Misplaced Pages

Allantoin: Difference between revisions

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 08:14, 30 December 2011 editNotWith (talk | contribs)61,905 edits Category:Chemical compounds found in animals← Previous edit Latest revision as of 08:19, 21 December 2024 edit undoPreimage (talk | contribs)Extended confirmed users1,364 edits →Lede: Clarify: allantoin is not a (major) metabolic intermediate in humans 
(151 intermediate revisions by 88 users not shown)
Line 1: Line 1:
{{redirect2|Paxyl|udder cream|the antidepressant Paxil|Paroxetine|the ointment|Bag Balm}}
{{chembox
{{Chembox
| verifiedrevid = 443375405
| Verifiedfields = changed
| ImageFile = Allantoin_chemical_structure.png
| Watchedfields = changed
| ImageSize = 150px
| verifiedrevid = 477317673
| IUPACName = (2,5-Dioxo-4-imidazolidinyl) urea
| ImageFile = Allantoin.svg
| OtherNames = • Alcloxa<br>• Aldioxa<br>• Ureidohydantoin<br>•Glyoxyldiureide<br>•Hemocane<br>• 5-Ureidohydantoin<br>• Vitamin U (formerly)<ref>{{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=0-89087-481-6 }}</ref>
| ImageSize = 180
| Section1 = {{Chembox Identifiers
| ImageAlt = Skeletal formula of allantoin
| ImageFile1 = Allantoïne.JPG
| ImageSize1 = 180
| ImageAlt1 = Heap of white powder on a watch glass
| ImageFile2 = Allantoin-3D-balls.png
| ImageSize2 = 180
| ImageAlt2 = Ball-and-stick model of the allantoin molecule
| IUPACName = ''N''-(2,5-Dioxoimidazolidin-4-yl)urea
| OtherNames = 1-(2,5-Dioxoimidazolidin-4-yl)urea<br>Glyoxyldiureide<br>5-Ureidohydantoin
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 199 | ChemSpiderID = 199
Line 23: Line 33:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 97-59-6 | CASNo = 97-59-6
| PubChem = | PubChem = 204
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15676 | ChEBI = 15676
| SMILES = O=C1NC(=O)NC1NC(=O)N | SMILES = O=C1NC(=O)NC1NC(=O)N
| EINECS = 202-592-8
}}
| RTECS = YT1600000
| Section2 = {{Chembox Properties
}}
|C=4|H=6|N=4|O=3
|Section2={{Chembox Properties
| C=4 | H=6 | N=4 | O=3
| Appearance = colourless crystalline powder | Appearance = colourless crystalline powder
| Density = 1.45g/cm3 | Odor = odorless
| Density = 1.45 g/cm<sup>3</sup>
| MeltingPtC = 230 | MeltingPtC = 230
| MeltingPt_notes = (decomposes)
| BoilingPt =
| Solubility = 0.5% at 25 °C | BoilingPtC = 478
| BoilingPt_notes = {{Dubious|Decomposes before melting, then allegedly boils|date=November 2020|reason=Solids that decompose rather than melting rarely have a boiling point. Especially not a boiling point 200 degrees above decomposition.}}
}}
| Solubility = 0.57 g/100 mL (25&nbsp;°C) <br /> 4.0 g/100 mL (75&nbsp;°C)
| Section3 = {{Chembox Hazards
| SolubleOther = soluble in ], ], ] <br /> insoluble in ]
| ExternalMSDS =
| LogP = −3.14
| pKa = 8.48
}}
|Section3={{Chembox Hazards
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| LD50 = > 5000 mg/kg (oral, rat)
}}
}}
}} }}


