50-71-5

Usage

Uses

Used in Biochemical Research:
Alloxan is utilized as a research tool in the field of biochemistry, particularly for studying the mechanisms of diabetes and the effects of various compounds on pancreatic beta cells. It is also used to induce diabetes in experimental animal models for research purposes.
Used in Cosmetics:
In the cosmetics industry, Alloxan is employed as an ingredient in various formulations due to its ability to impart a pink color to the skin. This property makes it useful for creating color effects in products such as blushes, lipsticks, and other makeup items.
Used in Organic Synthesis:
Alloxan serves as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals and other specialty chemicals. Its unique structure and reactivity make it a valuable building block for the development of new molecules with potential applications in various industries.

Safety Profile

Poison by intraperitoneal, intravenous, subcutaneous, and rectal routes. Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Produces dlabetes in experimental animals. Decomposes in storage to release CO2. Do not store in sealed container. Explodes when heated above 170℃. When heated to decomposition it emits toxic fumes of NOx,.

Purification Methods

Crystallisation from water gives the tetrahydrate. Anhydrous crystals are obtained by crystallisation from acetone, glacial acetic acid or by sublimation in vacuo. [See below and Beilstein 24 H 500, 24 I 428, 24 II 301, 24 III/IV 2137.]

InChI:InChI=1/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)

Synthetic route

BARBITURIC ACID (67-52-7) → 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5)

Conditions	Yield
With chromium(VI) oxide In acetic acid

3,5-dihydroxyphenol (108-73-6) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 5-hydroxy-5-[2,4,6-trihydroxy-3,5-bis(5-hydroxy-2,4,6-trioxo-3,5-dihydro-1H-pyrimidin-5-yl)phenyl]-3,5-dihydro-1H-pyrimidine-2,4,6-trione

Conditions	Yield
With acetic acid at 20℃; for 24h;	92%

1,2-diamino-benzene (95-54-5) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → alloxazine (490-59-5)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	86%

benzyl (2-amino-3-(cyclohexylamino)phenyl)carbamate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → benzyl (10-cyclohexyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]-pteridine-6-yl)carbamate

Conditions	Yield
With boron trioxide; acetic acid at 20℃; for 18h;	82%

dibenzyl ((((1‘‘R,2‘‘R)-cyclohexane-1‘‘,2‘‘-diyl)bis(azanediyl))bis(2-amino-3,1-phenylene))dicarbamate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → dibenzyl (((1‘‘R,2‘‘R)-cyclohexane-1‘‘,2‘‘-diyl)bis(2,4-dioxo-2,3,4,4a-tetrahydrobenzo[g]pteridine-9a,6-diyl))dicarbamate

Conditions	Yield
With boron trioxide; acetic acid at 20℃; for 14h;	78%

pyrene‐4,5‐diamine + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → pyreno[4,5-g]pteridine-11,13(10H,12H)-dione

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	75%

2,3-Diaminonaphthalene (771-97-1) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → naphtho[2,3-g]pteridine-2,4(1H,3H)-dione (4794-65-4)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	73%

copper(II) choride dihydrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → Cu(2+)*C4N2O4(2-)*3H2O=Cu(C4N2O4)*3H2O

Conditions	Yield
With water In water gradual addn. of an aq. soln. of CuCl2*2H2O to an aq. soln. of alloxane; simultaneous addn. of 10% aq. NaOH (->pH=7.5); pH=5 or pH=6 for a few hours;; ppt.; washing with cold H2O; drying in vac. at ambient temp. over CaCl2;;	72%
With H2O In water gradual addn. of an aq. soln. of CuCl2*2H2O to an aq. soln. of alloxane; simultaneous addn. of 10% aq. NaOH (->pH=7.5); pH=5 or pH=6 for a few hours;; ppt.; washing with cold H2O; drying in vac. at ambient temp. over CaCl2;;	72%

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) + cobalt(II) chloride (7646-79-9) → alloxane, Co-salt * pentahydrate

Conditions	Yield
With sodium hydroxide In water addition of CoCl2 in H2O to a solution of alloxane in H2O under addition of NaOH-solution until pH=7.5; then pH=5-6; seperation of the ppt. after some hours;; washing the product with cold H2O; drying in vac. at normal temperature over CaCl2;;	69%
With NaOH In water

nickel(II) nitrate hexahydrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → Ni(2+)*C4N2O4(2-)*5H2O=NiC4N2O4*5H2O

Conditions	Yield
With sodium hydroxide In water gradual addn. of equimolar amt. of aq. Ni(NO3)2*6H2O soln. to aq. soln. of alloxan, addn. of 10% NaOH soln. to pH 7.5, then adjusting to pH 5-6;; pptn., sepg. after several hours, washing with cold H2O, drying in vac. at ambient temp. over CaCl2;;	66%

2-amino-4,5-difluoroaniline (76179-40-3) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 8,9-difluoronaphtho[2,3-g]pteridine-2,4(1H,3H)-dione

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	58%

2,3-diaminephenazine (655-86-7) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → pteridino[6,7-b]phenazine-2,4(1H,3H)-dione

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	57%

1-(N-octylamino)-2-aminobenzene (38423-40-4) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 10-octylisoalloxazine

Conditions	Yield
With boric acid; acetic acid at 60℃; for 1h;	41%

N-butyl-4-trifluoromethylbenzene-1,2-diamine (320406-61-9) + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → 10-butyl-7-(trifluoromethyl)isoalloxazine

Conditions	Yield
With boric acid; acetic acid at 70℃; for 3h;	39%

C26H30N4 + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → C30H28N6O2

Conditions	Yield
With boric acid; acetic acid at 60℃; for 1h;	33.7%

5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) + 2,3-diaminomaleonitrile (18514-52-8) → 2,4-dioxo-1,2,3,4-tetrahydropteridine-6,7-dicarbonitrile (55408-53-2)

Conditions	Yield
With boric acid In acetic acid at 60℃; for 15h; Inert atmosphere;	32%

mercury(II) nitrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → alloxane*mercury(II) oxide*7H2O

Conditions	Yield
With H2O In water pptn. from alloxane soln. with Hg(NO3)2;;

ferric sulfate nonahydrate + 5,5-dihydroxypyrimidine-2,4,6(1H,3H,5H)-trione (50-71-5) → Fe(OH)(SO4H)2(NH(CO)3NH(CO))H2O

Conditions	Yield
In water mixing ratio Fe2(SO4)3*9H2O:alloxan = 1:2 at pH=2; evapd. (water bath); sepn. of crystals; dried; elem.anal.; X-ray diffraction;

Upstream product

• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 67-52-7 BARBITURIC ACID 

Downstream Products

• 21708-43-0 10-benzylbenzo[g]pteridine-2,4(3H,10H)-dione 
• 490-59-5 alloxazine 

Relevant academic research and scientific papers

Novel riboflavin-inspired conjugated bio-organic semiconductors

Flavins are known to be extremely versatile, thus enabling routes to innumerable modifications in order to obtain desired properties. Thus, in the present paper, the group of bio-inspired conjugated materials based on the alloxazine core is synthetized using two efficient novel synthetic approaches providing relatively high reaction yields. The comprehensive characterization of the materials, in order to evaluate the properties and application potential, has shown that the modification of the initial alloxazine core with aromatic substituents allows fine tuning of the optical bandgap, position of electronic orbitals, absorption and emission properties. Interestingly, the compounds possess multichromophoric behavior, which is assumed to be the results of an intramolecular proton transfer.