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Allantoin

|Section2={{Chembox Properties | C=4 | H=6 | N=4 | O=3 | Appearance = colourless crystalline powder | Odor = odorless | Density = 1.45 g/cm3 | MeltingPtC = 230 | MeltingPt_notes = (decomposes) | BoilingPtC = 478 | Solubility = 0.57 g/100 mL (25 °C) 4.0 g/100 mL (75 °C) | SolubleOther = soluble in alcohol, pyridine, NaOH insoluble in ethyl ether | LogP = -3.14 | pKa = 8.48 }} |Section3={{Chembox Hazards | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 | ExternalSDS = Allantoin MSDS | MainHazards = | FlashPt = | AutoignitionPt = | LD50 = > 5000 mg/kg (oral, rat) }} }} Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide.https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204http://www.chemblink.com/products/97-59-6.htm It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria. It is produced from uric acid, which is a degradation product of purine nucleobases, by urate oxidase (or uricase).

History

Allantoin was first isolated in 1800 by the Italian physician Michele Francesco Buniva (1761–1834) and the French chemist Louis Nicolas Vauquelin, who mistakenly believed it to be present in the amniotic fluid.See:

Animals

Named after the allantois (an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and other 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 other 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 has been shown to improve insulin resistance when administered to rats and increased lifespan when administered to the nematode worm Caenorhabditis elegans.

Bacteria

In bacteria, purines and their derivatives (such as allantoin) are used as secondary sources of nitrogen under nutrient-limiting conditions. Their degradation yields ammonia, which can then be utilized. For instance, Bacillus subtilis is able to utilize allantoin as its sole nitrogen source. Mutants in the B. subtilis pucI gene were unable to grow on allantoin, indicating that it encodes an allantoin transporter. In Streptomyces coelicolor, allantoinase ( EC 3.5.2.5) and allantoicase (EC 3.5.3.4) are essential for allantoin metabolism. In this species the catabolism of allantoin, and the subsequent release of ammonium, inhibits antibiotic production (Streptomyces species synthesize about half of all known antibiotics of microbial origin).

Applications

Allantoin is present in botanical extracts of the comfrey plant and in the urine of most mammals. Chemically synthesized bulk allantoin, which is chemically equivalent to natural allantoin, is safe, non-toxic, compatible with cosmetic raw materials and meets CTFA and JSCI requirements. Over 10,000 patents reference allantoin. Patent Lens search

Cosmetics and toiletries

Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics, including: 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. An animal study in 2010 found that based on the results from histological analyses, a soft lotion with 5% allantoin ameliorates the wound healing process, by modulating the inflammatory response. The study also suggests that quantitative analysis lends support to the idea that allantoin also promotes fibroblast proliferation and synthesis of the extracellular matrix. A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical nonsteroidal agent containing allantoin.

Pharmaceuticals

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.

Biomarker of oxidative stress

Since uric acid is the end product of the purine metabolism in humans, only non-enzymatic processes with reactive oxygen species will give rise to allantoin, which is thus a suitable biomarker to measure oxidative stress in chronic illnesses and senescence.

See also

References

External links

"green air" © 2007 - Ingo Malchow, Webdesign Neustrelitz
This article based upon the http://en.wikipedia.org/wiki/Allantoin, the free encyclopaedia Wikipedia and is licensed under the GNU Free Documentation License.
Further informations available on the list of authors and history: http://en.wikipedia.org/w/index.php?title=Allantoin&action=history
presented by: Ingo Malchow, Mirower Bogen 22, 17235 Neustrelitz, Germany