Chemistry:Allantoin

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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
EC Number
  • 202-592-8
KEGG
RTECS number
  • YT1600000
UNII
Properties
C4H6N4O3
Molar mass 158.117 g·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 in alcohol, pyridine, NaOH
insoluble in ethyl ether
log P −3.14
Acidity (pKa) 8.48
Hazards
Safety data sheet Allantoin MSDS
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Lethal dose or concentration (LD, LC):
> 5000 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide.[1][2] 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 itself is a degradation product of nucleic acids, by action of urate oxidase (uricase).[3][4][5] The occurs as a natural mineral compound (IMA symbol Aan[6]).

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.[7] In 1821, the French chemist Jean Louis Lassaigne found it in the fluid of the allantois; he called it "l'acide allantoique".[8] In 1837, the German chemists Friedrich Wöhler and Justus Liebig synthesized it from uric acid and renamed it "allantoïn".[9]

Animals

Named after the allantois (an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and other hominids), 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.[10] 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.[11]

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

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

Mutants in the B. subtilis pucI gene were unable to grow on allantoin, indicating that it encodes an allantoin transporter.[16]

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).[17]

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.[18]

Cosmetics

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

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.[19]

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.[20][21]

See also

References

  1. ↑ "Allantoin". https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204. 
  2. ↑ "CAS # 97-59-6, Allantoin, 5-Ureidohydantoin, Glyoxyldiureide, Glyoxylic diureide, Cordianine, Glyoxyldiureid, (2,5-Dioxo-4-imidazolidinyl)urea". http://www.chemblink.com/products/97-59-6.htm. 
  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. PMID 8795700. 
  4. ↑ Xi, H.; Schneider, B. L.; Reitzer, L. (2000-10-01). "Purine catabolism in Escherichia coli and function of xanthine dehydrogenase in purine salvage". Journal of Bacteriology 182 (19): 5332–5341. doi:10.1128/jb.182.19.5332-5341.2000. ISSN 0021-9193. PMID 10986234. 
  5. ↑ Johnson, Richard J.; Sautin, Yuri Y.; Oliver, William J.; Roncal, Carlos; Mu, Wei; Gabriela Sanchez-Lozada, L.; Rodriguez-Iturbe, Bernardo; Nakagawa, Takahiko et al. (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. ISSN 1432-136X. PMID 18649082. 
  6. ↑ Warr, L.N. (2021). "IMA-CNMNC approved mineral symbols". Mineralogical Magazine 85 (3): 291–320. doi:10.1180/mgm.2021.43. Bibcode: 2021MinM...85..291W. 
  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 sind Allantoïssäure, oder dieselbe Substance, die man in der Allantoïsflussigkeit der Kühe gefunden hat; wir werden sie von nun an Allantoïn nennen." (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. http://jpet.aspetjournals.org/cgi/reprint/81/1/1. 
  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. PMID 7492331. 
  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. PMID 18926881. 
  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 in C. elegans". Aging Cell 15 (2): 256–266. doi:10.1111/acel.12432. PMID 26676933. 
  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, from Bacillus subtilis: evolutionary relationships, amplified expression, activity and specificity". Microbiology 162 (5): 823–836. doi:10.1099/mic.0.000266. ISSN 1465-2080. PMID 26967546. 
  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. ISSN 1752-0509. PMID 18302748. 
  16. ↑ Schultz, A. C.; Nygaard, P.; Saxild, H. H. (2001-06-01). "Functional analysis of 14 genes that constitute the purine catabolic pathway in Bacillus subtilis and 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. ISSN 0021-9193. PMID 11344136. 
  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 in Streptomyces coelicolor" (in en). Applied Microbiology and Biotechnology 98 (1): 351–360. doi:10.1007/s00253-013-5372-1. ISSN 0175-7598. PMID 24292080. 
  18. ↑ Patent Lens search[yes|permanent dead link|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. PMID 16029681. 
  20. ↑ "Allantoin as a marker of oxidative stress in human erythrocytes". Clinical Chemistry and Laboratory Medicine 46 (9): 1270–4. 2008. doi:10.1515/CCLM.2008.244. PMID 18636793. 
  21. ↑ "Uric acid and allantoin levels in Down syndrome: Antioxidant and oxidative stress mechanisms?". Clinica Chimica Acta 341 (1–2): 139–46. 2004. doi:10.1016/j.cccn.2003.11.020. PMID 14967170. 

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