Homogentisic acid

Homogentisic acid
Homogentisic acid
Identifiers
CAS number 451-13-8
PubChem 780
ChemSpider 759 YesY
DrugBank DB08327
KEGG C00544 YesY
MeSH Homogentisic+acid
ChEBI CHEBI:44747 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O4
Molar mass 168.15 g mol−1
Melting point

150-152 °C, 423-425 K, 302-306 °F

 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 is a result of the failure of the enzyme homogentisic acid 1,2-dioxygenase (typically due to a mutation) and is associated with alkaptonuria.[4]

Intermediate

It is an intermediate in the metabolism of aromatic amino acids such as phenylalanine and tyrosine.

References

  1. ^ Paolo Cabras, Alberto Angioni, Carlo Tuberoso, Ignazio Floris, Fabiano Reniero, Claude Guillou and 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. 
  2. ^ Goodwin PH and Sopher CR (1994). "Brown pigmentation of Xanthomonas campestris pv. phaseoli associated with homogentisic acid". Canadian Journal of Microbiology 40 (1): 28–34. http://cat.inist.fr/?aModele=afficheN&cpsidt=3978055. 
  3. ^ Alexandra Carreira, Luísa M. Ferreira and 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. 
  4. ^ Phornphutkul C, Introne WJ, Perry MB, et al. (2002). "Natural history of alkaptonuria". New England Journal Medicine 347 (26): 2111–21. doi:10.1056/NEJMoa021736. PMID 12501223. http://content.nejm.org/cgi/content/full/347/26/2111. 

Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать курсовую

Look at other dictionaries:

  • homogentisic acid — homogentisic acid. См. гомогентизиновая кислота. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • homogentisic acid — Glycosuric acid; (2,5 dihydroxyphenyl)acetic acid; an intermediate in l phenylalanine and l tyrosine catabolism; if made alkaline, it oxidizes rapidly in air to a quinone that polymerizes to a melaninlike material; elevated levels are observed in …   Medical dictionary

  • homogentisic acid — a product formed during the metabolism of the amino acids phenylalanine and tyrosine. In normal individuals homogentisic acid is oxidized by the enzyme homogentisic acid oxidase. In rare cases this enzyme is lacking and a condition known as… …   The new mediacal dictionary

  • homogentisic acid — homogentizo rūgštis statusas T sritis chemija formulė (HO)₂C₆H₃CH₂COOH atitikmenys: angl. homogentisic acid rus. гомогентизиновая кислота ryšiai: sinonimas – 2,5 dihidroksifeniletano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • homogentisic acid — acid found in the blood and urine of people suffering from alkaptonuria …   English contemporary dictionary

  • homogentisic acid — noun an acid formed as an intermediate product of the metabolism of tyrosine and phenylalanine • Syn: ↑alkapton, ↑alcapton • Hypernyms: ↑acid * * * pronunc at homo +|jen|tizik noun Etymology …   Useful english dictionary

  • homogentisic acid — noun 2,5 dihydroxyphenylacetic acid. Syn: alcapton, alkapton, melanic acid …   Wiktionary

  • homogentisic acid — /hoh meuh jen tis ik, tiz , hoh / an intermediate compound in the metabolism of tyrosine and of phenylalanine, found in excess in the blood and urine of persons affected with alkaptonuria. Also called alkapton. [1890 95; HOMO + GENTISIC ACID] * * …   Universalium

  • Кислота Гомогентизиновая (Homogentisic Acid) — вещество, образующееся во время метаболизма аминокислот фенилаланина и тирозина. У нормальных, здоровых индивидуумов гомогентизиновая кислота окисляется с помощью фермента оксидазы гомогентизиновой кислоты (homogentisic acid oxidase). В редких… …   Медицинские термины

  • homogentisic acid oxidase — ho·mo·gen·tis·ic ac·id ox·i·dase (ho″mo jen tisґik asґid okґsĭ dās) homogentisate 1,2 dioxygenase …   Medical dictionary

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”