ALLANTOIN

Synonyms:
ALLANTOINE; Allantoïne; ALLANTOİNE; allantoin; 97-59-6; 5-Ureidohydantoin; Glyoxyldiureide; 1-(2,5-dioxoimidazolidin-4-yl)urea; Glyoxyldiureid; Allantol; Cordianine; Sebical; Alantan; AVC/Dienestrolcream; Urea, (2,5-dioxo-4-imidazolidinyl)-; Hydantoin, 5-ureido-Cutemol emollient; Uniderm A; (2,5-Dioxo-4-imidazolidinyl)urea; Glyoxylic diureide; Glyoxylic(acid) diureide; Psoralon; Septalan; Caswell No. 024; (2,5-dioxoimidazolidin-4-yl)urea; NSC 7606; 5-Ureido-2,4-imidazolidindion;ALLANTOINE; Allantoïne; ALLANTOİNE; allantoin; 97-59-6; 5-Ureidohydantoin; Glyoxyldiureide; 1-(2,5-dioxoimidazolidin-4-yl)urea; Glyoxyldiureid; Allantol; Cordianine; Sebical; Alantan; AVC/Dienestrolcream;ALLANTOINE; Allantoïne; ALLANTOİNE; allantoin; 97-59-6; 5-Ureidohydantoin; Glyoxyldiureide; 1-(2,5-dioxoimidazolidin-4-yl)urea; Glyoxyldiureid; Allantol; Cordianine; Sebical; Alantan; AVC/Dienestrolcream; Urea, (2,5-dioxo-4-imidazolidinyl)-; Hydantoin, 5-ureido-Cutemol emollient; Uniderm A; (2,5-Dioxo-4-imidazolidinyl)urea; Glyoxylic diureide; Glyoxylic(acid) diureide; Psoralon; Septalan; Caswell No. 024; (2,5-dioxoimidazolidin-4-yl)urea; NSC 7606; 5-Ureido-2,4-imidazolidindion;ALLANTOINE; Allantoïne; ALLANTOİNE; allantoin; 97-59-6; 5-Ureidohydantoin; Glyoxyldiureide; 1-(2,5-dioxoimidazolidin-4-yl)urea; Glyoxyldiureid; Allantol; Cordianine; Sebical; Alantan; AVC/Dienestrolcream; Urea, (2,5-dioxo-4-imidazolidinyl)-; Hydantoin, 5-ureido-Cutemol emollient; Uniderm A; (2,5-Dioxo-4-imidazolidinyl)urea; Glyoxylic diureide; Glyoxylic(acid) diureide; Psoralon; Septalan; Caswell No. 024; (2,5-dioxoimidazolidin-4-yl)urea; NSC 7606; 5-Ureido-2,4-imidazolidindion; N-(2,5-Dioxo-4-imidazolidinyl)urea; CCRIS 1958; Allantoin [USAN:BAN]; 2,5-Dioxo-4-imidazolidinyl-urea; Fancol TOIN; 5-Ureidohydrantoin; Allantoïne ; Allantoin; Allantoine; N-(2,5-Dioxo-4-imidazolidinyl)urea; CCRIS 1958; Allantoin [USAN:BAN]; 2,5-Dioxo-4-imidazolidinyl-urea; Fancol TOIN; 5-Ureidohydrantoin; Allantoïne ; Allantoin; Allantoine; Alantoïne ; Alantoin; Alantoine;  Urea, (2,5-dioxo-4-imidazolidinyl)-; Hydantoin, 5-ureido-Cutemol emollient; Uniderm A; (2,5-Dioxo-4-imidazolidinyl)urea; Glyoxylic diureide; Glyoxylic(acid) diureide; Psoralon; Septalan; Caswell No. 024; (2,5-dioxoimidazolidin-4-yl)urea; NSC 7606; 5-Ureido-2,4-imidazolidindion; N-(2,5-Dioxo-4-imidazolidinyl)urea; CCRIS 1958; Allantoin [USAN:BAN]; 2,5-Dioxo-4-imidazolidinyl-urea; Fancol TOIN; 5-Ureidohydrantoin; Allantoïne ; Allantoin; Allantoine; N-(2,5-Dioxo-4-imidazolidinyl)urea; CCRIS 1958; Allantoin [USAN:BAN]; 2,5-Dioxo-4-imidazolidinyl-urea; Fancol TOIN; 5-Ureidohydrantoin; Allantoïne ; Allantoin; Allantoine; Alantoïne ; Alantoin; Alantoine; ALLANTOİNE; ALLANTOINE ; ALLANTOİN ; ALLANTOIN ; Allantoïne; Allantoïn

