Product Name

  • Name

    6-Hydroxypurine

  • EINECS 200-697-3
  • CAS No. 68-94-0
  • Article Data148
  • CAS DataBase
  • Density 1.892 g/cm3
  • Solubility practically insoluble in water
  • Melting Point 250 °C
  • Formula C5H4N4O
  • Boiling Point 533.428 °C at 760 mmHg
  • Molecular Weight 136.113
  • Flash Point 276.407 °C
  • Transport Information
  • Appearance White to off-white powder
  • Safety 22-24/25-37/39-26-36
  • Risk Codes 36/37/38-22-40
  • Molecular Structure Molecular Structure of 68-94-0 (6-Hydroxypurine)
  • Hazard Symbols HarmfulXn
  • Synonyms Sarcine;9H-Purin-6-ol (VAN);Hypoxanthine enol;3,7-dihydropurin-6-one;3,5-dihydropurin-6-one;Hypoxanthine (VAN) (8CI);3H-Purin-6-ol;9H-Purin-6(1H)-one;1,9-Dihydro-purin-6-one;Sarkine;Hyp;Purin-6(3H)-one;25991-09-7;HX;Sarkin;Purine-6-ol;Purin-6(1H)-one;6H-Purin-6-one, 1,7-dihydro-;6(1H)-purinone;1,7-Dihydro-6H-purin-6-one;6H-Purin-6-one,1,7-dihydro-;39464-15-8;Purin-6-ol;9H-purin-6-ol;6-Hydroxypurine;6-Hydroxypurine (Hypoxanthine);
  • PSA 74.43000
  • LogP -0.35380

Synthetic route

formic acid
64-18-6

formic acid

6-chloro-4,5-diaminopyrimidine
4316-98-7

6-chloro-4,5-diaminopyrimidine

A

6-amino-5-formylamino-3H-pyrimidin-4-one
64194-58-7

6-amino-5-formylamino-3H-pyrimidin-4-one

B

1,7-dihydro-6H-purin-6-one
68-94-0

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

uric Acid
69-93-2

uric Acid

A

1,7-dihydro-6H-purin-6-one
68-94-0

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

B

xanthin
69-89-6

xanthin

Conditions
ConditionsYield
With water at 180 - 200℃;
formic acid
64-18-6

formic acid

5-amino-3-β-D-ribofuranosyl-3H-imidazole-4-carboxylic acid amide
7132-71-0

5-amino-3-β-D-ribofuranosyl-3H-imidazole-4-carboxylic acid amide

acetic anhydride
108-24-7

acetic anhydride

A

7-β-D-ribofuranosyl-1,7-dihydro-purin-6-one
5627-15-6, 5627-18-9, 10280-01-0, 10280-02-1, 19895-30-8

7-β-D-ribofuranosyl-1,7-dihydro-purin-6-one

B

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts mit wss.KHCO3;
5,6-diamino-3H-pyrimidin-4-one; sulfate
52502-66-6, 102783-18-6, 120568-21-0

5,6-diamino-3H-pyrimidin-4-one; sulfate

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With formic acid
acetic anhydride
108-24-7

acetic anhydride

aminomalonamamidine dihydrochloride
16014-63-4

aminomalonamamidine dihydrochloride

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1,7-dihydro-6H-purin-6-one
68-94-0

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

5,6-diamino-3H-pyrimidin-4-one; sulfate
52502-66-6, 102783-18-6, 120568-21-0

5,6-diamino-3H-pyrimidin-4-one; sulfate

1,7-dihydro-6H-purin-6-one
68-94-0

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

N-(5-amino-6-chloropyrimidin-4-yl)formamide
7501-32-8

N-(5-amino-6-chloropyrimidin-4-yl)formamide

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
zeitlicher Verlauf der Hydrolyse.Hydrolysis;
7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
durch Enzymwirkung; z. B. durch faulenden Pankreasextrakt unter Luftabschluss;
durch Faeulnisbakterien;
durch Schweinemilzferment;
ammonium acetate
631-61-8

ammonium acetate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

ethyl 2-acetamido-2-cyanoacetate
90877-70-6, 4977-62-2

ethyl 2-acetamido-2-cyanoacetate

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With ammonia at 180℃;
chloroform
67-66-3

chloroform

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

xanthin
69-89-6

xanthin

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
at 60 - 70℃;
xanthin
69-89-6

xanthin

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
at 200℃;
xanthin
69-89-6

xanthin

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With sodium hydroxide; chloroform at 60 - 70℃;
With garcinielliptone HA; xanthine oxidase In water at 25℃; for 0.0833333h; pH=7.5; Kinetics; Reagent/catalyst; Time; Concentration; aq. phosphate buffer; Enzymatic reaction;
adenosine
58-61-7

adenosine

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
mit Hilfe von Bacterium-coli;
Hydrolyse und Desaminierung bei der Einwirkung von Escherichia coli und anderen Bakterien.Hydrolysis;
Conditions
ConditionsYield
With nucleoside phosphorylase
With Pi; nucleoside phosphorylase (enzyme) Rate constant;
1,7-dihydro-<1 or 3-15N>purin-6-one