'''Allantoin''' is a chemical compound with formula C<sub>4</sub>H<sub>6</sub>N<sub>4</sub>O<sub>3</sub>. It is also called '''5-ureidohydantoin''' or '''glyoxyldiureide'''.<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204 | title=Allantoin}}</ref><ref>{{Cite web | url=http://www.chemblink.com/products/97-59-6.htm | title=CAS # 97-59-6, Allantoin, 5-Ureidohydantoin, Glyoxyldiureide, Glyoxylic diureide, Cordianine, Glyoxyldiureid, (2,5-Dioxo-4-imidazolidinyl)urea}}</ref> It is a ] of ]. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria, though not humans. It is produced from ], which itself is a degradation product of ], by action of ] (uricase).<ref>{{Cite journal|last1=Pizzichini|first1=Maria|last2=Pandolfi|first2=Maria Luisa|last3=Arezzini|first3=Laura|last4=Terzuoli|first4=Lucia|last5=Fè|first5=Linda|last6=Bontemps|first6=Francois|last7=Van den Berghe|first7=Georges|last8=Marinello|first8=Enrico|date=1996-08-09|title=Labelling of uric acid and allantoin in different purine organs and urine of the rat|journal=Life Sciences|volume=59|issue=11|pages=893–899|doi=10.1016/0024-3205(96)00387-6|pmid=8795700}}</ref><ref>{{Cite journal|last1=Xi|first1=H.|last2=Schneider|first2=B. L.|last3=Reitzer|first3=L.|date=2000-10-01|title=Purine catabolism in ''Escherichia coli'' and function of xanthine dehydrogenase in purine salvage|journal=Journal of Bacteriology|volume=182|issue=19|pages=5332–5341|issn=0021-9193|pmc=110974|pmid=10986234|doi=10.1128/jb.182.19.5332-5341.2000}}</ref><ref>{{Cite journal|last1=Johnson|first1=Richard J.|last2=Sautin|first2=Yuri Y.|last3=Oliver|first3=William J.|last4=Roncal|first4=Carlos|last5=Mu|first5=Wei|last6=Gabriela Sanchez-Lozada|first6=L.|last7=Rodriguez-Iturbe|first7=Bernardo|last8=Nakagawa|first8=Takahiko|last9=Benner|first9=Steven A.|date=2009-01-01|title=Lessons from comparative physiology: could uric acid represent a physiologic alarm signal gone awry in western society?|journal=Journal of Comparative Physiology B|volume=179|issue=1|pages=67–76|doi=10.1007/s00360-008-0291-7|issn=1432-136X|pmc=2684327|pmid=18649082}}</ref> Allantoin also occurs as a natural mineral compound (] ] Aan<ref>{{Cite journal|last=Warr|first=L.N.|date=2021|title=IMA-CNMNC approved mineral symbols|journal=Mineralogical Magazine|volume=85|issue=3 |pages=291–320|doi=10.1180/mgm.2021.43 |bibcode=2021MinM...85..291W |s2cid=235729616 |doi-access=free}}</ref>).
'''Allantoin''' is a chemical compound with formula C<sub>4</sub>H<sub>6</sub>N<sub>4</sub>O<sub>3</sub>. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a ] of ].


== History ==
Named after the ], an ] embryonic excretory organ in which it concentrates during development in most ]s except humans and higher apes, it is a product of oxidation of ] by ] ]. After birth, it is the predominant means by which ] is excreted in the ] of these animals.<ref>{{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 | issue=1}}</ref> In humans and higher apes, the metabolic pathway for conversion of ] to allantoin is not present, so the former is excreted. Recombinant ] is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ]) before excretion.<ref>{{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 |pmid=7492331 |pmc=1136261 }}</ref> Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.

Allantoin was first isolated in 1800 by the Italian physician Michele Francesco Buniva (1761–1834) and the French chemist ], who mistakenly believed it to be present in the ].<ref>See:
* Buniva and Vauquelin (1800) (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, </ref> In 1821, the French chemist ] found it in the fluid of the ]; he called it ''"l'acide allantoique"''.<ref>Lassaigne (1821) (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).</ref> In 1837, the German chemists ] and ] synthesized it from ] and renamed it "allantoïn".<ref>See:
* Liebig and Wöhler (1837) (On the nature of uric acid), ''Annalen der Physik und Chemie'', '''41''' (8) : 561-569. Allantoin is named on 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 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) (Investigations into the nature of uric acid), ''Annalen der Pharmacie'', '''26''' : 241-340.</ref>

==Animals==
Named after the ] (an ] embryonic excretory organ in which it concentrates during development in most ]s except humans and other hominids), it is a product of oxidation of ] by ] ]. After birth, it is the predominant means by which ] is excreted in the ] of these animals.<ref>{{cite journal |title= The absorption and excretion of allantoin in mammals|author1=Young E. G. |author2=Wentworth H. P. |author3=Hawkins W. W. | journal= J. Pharmacol. Exp. Ther. | volume= 81 | pages= 1–9| year= 1944 | url=http://jpet.aspetjournals.org/cgi/reprint/81/1/1 | issue=1}}</ref> In humans and other higher apes, the metabolic pathway for conversion of ] to allantoin is not present, so the former is excreted. Recombinant ] is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ]) before excretion.<ref>{{cite journal |last=Fujiwara |first=S |author2=Noguchi T |year=1995|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 |pmid=7492331 |pmc=1136261 |doi=10.1042/bj3120315 }}</ref>

