5-Hydantoinacetic acid

Base Information

• Chemical Name: 5-Hydantoinacetic acid
• CAS No.: 5427-26-9
• Molecular Formula: C5H6 N2 O4
• Molecular Weight: 158.114
• Hs Code.: 2933990090
• European Community (EC) Number: 226-574-4
• NSC Number: 49347,14985
• DSSTox Substance ID: DTXSID20875595
• Nikkaji Number: J216J
• Mol file: 5427-26-9.mol

Synonyms:5427-26-9;5-Hydantoinacetic acid;Hydantoin-5-acetic acid;2-(2,5-dioxoimidazolidin-4-yl)acetic acid;(2,5-dioxoimidazolidin-4-yl)acetic acid;5-Hydantoin acetic acid;4-Imidazolidineacetic acid, 2,5-dioxo-;2,5-Dioxo-1,3-diazolidin-4-ylacetic acid;EINECS 226-574-4;MFCD00005267;5-Hydantoinaceticacid;dl-Hydantoin-5-acetic acid;SCHEMBL337478;DL-5-(Carboxymethyl)hydantoin;(+/-)hydantoin-5-acetic acid;Hydantoin-5-acetic acid, 98%;(+/-) hydantoin-5-acetic acid;DTXSID20875595;HMS1654E10;NSC14985;NSC49347;BBL010048;NSC 14985;NSC 49347;NSC-14985;NSC-49347;STK500369;AKOS000269789;AKOS016039846;CS-W017961;SB46778;AS-65256;2-(2,5-dioxoimidazolidin-4-yl)aceticacid;(2,5-Dioxo-4-imidazolidinyl)acetic acid #;(2,5-dioxo-imidazolidin-4-yl)-acetic acid;FT-0620459;2-oxo-2-(5-oxoimidazolidin-4-yl)acetic acid;EN300-25868;D77819;H-3520;A830074;Z57662377

Chemical Property of 5-Hydantoinacetic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 214-215 °C (dec.)(lit.)
• Refractive Index: 1.5090 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: °C
• PSA: 95.50000
• Density: 1.491g/cm³
• LogP: -0.67330
• Water Solubility.: 11.15g/L(temperature not stated)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 158.03275668
• Heavy Atom Count: 11
• Complexity: 225

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2,5-Dioxoimidazolidin-4-yl)aceticAcid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(=O)NC(=O)N1)C(=O)O
• 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

Technology Process of 5-Hydantoinacetic acid

There total 15 articles about 5-Hydantoinacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

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

Guidance literature:

With hydrogenchloride;

Reference yield:

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

Guidance literature:

With potassium hydroxide;

DOI:10.1021/ja01195a062

Reference yield:

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

Guidance literature:

Multi-step reaction with 2 steps

1: platinum; ethanol / Hydrogenation

2: KOH

With potassium hydroxide; ethanol; platinum;

DOI:10.1021/ja01195a062

upstream raw materials:

hydantoin-5-acetic acid ethyl ester

potassium cyanate

L-Aspartic acid

ureidosuccinic acid

Downstream raw materials:

2-(2,5-dioxoimidazolidin-4-yl)-N-(3-(2-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)acetamide

2-(2,5-dioxoimidazolidin-4-yl)-N-(3-(4-nitrophenyl)-4-phenylthiazol-2(3H)-ylidene)acetamide

N-(3-(4-chlorophenyl)-4-phenylthiazol-2(3H)-ylidene)-2-(2,5-dioxoimidazolidin-4-yl)acetamide

4-methylaniline derivative of hydantoin-5-acetic acid

Refernces

• 1、 Mitchell,Nyc. "-". . p. 674. Retrieved 1947.
• 2、 Kaminskyy, Danylo,Zimenkovsky, Borys,Lesyk, Roman. "Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives". scheme or table. p. 3627 - 3636. Retrieved 2009/12/04.
• 3、 Christy, M. Robert,Koch, Tad H.. "Chemical Reactivity of the New Amino Acid β-Carboxyaspartic Acid (Asa)". . p. 1771 - 1772. Retrieved 2007/10/02.