-H from xanthine/xanthine oxidase were consistent with those measured by cytochrome c reduction but detection sensitivity was 10- to 100-fold higher. EPR detection of CT02-H enabled measurement of very low O2?- flux with a detection limit of 0.34 nM/min over 120 min. HPLC in tandem with electrochemical detection was used to quantitatively detect the stable quinone methide product and is a highly sensitive and specific method for measurement of O2 ?-, with a sensitivity limit of ~2×10-13 mol (10 nM with 20-μl injection volume). Based on the O2-dependent linewidth broadening of its EPR spectrum, CT02-H also enables simultaneous measurement of O2 concentration and O2?- generation and was shown to provide sensitive detection of extracellular O 2?- generation in endothelial cells stimulated either by menadione or with anoxia/reoxygenation. Thus, CT02-H is a unique probe that provides very high sensitivity and specificity for measurement of O 2?- by either EPR or HPLC methods.

Inhibition studies of bovine xanthine oxidase by luteolin, silibinin, quercetin, and curcumin

Pauff, James M.,Hille, Russ

, p. 725 - 731 (2009)

Xanthine oxidoreductase (XOR) is a molybdenum-containing enzyme that under physiological conditions catalyzes the final two steps in purine catabolism, ultimately generating uric acid for excretion. Here we have investigated four naturally occurring compounds that have been reported to be inhibitors of XOR in order to examine the nature of their inhibition utilizing in vitro steady-state kinetic studies. We find that luteolin and quercetin are competitive inhibitors and that silibinin is a mixed-type inhibitor of the enzyme in vitro, and, unlike allopurinol, the inhibition is not time-dependent. These three natural products also decrease the production of superoxide by the enzyme. In contrast, and contrary to previous reports in the literature based on in vivo and other nonmechanistic studies, we find that curcumin did not inhibit the activity of purified XO nor its superoxide production in vitro.

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Horbaczewski

, p. 356 ()

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Kinetic model of oxidation catalyzed by xanthine oxidase - The final enzyme in degradation of purine nucleosides and nucleotides

Banach, Kinga,Bojarska, Elzbieta,Kazimierczuk, Zygmunt,Magnowska, Lucyna,Bzowska, Agnieszka

, p. 465 - 469 (2005)

A new kinetic model is presented for analysis of experimental data of oxidation process catalyzed by milk xanthine oxidase. The kinetics for two substrates, xanthine and its analog 2-chloroadenine, in a broad pH range (5.8-9.0) are best described by an equation which is a rational function of degree 2:3 and 2:2, respectively. Copyright Taylor & Francis, Inc.

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Horbaczewski

, p. 201 (1887)

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Hydrogen peroxide is the major oxidant product of xanthine oxidase

Kelley, Eric E.,Khoo, Nicholas K.H.,Hundley, Nicholas J.,Malik, Umair Z.,Freeman, Bruce A.,Tarpey, Margaret M.

, p. 493 - 498 (2010)

Xanthine oxidase (XO) is a critical source of reactive oxygen species (ROS) in inflammatory disease. Focus, however, has centered almost exclusively on XO-derived superoxide (O2?-), whereas direct H2O2 production from XO has been less well investigated. Therefore, we examined the relative quantities of O2?- and H2O2 produced by XO under a range (1-21%) of O2 tensions. At O2 concentrations between 10 and 21%, H2O2 accounted for ~75% of ROS production. As O2 concentrations were lowered, there was a concentration-dependent increase in H2O2 formation, accounting for 90% of ROS production at 1% O2. Alterations in pH between 5.5 and 7.4 did not affect the relative proportions of H2O2 and O2?- formation. Immobilization of XO, by binding to heparin-Sepharose, further enhanced relative H2O2 production by ~30%, under both normoxic and hypoxic conditions. Furthermore, XO bound to glycosaminoglycans on the apical surface of bovine aortic endothelial cells demonstrated a similar ROS production profile. These data establish H2O2 as the dominant (70-95%) reactive product produced by XO under clinically relevant conditions and emphasize the importance of H2O2 as a critical factor when examining the contributory roles of XO-catalyzed ROS in inflammatory processes as well as cellular signaling.

Structure-activity relationship of xanthones as inhibitors of xanthine oxidase

Zhou, Ling-Yun,Peng, Jia-Le,Wang, Jun-Ming,Geng, Yuan-Yuan,Zuo, Zhi-Li,Hua, Yan

, (2018/02/17)

Polygala plants contain a large number of xanthones with good physiological activities. In our previous work, 18 xanthones were isolated from Polygala crotalarioides. Extented study of the chemical composition of the other species Polygala sibirica led to the separation of two new xanthones-3-hydroxy-1,2,6,7,8-pentamethoxy xanthone (A) and 6-O--D-glucopyranosyl-1,7- dimethoxy xanthone (C)-together with 14 known xanthones. Among them, some xanthones have a certain xanthine oxidase (XO) inhibitory activity. Furthemore, 14 xanthones as XO inhibitors were selected to develop three-dimensional quantitative structure-activity relationship (3D-QSAR) using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) models. The CoMFA model predicted a q2 value of 0.613 and an r2 value of 0.997. The best CoMSIA model predicted a q2 value of 0.608 and an r2 value of 0.997 based on a combination of steric, electrostatic, and hydrophobic effects. The analysis of the contour maps from each model provided insight into the structural requirements for the development of more active XO inhibitors.

Real-Time Monitoring of Enzyme-Catalysed Reactions using Deep UV Resonance Raman Spectroscopy

Westley, Chloe,Fisk, Heidi,Xu, Yun,Hollywood, Katherine A.,Carnell, Andrew J.,Micklefield, Jason,Turner, Nicholas J.,Goodacre, Royston

, p. 6983 - 6987 (2017/05/29)

For enzyme-catalysed biotransformations, continuous in situ detection methods minimise the need for sample manipulation, ultimately leading to more accurate real-time kinetic determinations of substrate(s) and product(s). We have established for the first time an on-line, real-time quantitative approach to monitor simultaneously multiple biotransformations based on UV resonance Raman (UVRR) spectroscopy. To exemplify the generality and versatility of this approach, multiple substrates and enzyme systems were used involving nitrile hydratase (NHase) and xanthine oxidase (XO), both of which are of industrial and biological significance, and incorporate multistep enzymatic conversions. Multivariate data analysis of the UVRR spectra, involving multivariate curve resolution-alternating least squares (MCR-ALS), was employed to effect absolute quantification of substrate(s) and product(s); repeated benchmarking of UVRR combined with MCR-ALS by HPLC confirmed excellent reproducibility.

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