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
ECHA InfoCard
 100.002.358 Edit 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-N checkY
  • 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 158.117 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
ethyl ether
log P −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 dose or concentration (LD, LC):
> 5000 mg/kg (oral, rat)
Safety data sheet (SDS) Allantoin MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide.

nucleic acids, by action of urate oxidase (uricase).[3][4][5] Allantoin also 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

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

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".
  2. ^ "CAS # 97-59-6, Allantoin, 5-Ureidohydantoin, Glyoxyldiureide, Glyoxylic diureide, Cordianine, Glyoxyldiureid, (2,5-Dioxo-4-imidazolidinyl)urea".
  3. PMID 8795700
    .
  4. PMID 10986234
    .
  5. PMID 18649082
    .
  6. S2CID 235729616
    .
  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.
  11. PMID 7492331
    .
  12. S2CID 207127849
    .
  13. PMID 26676933
    .
  14. PMID 26967546
    .
  15. PMID 18302748
    .
  16. PMID 11344136
    .
  17. S2CID 216898
    .
  18. ^ Patent Lens search[permanent dead link]
  19. PMID 16029681
    .
  20. S2CID 6420729
    .
  21. PMID 14967170
    .

External links
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