Wikipedia

Allantoin

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Allantoinis a chemical compound with formula C4H6N4O3.It is also called5-ureidohydantoinorglyoxyldiureide.[1][2]It is adiureideofglyoxylic acid.Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria, though not humans. It is produced fromuric acid,which itself is a degradation product ofnucleic acids,by action ofurate oxidase(uricase).[3][4][5]Allantoin also occurs as a natural mineral compound (IMAsymbolAan[6]).

Allantoin
Skeletal formula of allantoin
Heap of white powder on a watch glass
Ball-and-stick model of the allantoin molecule
Names
IUPAC name
N-(2,5-Dioxoimidazolidin-4-yl)urea
Other names
1-(2,5-Dioxoimidazolidin-4-yl)urea
Glyoxyldiureide
5-Ureidohydantoin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.358Edit this at Wikidata
EC Number
  • 202-592-8
KEGG
RTECS number
  • YT1600000
UNII
  • 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)checkY
    Key: POJWUDADGALRAB-UHFFFAOYSA-NcheckY
  • 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
  • O=C1NC(=O)NC1NC(=O)N
  • C1(C(=O)NC(=O)N1)NC(=O)N
Properties
C4H6N4O3
Molar mass 158.117g·mol−1
Appearance colourless crystalline powder
Odor odorless
Density 1.45 g/cm3
Melting point 230 °C (446 °F; 503 K) (decomposes)
Boiling point 478 °C (892 °F; 751 K)[dubious–discuss]
0.57 g/100 mL (25 °C)
4.0 g/100 mL (75 °C)
Solubility soluble inalcohol,pyridine,NaOH
insoluble inethyl ether
logP −3.14
Acidity(pKa) 8.48
Hazards
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Lethal doseor concentration (LD, LC):
> 5000 mg/kg (oral, rat)
Safety data sheet(SDS) Allantoin MSDS
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

History

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Allantoin was first isolated in 1800 by the Italian physician Michele Francesco Buniva (1761–1834) and the French chemistLouis Nicolas Vauquelin,who mistakenly believed it to be present in theamniotic fluid.[7]In 1821, the French chemistJean Louis Lassaignefound it in the fluid of theallantois;he called it"l'acide allantoique".[8]In 1837, the German chemistsFriedrich WöhlerandJustus Liebigsynthesized it fromuric acidand renamed it "allantoïn".[9]

Animals

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Named after theallantois(anamnioteembryonic excretory organ in which it concentrates during development in mostmammalsexcept humans and other hominids), it is a product of oxidation ofuric acidbypurinecatabolism.After birth, it is the predominant means by whichnitrogenous wasteis excreted in theurineof these animals.[10]In humans and other higher apes, the metabolic pathway for conversion ofuric acidto allantoin is not present, so the former is excreted. Recombinantrasburicaseis sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (intoammonia) before excretion.[11]

Allantoin has been shown to improve insulin resistance when administered to rats and to increase lifespan when administered to the nematode wormCaenorhabditis elegans.[12][13]

Bacteria

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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.[14]For instance,Bacillus subtilisis able to utilize allantoin as its sole nitrogen source.[15]

Mutants in theB. subtilispucIgene were unable to grow on allantoin, indicating that it encodes an allantoin transporter.[16]

InStreptomyces coelicolor,allantoinase (EC3.5.2.5) 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 (Streptomycesspecies synthesize about half of all known antibiotics of microbial origin).[17]

Applications

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Allantoin is present in botanicalextractsof thecomfreyplant and in theurineof most mammals. Chemically synthesized bulk allantoin, which is chemically equivalent to natural allantoin, is safe, non-toxic, compatible with cosmetic raw materials and meetsCTFAandJSCIrequirements. Over 10,000patentsreference allantoin.[18]

Cosmetics

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Manufacturers may use allantoin as an ingredient in over-the-counter cosmetics.[citation needed]

Pharmaceuticals

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It is frequently present intoothpaste,mouthwash,and otheroral hygieneproducts, inshampoos,lipsticks,anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.[19]

Biomarker of oxidative stress

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Sinceuric acidis the end product of thepurine metabolismin humans, only non-enzymatic processes withreactive oxygen specieswill give rise to allantoin, which is thus a suitablebiomarkerto measureoxidative stressin chronic illnesses andsenescence.[20][21]

