- 関
- homogentisic acid
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/02/25 17:12:22」(JST)
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Homogentisic acid
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| Names |
| IUPAC name
(2,5-Dihydroxyphenyl)acetic acid
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| Other names
Melanic acid
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| Identifiers |
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CAS Number
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451-13-8 Y |
| 3D model (Jmol) |
Interactive image |
| ChEBI |
CHEBI:44747 Y |
| ChemSpider |
759 Y |
| DrugBank |
DB08327 Y |
| ECHA InfoCard |
100.006.540 |
| KEGG |
C00544 Y |
| MeSH |
Homogentisic+acid |
| PubChem |
780 |
InChI
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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
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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 |
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Chemical formula
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C8H8O4 |
| Molar mass |
168.15 g·mol−1 |
| Melting point |
150 to 152 °C (302 to 306 °F; 423 to 425 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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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
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
It is an intermediate in the catabolism of aromatic amino acids such as phenylalanine and tyrosine.
References
- ^ Paolo Cabras; Alberto Angioni; Carlo Tuberoso; Ignazio Floris; Fabiano Reniero; Claude Guillou; 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, Sopher CR (1994). "Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid". Canadian Journal of Microbiology. 40 (1): 28–34. doi:10.1139/m94-005.
- ^ Alexandra Carreira; Luísa M. Ferreira; 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 of 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-Ketoadipate
- Glutaryl-CoA
- Glutaconyl-CoA
- Crotonyl-CoA
- β-Hydroxybutyryl-CoA
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leucine→
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- α-Ketoisocaproic acid
- β-hydroxy β-methylbutyric acid
- β-hydroxy β-methylbutyryl-CoA
- 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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- Agmatine
- Ornithine
- Citrulline
- Cadaverine
- Putrescine
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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-Maleylacetoacetic acid
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G→oxaloacetate
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| Other |
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Phenolic acids (C6-C1) and their glycosides
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| Monohydroxybenzoic acids |
- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid (2-Hydroxybenzoic acid)
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Glycosides
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- p-Hydroxybenzoic acid glucoside
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Acetylated
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- Methylparaben (Methyl p-hydroxybenzoic acid)
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| Dihydroxybenzoic acids |
- 2,3-Dihydroxybenzoic acid (Hypogallic acid)
- 2,4-Dihydroxybenzoic acid
- 2,5-Dihydroxybenzoic acid (Gentisic acid)
- 2,6-Dihydroxybenzoic acid
- 3,4-Dihydroxybenzoic acid (Protocatechuic acid)
- 3,5-Dihydroxybenzoic acid
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Acetylated
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- Ethyl protocatechuate
- Orsellinic acid
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| Trihydroxybenzoic acids |
- Gallic acid
- Phloroglucinol carboxylic acid
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Glycosides
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- Bergenin
- Norbergenin
- Theogallin
- Chebulic acid
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Acetylated
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- Ethyl gallate
- Eudesmic acid
- Methyl gallate
- Syringic acid
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English Journal
- Oxidative stress and mechanisms of ochronosis in alkaptonuria.
- Braconi D1, Millucci L1, Bernardini G1, Santucci A2.
- Free radical biology & medicine.Free Radic Biol Med.2015 Nov;88(Pt A):70-80. doi: 10.1016/j.freeradbiomed.2015.02.021. Epub 2015 Feb 28.
- Alkaptonuria (AKU) is a rare metabolic disease due to a deficient activity of the enzyme homogentisate 1,2-dioxygenase (HGD), involved in Phe and Tyr catabolism. Due to such a deficiency, AKU patients undergo accumulation of the metabolite homogentisic acid (HGA), which is prone to oxidation/polymer
- PMID 25733348
- Homogentisate phytyltransferase from the unicellular green alga Chlamydomonas reinhardtii.
- Gálvez-Valdivieso G1, Cardeñosa R2, Pineda M2, Aguilar M2.
- Journal of plant physiology.J Plant Physiol.2015 Sep 28;188:80-88. doi: 10.1016/j.jplph.2015.09.010. [Epub ahead of print]
- Homogentisate phytyltransferase (HPT) (EC 2.5.1.-) catalyzes the first committed step of tocopherol biosynthesis in all photosynthetic organisms. This paper presents the molecular characterization and expression analysis of HPT1 gene, and a study on the accumulation of tocopherols under different en
- PMID 26454640
- Renal and prostate stones composition in alkaptonuria: a case report.
- Wolff F, Biaou I, Koopmansch C, Vanden Bossche M, Pozdzik A, Roumeguère T, Cotton F.
- Clinical nephrology.Clin Nephrol.2015 Sep 23. [Epub ahead of print]
- Alkaptonuria is a genetic disorder characterized by an accumulation of homogentisic acid due to an enzymatic defect of homogentisate 1,2 dioxygenase. The homogentisic acid is excreted exclusively by both glomerular filtration and tubular secretion leading to the renal parenchyma being exposed to hig
- PMID 26396096
Japanese Journal
- Generation of transgenic tobacco plants with enhanced tocotrienol levels through the ectopic expression of rice homogentisate geranylgeranyl transferase
- Generation of transgenic tobacco plants with enhanced tocotrienol levels through the ectopic expression of rice homogentisate geranylgeranyl transferase
- NMR-based metabolomics of urine in a mouse model of Alzheimer's disease: identification of oxidative stress biomarkers
- Journal of Clinical Biochemistry and Nutrition 52(2), 133-138, 2013
- NAID 130004466706
Related Links
- Homogentisate 1,2-dioxygenase (homogentisic acid oxidase, homogentisicase) is an enzyme, which catalyzes the conversion of homogentisate to 4- maleylacetoacetate. Homogentisate 1,2-dioxygenase or HGD is involved in the catabolism of ...
- InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) Yes Y Key: IGMNYECMUMZDDF-UHFFFAOYSA-N Yes 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- ...
★リンクテーブル★
[★]
- 英
- homogentisic acid, homogentisate
- 関
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臨床関連
[★]
ホモゲンチジン酸
- 関
- homogentisate
[★]
ホモゲンチジン酸-1
- 関
- homogentisic acid oxidase