Allantoin has been shown to improve insulin resistance when administered to rats and to increase lifespan when administered to the nematode worm '']''.<ref>{{cite journal|author1=Ko, W.C. |author2=Liu, I.M. |author3=Chung, H.H. |author4=Cheng, J.T.|title=Activation of I<sub>2</sub>-imidazoline receptors may ameliorate insulin resistance in fructose-rich chow-fed rats|journal=Neuroscience Letters|volume=448|issue=1|date=2008|pages=90–93|doi=10.1016/j.neulet.2008.10.002|pmid=18926881|s2cid=207127849 }}</ref><ref>{{cite journal|author1=Shaun Calvert |author2=Robi Tacutu |author3=Samim Sharifi |author4=Rute Teixeira |author5=Pratul Ghosh |author6=João Pedro de Magalhães|year=2016|title=A network pharmacology approach reveals new candidate caloric restriction mimetics in ''C. elegans''|journal=Aging Cell|volume=15 |issue=2|pages=256–266|doi= 10.1111/acel.12432|pmid=26676933|pmc=4783339}}</ref>

== 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.<ref>{{Cite journal|last1=Ma|first1=Pikyee|last2=Patching|first2=Simon G.|last3=Ivanova|first3=Ekaterina|last4=Baldwin|first4=Jocelyn M.|last5=Sharples|first5=David|last6=Baldwin|first6=Stephen A.|last7=Henderson|first7=Peter J. F.|date=2016-05-01|title=Allantoin transport protein, PucI, from ''Bacillus subtilis'': evolutionary relationships, amplified expression, activity and specificity|journal=Microbiology|volume=162|issue=5|pages=823–836|doi=10.1099/mic.0.000266|doi-access=free |issn=1465-2080|pmc=4851255|pmid=26967546}}</ref> For instance, '']'' is able to utilize allantoin as its sole nitrogen source.<ref>{{Cite journal|last1=Goelzer|first1=Anne|last2=Bekkal Brikci|first2=Fadia|last3=Martin-Verstraete|first3=Isabelle|last4=Noirot|first4=Philippe|last5=Bessières|first5=Philippe|last6=Aymerich|first6=Stéphane|last7=Fromion|first7=Vincent|date=2008-02-26|title=Reconstruction and analysis of the genetic and metabolic regulatory networks of the central metabolism of Bacillus subtilis|journal=BMC Systems Biology|volume=2|pages=20|doi=10.1186/1752-0509-2-20|issn=1752-0509|pmc=2311275|pmid=18302748 |doi-access=free }}</ref>

Mutants in the ''B. subtilis'' ''pucI'' gene were unable to grow on allantoin, indicating that it encodes an allantoin transporter.<ref>{{Cite journal|last1=Schultz|first1=A. C.|last2=Nygaard|first2=P.|last3=Saxild|first3=H. H.|date=2001-06-01|title=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=Journal of Bacteriology|volume=183|issue=11|pages=3293–3302|doi=10.1128/JB.183.11.3293-3302.2001|issn=0021-9193|pmc=99626|pmid=11344136}}</ref>

In '']'', allantoinase (] 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).<ref>{{Cite journal|last1=Navone|first1=Laura|last2=Casati|first2=Paula|last3=Licona-Cassani|first3=Cuauhtémoc|last4=Marcellin|first4=Esteban|last5=Nielsen|first5=Lars K.|last6=Rodriguez|first6=Eduardo|last7=Gramajo|first7=Hugo|date=2013-11-29|title=Allantoin catabolism influences the production of antibiotics in ''Streptomyces coelicolor''|journal=Applied Microbiology and Biotechnology|language=en|volume=98|issue=1|pages=351–360|doi=10.1007/s00253-013-5372-1|issn=0175-7598|pmid=24292080|hdl=11336/7859|s2cid=216898|hdl-access=free}}</ref>


== Applications == == Applications ==
Allantoin is present in botanical ]s of the ] plant and ] from cows and most mammals. Chemically synthesized bulk allantoin is nature-identical, safe, non-toxic, compatible with cosmetic raw materials and meets CTFA and JSCI requirements.<ref>Akema (an allantoin manufacturer) </ref> Over 10,000 ] reference allantoin. <ref>Patent Lens search </ref> Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics: a moisturizing and ] effect, increasing the water content of the ] and enhancing the ] 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.<ref>www.in-cosmetics.com trade exhibition </ref> A study published in 2009 reported the treatment of ] in mild-to-moderate atopic dermatitis with a topical non-steroidal agent containing Allantoin.<ref>J Drugs Dermatol. 2009 Jun;8(6):537-9.</ref> Allantoin is present in botanical ]s of the ] plant and in the ] 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 ] and ] requirements. Over 10,000 ]s reference allantoin.<ref>{{Dead link|date=May 2019 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>


