Allantoin
Encyclopedia
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid
.
Named after the allantois
, an amniote
embryonic excretory organ in which it concentrates during development in most mammal
s except humans and 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. In humans and 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 is a major metabolic intermediate in many other organisms including plants and bacteria.
s of the comfrey
plant and urine
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. Over 10,000 patents reference allantoin. Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics: 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. A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent containing Allantoin.
It is frequently present in toothpaste
, mouthwash
, and other oral hygiene
products, in shampoo
s, lipstick
s, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.
Glyoxylic acid
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially....
.
Named after the allantois
Allantois
Allantois is a part of a developing animal conceptus . It helps the embryo exchange gases and handle liquid waste....
, an amniote
Amniote
The amniotes are a group of tetrapods that have a terrestrially adapted egg. They include synapsids and sauropsids , as well as their fossil ancestors. Amniote embryos, whether laid as eggs or carried by the female, are protected and aided by several extensive membranes...
embryonic excretory organ in which it concentrates during development in most mammal
Mammal
Mammals are members of a class of air-breathing vertebrate animals characterised by the possession of endothermy, hair, three middle ear bones, and mammary glands functional in mothers with young...
s except humans and higher apes, it is a product of oxidation of uric acid
Uric acid
Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid urates such as ammonium acid urate. Uric acid is created when the body breaks down purine nucleotides. High blood concentrations of uric acid...
by purine
Purine
A purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature....
catabolism
Catabolism
Catabolism is the set of metabolic pathways that break down molecules into smaller units and release energy. In catabolism, large molecules such as polysaccharides, lipids, nucleic acids and proteins are broken down into smaller units such as monosaccharides, fatty acids, nucleotides, and amino...
. After birth, it is the predominant means by which nitrogenous waste is excreted in the urine
Urine
Urine is a typically sterile liquid by-product of the body that is secreted by the kidneys through a process called urination and excreted through the urethra. Cellular metabolism generates numerous by-products, many rich in nitrogen, that require elimination from the bloodstream...
of these animals. In humans and higher apes, the metabolic pathway for conversion of uric acid
Uric acid
Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid urates such as ammonium acid urate. Uric acid is created when the body breaks down purine nucleotides. High blood concentrations of uric acid...
to allantoin is not present, so the former is excreted. Recombinant rasburicase
Rasburicase
Rasburicase is a recombinant version of a urate oxidase enzyme that occurs in many mammals but not in humans.-Uses:Rasburicase is approved for use by the U.S...
is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
) before excretion. Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.
Applications
Allantoin is present in botanical extractExtract
An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol or water. Extracts may be sold as tinctures or in powder form....
s of the comfrey
Comfrey
Comfrey is an important herb in organic gardening. It is used as a fertilizer and also has many purported medicinal uses...
plant and urine
Urine
Urine is a typically sterile liquid by-product of the body that is secreted by the kidneys through a process called urination and excreted through the urethra. Cellular metabolism generates numerous by-products, many rich in nitrogen, that require elimination from the bloodstream...
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. Over 10,000 patents reference allantoin. Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics: a moisturizing and keratolytic
Keratolytic
Keratolytic therapy is treatment to remove warts and other lesions in which the epidermis produces excess skin. In this therapy, acid medicine, such as salicylic acid is put on the lesion. Keratolytic therapy thins the skin on and around the lesion. It causes the outer layer of the skin to loosen...
effect, increasing the water content of the extracellular matrix
Extracellular matrix
In biology, the extracellular matrix is the extracellular part of animal tissue that usually provides structural support to the animal cells in addition to performing various other important functions. The extracellular matrix is the defining feature of connective tissue in animals.Extracellular...
and enhancing the desquamation
Desquamation
Desquamation , also called skin peeling, is the shedding of the outermost membrane or layer of a tissue, such as the skin.-Skin:Normal, nonpathologic desquamation of the skin occurs when keratinocytes, after moving apically over about 14 days, are individually shed unnoticeably...
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. A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent containing Allantoin.
It is frequently present in toothpaste
Toothpaste
Toothpaste is a paste or gel dentifrice used with a toothbrush as an accessory to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it serves as an abrasive that aids in removing the dental plaque and food from the teeth, assists in suppressing...
, mouthwash
Mouthwash
Mouthwash or mouth rinse is a product used to enhance oral hygiene. Some manufacturers of mouthwash claim that antiseptic and anti-plaque mouth rinse kill the bacterial plaque causing cavities, gingivitis, and bad breath. Anti-cavity mouth rinse uses fluoride to protect against tooth decay...
, and other oral hygiene
Oral hygiene
Teeth cleaning is part of oral hygiene and involves the removal of dental plaque from teeth with the intention of preventing cavities , gingivitis, and periodontal disease. People routinely clean their own teeth by brushing and interdental cleaning, and dental hygienists can remove hardened...
products, in shampoo
Shampoo
Shampoo is a hair care product used for the removal of oils, dirt, skin particles, dandruff, environmental pollutants and other contaminant particles that gradually build up in hair...
s, lipstick
Lipstick
Lipstick is a cosmetic product containing pigments, oils, waxes, and emollients that applies color, texture, and protection to the lips. Many varieties of lipstick are known. As with most other types of makeup, lipstick is typically, but not exclusively, worn by women...
s, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.
See also
- Imidazolidinyl ureaImidazolidinyl ureaImidazolidinyl urea is an antimicrobial preservative used in cosmetics . It is chemically related to diazolidinyl urea which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser.- Safety :...
and diazolidinyl ureaDiazolidinyl ureaDiazolidinyl urea is an antimicrobial preservative used in cosmetics. It is chemically related to imidazolidinyl urea which is used in the same way. Diazolidinyl urea acts as a formaldehyde releaser....
, antimicrobialAntimicrobialAn anti-microbial is a substance that kills or inhibits the growth of microorganisms such as bacteria, fungi, or protozoans. Antimicrobial drugs either kill microbes or prevent the growth of microbes...
condensation products of allantoin with formaldehydeFormaldehydeFormaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...