Allantoin
| Allantoin | |
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(2,5-Dioxo-4-imidazolidinyl) urea |
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Other names
• Alcloxa |
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| Identifiers | |
| CAS number | 97-59-6  |
| ChemSpider | 199 |
| UNII | 344S277G0Z |
| KEGG | D00121 |
| ChEBI | CHEBI:15676 |
| ChEMBL | CHEMBL593429 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C4H6N4O3 |
| Molar mass | 158.12 g mol−1 |
| Appearance | colourless crystalline powder |
| Density | 1.45g/cm3 |
| Melting point |
230 °C, 503 K, 446 °F |
| Solubility in water | 0.5% at 25 °C |
| Hazards | |
| MSDS | Allantoin MSDS |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.[2] 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.[3] Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.
[edit] 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.[4] Over 10,000 patents reference allantoin. [5] 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.[6] A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent containing Allantoin.[7]
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.[8]
[edit] See also
- Imidazolidinyl urea and diazolidinyl urea, antimicrobial condensation products of allantoin with formaldehyde
[edit] References
- ^ Haas, Elson M. (1992). Staying Healthy With Nutrition: The Complete Guide to Diet and Nutritional Medicine. Celestial Arts. ISBN 0-89087-481-6.
- ^ 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. http://jpet.aspetjournals.org/cgi/reprint/81/1/1.
- ^ 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. PMC 1136261. PMID 7492331. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1136261.
- ^ Akema (an allantoin manufacturer) [1]
- ^ Patent Lens search [2]
- ^ www.in-cosmetics.com trade exhibition [www.in-cosmetics.com/ExhibitorLibrary/58/ALLANTOIN_CTFA.pdf]
- ^ J Drugs Dermatol. 2009 Jun;8(6):537-9.
- ^ Thornfeldt, C (July 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.
