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Homogentisic acid

February 12, 2024

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.

Homogentisic acid
Names
Preferred IUPAC name
(2,5-Dihydroxyphenyl)acetic acid
Other names
Melanic acid
Identifiers
  • 451-13-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:44747 Y
ChemSpider
  • 759 Y
DrugBank
  • DB08327 Y
ECHA InfoCard 100.006.540
KEGG
  • C00544 Y
MeSH Homogentisic+acid
  • 780
UNII
  • NP8UE6VF08 Y
  • DTXSID1060005
  • 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
  • O=C(O)Cc1cc(O)ccc1O
Properties
C8H8O4
Molar mass 168.148 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).
Y verify (what is YN ?)

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.

4-Hydroxyphenylpyruvate (produced by transamination of tyrosine) is acted upon by the enzyme 4-hydroxyphenylpyruvate dioxygenase to yield homogentisate.[5] If active and present, the enzyme homogentisate 1,2-dioxygenase further degrades homogentisic acid to yield 4-maleylacetoacetic acid.[6]

References edit

  1. ^ 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. PMID 10552766.
  2. ^ Goodwin PH, Sopher CR (1994). . Canadian Journal of Microbiology. 40 (1): 28–34. doi:10.1139/m94-005. Archived from the original on 21 July 2011. Retrieved 25 February 2011.
  3. ^ 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. CiteSeerX 10.1.1.319.523. doi:10.1128/AEM.67.8.3463-3468.2001. PMC 93044. PMID 11472920.
  4. ^ 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.
  5. ^ Lindstedt, Sven; Odelhog, Birgit; Rundgren, Marianne (1977). "Purification and Some Properties of 4-Hydroxyphenylpyruvate Dioxygenase from Pseudomonas sp. P.J. 814". Biochemistry. 16 (15): 3369–3377. doi:10.1021/bi00634a013.
  6. ^ Knox WE, LeMay-Knox M (October 1951). "The oxidation in liver of l-tyrosine to acetoacetate through p-hydroxyphenylpyruvate and homogentisic acid". The Biochemical Journal. 49 (5): 686–93. doi:10.1042/bj0490686. PMC 1197578. PMID 14886367.

February 12, 2024
homogentisic, acid, dihydroxyphenylacetic, acid, phenolic, acid, usually, found, arbutus, unedo, strawberry, tree, honey, also, present, bacterial, plant, pathogen, xanthomonas, campestris, phaseoli, well, yeast, yarrowia, lipolytica, where, associated, with, . 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 Homogentisic acid NamesPreferred IUPAC name 2 5 Dihydroxyphenyl acetic acidOther names Melanic acidIdentifiersCAS Number 451 13 8 Y3D model JSmol Interactive imageChEBI CHEBI 44747 YChemSpider 759 YDrugBank DB08327 YECHA InfoCard 100 006 540KEGG C00544 YMeSH Homogentisic acidPubChem CID 780UNII NP8UE6VF08 YCompTox Dashboard EPA DTXSID1060005InChI InChI 1S C8H8O4 c9 6 1 2 7 10 5 3 6 4 8 11 12 h1 3 9 10H 4H2 H 11 12 YKey IGMNYECMUMZDDF UHFFFAOYSA N YInChI 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 UHFFFAOYAKSMILES O C O Cc1cc O ccc1OPropertiesChemical formula C 8H 8O 4Molar mass 168 148 g mol 1Melting 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 Y verify what is Y N Infobox references It is less commonly known as melanic acid the name chosen by William Prout Human pathology editAccumulation 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 editIt is an 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 5 If active and present the enzyme homogentisate 1 2 dioxygenase further degrades homogentisic acid to yield 4 maleylacetoacetic acid 6 References edit 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 PMID 10552766 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 Archived from the original on 21 July 2011 Retrieved 25 February 2011 Alexandra Carreira Luisa M Ferreira Virgilio Loureiro 2001 Brown Pigments Produced by Yarrowia lipolytica Result from Extracellular Accumulation of Homogentisic Acid Appl Environ Microbiol 67 8 3463 3468 CiteSeerX 10 1 1 319 523 doi 10 1128 AEM 67 8 3463 3468 2001 PMC 93044 PMID 11472920 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 Lindstedt Sven Odelhog Birgit Rundgren Marianne 1977 Purification and Some Properties of 4 Hydroxyphenylpyruvate Dioxygenase from Pseudomonas sp P J 814 Biochemistry 16 15 3369 3377 doi 10 1021 bi00634a013 Knox WE LeMay Knox M October 1951 The oxidation in liver of l tyrosine to acetoacetate through p hydroxyphenylpyruvate and homogentisic acid The Biochemical Journal 49 5 686 93 doi 10 1042 bj0490686 PMC 1197578 PMID 14886367 Retrieved from https en wikipedia org w index php title Homogentisic acid amp oldid 1171334074, wikipedia, wiki, book, books, library,

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