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Allantoin

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Allantoin
Names
IUPAC name (2,5-Dioxo-4-imidazolidinyl) urea
Other names • Alcloxa
• Aldioxa
• Ureidohydantoin
•Glyoxyldiureide
•Hemocane
• 5-Ureidohydantoin
• Vitamin U (formerly)
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.358 Edit this at Wikidata
KEGG
UNII
CompTox Dashboard (EPA)
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)Key: POJWUDADGALRAB-UHFFFAOYSA-N
  • InChI=1/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)Key: POJWUDADGALRAB-UHFFFAOYAE
SMILES
  • O=C1NC(=O)NC1NC(=O)N
  • C1(C(=O)NC(=O)N1)NC(=O)N
Properties
Chemical formula C4H6N4O3
Molar mass 158.117 g·mol
Appearance colourless crystalline powder
Density 1.45g/cm3
Melting point 230 °C (446 °F; 503 K)
Solubility in water 0.5% at 25 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid.

Named after the allantois, an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and higher apes, it is a product of oxidation of uric acid by purine catabolism. After birth, it is the predominant means by which nitrogenous waste is excreted in the urine of these animals. In humans and higher apes, the metabolic pathway for conversion of uric acid to allantoin is not present, so the former is excreted. Recombinant rasburicase is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ammonia) before excretion. Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.

Applications

Allantoin is present in botanical extracts of the comfrey plant and urine from cows and most mammals. Chemically synthesized bulk allantoin is nature-identical, safe, non-toxic, compatible with cosmetic raw materials and meets CTFA and JSCI requirements. Over 10,000 patents reference allantoin. Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics: a moisturizing and keratolytic effect, increasing the water content of the extracellular matrix and enhancing the desquamation of upper layers of dead skin cells, increasing the smoothness of the skin; promoting cell proliferation and wound healing; and a soothing, anti-irritant, and skin protectant effect by forming complexes with irritant and sensitizing agents. A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent containing Allantoin.

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.

See also

References

  1. Haas, Elson M. (1992). Staying Healthy With Nutrition: The Complete Guide to Diet and Nutritional Medicine. Celestial Arts. ISBN 0-89087-481-6.
  2. Young E. G., Wentworth H. P., Hawkins W. W. (1944). "The absorption and excretion of allantoin in mammals". J. Pharmacol. Experi. Therapeutics. 81 (1): 1–9.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Fujiwara, S (1995). "Degradation of purines: only ureidoglycollate lyase out of four allantoin-degrading enzymes is present in mammals". The Biochemical Journal. 312 (Pt 1): 315–8. PMC 1136261. PMID 7492331. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
  4. Akema (an allantoin manufacturer)
  5. Patent Lens search
  6. www.in-cosmetics.com trade exhibition
  7. J Drugs Dermatol. 2009 Jun;8(6):537-9.
  8. Thornfeldt, C (2005). "Cosmeceuticals containing herbs: fact, fiction, and future". Dermatologic Surgery. 31 (7 Pt 2): 873–80. doi:10.1111/j.1524-4725.2005.31734. PMID 16029681. {{cite journal}}: Unknown parameter |month= ignored (help)
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