| 词条 | Homogentisic acid |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443859706 | ImageFile=Homogentisic acid.svg | ImageFile1 = Homogentisic Acid 3D balls.png | IUPACName=(2,5-Dihydroxyphenyl)acetic acid | OtherNames=Melanic acid |Section1={{Chembox Identifiers | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C00544 | InChI = 1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) | InChIKey = IGMNYECMUMZDDF-UHFFFAOYAK | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IGMNYECMUMZDDF-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo=451-13-8 | PubChem=780 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 759 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB08327 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 44747 | SMILES = O=C(O)Cc1cc(O)ccc1O | MeSHName=Homogentisic+acid |Section2={{Chembox Properties | C=8 | H=8 | O=4 | Appearance= | Density= | MeltingPtC=150 to 152 | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} Homogentisic acid (2,5-dihydroxyphenylacetic acid) is a phenolic acid usually 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 oxidatively dimerised to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses. It is less commonly known as melanic acid, the name chosen by William Prout. Human pathologyAccumulation 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] IntermediateIt is an intermediate in the catabolism of aromatic amino acids such as phenylalanine and tyrosine. References1. ^{{cite journal | title = Homogentisic Acid: A Phenolic Acid as a Marker of Strawberry-Tree (Arbutus unedo) Honey |author1=Paolo Cabras |author2=Alberto Angioni |author3=Carlo Tuberoso |author4=Ignazio Floris |author5=Fabiano Reniero |author6=Claude Guillou |author7=Stefano Ghelli | journal = J. Agric. Food Chem. | year = 1999 | volume = 47 | issue = 10 | pages = 4064–4067 | doi = 10.1021/jf990141o}} {{Amino acid metabolism intermediates}}{{Phenolic acid}}{{Use dmy dates|date=March 2011}}{{DEFAULTSORT:Homogentisic Acid}}2. ^{{cite journal | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=3978055 | title = Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid |vauthors=Goodwin PH, Sopher CR| journal = Canadian Journal of Microbiology | volume = 40 | issue = 1 | pages = 28–34 | year = 1994 | doi=10.1139/m94-005}} 3. ^{{cite journal | title = Brown Pigments Produced by Yarrowia lipolytica Result from Extracellular Accumulation of Homogentisic Acid |author1=Alexandra Carreira |author2=Luísa M. Ferreira |author3=Virgílio Loureiro | journal = Appl Environ Microbiol | year = 2001 | volume = 67 | issue = 8 | pages = 3463–3468 | doi = 10.1128/AEM.67.8.3463-3468.2001|citeseerx=10.1.1.319.523 }} 4. ^{{cite journal |vauthors=Phornphutkul C, Introne WJ, Perry MB, etal |title=Natural history of alkaptonuria |journal=New England Journal of Medicine |volume=347 |issue=26 |pages=2111–21 |year=2002 |pmid=12501223 |doi=10.1056/NEJMoa021736| url=http://content.nejm.org/cgi/content/full/347/26/2111}} 3 : Hydroquinones|Acetic acids|Hydroxy acids |
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