See also

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References

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  1. ^"Allantoin".
  2. ^"CAS # 97-59-6, Allantoin, 5-Ureidohydantoin, Glyoxyldiureide, Glyoxylic diureide, Cordianine, Glyoxyldiureid, (2,5-Dioxo-4-imidazolidinyl)urea".
  3. ^Pizzichini, Maria; Pandolfi, Maria Luisa; Arezzini, Laura; Terzuoli, Lucia; Fè, Linda; Bontemps, Francois; Van den Berghe, Georges; Marinello, Enrico (1996-08-09). "Labelling of uric acid and allantoin in different purine organs and urine of the rat".Life Sciences.59(11):893–899.doi:10.1016/0024-3205(96)00387-6.PMID8795700.
  4. ^Xi, H.; Schneider, B. L.; Reitzer, L. (2000-10-01)."Purine catabolism inEscherichia coliand function of xanthine dehydrogenase in purine salvage ".Journal of Bacteriology.182(19):5332–5341.doi:10.1128/jb.182.19.5332-5341.2000.ISSN0021-9193.PMC110974.PMID10986234.
  5. ^Johnson, Richard J.; Sautin, Yuri Y.; Oliver, William J.; Roncal, Carlos; Mu, Wei; Gabriela Sanchez-Lozada, L.; Rodriguez-Iturbe, Bernardo; Nakagawa, Takahiko; Benner, Steven A. (2009-01-01)."Lessons from comparative physiology: could uric acid represent a physiologic alarm signal gone awry in western society?".Journal of Comparative Physiology B.179(1):67–76.doi:10.1007/s00360-008-0291-7.ISSN1432-136X.PMC2684327.PMID18649082.
  6. ^Warr, L.N. (2021)."IMA-CNMNC approved mineral symbols".Mineralogical Magazine.85(3):291–320.Bibcode:2021MinM...85..291W.doi:10.1180/mgm.2021.43.S2CID235729616.
  7. ^See:
    • Buniva and Vauquelin (1800)"Sur l'eau de l'amnios de femme et de vache"(On the amniotic fluid of women and cows),Annales de chimie,33:269-282.
    • See also: Leopold Gmelin with Henry Watts, trans.,Hand-book of Chemistry(London, England: The Cavendish Society, 1856), vol. 10,p. 260.
  8. ^Lassaigne (1821)"Nouvelles recherches sur la composition les eaux de l'allantoïde et de l'amnios de la vache"(New investigations into the composition of the allantoic and amniotic fluids of the cow),Annales de chimie et de physique,2nd series,17:295-305. On pp. 300 ff, Lassaigne names and characterizes "l'acide allantoique" (allantoic acid).
  9. ^See:
    • Liebig and Wöhler (1837)"Ueber die Natur der Harnsäure"(On the nature of uric acid),Annalen der Physik und Chemie,41(8): 561-569. Allantoin is named on p. 563.From p. 563:"Sie sindAllantoïssäure,oder dieselbe Substance, die man in der Allantoïsflussigkeit der Kühe gefunden hat; wir werden sie von nun anAllantoïnnennen. "(They [i.e., the crystals previously isolated] are allantois acid, or the same substance that one found in the allantois fluid of cows; we will call it "allantoin" from now on.)
    • Reprinted in: F. Wöhler and J. Liebig (1838)"Untersuchungen über die Natur der Harnsäure"(Investigations into the nature of uric acid),Annalen der Pharmacie,26:241-340.
  10. ^Young E. G.; Wentworth H. P.; Hawkins W. W. (1944)."The absorption and excretion of allantoin in mammals".J. Pharmacol. Exp. Ther.81(1):1–9.
  11. ^Fujiwara, S; Noguchi T (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.doi:10.1042/bj3120315.PMC1136261.PMID7492331.
  12. ^Ko, W.C.; Liu, I.M.; Chung, H.H.; Cheng, J.T. (2008). "Activation of I2-imidazoline receptors may ameliorate insulin resistance in fructose-rich chow-fed rats ".Neuroscience Letters.448(1):90–93.doi:10.1016/j.neulet.2008.10.002.PMID18926881.S2CID207127849.
  13. ^Shaun Calvert; Robi Tacutu; Samim Sharifi; Rute Teixeira; Pratul Ghosh; João Pedro de Magalhães (2016)."A network pharmacology approach reveals new candidate caloric restriction mimetics inC. elegans".Aging Cell.15(2):256–266.doi:10.1111/acel.12432.PMC4783339.PMID26676933.
  14. ^Ma, Pikyee; Patching, Simon G.; Ivanova, Ekaterina; Baldwin, Jocelyn M.; Sharples, David; Baldwin, Stephen A.; Henderson, Peter J. F. (2016-05-01)."Allantoin transport protein, PucI, fromBacillus subtilis:evolutionary relationships, amplified expression, activity and specificity ".Microbiology.162(5):823–836.doi:10.1099/mic.0.000266.ISSN1465-2080.PMC4851255.PMID26967546.
  15. ^Goelzer, Anne; Bekkal Brikci, Fadia; Martin-Verstraete, Isabelle; Noirot, Philippe; Bessières, Philippe; Aymerich, Stéphane; Fromion, Vincent (2008-02-26)."Reconstruction and analysis of the genetic and metabolic regulatory networks of the central metabolism of Bacillus subtilis".BMC Systems Biology.2:20.doi:10.1186/1752-0509-2-20.ISSN1752-0509.PMC2311275.PMID18302748.
  16. ^Schultz, A. C.; Nygaard, P.; Saxild, H. H. (2001-06-01)."Functional analysis of 14 genes that constitute the purine catabolic pathway inBacillus subtilisand evidence for a novel regulon controlled by the PucR transcription activator ".Journal of Bacteriology.183(11):3293–3302.doi:10.1128/JB.183.11.3293-3302.2001.ISSN0021-9193.PMC99626.PMID11344136.
  17. ^Navone, Laura; Casati, Paula; Licona-Cassani, Cuauhtémoc; Marcellin, Esteban; Nielsen, Lars K.; Rodriguez, Eduardo; Gramajo, Hugo (2013-11-29). "Allantoin catabolism influences the production of antibiotics inStreptomyces coelicolor".Applied Microbiology and Biotechnology.98(1):351–360.doi:10.1007/s00253-013-5372-1.hdl:11336/7859.ISSN0175-7598.PMID24292080.S2CID216898.
  18. ^Patent Lens search[permanent dead link‍]
  19. ^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.PMID16029681.
  20. ^Kanďár R, Záková P (2008). "Allantoin as a marker of oxidative stress in human erythrocytes".Clinical Chemistry and Laboratory Medicine.46(9):1270–4.doi:10.1515/CCLM.2008.244.PMID18636793.S2CID6420729.
  21. ^Zitnanová I, Korytár P, Aruoma OI, Sustrová M, Garaiová I, Muchová J, Kalnovicová T, Pueschel S, Duracková Z (2004). "Uric acid and allantoin levels in Down syndrome: Antioxidant and oxidative stress mechanisms?".Clinica Chimica Acta.341(1–2):139–46.doi:10.1016/j.cccn.2003.11.020.PMID14967170.
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