Homogentisic acid: Difference between revisions

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+{{Use dmy dates|date=August 2021}}
 {{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
 | 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 = IGMNYECMUMZDDF-UHFFFAOYSA-N
+| CASNo_Ref = {{cascite|correct|??}}
 | 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
-|  DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank = DB08327
 | ChEBI_Ref = {{ebicite|correct|EBI}}
 | ChEBI = 44747
 | 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
+|Section3={{Chembox Hazards
-|  MainHazards=
+| MainHazards=
-|  FlashPt=
+| FlashPt=
+| AutoignitionPt =
-|  Autoignition=
   }}
 }}
-'''Homogentisic acid''' (2,5-dihydroxyphenylacetic acid) is a [[phenolic acid]] found in ''[[Arbutus unedo]]'' (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 ''[[Xanthomonas campestris pv. phaseoli]]''<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 ''[[Yarrowia lipolytica]]''<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 [[phenolic acid]] usually found in ''[[Arbutus unedo]]'' (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 [[Xanthomonas campestris pv. phaseoli|''Xanthomonas campestris'' pv. ''phaseoli'']]<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 ''[[Yarrowia lipolytica]]''<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 [[dimer (chemistry)|dimerised]] to form [[hipposudoric acid]], one of the main constituents of the 'blood sweat' of [[hippopotamus]]es.
 It is less commonly known as '''melanic acid''', the name chosen by [[William Prout]].
 ==Human pathology==
-Accumulation of excess homogentisic acid is a result of the failure of the enzyme [[homogentisic acid 1,2-dioxygenase]] (typically due to a mutation) and is associated with [[alkaptonuria]].<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 [[homogentisic acid 1,2-dioxygenase]] (typically due to a mutation) in the degradative pathway of [[tyrosine]], consequently associated with [[alkaptonuria]].<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==
-It is an intermediate in the metabolism of aromatic amino acids such as [[phenylalanine]] and [[tyrosine]].
+It is an [[Metabolic intermediate|intermediate]] in the [[catabolism]] of aromatic amino acids such as [[phenylalanine]] and [[tyrosine]].
+[[4-Hydroxyphenylpyruvate]] (produced by [[transamination]] of tyrosine) is acted upon by the enzyme [[4-hydroxyphenylpyruvate dioxygenase]] 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 [[homogentisate 1,2-dioxygenase]] further degrades homogentisic acid to yield [[4-maleylacetoacetic acid]].<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==
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 {{Phenolic acid}}
-{{Use dmy dates|date=March 2011}}
 {{DEFAULTSORT:Homogentisic Acid}}
 [[Category:Hydroquinones]]
-[[Category:Carboxylic acids]]
+[[Category:Acetic acids]]
+[[Category:Hydroxy acids]]
+[[Category:Phenylethanoids]]
-[[de:Homogentisinsäure]]
-[[es:Ácido homogentísico]]
-[[fr:Acide homogentisique]]
-[[ja:ホモゲンチジン酸]]
-[[pl:Kwas homogentyzynowy]]
-[[pt:Ácido homogentísico]]