Allantoin
Allantoin is a widely used ingredient found in many popular skin care products. Also, Allantoin is one of the versatile ingredients as a chemical compound that is good for the skin.

Its use goes back to ancient Egypt and China. As a component; It is known that its chemical composition does not have any side effects and is valid for all skin types and is safe when applied to the skin.

Benefits;

Moisturizer: Increases the skin's water content.
Desquamation: It promotes natural shedding in the stratum corneum, which is the outer layer of the skin.
Restorative effect: It is known for its ability to stimulate cell proliferation by promoting new tissue growth. It promotes the regeneration of cells. Known research on wound healing has shown that it clears necrotic scar tissue and gives rise to a healthy new tissue.
Recovery: An active skin protectant, naturally promotes the healing process of the skin; It is a suitable ingredient for treating minor wounds and irritations.
Relieves skin dryness: Promotes cellular regeneration, prevents dryness, and Allantoin encourages sensitive skin to be more flexible.
Protection: It is an ingredient that really softens the skin, protects chapped, sun damaged skin, studies have shown that it protects against UV-induced cell damage.
Soothing: Considered an excellent sedative. Therefore, it is used even in baby products to prevent skin irritation.
Anti-aging - Antioxidant effect: It helps to reduce free radical activity in the skin with topical application of 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
(2,5-Dioxo-4-imidazolidinyl) urea
Other names
Glyoxyldiureide; 5-Ureidohydantoin
Identifiers
CAS Number    
97-59-6 ☑
3D model (JSmol)    
Interactive image
Interactive image
ChEBI    
CHEBI:15676 ☑
ChEMBL    
ChEMBL593429 ☑
ChemSpider    
199 ☑
ECHA InfoCard    100.002.358 Edit this at Wikidata
EC Number    
202-592-8
KEGG    
D00121 ☑
PubChem CID    
204
RTECS number    
YT1600000
UNII    
344S277G0Z ☑
CompTox Dashboard (EPA)    
DTXSID3020043 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    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)
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
Safety data sheet    Allantoin MSDS
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
120
Lethal dose or concentration (LD, LC):
LD50 (median dose)    > 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
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]

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

Animals
Named after the allantois (an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and other 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.[9] 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.[10]

Allantoin has been shown to improve insulin resistance when administered to rats and increased lifespan when administered to the nematode worm Caenorhabditis elegans.[11][12]

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

Mutants in the B. subtilis pucI gene were unable to grow on allantoin, indicating that it encodes an allantoin transporter.[15]

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).[16]

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.[17]

Cosmetics and toiletries
Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics, including: 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; promoting cell proliferation and wound healing; and a soothing, anti-irritant, and skin protectant effect by forming complexes with irritant and sensitizing agents.

An animal study in 2010 found that based on the results from histological analyses, a soft lotion with 5% allantoin ameliorates the wound healing process, by modulating the inflammatory response. The study also suggests that quantitative analysis lends support to the idea that allantoin also promotes fibroblast proliferation and synthesis of the extracellular matrix.[18]

A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical nonsteroidal agent containing allantoin.[19]

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.[20]

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.[21][22]

See also
Imidazolidinyl urea and diazolidinyl urea, are antimicrobial condensation products of allantoin with formaldehyde.

