ホモゲンチジン酸
- 関
- homogentisate
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）』「2013/12/31 22:33:51」(JST)
[Wiki en表示]
| Homogentisic acid |
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IUPAC name
(2,5-Dihydroxyphenyl)acetic acid
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| Identifiers |
| CAS number |
451-13-8 Y |
| PubChem |
780 |
| ChemSpider |
759 Y |
| DrugBank |
DB08327 |
| KEGG |
C00544 Y |
| MeSH |
Homogentisic+acid |
| ChEBI |
CHEBI:44747 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) Y
Key: IGMNYECMUMZDDF-UHFFFAOYSA-N Y
InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
Key: IGMNYECMUMZDDF-UHFFFAOYAK
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| Properties |
| Molecular formula |
C8H8O4 |
| Molar mass |
168.15 g mol−1 |
| Melting point |
150 to 152 °C; 302 to 306 °F; 423 to 425 K |
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 |
Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid found in Arbutus unedo (strawberry-tree) honey.[1] It is also present in the bacterial plant pathogen Xanthomonas campestris pv. phaseoli[2] as well as in the yeast Yarrowia lipolytica[3] where it is associated with the production of brown pigments.
It is less commonly known as melanic acid, the name chosen by William Prout.
Human pathology[edit]
Accumulation of excess homogentisic acid and its oxide, named alkapton, is a result of the failure of the enzyme homogentisic acid 1,2-dioxygenase (typically due to a mutation) in the degradative pathway of tyrosine, consequently associated with alkaptonuria.[4]
Intermediate[edit]
It is an intermediate in the catabolism of aromatic amino acids such as phenylalanine and tyrosine.
References[edit]
- ^ Paolo Cabras, Alberto Angioni, Carlo Tuberoso, Ignazio Floris, Fabiano Reniero, Claude Guillou and Stefano Ghelli (1999). "Homogentisic Acid: A Phenolic Acid as a Marker of Strawberry-Tree (Arbutus unedo) Honey". J. Agric. Food Chem. 47 (10): 4064–4067. doi:10.1021/jf990141o.
- ^ Goodwin PH and Sopher CR (1994). "Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid". Canadian Journal of Microbiology 40 (1): 28–34.
- ^ Alexandra Carreira, Luísa M. Ferreira and Virgílio Loureiro (2001). "Brown Pigments Produced by Yarrowia lipolytica Result from Extracellular Accumulation of Homogentisic Acid". Appl Environ Microbiol 67 (8): 3463–3468. doi:10.1128/AEM.67.8.3463-3468.2001.
- ^ Phornphutkul C, Introne WJ, Perry MB, et al. (2002). "Natural history of alkaptonuria". New England Journal Medicine 347 (26): 2111–21. doi:10.1056/NEJMoa021736. PMID 12501223.
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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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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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Phenolic acids and their glycosides
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| Monohydroxybenzoic acids |
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Aglycones
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- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid
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Glycosides
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- p-Hydroxybenzoic acid glucoside
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| Dihydroxybenzoic acids |
- 2,3-Dihydroxybenzoic acid (Hypogallic acid)
- 2,4-Dihydroxybenzoic acid
- 2,6-Dihydroxybenzoic acid
- 3,5-Dihydroxybenzoic acid
- Ethyl protocatechuate
- Gentisic acid
- Homogentisic acid
- Orsellinic acid
- Protocatechuic acid
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| Trihydroxybenzoic acids |
- Bergenin
- Chebulic acid
- Ethyl gallate
- Eudesmic acid
- Gallic acid
- Norbergenin
- Phloroglucinol carboxylic acid
- Syringic acid
- Theogallin
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UpToDate Contents
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English Journal
- Alkaptonuria - Case report.
- Craide FH1, Fonseca JS2, Mariano PC1, Fernandez NM3, Castro CG1, Mene Yde S1.
- Anais brasileiros de dermatologia.An Bras Dermatol.2014 Sep;89(5):799-801.
