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97-59-6

Basic Information
CAS No.: 97-59-6
Name: Allantoin
Molecular Structure:
Molecular Structure of 97-59-6 (Allantoin)
Formula: C4H6N4O3
Molecular Weight: 158.12
Synonyms: (2,5-dioxoimidazolidin-4-yl)urea;Glyoxylic(acid) diureide;urea, N-(2,5-dioxo-4-imidazolidinyl)-;Cutemol emollient;[(4S)-2,5-dioxoimidazolidin-4-yl]urea;5-Ureido-2,4-imidazolidindion;[(4R)-2,5-dioxoimidazolidin-4-yl]urea;Urea, (2,5-dioxo-4-imidazolidinyl)-;Urea, (2,5-dioxo-4-imidazolidinyl)- (9CI);Glyoxyldiureide;Urea, (2, 5-dioxo-4-imidazolidinyl)-;Glyoxylic diureide;(2,5-Dioxo-4-imidazolidinyl)urea;5-Ureidohydantoin;Allantoin (5-Ureidohydantoin);Urea,(2,5-dioxo-4-imidazolidinyl)-;
EINECS: 202-592-8
Density: 1.652 g/cm3
Melting Point: 230 °C (dec.)(lit.)
Boiling Point: 478oC
Flash Point: 230-234 °C
Solubility: Slightly soluble in water. Freely soluble in alkalis
Appearance: White crystalline powder
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 22-36/37/38
Safety: 22-24/25-36-26
Transport Information:
PSA: 113.32000
LogP: -0.43100
Synthetic route
298-12-4

Glyoxilic acid

97-59-6

Allantoin

Conditions
ConditionsYield
With Co[PyPS]2Mo11VO40 at 90℃; for 10h; Temperature; Reagent/catalyst; Microwave irradiation;89.3%
With titanium dioxide-based composite solid catalyst A1 at 75℃; for 4h;85%
at 60℃; for 1.5h; Concentration;82.4%
69-93-2

uric Acid

A

120-89-8

parabanic acid

B

5676-27-7

Oxalyldiurea

C

105245-87-2

dehydro-allantoin

D

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;
69-93-2

uric Acid

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
69-93-2

uric Acid

A

121669-46-3

potassium salt of uroxanate

B

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%
32282-43-2

DL-5-chlorohydantoin

97-59-6

Allantoin

Conditions
ConditionsYield
In nitromethane for 1h; Reflux;15%
69-93-2

uric Acid

A

508-37-2

uroxanate

B

97-59-6

Allantoin

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate In water for 4h; Ambient temperature; Yield given;A n/a
B 14%
461-72-3

2,4-imidazolidinedione

97-59-6

Allantoin

Conditions
ConditionsYield
With bromine; acetic acid
496-46-8

glycoluril

97-59-6

Allantoin

Conditions
ConditionsYield
With dihydrogen peroxide; copper dichloride
444-15-5

5-hydroxybarbituric acid

97-59-6

Allantoin

Conditions
ConditionsYield
With potassium nitrite; acetic acid
99-16-1

allantoic acid

97-59-6

Allantoin

Conditions
ConditionsYield
With water
874531-63-2

4,5-dihydroxy-2-oxo-5-ureido-imidazolidine-4-carboxylic acid

97-59-6

Allantoin

Conditions
ConditionsYield
With water at 60 - 80℃;
With nitric acid
79-43-6

dichloro-acetic acid

97-59-6

Allantoin

473-90-5

acetonedicarboxylic acid

97-59-6

Allantoin

Conditions
ConditionsYield
With water at 110 - 115℃;
at 110℃;
at 110℃;
6065-82-3

Ethyl diethoxyacetate

97-59-6

Allantoin

69-93-2

uric Acid

A

120-89-8

parabanic acid

B

61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

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

C

36597-25-8

4-hydroxy-2,5-dioxoimidazolidine-4-carboxamide

D

3237-50-1

5,5-dihydroxy-pyrimidine-2,4,6-trione

E

57-13-6

urea

F

97-59-6

Allantoin

Conditions
ConditionsYield
In methanol Mechanism; electrochemical oxidation;
69-93-2

uric Acid

A

61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

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

B

57-13-6

urea

C

97-59-6

Allantoin

Conditions
ConditionsYield
at 25℃; Product distribution; Mechanism; Rate constant; electrochemical oxidation; buffer (pH=2-10); various times, potentials and electrodes;
In phosphate buffer at 24℃; pH=2.3 - 11.2; Product distribution; Further Variations:; effect of surfactants; differential pulse voltammetric oxidation; Electrochemical reaction;
81129-52-4

1-carboxy-2,4,6,8-tetraazabicyclo<3.3.0>octa-4-ene-3,7-dione

97-59-6

Allantoin

Conditions
ConditionsYield
With hydroxide at 25℃; Rate constant;
69-89-6

xanthin

97-59-6

Allantoin

Conditions
ConditionsYield
at 25℃; Product distribution; Mechanism; Rate constant; electrochemical oxidation; buffer (pH=6-10); various times, potentials and electrodes;
6960-30-1, 151359-24-9