ALLANTOIN
Allantoin, which has soothing and healing effects on the skin, is used in creams and topical substances prepared for medical purposes. It is found in allantoic fluid and in fetal urine of some mammals, but in many plants (especially comfrey-comfrey).
The main function of allantoin is to stimulate cell proliferation and improve the restructuring of granulation tissue.
For cosmetic purposes, Allantoin is mostly obtained from comfrey plant. Besides, the self-renewal property of snails is due to the Allantoin substance in their secretions. Today, many creams containing snail extract are produced in the cosmetics industry.
Allantoin and Cosmetic Applications
Allantoin provides cell renewal in the skin. It greatly supports skin regeneration and repair in problematic and weakened skin.
Although mostly used in lotions and skin creams; It is used extensively in lip care products, baby creams and lotions, oral care products, toothpastes, shampoos, hair dyes, sunscreens, wet wipes, after-shave care products and color cosmetics. Allantoin in this kind of cosmetic products; It has anti-irritation, healing and regenerating activity. It protects the skin from damage.
In drug applications; It is also used in the treatment of skin diseases such as skin ulcers, wounds, scars, burns, sunburns, carbuncles, acne, skin eruptions, fissures, skin abrasions, impetigo, eczema, psoriasis and psoriasis.
 
Allantoin for sensitive skin and skin rashes
Skin care for sensitive skin is a very demanding job. Care methods applied for normal skin can cause rash and allergic reactions in sensitive skin, so a different care should be applied from other skin types.
Sensitive skin also has a dry skin structure. First of all, products with soft texture and designed for sensitive skin should be used. Therefore, the content and active ingredients of sensitive skin care products are very important.
Allantoin, the active ingredient that adapts to the skin with its natural structure, is an ideal ingredient for use especially on sensitive skin. Soothes skin rashes, is antiseptic. It soothes, calms, moisturizes the skin and helps it renew its natural functions.
What is Allantoin? What Are Its Benefits For The Skin?
March 14, 2019
Allantoin is a widely used ingredient found in many popular skin care products. It is also one of the versatile ingredients as a chemical compound that is good for the skin.

It usually comes from the herbal extracts found in the roots of the comfrey plant (Symphytum Officinale), aloe vera, chamomile, lotus, yam and other herbs.

Its use goes back to ancient Egypt and China. As a component; It is known that its chemical composition does not have any side effects and is valid for all skin types and is safe when applied to the skin.

We can say that allantoin is a versatile, safe and effective skin care ingredient with many different benefits, including softening and moisturizing the skin. According to the International Toxicology journal, allantoin is an ingredient that has been found to be non-toxic and safe for use in a variety of cosmetic applications.

HOW IS ALLANTOIN EFFECT MECHANISM?
Allantoin is a known keratolytic, meaning it can increase the water content of cells. It also helps in marking the outer layers of the skin.

Keratolytic feature; It is especially used to treat skin and scalp disorders such as warts, acne, dandruff and psoriasis. The outer layer of our skin, which performs keratolytic effect, protective and regulatory functions, is the epidermis. It synthesizes a large number of proteins and oils (lipids) found naturally in the Stratum Corneum.

Allantoin is smart; It interacts with the skin's keratin to thin an abnormal and thick Stratum corneum. This is what allantoin provides to make your skin feel smooth. An allantoin at a concentration of 0.2% that you will use on your skin has keratolytic properties. Allantoin is very active in low concentrations (up to 0.5%) and its biggest advantage is that it is non-irritating and non-toxic to the skin.

WHAT ARE ALLANTOIN SCIENTIFIC STUDIES?
Allantoin is also known to be effective in healing and regenerating the skin. A 2015 study by the University of Liverpool confirmed the beneficial properties and scientific functions that Allantoin offers through skin care products.

According to a study on allantoin; Thanks to the ingredient with an allantoin content of only 0.2%, the symptoms of redness and cracking in women's skin improved by more than 90%. The fact that allantoin has active keratolytic properties means it is an ideal ingredient in combating dandruff, and it does this by breaking down large particles in dead skin cells.