- Alkaptonuria, also called endogenous ochronosis, is a rare metabolic autosomal recessive disorder. It occurs by complete inhibition of homogentisic acid oxidase enzyme having its deposition in various tissues. Male patient, 52 years old, sought medical help complaining about progressive appearance o
- PMID 25184921
- Two novel mutations in the homogentisate-1,2-dioxygenase gene identified in Chinese Han Child with Alkaptonuria.
- Li H, Zhang K, Xu Q, Ma L, Lv X, Sun R.
- Journal of pediatric endocrinology & metabolism : JPEM.J Pediatr Endocrinol Metab.2014 Aug 12. pii: /j/jpem.ahead-of-print/jpem-2014-0122/jpem-2014-0122.xml. doi: 10.1515/jpem-2014-0122. [Epub ahead of print]
- Abstract Alkaptonuria (AKU) is an autosomal recessive disorder of tyrosine metabolism, which is caused by a defect in the enzyme homogentisate 1,2-dioxygenase (HGD) with subsequent accumulation of homogentisic acid. Presently, more than 100 HGD mutations have been identified as the cause of the inbo
- PMID 25153563
- Urine homogentisic acid and tyrosine: simultaneous analysis by liquid chromatography tandem mass spectrometry.
- Hughes AT1, Milan AM2, Christensen P3, Ross G3, Davison AS4, Gallagher JA5, Dutton JJ4, Ranganath LR1.
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2014 Jul 15;963:106-12. doi: 10.1016/j.jchromb.2014.06.002. Epub 2014 Jun 7.
- Alkaptonuria (AKU) is a rare debilitating autosomal recessive disorder of tyrosine metabolism. Deficiency of homogentisate 1,2-dioxygenase results in increased homogentisic acid (HGA) which although excreted in gram quantities in the urine, is deposited as an ochronotic pigment in connective tissues
- PMID 24952314
Japanese Journal
- A Rare Case of Acquired Methemoglobinemia Associated with Alkaptonuria
- , , , , , , , ,
- Internal Medicine 53(16), 1797-1800, 2014
- … Alkaptonuria is a congenital error of metabolism caused by the deficiency of homogentisic acid oxidase, which subsequently results in the accumulation of homogentisic acid (HGA) in body tissues. …
- NAID 130004678402
- 近藤 超子,大塚 和孝,森田 馨,井手 迪
- 整形外科と災害外科 62(4), 697-702, 2013-09-25
- 比較的まれな疾患であるアルカプトン尿性関節症を経験したので報告する．52歳男性．以前より両側膝関節症あり．近医にて治療受けていたが，症状増悪にて当院受診．健側アキレス腱断裂手術時にアキレス腱の色素沈着を指摘されている．既往に腎結石あり．関節穿刺にて右膝より約30ml程度の排液をみとめ，関節液内に黒褐色針状浮遊物多数散見された．関節液外観に感染所見はなく，病理組織検査では，浮遊物は色素沈着した変性軟 …
- NAID 10031200317
- 1P-118 放線菌による芳香族化合物ホモゲンチジン酸の生産(一般講演(発酵生理学,発酵工学),第65回日本生物工学会大会)
Related Links
- homogentisic acid ho·mo·gen·tis·ic acid (hō'mō-jěn-tĭz'ĭk) n. An intermediate of the metabolic breakdown of tyrosine and phenylalanine; it occurs in the urine in cases of alkaptonuria. Also called alkapton.
- homogentisic acid [ho″mo-jen-tis´ik] 2,5-dihydroxyphenyl acetic acid, an intermediate product in the metabolism of tyrosine and phenylalanine, excreted in the urine in the inborn error of metabolism known as phenylketonuria. ho·mo ...
Related Pictures
★リンクテーブル★
[★]
- 英
- homogentisic acid, homogentisate
- 関
- [[]]
臨床関連
[★]
- 関
- homogentisic acid
[★]
ホモゲンチジン酸酸化酵素