5-hydroxyisourate

97-59-6

Allantoin

Conditions
ConditionsYield
With phosphate buffer In water at 22℃; Rate constant; var. ionic strength of buffer;

Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2,6,8-trioxo-1,2,6,8-tetrahydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester

A

36597-25-8

4-hydroxy-2,5-dioxoimidazolidine-4-carboxamide

B

36468-53-8

β-D-ribofuranose

C

Phosphoric acid mono-[(2R,3S,4R,5R)-5-(2,5-dioxo-4-ureido-imidazolidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

D

97-59-6

Allantoin

Conditions
ConditionsYield
In water at 22℃; Rate constant; pH 7.0; decomposition rate constants;
74333-71-4

4,5-dimethoxy-4,5-dihydrouric acid

97-59-6

Allantoin

590-28-3

potassium cyanate

24764-63-4

5-amino-imidazolidine-2,4-dione

97-59-6

Allantoin

69-93-2

uric Acid

7722-84-1

dihydrogen peroxide

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

97-59-6

Allantoin

Conditions
ConditionsYield
at 38℃;
461-72-3

2,4-imidazolidinedione

7726-95-6

bromine

64-19-7

acetic acid

97-59-6

Allantoin

69-93-2

uric Acid

air oxygen

air oxygen

alkaline solution

alkaline solution

97-59-6

Allantoin

Conditions
ConditionsYield
saeuert man die alkal.Loesung mit Essigsaeure, und nach weiterem Stehenlassen oder Eindampfen der Loesung;
allantoin-imide-(4)

allantoin-imide-(4)

97-59-6

Allantoin

Conditions
ConditionsYield
With hydrogenchloride
With water
allantoinoic acid ethyl ester

allantoinoic acid ethyl ester

97-59-6

Allantoin

Conditions
ConditionsYield
With ammonia
With potassium hydroxide
With potassium hydroxide
alloxanate urea

alloxanate urea

97-59-6

Allantoin

Conditions
ConditionsYield
With acetic anhydride
470-44-0

alloxanoic acid

108-24-7

acetic anhydride

alloxanate urea

alloxanate urea

97-59-6

Allantoin

97-59-6

Allantoin

2207-75-2

monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate

Conditions
ConditionsYield
With N-Bromosuccinimide; potassium iodide; potassium hydroxide In water at 0 - 25℃; for 3h; Temperature; Reagent/catalyst; Darkness;91.32%
127099-85-8, 780722-26-1

N-Cyanoguanidine

97-59-6

Allantoin

N-[(2,5-dioxoimidazolidin-4-yl)carbamoyl]imidodicarbonimidic diamide

Conditions
ConditionsYield
With sulfuric acid In water for 20h; Heating; Green chemistry;81%
1590389-14-2

potassium (4-fluorobenzoyl)trifluoroborate

97-59-6

Allantoin

N-((2,5-dioxoimidazolidin-4-yl)carbamoyl)-4-fluorobenzamide

Conditions
ConditionsYield
With 1,3-dichloro-5,5-dimethylhydantoin In tetrahydrofuran at 40℃; for 4h; pH=3; chemoselective reaction;80%
64-19-7

acetic acid

97-59-6

Allantoin

2207-75-2

monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate

Conditions
ConditionsYield
Stage #1: Allantoin With bromine; potassium iodide; potassium hydroxide In water at 0 - 25℃; for 30h;
Stage #2: acetic acid In water at 0 - 5℃; pH=5; Time;
76.1%
69812-30-2

2-(acetylamino)-1,3-thiazole-5-sulfonyl chloride

97-59-6

Allantoin

C9H10N6O6S2

Conditions
ConditionsYield
With potassium carbonate In ethanol for 3h; Heating;52%
60971-83-7

1-(3-iodopropyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-2,6-purinedione

97-59-6

Allantoin

{1-[3-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-purin-1-yl)-propyl]-2,5-dioxo-imidazolidin-4-yl}-urea

Conditions
ConditionsYield
Stage #1: Allantoin With sodium methylate In methanol for 1.5h; Heating;
Stage #2: 1-(3-iodopropyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-2,6-purinedione In methanol for 36h; Heating;
40%
97-59-6

Allantoin

108-95-2

phenol

A

2420-17-9

5-(4-hydroxy-phenyl)-imidazolidine-2,4-dione

B

77972-18-0

D,L-5-(2'-hydroxyphenyl)hydantoin

Conditions
ConditionsYield
hydrogenchloride at 65℃; for 24h;A 19.2%
B 8%
hydrogenchloride at 65℃; for 24h;A 19.2%
B 8%
77-78-1

dimethyl sulfate

97-59-6

Allantoin

22494-77-5

3-methyl-5-ureidohydantoin

Conditions
ConditionsYield
With potassium hydroxide
Darstellung;
97-59-6

Allantoin

592-18-7

carbamoylimino-acetic acid

Conditions
ConditionsYield
With hydrogenchloride nachfolgende Einw. von salpetriger Saeure;
97-59-6

