ウロカニン酸
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/02/17 17:36:50」(JST)
[Wiki en表示]
| Urocanic acid |
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IUPAC name
(E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
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| Identifiers |
| CAS number |
104-98-3 |
| PubChem |
1178 |
| MeSH |
Urocanic+acid |
| Jmol-3D images |
Image 1 |
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| Properties |
| Molecular formula |
C6H6N2O2 |
| Molar mass |
138.124 g/mol |
| Melting point |
225°C |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Infobox references |
Urocanic acid is an intermediate in the catabolism of L-histidine.
Contents
- 1 Metabolism
- 2 Clinical significance
- 3 Function
- 4 History
- 5 See also
- 6 References
- 7 External links
Metabolism[edit]
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.
Clinical significance[edit]
Inherited deficiency of urocanase leads to elevated levels of urocanic acid in the urine, a condition known as urocanic aciduria.
Function[edit]
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 the cis isomer. The cis form is known to activate regulatory T cells.
History[edit]
Urocanic acid was first isolated in 1874 by the chemist M. Jaffé from the urine of a dog,[1] hence the name (Latin: urina = urine, and canis = dog).
See also[edit]
- Histidinemia
- Inborn error of metabolism
References[edit]
- ^ Jaffé, M. (1874). "Concerning a new constituent in the urine of dogs". Ber. Deut. Chem. Ges. 7: 1669–1673.
External links[edit]
- The Online Metabolic and Molecular Bases of Inherited Disease - Chapter 80 - An overview of disorders of histidine metabolism, including urocanic aciduria.
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Amino acid metabolism metabolic intermediates
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| K→acetyl-CoA |
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lysine→
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- Saccharopine
- Allysine
- α-Aminoadipic acid
- α-Aminoadipate
- Glutaryl-CoA
- Glutaconyl-CoA
- Crotonyl-CoA
- β-Hydroxybutyryl-CoA
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leucine→
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- α-Ketoisocaproic acid
- Isovaleryl-CoA
- 3-Methylcrotonyl-CoA
- 3-Methylglutaconyl-CoA
- HMG-CoA
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|
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tryptophan→alanine→
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- N'-Formylkynurenine
- Kynurenine
- Anthranilic acid
- 3-Hydroxykynurenine
- 3-Hydroxyanthranilic acid
- 2-Amino-3-carboxymuconic semialdehyde
- 2-Aminomuconic semialdehyde
- 2-Aminomuconic acid
- Glutaryl-CoA
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| G |
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G→pyruvate→citrate
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glycine→serine→
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- glycine→creatine: Glycocyamine
- Phosphocreatine
- Creatinine
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G→glutamate→
α-ketoglutarate
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histidine→
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- Urocanic acid
- Imidazol-4-one-5-propionic acid
- Formiminoglutamic acid
- Glutamate-1-semialdehyde
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proline→
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- 1-Pyrroline-5-carboxylic acid
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arginine→
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- Ornithine
- Putrescine
- Agmatine
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other
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- cysteine+glutamate→glutathione: γ-Glutamylcysteine
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G→propionyl-CoA→
succinyl-CoA
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valine→
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- α-Ketoisovaleric acid
- Isobutyryl-CoA
- Methacrylyl-CoA
- 3-Hydroxyisobutyryl-CoA
- 3-Hydroxyisobutyric acid
- 2-Methyl-3-oxopropanoic acid
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isoleucine→
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- 2,3-Dihydroxy-3-methylpentanoic acid
- 2-Methylbutyryl-CoA
- Tiglyl-CoA
- 2-Methylacetoacetyl-CoA
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methionine→
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- generation of homocysteine: S-Adenosyl methionine
- S-Adenosyl-L-homocysteine
- Homocysteine
- conversion to cysteine: Cystathionine
- alpha-Ketobutyric acid+Cysteine
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threonine→
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propionyl-CoA→
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G→fumarate
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phenylalanine→tyrosine→
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- 4-Hydroxyphenylpyruvic acid
- Homogentisic acid
- 4-Maleylacetoacetate
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G→oxaloacetate
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| Other |
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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- Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- Amino acids / intermediates
- tetrapyrroles / intermediates
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UpToDate Contents
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English Journal
- Determination of biogenic amines in beer and wine by capillary electrophoresis-tandem mass spectrometry.
- Daniel D1, Dos Santos VB2, Vidal DT3, do Lago CL4.
- Journal of chromatography. A.J Chromatogr A.2015 Oct 16;1416:121-8. doi: 10.1016/j.chroma.2015.08.065. Epub 2015 Sep 3.
- A capillary electrophoresis-tandem mass spectrometry (CE-MS/MS) method for the simultaneous assessment of nine biogenic amines (spermine, spermidine, putrescine, cadaverine, histamine, phenylethylamine, tryptamine, tyramine, and urocanic acid) in commercial samples of beer and wine is introduced. Th
- PMID 26362807
- Confocal Raman spectroscopy: In vivo biochemical changes in the human skin by topical formulations under UV radiation.
- Tosato MG1, Orallo DE2, Ali SM3, Churio MS2, Martin AA3, Dicelio L1.
- Journal of photochemistry and photobiology. B, Biology.J Photochem Photobiol B.2015 Sep 1;153:51-58. doi: 10.1016/j.jphotobiol.2015.08.030. [Epub ahead of print]
- A new approach to the study of the effects on human skin of mycosporine-like amino acids (MAAs) and gadusol (Gad) incorporated in polymer gel is proposed in this work. The depth profile and photoprotector effects of Pluronic F127® gels containing each of the natural actives were evaluated by in viv
- PMID 26398811
- Investigation of a Degradant in a Biologics Formulation Buffer Containing L-Histidine.
- Wang C1, Yamniuk A, Dai J, Chen S, Stetsko P, Ditto N, Zhang Y.
- Pharmaceutical research.Pharm Res.2015 Aug;32(8):2625-35. doi: 10.1007/s11095-015-1648-8. Epub 2015 Feb 12.
- PURPOSE: An unknown UV 280 nm absorbing peak was observed by SEC for protein stability samples formulated in L-histidine during a stress stability study. Understanding the source would enhance the confidence in the SEC results. We identified the unknown peak, studied the cause, and evaluated ways t
- PMID 25670525
Japanese Journal
- Efficient preparation of urocanic acid derivatives from histidine
- Lovely Carl J.,Sivappa Rasapalli,Mukherjee Sabuj [他]
- Heterocycles 80(2), 1353-1358, 2010-03-01
- NAID 40016991498
- Histidase expression in human epidermal keratinocytes : Regulation by differentiation status and all-trans retinoic acid
- ECKHART Leopold,SCHMIDT Martina,MILDNER Michael,MLITZ Veronika,ABTIN Arby,BALLAUN Claudia,FISCHER Heinz,MRASS Paul,TSCHACHLER Erwin
- Journal of dermatological science 50(3), 209-215, 2008-06-01
- NAID 10024119134
Related Links
- 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 ...
★リンクテーブル★
[★]
- 英
- urocanic acid, urocanate
- 同
- 4-イミダゾールアクリル酸 4-imidazoleacrylic acid
- 関
- ヒスチジン