5427-26-9

Basic information

• Product Name: HYDANTOIN-5-ACETIC ACID
• Synonyms: LABOTEST-BB LT00440975;HYDANTOIN-5-ACETIC ACID;DL-5-(CARBOXYMETHYL)HYDANTOIN;(2,5-DIOXO-IMIDAZOLIDIN-4-YL)-ACETIC ACID;2,5-DIOXO-4-IMIDAZOLIDINEACETIC ACID;2,4-DIOXOIMIDAZOLIDINE-5-ACETIC ACID;5-HYDANTOIN ACETIC ACID;AKOS BBS-00005331
• CAS NO: 5427-26-9
• Molecular Formula: C5H6N2O4
• Molecular Weight: 158.11
• EINECS: 226-574-4
• Product Categories: Acetics acid and esters
• Mol File: 5427-26-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 214-215 °C (dec.)(lit.)
• Boiling Point: 283.16°C (rough estimate)
• Flash Point: °C
• Appearance: White/Crystalline Powder
• Density: 1.5902 (rough estimate)
• Refractive Index: 1.5090 (estimate)
• PKA: 3.79±0.10(Predicted)
• Water Solubility: 11.15g/L(temperature not stated)
• BRN: 83035
• CAS DataBase Reference: HYDANTOIN-5-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: HYDANTOIN-5-ACETIC ACID(5427-26-9)
• EPA Substance Registry System: HYDANTOIN-5-ACETIC ACID(5427-26-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5427-26-9(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Reactant for synthesis of:Nonfolate compounds as antiparasitic agents inhibiting pteridine reductase2,4-Azolidinedione-acetic acid derivatives as anticancer agentsAnti-inflammatory and analgesic drugsAmides via polystyrene-supported N-hydroxybenxotriazole resin

InChI:InChI=1/C5H6N2O4/c8-3(9)1-2-4(10)7-5(11)6-2/h2H,1H2,(H,8,9)(H2,6,7,10,11)/p-1/t2-/m0/s1

Synthetic route

ureidosuccinic acid (923-37-5, 173298-46-9) → 5-hydantoinacetic acid (5427-26-9)

hydantoin-5-acetic acid ethyl ester (58063-94-8) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With potassium hydroxide

potassium cyanate (590-28-3) + L-Aspartic acid (56-84-8) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With water anschliessend Kochen des Rueckstandes mit verd. Salzsaeure; hydantoin-acetic acid-(5), optically active form;

[(2,5-dioxo-imidazolidin-4-yl)-acetyl]-urea (198337-26-7) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With potassium hydroxide

(2E)-but-2-enedioic acid (110-17-8) + urea (57-13-6) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
at 135 - 140℃;

urea (57-13-6) + aspartic Acid (617-45-8) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
at 125 - 130℃;
With water man dampft das Reaktionsgemisch mit Salzsaeure ein;

potassium cyanate (590-28-3) + aspartic Acid (617-45-8) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With potassium hydroxide man dampft das Reaktionsgemisch mit Salzsaeure ein;
Stage #1: potassium cyanate; aspartic Acid With potassium hydroxide Stage #2: With hydrogenchloride In water

maleic acid monoureide monopotassium salt (38516-69-7) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With bromine In water

5-hydantoinmalonic acid (80754-77-4) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With hydrogenchloride at 70℃; for 30h; Rate constant;

5-carboxymethylene-hydantoin → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With phosphonium iodide; hydrogen iodide

anhydroureidosuccinic acid amide → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With hydrogenchloride

hydantoin-acetic acid-(5), optically active form → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With sodium hydroxide hydantoin-acetic acid-(5), optically inactive form;

ureidosuccinic acid monoamide → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
With hydrogenchloride

(2,5-dioxo-imidazolidin-4-ylidene)-acetic acid ethyl ester (943-18-0) → 5-hydantoinacetic acid (5427-26-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: platinum; ethanol / Hydrogenation 2: KOH View Scheme

furan-2-ylmethanamine (617-89-0) + 5-hydantoinacetic acid (5427-26-9) → 2-(2,5-dioxoimidazolidin-4-yl)-N-(furan-2-yl-methyl)acetamide (1114372-33-6)

Conditions	Yield
for 0.166667h; microwave irradiation;	90%

3-(4-nitro-phenyl)-4-phenyl-3H-thiazol-2-ylideneamine (109902-46-7) + 5-hydantoinacetic acid (5427-26-9) → 2-(2,5-dioxoimidazolidin-4-yl)-N-(3-(4-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)acetamide (1147735-20-3)

Conditions	Yield
for 0.333333h; Microwave irradiation;	84%

4-aminophenyl methacrylate (23679-72-3) + 5-hydantoinacetic acid (5427-26-9) → 4-(2-(2,5-dioxoimidazolidin-4yl)acetamido)phenyl methacrylate

Conditions	Yield
Stage #1: 5-hydantoinacetic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.166667h; Stage #2: 4-aminophenyl methacrylate In N,N-dimethyl-formamide for 12h;	75%