===Cosmetics===
It is frequently present in ], ], and other ] products, in ]s, ]s, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.<ref>{{cite journal |doi=10.1111/j.1524-4725.2005.31734 |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 }}</ref>
Manufacturers may use allantoin as an ingredient in over-the-counter cosmetics.{{cn|date=March 2023}}

===Pharmaceuticals===
It is frequently present in ], ], and other ] products, in ]s, ]s, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.<ref>{{cite journal |doi=10.1111/j.1524-4725.2005.31734 |last=Thornfeldt |first=C |year=2005|title=Cosmeceuticals containing herbs: fact, fiction, and future |journal=Dermatologic Surgery |volume=31 |issue=7 Pt 2 |pages=873–80 |pmid=16029681 }}</ref>

===Biomarker of oxidative stress===
Since ] is the end product of the ] in humans, only non-enzymatic processes with ] will give rise to allantoin, which is thus a suitable ] to measure ] in chronic illnesses and ].<ref>{{cite journal|vauthors=Kanďár R, Záková P |pmid=18636793|year=2008|title=Allantoin as a marker of oxidative stress in human erythrocytes|volume=46|issue=9|pages=1270–4|doi=10.1515/CCLM.2008.244|journal=Clinical Chemistry and Laboratory Medicine|s2cid=6420729}}</ref><ref>{{cite journal|vauthors=Zitnanová I, Korytár P, Aruoma OI, Sustrová M, Garaiová I, Muchová J, Kalnovicová T, Pueschel S, Duracková Z |pmid=14967170|year=2004|title=Uric acid and allantoin levels in Down syndrome: Antioxidant and oxidative stress mechanisms?|volume=341|issue=1–2|pages=139–46|doi=10.1016/j.cccn.2003.11.020|journal=Clinica Chimica Acta}}</ref>


== See also == == See also ==
{{Portal|Biology|Medicine|Chemistry}}
* ] and ], ] condensation products of allantoin with ]
* ] and ], are ] condensation products of allantoin with ].


== References == == References ==
{{reflist|2}} {{reflist}}

== External links ==
* '']'' (AllB) in ] ()
*


]
] ]
] ]
] ]
] ]

]
]
]
]
]
]
]
]
]
]
]
]
]
]
]
]
]
]

Latest revision as of 08:19, 21 December 2024

"Paxyl" and "udder cream" redirect here. For the antidepressant Paxil, see Paroxetine. For the ointment, see Bag Balm.
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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.358 Edit this at Wikidata
EC Number
  • 202-592-8
KEGG
PubChem CID
RTECS number
  • YT1600000
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: POJWUDADGALRAB-UHFFFAOYSA-N
  • 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
SMILES
  • O=C1NC(=O)NC1NC(=O)N
  • C1(C(=O)NC(=O)N1)NC(=O)N
Properties
Chemical formula C4H6N4O3
Molar mass 158.117 g·mol
Appearance colourless crystalline powder
Odor odorless
Density 1.45 g/cm
Melting point 230 °C (446 °F; 503 K) (decomposes)
Boiling point 478 °C (892 °F; 751 K)
Solubility in water 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
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):
LD50 (median dose) > 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria, though not humans. It is produced from uric acid, which itself is a degradation product of nucleic acids, by action of urate oxidase (uricase). Allantoin also occurs as a natural mineral compound (IMA symbol Aan).

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

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. 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 to increase 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.

Cosmetics

Manufacturers may use allantoin as an ingredient in over-the-counter cosmetics.

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

  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. 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. PMC 110974. 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; 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. ISSN 1432-136X. PMC 2684327. PMID 18649082.
  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. 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 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. PMC 1136261. 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. S2CID 207127849.
  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. PMC 4783339. 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. PMC 4851255. 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. PMC 2311275. 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. PMC 99626. 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". Applied Microbiology and Biotechnology. 98 (1): 351–360. doi:10.1007/s00253-013-5372-1. hdl:11336/7859. ISSN 0175-7598. PMID 24292080. S2CID 216898.
  18. Patent Lens search
  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. 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. PMID 18636793. S2CID 6420729.
  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. PMID 14967170.

External links

Categories:
Allantoin: Difference between revisions Add topic