1,7-dihydro-<1 or 3-15N>purin-6-one

1,7-dihydro-6H-purin-6-one
68-94-0

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

1,7-dihydro-<4-14C>purin-6-one

1,7-dihydro-<4-14C>purin-6-one

1,7-dihydro-6H-purin-6-one
68-94-0

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

1,7-dihydro-<8-14C>purin6-one

1,7-dihydro-<8-14C>purin6-one

1,7-dihydro-6H-purin-6-one
68-94-0

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

2.8-dichloro-6-ethoxy-purine

2.8-dichloro-6-ethoxy-purine

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
2.8-dichloro-6-oxy-purine

2.8-dichloro-6-oxy-purine

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
2-mercapto-adenine

2-mercapto-adenine

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With nitric acid
2-thio-xanthine

2-thio-xanthine

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With nitric acid
6-amino-3,7-dihydro-purine-2-thione
3647-48-1

6-amino-3,7-dihydro-purine-2-thione

nitric acid
7697-37-2

nitric acid

1,7-dihydro-6H-purin-6-one
68-94-0

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

2-thioxanthine
2487-40-3

2-thioxanthine

nitric acid
7697-37-2

nitric acid

1,7-dihydro-6H-purin-6-one
68-94-0

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

2-formylamino-malonomonoimidic acid diamide hydrochloride

2-formylamino-malonomonoimidic acid diamide hydrochloride

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
at 185℃;
sodium ethanolate
141-52-6

sodium ethanolate

5-amino-1(3)H-imidazole-4-carboxylic acid formylamide

5-amino-1(3)H-imidazole-4-carboxylic acid formylamide

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
With ethanol
With potassium hydrogencarbonate
5-amino-1(3)H-imidazole-4-carboxylic acid

5-amino-1(3)H-imidazole-4-carboxylic acid

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
at 185℃;
AMP

AMP

1,7-dihydro-6H-purin-6-one
68-94-0

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

Conditions
ConditionsYield
mit Hilfe von Bacterium-coli;
1,7-dihydro-6H-purin-6-one
68-94-0

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

6-chloropurine hydrochloride

6-chloropurine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; trichlorophosphate In dichloromethane; N,N-dimethyl-aniline99%
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

1,7-dihydro-6H-purin-6-one
68-94-0

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

kinetin
525-79-1

kinetin

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 72h;90%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 72h;90 % Chromat.
1,7-dihydro-6H-purin-6-one
68-94-0

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

13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose
503173-75-9

13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose

[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)hypoxanthine
503173-78-2

[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)hypoxanthine

Conditions
ConditionsYield
Stage #1: 1,7-dihydro-6H-purin-6-one With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Heating;
Stage #2: 13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2.5h; Heating;
86%
copper(II) perchlorate hexahydrate

copper(II) perchlorate hexahydrate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

1,7-dihydro-6H-purin-6-one
68-94-0

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

[(Cu(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3

[(Cu(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3

Conditions
ConditionsYield
With NaOH In methanol; water an aq. soln. of hypoxanthine and a MeOH soln. of N(C2H4NH2)3 and Cu saltmixed, pH adjusted to 8-9 with NaOH soln.; crystd. at room temp. for 3 wk; elem. anal.;81%
1,7-dihydro-6H-purin-6-one
68-94-0

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

6-chloropurine methanesulfonate
88166-56-7

6-chloropurine methanesulfonate

Conditions
ConditionsYield
With trichlorophosphate In methanesulfonic acid; dichloromethane; N,N-dimethyl-aniline78%
zinc perchlorate

zinc perchlorate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

1,7-dihydro-6H-purin-6-one
68-94-0

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

[Zn(tris(2-aminoethyl)amine)(hypoxanthinato)]ClO4*H2O
1145782-16-6

[Zn(tris(2-aminoethyl)amine)(hypoxanthinato)]ClO4*H2O

Conditions
ConditionsYield
With NaOH In methanol; water an aq. soln. of hypoxanthine and a MeOH soln. of N(C2H4NH2)3 and Zn saltmixed, pH adjusted to 8-9 with NaOH soln.; crystd. at room temp. for 3 wk; elem. anal.;78%
cadmium(II) perchlorate hexahydrate

cadmium(II) perchlorate hexahydrate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

1,7-dihydro-6H-purin-6-one
68-94-0

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

[(Cd(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3*0.5H2O

[(Cd(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3*0.5H2O

Conditions
ConditionsYield
With NaOH In methanol; water an aq. soln. of hypoxanthine and a MeOH soln. of N(C2H4NH2)3 and Cd saltmixed, pH adjusted to 8-9 with NaOH soln.; crystd. at room temp. for 1 mo; elem. anal.;54%
bromobenzene
108-86-1

bromobenzene

1,7-dihydro-6H-purin-6-one
68-94-0

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

A

1,9-dihydro-9-phenyl-6H-purin-6-one
6334-42-5

1,9-dihydro-9-phenyl-6H-purin-6-one

B

7-phenylhypoxanthine
62382-64-3

7-phenylhypoxanthine

Conditions
ConditionsYield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 32h; Inert atmosphere; Sealed tube; regioselective reaction;A 48%
B 11%
iodobenzene
591-50-4

iodobenzene

1,7-dihydro-6H-purin-6-one
68-94-0

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

A

1,9-dihydro-9-phenyl-6H-purin-6-one
6334-42-5

1,9-dihydro-9-phenyl-6H-purin-6-one

B

7-phenylhypoxanthine
62382-64-3

7-phenylhypoxanthine

Conditions
ConditionsYield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere; Sealed tube; regioselective reaction;A 43%
B 14%
1,7-dihydro-6H-purin-6-one
68-94-0