3-(2-nitro-phenyl)-4-phenyl-3H-thiazol-2-ylideneamine (37671-55-9) + 5-hydantoinacetic acid (5427-26-9) → 2-(2,5-dioxoimidazolidin-4-yl)-N-(3-(2-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)acetamide (1147735-21-4)

Conditions	Yield
for 0.333333h; Microwave irradiation;	74%

methanol (67-56-1) + 5-hydantoinacetic acid (5427-26-9) → D,L-aspartic acid methyl ester hydantoin (78212-20-1)

Conditions	Yield
With thionyl chloride for 1h; Ambient temperature;	72%

1-amino-2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl (41355-50-4) + 5-hydantoinacetic acid (5427-26-9) → 2,3,4,6-tetra-O-acetyl-N-(5-hydantoinacetyl)-β-D-mannopyranosylamine (74761-73-2)

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide; acetonitrile for 18h; Ambient temperature;	72%

5-hydantoinacetic acid (5427-26-9) → (2Z)-(2,5-dioxoimidazolidin-4-ylidene)acetic acid (153816-00-3)

Conditions	Yield
With bromine In acetic acid at 100℃; for 4h;	71%

1-(2-tert-butylphenyl)piperazine dihydrochloride + 5-hydantoinacetic acid (5427-26-9) → 5-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dione (1252656-48-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;	70%

5-hydantoinacetic acid (5427-26-9) + 3-(p-chlorophenyl)-4-phenyl-2-imino-4-thiazoline (109902-44-5) → N-(3-(4-chlorophenyl)-4-phenylthiazol-2(3H)-ylidene)-2-(2,5-dioxoimidazolidin-4-yl)acetamide (1147735-19-0)

Conditions	Yield
for 0.333333h; Microwave irradiation;	67%

4-oxo-N-[(3-piperazin-1-ylphenyl)methyl]-3,4-dihydroquinazoline-2-carboxamide dihydrochloride + 5-hydantoinacetic acid (5427-26-9) → N-[(3-{4-[(2,5-dioxoimidazolidin-4-yl)acetyl]piperazin-1-yl}phenyl)methyl]-4-oxo-3,4-dihydroquinazoline-2-carboxamide (935759-86-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 13h;	62%
Stage #1: 4-oxo-N-[(3-piperazin-1-ylphenyl)methyl]-3,4-dihydroquinazoline-2-carboxamide dihydrochloride; 5-hydantoinacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	62%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 5-hydantoinacetic acid (5427-26-9) → (2,5-dioxo-imidazolidin-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	55%

2-Bromo-4'-phenylacetophenone (135-73-9) + 5-hydantoinacetic acid (5427-26-9) → 2-(1,1'-biphenyl-4-yl)-2-oxoethyl (2,5-dioxoimidazolidin-4-yl)acetate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 50℃; for 3h;	50.1%

4-Methoxyphenylacetic acid (104-01-8) + isobutylamine (78-81-9) + 5-hydantoinacetic acid (5427-26-9) + toluene-4-sulfonic acid 3-azido-2-hydroxy-5-methyl-hexyl ester → 2-(2,5-dioxo-imidazolidin-4-yl)-N-{2-hydroxy-3-[2-(4-methoxy-phenyl)-acetylamino]-5-methyl-hexyl}-N-isobutyl-acetamide

Conditions	Yield
Multistep reaction;	50%

5-hydantoinacetic acid (5427-26-9) + (5-methylpyrazine-2-yl)methylamine (132664-85-8) → 2-(2,5-dioxoimidazolidin-4-yl)-N-((5-methylpyrazin-2-yl)methyl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	46%

5-hydantoinacetic acid (5427-26-9) → (2,5-dioxo-imidazolidin-4-yl)-acetyl chloride (51876-11-0)

Conditions	Yield
With thionyl chloride at 89℃; for 120h; Heating / reflux;	22%
With thionyl chloride In 1,4-dioxane for 0.5h; Reflux;

1-(4-morpholin-4-ylphenyl)methanamine (214759-74-7) + 5-hydantoinacetic acid (5427-26-9) → 2-(2,5-Dioxoimidazolidin-4-yl)-N-(4-morpholinobenzyl)acetamide

Conditions	Yield
Stage #1: 5-hydantoinacetic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1-(4-morpholin-4-ylphenyl)methanamine In N,N-dimethyl-formamide at 0 - 20℃; for 16.5h; Inert atmosphere;	13%

5-hydantoinacetic acid (5427-26-9) → (2,5-dioxo-imidazolidin-4-yliden)-acetic acid (58668-24-9)

Conditions	Yield
With bromine; acetic acid Beim Erhitzen des Reaktionsprodukts mit H2O;

ethanol (64-17-5) + 5-hydantoinacetic acid (5427-26-9) → hydantoin-5-acetic acid ethyl ester (58063-94-8)

