Allantoin

Allantoin

Chembox new
ImageFile = Allantoin_chemical_structure.png ImageSize = 150px
IUPACName = (2,5-Dioxo-4-imidazolidinyl) urea
OtherNames = • Alcloxa
• Aldioxa
• Udder cream
• Ureidohydantoin
•Glyoxyldiureide
•Hemocane
• 5-Ureidohydantoin
• Vitamin U (formerly) [cite book |title=Staying Healthy With Nutrition: The Complete Guide to Diet and Nutritional Medicine |last=Haas |first=Elson M. |year=1992 |publisher=Celestial Arts |isbn=0890874816 ]
Section1 = Chembox Identifiers
CASNo = 97-59-6
PubChem =
SMILES = O=C1C(NC(=O)N1)NC(=O)N

Section2 = Chembox Properties
C=4|H=6|N=4|O=3
Appearance =
Density =
MeltingPtC = 239
BoilingPt =
Solubility = 0.5% at 25 °C

Section3 = Chembox Hazards
ExternalMSDS = [http://www.sciencelab.com/xMSDS-Allantoin-9922829 Allantoin MSDS (PDF)]
MainHazards =
FlashPt =
Autoignition =

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. [cite journal |title= The absorption and excretion of allantoin in mammals| author= Young E. G., Wentworth H. P., Hawkins W. W. | journal= J. Pharmacol. Experi. Therapeutics | volume= 81 | pages= 1–9| year= 1944 | url=http://jpet.aspetjournals.org/cgi/reprint/81/1/1 ] 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. [cite journal |last=Fujiwara |first=S |coauthors=Noguchi T |year=1995 |month=November |title=Degradation of purines: only ureidoglycollate lyase out of four allantoin-degrading enzymes is present in mammals |journal=The Biochemical Journal |volume=312 |issue=Pt 1 |pages=315–8 |accessdate= 2007-12-21 |pmid=7492331 ] 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 uric acid from cows, most mammals. Chemically synthesized bulk allantoin is natural-identical, safe, non-toxic, compatible with cosmetic raw materials, and meets CTFA and JSCI requirements. [Akema (an allantoin manufacturer) [http://www.akema.it/allantoin.htm] ] Over 10,000 patents reference allantoin. [Patent Lens search [http://www.patentlens.com/patentlens/structured.cgi?q=allantoin+#list] ] 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. [www.in-cosmetics.com trade exhibition [www.in-cosmetics.com/ExhibitorLibrary/58/ALLANTOIN_CTFA.pdf] ] 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 proven scientifically to reduce the appearance of aging. [cite journal |last=Thornfeldt |first=C |year=2005 |month=July |title=Cosmeceuticals containing herbs: fact, fiction, and future |journal=Dermatologic Surgery |volume=31 |issue=7 Pt 2 |pages=873–80 |pmid=16029681 |url=http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=pubmed&dopt=AbstractPlus&list_uids=16029681 |accessdate= 2007-12-21 ]

See also

* Imidazolidinyl urea and diazolidinyl urea, antimicrobial condensation products of allantoin with formaldehyde

References


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Look at other dictionaries:

  • Allantoin — Al*lan to*in, n. (Chem.) A crystalline, transparent, colorless substance found in the allantoic liquid of the fetal calf; formerly called allantoic acid and amniotic acid. [1913 Webster] || …   The Collaborative International Dictionary of English

  • Allantoīn — (Allantoinsäure. Amniossäure), C8H6N4O6, der Harnsäure ähnlicher, nach Vauquelin u. Buniva, aus der vorher durch Abdampfen concentrirten allantolschen Flüssigkeit der Kühe sich absetzender u. bei der Oxydation der Harnsäure mittelst Bleisuperoxyd …   Pierer's Universal-Lexikon

  • Allantoīn — (Allantoissäure, Amniossäure) C4H6N4O3 findet sich in der Allantoisflüssigkeit der Kühe, im Kälberharn, nach Genuß von Gerbsäure im Menschenharn, auch im Rübensaft, in Roßkastanienrinde, in jungen Platanentrieben und entsteht durch Oxydation der… …   Meyers Großes Konversations-Lexikon

  • Allantoïn — Allantoïn, der Harnsäure ähnlicher Stoff, findet sich in der Allantoisflüssigkeit, kann auch durch Abdampfen der Harnsäure mit braunem Bleisuperoxyd dargestellt werden …   Herders Conversations-Lexikon

  • Allantoin — Strukturformel Allgemeines Name Allantoin Andere Namen …   Deutsch Wikipedia

  • Allantoin — Al|lan|to|in 〈n. 11; unz.; bei manchen Wirbeltieren〉 Endprodukt des Harnstoffwechsels [<grch. allas, Gen. allantos „Wurst“] * * * Al|lan|to|in [biol. fachspr. Allantois = Urharnsack (griech. allãs, Gen.: allãntos = Wurst); ↑ in (3)], das; s;… …   Universal-Lexikon

  • allantoin — alantoinas statusas T sritis chemija formulė Formulę žr. priede. priedas( ai) Grafinis formatas atitikmenys: angl. allantoin rus. аллантоин ryšiai: sinonimas – 5 ureidohidantoinas …   Chemijos terminų aiškinamasis žodynas

  • allantoin — noun Etymology: probably from German, from New Latin allantois + German in Date: circa 1844 a crystalline oxidation product C4H6N4O3 of uric acid used to promote healing of local wounds and infections …   New Collegiate Dictionary

  • allantoin — n. [Gr. allas, sausage] The resultant of purine and pyrimidine metabolism occurring in allantoic fluid and urine of various invertebrates …   Dictionary of invertebrate zoology

  • allantoin — /euh lan toh in/, n. Biochem., Pharm. a white powder, C4H6N4O3, produced by oxidation of uric acid and the major excretory product of purine degradation in many vertebrates: used medicinally to heal skin ulcers and in lotions, lipsticks, etc.,… …   Universalium

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