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97-59-6

Basic Information
CAS No.: 97-59-6
Name: Allantoin
Article Data: 114
Cas Database
Molecular Structure:
Molecular Structure of 97-59-6 (Allantoin)
Formula: C4H6N4O3
Molecular Weight: 158.117
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: N/A
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
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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