Names | |
---|---|
Preferred IUPAC name (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid | |
Other names (E)-3-(1H-imidazol-4-yl)acrylic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.963 |
MeSH | Urocanic+acid |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C6H6N2O2 | |
Molar mass | 138.124 g/mol |
Melting point | 225 °C (437 °F; 498 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Urocanic acid (formally trans-Urocanic acid) is an intermediate in the catabolism of L-histidine. The cis-urocanic acid isomer is rare.
It is formed from L-histidine through the action of histidine ammonialyase (also known as histidase or histidinase) by elimination of ammonium.
In the liver, urocanic acid is transformed by urocanate hydratase (or urocanase) to 4-imidazolone-5-propionic acid and subsequently to glutamic acid.
Inherited deficiency of urocanase leads to elevated levels of urocanic acid in the urine, a condition known as urocanic aciduria.
An important role for the onset of atopic dermatitis and asthma has been attributed to filaggrin, a skin precursor of urocanic acid. [1] [2]
Urocanic acid is thought to be a significant attractant of the nematode parasite Strongyloides stercoralis , [3] in part because of relatively high levels in the plantar surfaces of the feet, the site through which this parasite often enters the body.
Urocanic acid was detected in animal sweat and skin where, among other possible functions, it acts as an endogenous sunscreen or photoprotectant against UVB-induced DNA damage. Urocanic acid is found predominantly in the stratum corneum of the skin and it is likely that most of it is derived from filaggrin catabolism (a histidine-rich protein). When exposed to UVB irradiation, trans-urocanic acid is converted in vitro and in vivo to cis-urocanic acid (cis-UCA). [4] The cis form is known to activate regulatory T cells. [5]
Some studies attribute filaggrin an important role in keeping the skin surface slightly acidic, through a breaking down mechanism to form histidine and subsequently trans-urocanic acid, [6] however others have shown that the filaggrin–histidine–urocanic acid cascade is not essential for skin acidification. [7]
Urocanic acid was first isolated in 1874 by the chemist Max Jaffé from the urine of a dog, [8] [9] hence the name (Latin : urina = urine, and canis = dog).
Strongyloides stercoralis is a human pathogenic parasitic roundworm causing the disease strongyloidiasis. Its common name in the US is threadworm. In the UK and Australia, however, the term threadworm can also refer to nematodes of the genus Enterobius, otherwise known as pinworms.
Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, is known as seborrhoeic dermatitis.
Irritant diaper dermatitis is a generic term applied to skin rash in the diaper area that are caused by various skin disorders and/or irritants.
In organic chemistry, the Knoevenagel condensation reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation.
The Japp–Klingemann reaction is a chemical reaction used to synthesize hydrazones from β-keto-acids and aryl diazonium salts. The reaction is named after the chemists Francis Robert Japp and Felix Klingemann.
Atopic dermatitis (AD), also known as atopic eczema, is a long-term type of inflammation of the skin. AD is also often called simply eczema but the same term is also used to refer to dermatitis, the larger group of skin conditions. AD results in itchy, red, swollen, and cracked skin. Clear fluid may come from the affected areas, which can thicken over time.
Aziridine is an organic compound consisting of the three-membered heterocycle C2H5N. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.
Diphenylchloroarsine (DA) is the organoarsenic compound with the formula (C6H5)2AsCl. It is highly toxic and was once used in chemical warfare. It is also an intermediate in the preparation of other organoarsenic compounds. The molecule consists of a pyramidal As(III) center attached to two phenyl rings and one chloride. It was also known as sneezing oil during World War I by the Allies.
Filaggrin is a filament-associated protein that binds to keratin fibers in epithelial cells. Ten to twelve filaggrin units are post-translationally hydrolyzed from a large profilaggrin precursor protein during terminal differentiation of epidermal cells. In humans, profilaggrin is encoded by the FLG gene, which is part of the S100 fused-type protein (SFTP) family within the epidermal differentiation complex on chromosome 1q21. In cetaceans and sirenians, the FLG family has lost its function, with the curious exception of manatees in the latter clade: manatees still retain some functional FLG genes.
The acid mantle is a very thin, delicate, slightly acidic film covering the entire surface of human skin, serving as a protective barrier against pathogens and reduces body odor. The acidic pH at the skin's surface mainly maintained by free amino acids and α-hydroxy acids excreted from sweat; free fatty acids and amino acids from sebum; and urocanic acid and pyroglutamic acid. While the viable epidermis below the stratum corneum has a neutral pH of around 7.0, the surface pH of the skin's acid mantle typically ranges between 4.5 and 6.5, with an average assumption of 5.0 to 6.0.
Hans Freiherr von Pechmann was a German chemist, renowned for his discovery of diazomethane in 1894. Pechmann condensation and Pechmann pyrazole synthesis. He also first prepared 1,2-diketones, acetonedicarboxylic acid, methylglyoxal and diphenyltriketone; established the symmetrical structure of anthraquinone.
Fischer glycosidation refers to the formation of a glycoside by the reaction of an aldose or ketose with an alcohol in the presence of an acid catalyst. The reaction is named after the German chemist, Emil Fischer, winner of the Nobel Prize in chemistry, 1902, who developed this method between 1893 and 1895.
Histidine ammonia-lyase is an enzyme that in humans is encoded by the HAL gene. It converts histidine into ammonia and urocanic acid. Its systematic name is L-histidine ammonia-lyase (urocanate-forming).
Urocanase is the enzyme that catalyzes the second step in the degradation of histidine, the hydration of urocanate into imidazolonepropionate.
Corneocytes are terminally differentiated keratinocytes and compose most of the stratum corneum, the outermost layer of the epidermis. They are regularly replaced through desquamation and renewal from lower epidermal layers and are essential for its function as a skin barrier.
Keratohyalin is a protein structure found in cytoplasmic granules of the keratinocytes in the stratum granulosum of the epidermis. Keratohyalin granules (KHG) mainly consist of keratin, profilaggrin, loricrin and trichohyalin proteins which contribute to cornification or keratinization, the process of the formation of epidermal cornified cell envelope. During the keratinocyte differentiation, these granules maturate and expand in size, which leads to the conversion of keratin tonofilaments into a homogenous keratin matrix, an important step in cornification.
Oskar Piloty was a German chemist.
Urocanic aciduria is an autosomal recessive metabolic disorder caused by a deficiency of the enzyme urocanase. It is a secondary disorder of histidine metabolism.
Skin sloughing is the process of shedding dead surface cells from the skin. It is most associated with cosmetic skin maintenance via exfoliation, but can also occur biologically or for medical reasons.
Alexander Ellinger was a German chemist and pharmacologist.