Conditions	Yield
With hydrogenchloride

Fmoc-Val-OH (68858-20-8) + (4R,5R,1''S)-1-methyl-1-(3'-carboxypropyl)-4,5-bis<1''-<(fluorenylmethyloxycarbonyl)amino>-2''-phenylethyl>-1,3-dioxolane (170117-43-8) + 5-hydantoinacetic acid (5427-26-9) → (S)-N-((1S,2R,3R,4S)-1-Benzyl-4-{(S)-2-[2-(2,5-dioxo-imidazolidin-4-yl)-acetylamino]-3-methyl-butyrylamino}-2,3-dihydroxy-5-phenyl-pentyl)-2-[2-(2,5-dioxo-imidazolidin-4-yl)-acetylamino]-3-methyl-butyramide

Conditions	Yield
Multistep reaction;

Fmoc-Val-OH (68858-20-8) + 10-<1'-<<(2''S,3''S,5''S)-2'',5''-bis<(fluorenylmethyloxycarbonyl)amino>-1'',5''-diphenylhex-3''-yl>oxy>ethoxy>decanoic acid (220784-31-6) + 5-hydantoinacetic acid (5427-26-9) → (S)-N-((1S,2S,4S)-1-Benzyl-4-{(S)-2-[2-(2,5-dioxo-imidazolidin-4-yl)-acetylamino]-3-methyl-butyrylamino}-2-hydroxy-5-phenyl-pentyl)-2-[2-(2,5-dioxo-imidazolidin-4-yl)-acetylamino]-3-methyl-butyramide

Conditions	Yield
Multistep reaction;

Upstream product

• 590-28-3 potassium cyanate 
• 56-84-8 L-Aspartic acid 
• 923-37-5 ureidosuccinic acid 
• 198337-26-7 [(2,5-dioxo-imidazolidin-4-yl)-acetyl]-urea 
• 110-17-8 (2E)-but-2-enedioic acid 
• 57-13-6 urea 
• 38516-69-7 maleic acid monoureide monopotassium salt 
• 943-18-0 (2,5-dioxo-imidazolidin-4-ylidene)-acetic acid ethyl ester 
• 80754-77-4 5-hydantoinmalonic acid 
• 617-45-8 aspartic Acid 
• 58063-94-8 hydantoin-5-acetic acid ethyl ester 

Downstream Products

• 51876-11-0 (2,5-dioxo-imidazolidin-4-yl)-acetyl chloride 
• 1009488-20-3 4-methylaniline derivative of hydantoin-5-acetic acid 
• 473254-24-9 phenylamine derivative of hydantoin-5-acetic acid 
• 1252657-48-9 5-{2-[4-(2-tert-Butyl-4-methylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dione 
• 1252656-48-6 5-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}imidazolidine-2,4-dione 
• 1147735-19-0 N-(3-(4-chlorophenyl)-4-phenylthiazol-2(3H)-ylidene)-2-(2,5-dioxoimidazolidin-4-yl)acetamide 
• 1147735-20-3 2-(2,5-dioxoimidazolidin-4-yl)-N-(3-(4-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)acetamide 
• 1147735-21-4 2-(2,5-dioxoimidazolidin-4-yl)-N-(3-(2-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)acetamide 
• 935759-86-7 N-[(3-{4-[(2,5-dioxoimidazolidin-4-yl)acetyl]piperazin-1-yl}phenyl)methyl]-4-oxo-3,4-dihydroquinazoline-2-carboxamide 
• 65-86-1 orotic acid 
• 144-62-7 oxalic acid 

Relevant articles and documents

EFFECT OF THE REACTION MEDIUM ON THE BROMOCYCLIZATION OF MALEIC AND FUMARIC ACID MONOUREIDES

The monopotassium salt of maleic acid monoureide is brominated in water in the same way as the free acid, whereas the trans isomer is not brominated at all. Bromocyclization of the monopotassium salt of the cis isomer to give 5-(bromocarboxymethyl)hydantoin and intramolecular cyclization to give 5-(carboxymethyl)hydantoin are realized at pH 4-6. erythro-2,3-Dibromosuccinic acid and 5-(bromo-carboxymethyl)hydantoin are formed in the bromination of the monopotassium salt of fumaric acid monoureide at pH 4-6.Bromination of the methyl ester of maleic acid monoureide in 1,2-dichloroethane proceeds in the same way as bromination in water to give 2-amino-5-oxazolid-4-one.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Formation of N-Carbamoylaspartic Acid and Its Cyclisation to Orotic Acid

The stereochemistries of the reactions between cyanate and aspartic acid and 3-methylaspartic acid have been examined.The product of the first reaction, N-carbamoylaspartic acid 3, can cyclise to give either dihydroorotic acid 5 or 5-carboxymethylmydantoin 4.Acid catalysed cyclisation gives the latter while catalysis by the enzyme dihydroorotase gives the former.Introduction of a double bond into 3 changes the course of non-enzymatic cyclisation and a six-membered ring compound orotic acid 1 is the product.It is proposed that the double bond prevents intramolecular hydrogen bonding.