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

isopropyl alcohol
67-63-0

isopropyl alcohol

4C5H2N4O(2-)*4C3H8O*5Li(1+)*3H(1+)

4C5H2N4O(2-)*4C3H8O*5Li(1+)*3H(1+)

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; lithium tert-butoxide In N,N-dimethyl-formamide at 100℃; for 72h;31%
ethanol
64-17-5

ethanol

1,7-dihydro-6H-purin-6-one
68-94-0

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

4C5H2N4O(2-)*4C2H6O*5Li(1+)*3H(1+)

4C5H2N4O(2-)*4C2H6O*5Li(1+)*3H(1+)

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; lithium tert-butoxide In N,N-dimethyl-formamide at 100℃; for 72h;13%
O-methylcaprolactim
2525-16-8

O-methylcaprolactim

1,7-dihydro-6H-purin-6-one
68-94-0

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

1,7-dimethylhypoxanthine
33155-83-8

1,7-dimethylhypoxanthine

7-ethoxy-3,4,5,6-tetrahydro-2H-azepine
13414-33-0

7-ethoxy-3,4,5,6-tetrahydro-2H-azepine

1,7-dihydro-6H-purin-6-one
68-94-0

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

1,7-diethyl-1,7-dihydro-purin-6-one
113977-05-2

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

4-diazobenzenesulfonic acid
305-80-6

4-diazobenzenesulfonic acid

1,7-dihydro-6H-purin-6-one
68-94-0

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

4-(6-oxo-6,7-dihydro-1H-purin-8-ylazo)-benzenesulfonic acid

4-(6-oxo-6,7-dihydro-1H-purin-8-ylazo)-benzenesulfonic acid

1,7-dihydro-6H-purin-6-one
68-94-0

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

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

5-phosphoribosyl-1-pyrophosphate

[5']inosinic acid
21214-07-3

[5']inosinic acid

Conditions
ConditionsYield
mit Hypoxanthin-phosphoribosyltransferase aus Hefe bzw.Rinderleber;
1,7-dihydro-6H-purin-6-one
68-94-0

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

triethylamine
121-44-8

triethylamine

6-diethylaminopurine
6284-24-8

6-diethylaminopurine

Conditions
ConditionsYield
With trichlorophosphate
Conditions
ConditionsYield
mit Enzym-Praeparat aus Rinderleber bzw. aus Taubenleber;
1,7-dihydro-6H-purin-6-one
68-94-0

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

methyl iodide
74-88-4

methyl iodide

1,7-dimethyl-1,7-dihydro-purin-6-one; sodium iodide compound

1,7-dimethyl-1,7-dihydro-purin-6-one; sodium iodide compound

Conditions
ConditionsYield
With sodium hydroxide
1,7-dihydro-6H-purin-6-one
68-94-0

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

6H-purine-6-thione
50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide; tetralin
With pyridine; tetraphosphorus decasulfide
Multi-step reaction with 2 steps
1: N,N-dimethyl-aniline; POCl3
2: ethanol
View Scheme
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

[5']inosinic acid
21214-07-3

[5']inosinic acid

Conditions
ConditionsYield
With by means of cultures of a(n) bacillus subtilis-mutant

Hypoxanthine Chemical Properties

Product Name:6-Hydroxypurine
Synonyms:1,7-dihydro-6h-purin-6-on;6-Hydroxy-1H-purine;6-Oxopurine;1,7-Dihydro-6H-purine-6-one;3H-Purin-6-ol;4-Hydroxy-1H-purine;6-Hydropurine;6H-Purin-6-one, 1,7-dihydro-;
1,7-dihydro-6h-purin-6-on is the chemical compound with the formula C5H4N4O.Its molecular weight is 136.11.It is white to off-white power.
Melting point:>300 °C(lit.)
storage temp.:2-8°C
solubility:1 M NaOH: 25 mg/mL
WATER Solubility:practically insoluble

Hypoxanthine Toxicity Data With Reference

1.   

ipr-mus LD50:750 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .

Hypoxanthine Consensus Reports

Reported in EPA TSCA Inventory.

Hypoxanthine Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.
Hypoxanthine's hazard Codes: Xn
Risk Statements:
20:Harmful by inhalation 
40:Limited evidence of a carcinogenic effect 
36/37/38:  Irritating to eyes, respiratory system and skin 
Hypoxanthine's safety Statements:
22:Do not breathe dust 
26:In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice 
36:Wear suitable protective clothing 
24/25:Avoid contact with skin and eyes 
37/39:Wear suitable gloves and eye/face protection 
WGK Germany:3
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