Allantoin

461-72-3

2,4-imidazolidinedione

Conditions
ConditionsYield
With hydrogen iodide
97-59-6

Allantoin

496-46-8

glycoluril

Conditions
ConditionsYield
With sodium amalgam; sulfuric acid
97-59-6

Allantoin

585-05-7

oxaluric acid

Conditions
ConditionsYield
With permanganate(VII) ion; acetic acid
97-59-6

Allantoin

A

585-05-7

oxaluric acid

B

5676-27-7

Oxalyldiurea

Conditions
ConditionsYield
With ammonium persulfate; sodium acetate
With potassium permanganate; bi carbonate .alkali
With potassium permanganate; acetic acid
97-59-6

Allantoin

556-99-0

triuret

Conditions
ConditionsYield
With dihydrogen peroxide
97-59-6

Allantoin

99-16-1

allantoic acid

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide; water
enzymatische Spaltung durch Brei oder Presssaft von Leguminosensamen;
With water Alkaline conditions;
97-59-6

Allantoin

462-60-2

N-carbamoylglycine

Conditions
ConditionsYield
With barium dihydroxide
97-59-6

Allantoin

861794-23-2

diureido-acetic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate
97-59-6

Allantoin

A

556-99-0

triuret

B

57-13-6

urea

Conditions
ConditionsYield
With lithium carbonate Bei der elektrochemischen Oxydation an einer Bleidioxydanode;
90-46-0

9-hydroxyxanthene

97-59-6

Allantoin

87980-02-7

1-(2,5-dioxo-imidazolidin-4-yl)-3-xanthen-9-yl-urea

Conditions
ConditionsYield
With acetic acid
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    Allantoin 97-59-6

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  • Casno:

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    ALLANTOIN Chemical Name: 5-Ureidohydantoin; Allantion; (2,5-dioxo-4-imidazolidinyl)-urea Trade Name: ALLANTOIN Structural Formula: Molecular Formula: C4H6N4O3 Molecular Weight: 158.1

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  • allantoin CAS:97-59-6 Safe delivery Free of customs clearance

  • Casno:

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Specification

The Allantoin, with the CAS registry number 97-59-6, is also known as 1-(2,5-Dioxo-4-imidazolidinyl)urea. It belongs to the product categories of Substrates; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. Its EINECS registry number is 202-592-8. This chemical's molecular formula is C4H6N4O3 and molecular weight is 158.12. What's more, its IUPAC name is called (2,5-Dioxoimidazolidin-4-yl)urea. It should be stored in a cool, dry and well-ventilated place. In fish, Allantoin is broken down further (into ammonia) before excretion. It is a major metabolic intermediate in many other organisms including plants and bacteria. It is frequently present in toothpaste, mouthwash, and other oral hygiene products, in shampoos, lipsticks, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.

Physical properties about Allantoin are: (1)ACD/LogP: -1.523; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.52; (4)ACD/LogD (pH 7.4): -1.62; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 3.53; (8)ACD/KOC (pH 7.4): 2.81; (9)#H bond acceptors: 7; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 113.32 Å2; (13)Index of Refraction: 1.616; (14)Molar Refractivity: 33.422 cm3; (15)Molar Volume: 95.701 cm3; (16)Polarizability: 13.25×10-24cm3; (17)Surface Tension: 82.625 dyne/cm; (18)Density: 1.652 g/cm3.

Preparation of Allantoin: this chemical can be prepared by 7,9-dihydro-3H-purine-2,6,8-trione. This reaction needs reagents I2, LiOH and solvent H2O at temperature of 4 °C. The yield is 70 %.

Allantoin can be prepared by 7,9-dihydro-3H-purine-2,6,8-trione.

Uses of Allantoin: it is used to produce other chemicals. For example, it can react with 1-(3-iodo-propyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione to get {1-[3-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-purin-1-yl)-propyl]-2,5-dioxo-imidazolidin-4-yl}-urea. The reaction occurs with reagent NaOMe and other condition of heating for 1.5 hours. The yield is 40 %.

Allantoin can react with 1-(3-iodo-propyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione to get {1-[3-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-purin-1-yl)-propyl]-2,5-dioxo-imidazolidin-4-yl}-urea.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. It has serious damage to eyes. If swallowed, it's harmful to health. Therefore, you should wear suitable protective clothing. The gas can not be breathed and you should avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: C1(C(=O)NC(=O)N1)NC(=O)N
(2) InChI: InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
(3) InChIKey: POJWUDADGALRAB-UHFFFAOYSA-N