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Allantoin



Allantoin
Chemical name
(2,5-Dioxo-4-imidazolidinyl) urea
General
Chemical formula C4H6N4O3
Molecular weight 158.1164 g/mol
Appearance white crystalline powder
CAS number 97-59-6
MSDS Allantoin MSDS
SMILES O=C1C(NC(=O)N1)NC(=O)N
Other names
  • ?
Physical properties
Density and phase at STP  ? g/cm3 (?)
Solubility 0.5% in water (25 °C)
0.2% in alcohol (25 °C ?)
Specific gravity  ?
Crystal structure  ?
pH (10% solution with water)  ?
Acidity constant (pKa)  ?
Thermal decomposition  ? °C (? K)
Phase behavior
Melting point 239 °C
Boiling point  ? °C (? K)
Triple point  ? K (? °C)
 ? bar
Critical point  ? K (? °C)
 ? bar
Heat of fusion
fusH)
 ? kJ/mol
Entropy of fusion
fusS)
 ? J/mol·K
Heat of vaporization
vapH)
 ? kJ/mol

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 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.[1] In humans and other higher apes, the metabolic pathway for conversion of uric acid to allantoin has been lost, 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, but most of the enzymes responsible have been lost in mammals.[2] Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.

Additional recommended knowledge

Applications

Allantoin is present in botanical extracts of the comfrey plant. Chemically synthesized bulk allantoin is natural-identical, safe, non-toxic, compatible with cosmetic raw materials, and meets CTFA and JSCI requirements. [3] Over 10,000 patents reference allantoin. [4] 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; promotion of cell proliferation and wound healing; and a soothing, anti-irritant, and skin protectant effect by forming complexes with irritant and sensitizing agents.[5] 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. Allantoin has not been proved scientifically to reduce the appearance of aging.[6]

Synonyms

  • Udder cream
  • Uureidohydantoin
  • Glyoxyldiureide
  • Hemocane
  • (2,5-dioxo-4-imidazolidinyl)-urea
  • 5-ureidohydantoin
  • (formerly) Vitamin U[7] - See also S-Methylmethionine

References

  1. ^ Young E. G., Wentworth H. P., Hawkins W. W. (1944). "The absorption and excretion of allantoin in mammals". J. Pharmacol. Experi. Therapeutics 81: 1-9.
  2. ^ Fujiwara, S; Noguchi T (November 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. PMID 7492331. Retrieved on 2007-12-21.
  3. ^ Akema (an allantoin manufacturer) [1]
  4. ^ Patent Lens search [2]
  5. ^ www.in-cosmetics.com trade exhibition [www.in-cosmetics.com/ExhibitorLibrary/58/ALLANTOIN_CTFA.pdf]
  6. ^ Thornfeldt, C (July 2005). "Cosmeceuticals containing herbs: fact, fiction, and future". Dermatologic Surgery 31 (7 Pt 2): 873-80. PMID 16029681. Retrieved on 2007-12-21.
  7. ^ Haas, Elson M. (1992). Staying Healthy With Nutrition: The Complete Guide to Diet and Nutritional Medicine. Celestial Arts. ISBN 0890874816. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Allantoin". A list of authors is available in Wikipedia.
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