Allantoin

Base Information

• Chemical Name: Allantoin
• CAS No.: 97-59-6
• Deprecated CAS: 37305-69-4,5377-33-3,58308-55-7,5377-33-3,58308-55-7
• Molecular Formula: C4H6N4O3
• Molecular Weight: 158.117
• Hs Code.: 29332100
• European Community (EC) Number: 202-592-8
• NSC Number: 757792,7606
• UNII: 344S277G0Z
• DSSTox Substance ID: DTXSID3020043
• Nikkaji Number: J3.978K
• Wikipedia: Allantoin
• Wikidata: Q409804
• NCI Thesaurus Code: C74277
• RXCUI: 508
• Metabolomics Workbench ID: 143220
• ChEMBL ID: CHEMBL593429
• Mol file: 97-59-6.mol

Synonyms:Allantoin;Herpecin L;Herpecin-L;HerpecinL;Sebical;Woun'dres

Chemical Property of Allantoin

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 230 °C (dec.)(lit.)
• Refractive Index: 1.615
• Boiling Point: 478oC
• PKA: 8.96(at 25℃)
• Flash Point: 230-234 °C
• PSA: 113.32000
• Density: 1.652 g/cm³
• LogP: -0.43100
• Storage Temp.: Refrigerator
• Solubility.: H2O: soluble0.1g/10 mL, clear, colorless
• Water Solubility.: Slightly soluble in water. Freely soluble in alkalis
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.04399007
• Heavy Atom Count: 11
• Complexity: 225

Purity/Quality:

99%, ^*data from raw suppliers

Allantoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: C1(C(=O)NC(=O)N1)NC(=O)N
• Recent ClinicalTrials: Study of Alwextin? Cream in Treating Epidermolysis Bullosa
• Recent EU Clinical Trials: An Open Label, Multi-center, Extension Study to Evaluate the Long-term Safety of Zorblisa (SD-101-6.0) in Patients with Epidermolysis Bullosa
• Chemical Composition: Allantoin, chemically known as (2,5-dioxo-4-imidazolidinyl)urea, consists of a heterocyclic compound with a five-membered ring containing a urea substituent in the 4th position.
• Biological Properties: Acts as an intermediate product of the purine catabolic pathway in plants, aiding in nitrogen mobilization.; Plays a role in increasing stress tolerance in plants, including drought, salt, cold, heavy metals, and irradiance.; Enhances wound healing process by modulating the inflammatory response, stimulating fibroblast proliferation, and extracellular matrix synthesis.; Facilitates inter-plant interactions and kin recognition in plants, acting as a signaling molecule.
• Applications in Skin Care: Widely used in skin care products due to its ability to promote healing of scar tissue and scars.; Found in over 1300 cosmetic products. Originally discovered in the callus of the Coffea Arabica plant.
• Synthetic Potential: Allantoin's availability and multifunctionality make it attractive for synthetic purposes, especially in the pharmaceutical industry. Its chemical properties include hydrolysis reactions, complexation with organic and inorganic substrates, and interactions with nucleophilic reagents.; Can serve as a basic azaheterocycle to manufacture a wide range of new compounds, including bioactive ones.

Technology Process of Allantoin

There total 78 articles about Allantoin 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: 89.3%

urea (57-13-6) + Glyoxilic acid (298-12-4) → Allantoin (97-59-6)

Guidance literature:

With Co[PyPS]2Mo₁₁VO₄₀; at 90 ℃; for 10h; Temperature; Reagent/catalyst; Microwave irradiation;

Reference yield: 75.0%

uric Acid (69-93-2) → parabanic acid (120-89-8) + Oxalyldiurea (5676-27-7) + dehydro-allantoin (105245-87-2) + Allantoin (97-59-6)

Guidance literature:

With lithium hydroxide; iodine; In water; for 0.0833333h; excess of I₂;

DOI:10.1016/S0040-4020(01)87480-9

Reference yield: 70.0%

uric Acid (69-93-2) → Allantoin (97-59-6)

Guidance literature:

With lithium hydroxide; iodine; In water; at 4 ℃; equimolar amount of I₂;

DOI:10.1016/S0040-4020(01)87480-9

upstream raw materials:

uric Acid

2,4-imidazolidinedione

urea

glycoluril

Downstream raw materials:

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

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

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

isocyanuric acid

Refernces

• 1、 Tawa,Etoh,Hirose. "A statistical method for the determination of serum uric acid.". . p. 3381 - 3384. Retrieved 1980.
• 2、 Kahn, Kalju,Tipton, Peter A.. "Kinetics and mechanism of allantoin racemization". . p. 62 - 72. Retrieved 2000.
• 3、 Patching, Simon G.. "Synthesis of highly pure 14C-labelled DL-allantoin and 13C NMR analysis of labelling integrity". . p. 401 - 404. Retrieved 2009.
• 4、 Kahn, Kalju,Serfozo, Peter,Tipton, Peter A.. "Identification of the true product of the urate oxidase reaction". . p. 5435 - 5442. Retrieved 1997.
• 5、 -. "Method for producing allantoin for cosmetics". Paragraph 0016-0017; 0019-0020; 0022-0023; 0025-0026; 0029. . Retrieved 2020/11/10.