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Revision as of 12:08, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Ch← Previous edit Latest revision as of 23:43, 5 August 2024 edit undoحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits removed Category:Acetic acids; added Category:Phenylacetic acids using HotCat 
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⚫ {{Use dmy dates|date=August 2021}}
{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 443858586 | verifiedrevid = 443859706
|ImageFile=Homogentisic acid.svg | ImageFile=Homogentisic acid.svg
⚫ |IUPACName=(2,5-Dihydroxyphenyl)acetic acid
| ImageFile1 = Homogentisic Acid 3D balls.png
⚫ |OtherNames=Melanic acid
⚫ | PIN=(2,5-Dihydroxyphenyl)acetic acid
⚫ |Section1= {{Chembox Identifiers
⚫ | OtherNames=Melanic acid
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
⚫ |Section1={{Chembox Identifiers
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00544 | 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) | InChI = 1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IGMNYECMUMZDDF-UHFFFAOYSA-N | StdInChIKey = IGMNYECMUMZDDF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=451-13-8 | CASNo=451-13-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=780
| UNII = NP8UE6VF08
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | PubChem=780
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 759 | ChemSpiderID = 759
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08327 | DrugBank = DB08327
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 44747 | ChEBI = 44747
| SMILES = O=C(O)Cc1cc(O)ccc1O | SMILES = O=C(O)Cc1cc(O)ccc1O
| MeSHName=Homogentisic+acid | MeSHName=Homogentisic+acid
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=8|H=8|O=4 | C=8 | H=8 | O=4
| Appearance= | Appearance=
| Density= | Density=
| MeltingPtCL=150 | MeltingPtC=150 to 152
| BoilingPt=
| MeltingPtCH=152
| BoilingPt= | Solubility=
⚫ }}
| Solubility=
⚫ |Section3={{Chembox Hazards
⚫ }}
⚫ | MainHazards=
⚫ |Section3= {{Chembox Hazards
⚫ | FlashPt=
⚫ | MainHazards=
| AutoignitionPt =
⚫ | FlashPt=
⚫ }}
| Autoignition=
⚫ }}
}} }}


'''Homogentisic acid''' (2,5-dihydroxyphenylacetic acid) is a ] found in '']'' (strawberry-tree) honey.<ref>{{cite journal | title = Homogentisic Acid: A Phenolic Acid as a Marker of Strawberry-Tree (Arbutus unedo) Honey | author = Paolo Cabras, Alberto Angioni, Carlo Tuberoso, Ignazio Floris, Fabiano Reniero, Claude Guillou and Stefano Ghelli | journal = J. Agric. Food Chem. | year = 1999 | volume = 47 | issue = 10 | pages = 4064–4067 | doi = 10.1021/jf990141o}}</ref> It is also present in the bacterial plant pathogen '']''<ref>{{cite journal | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=3978055 | title = Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid | author = Goodwin PH and Sopher CR | journal = Canadian Journal of Microbiology | volume = 40 | issue = 1 | pages = 28-34 | year = 1994}}</ref> as well as in the yeast '']''<ref>{{cite journal | title = Brown Pigments Produced by Yarrowia lipolytica Result from Extracellular Accumulation of Homogentisic Acid | author = Alexandra Carreira, Luísa M. Ferreira and Virgílio Loureiro | journal = Appl Environ Microbiol | year = 2001 | volume = 67 | issue = 8 | pages = 3463–3468 | doi = 10.1128/AEM.67.8.3463-3468.2001}}</ref> where it is associated with the production of brown pigments. '''Homogentisic acid''' (2,5-dihydroxyphenylacetic acid) is a ] usually found in '']'' (strawberry-tree) honey.<ref>{{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|pmid=10552766 }}</ref> It is also present in the bacterial plant pathogen ]<ref>{{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 | access-date = 25 February 2011 | archive-date = 21 July 2011 | archive-url = https://web.archive.org/web/20110721001238/http://cat.inist.fr/?aModele=afficheN&cpsidt=3978055 | url-status = dead}}</ref> as well as in the yeast '']''<ref>{{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|pmid=11472920 |pmc=93044 |citeseerx=10.1.1.319.523 }}</ref> where it is associated with the production of brown pigments. It is oxidatively ] to form ], one of the main constituents of the 'blood sweat' of ]es.


It is less commonly known as '''melanic acid''', the name chosen by ]. It is less commonly known as '''melanic acid''', the name chosen by ].


==Human pathology== ==Human pathology==
Accumulation of excess homogentisic acid is a result of the failure of the enzyme ] (typically due to a mutation) and is associated with ].<ref name=Phornphutkul>{{cite journal |author=Phornphutkul C, Introne WJ, Perry MB, ''et al.'' |title=Natural history of alkaptonuria |journal=New England Journal 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}}</ref> Accumulation of excess homogentisic acid and its oxide, named '''alkapton''', is a result of the failure of the enzyme ] (typically due to a mutation) in the degradative pathway of ], consequently associated with ].<ref name=Phornphutkul>{{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|doi-access=free }}</ref>


==Intermediate== ==Intermediate==
It is an intermediate in the metabolism of aromatic amino acids such as ] and ]. It is an ] in the ] of aromatic amino acids such as ] and ].

] (produced by ] of tyrosine) is acted upon by the enzyme ] to yield homogentisate.<ref>{{cite journal |last1=Lindstedt |first1=Sven |last2=Odelhog |first2=Birgit |last3=Rundgren |first3=Marianne |title=Purification and Some Properties of 4-Hydroxyphenylpyruvate Dioxygenase from Pseudomonas sp. P.J. 814 |journal=Biochemistry |date=1977 |volume=16 |issue=15 |pages=3369–3377 |doi=10.1021/bi00634a013}}</ref> If active and present, the enzyme ] further degrades homogentisic acid to yield ].<ref>{{cite journal | vauthors = Knox WE, LeMay-Knox M | title = The oxidation in liver of l-tyrosine to acetoacetate through p-hydroxyphenylpyruvate and homogentisic acid | journal = The Biochemical Journal | volume = 49 | issue = 5 | pages = 686–93 | date = October 1951 | pmid = 14886367 | pmc = 1197578 | doi = 10.1042/bj0490686 }}</ref>


==References== ==References==
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{{Phenolic acid}} {{Phenolic acid}}


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