Homogentisic acid
Organic compound involved in the metabolism of amino acids
| |
| IUPAC Name: | {{{IUPACName}}} |
| Other Names: | |
| Identifiers | |
| CAS Number | |
| PubChem | |
| ChemSpider | |
| SMILES | |
| InChI | |
| InChIKey | |
| StdInChI | |
| StdInChIKey | |
| Properties | |
| Chemical formula | CHNO |
| Appearance | |
| Density | |
| Melting Point | |
| Boiling Point | |
| Solubility | |
| Hazards | |
| Main Hazards | |
| Flash Point | |
| Autoignition Temperature | |
Homogentisic acid is an organic compound that plays a crucial role in the metabolism of the amino acids tyrosine and phenylalanine. It is a key intermediate in the catabolic pathway of these amino acids.
Biochemistry[edit | edit source]
Homogentisic acid is formed during the breakdown of tyrosine and phenylalanine through the action of the enzyme homogentisate 1,2-dioxygenase. This enzyme catalyzes the conversion of homogentisic acid to maleylacetoacetic acid, which is further processed in the metabolic pathway.
Medical significance[edit | edit source]
The accumulation of homogentisic acid in the body is associated with a rare genetic disorder known as alkaptonuria. This condition is caused by a deficiency in the enzyme homogentisate 1,2-dioxygenase, leading to the buildup of homogentisic acid in tissues and its excretion in urine. Over time, this can result in ochronosis, a condition characterized by the darkening of connective tissues, and can lead to arthritis and other complications.
Chemical properties[edit | edit source]
Homogentisic acid is a dihydroxyphenylacetic acid with the chemical formula C_8H_8O_4. It is a crystalline solid that is soluble in water. The compound has two hydroxyl groups attached to a benzene ring, which makes it a dihydroxy derivative of phenylacetic acid.
Related compounds[edit | edit source]
Homogentisic acid is structurally related to other phenolic acids, such as gallic acid and protocatechuic acid. It is also related to phenylacetic acid and its derivatives.
See also[edit | edit source]
References[edit | edit source]
.svg){kind=small} | This biochemistry article is a stub. You can help WikiMD by expanding it. |
Search WikiMD
Ad.Tired of being Overweight? Try W8MD's physician weight loss program.
Semaglutide (Ozempic / Wegovy and Tirzepatide (Mounjaro / Zepbound) available.
Advertise on WikiMD
|
WikiMD's Wellness Encyclopedia |
| Let Food Be Thy Medicine Medicine Thy Food - Hippocrates |
Translate this page: - East Asian
中文,
日本,
한국어,
South Asian
हिन्दी,
தமிழ்,
తెలుగు,
Urdu,
ಕನ್ನಡ,
Southeast Asian
Indonesian,
Vietnamese,
Thai,
မြန်မာဘာသာ,
বাংলা
European
español,
Deutsch,
français,
Greek,
português do Brasil,
polski,
română,
русский,
Nederlands,
norsk,
svenska,
suomi,
Italian
Middle Eastern & African
عربى,
Turkish,
Persian,
Hebrew,
Afrikaans,
isiZulu,
Kiswahili,
Other
Bulgarian,
Hungarian,
Czech,
Swedish,
മലയാളം,
मराठी,
ਪੰਜਾਬੀ,
ગુજરાતી,
Portuguese,
Ukrainian
Medical Disclaimer: WikiMD is not a substitute for professional medical advice. The information on WikiMD is provided as an information resource only, may be incorrect, outdated or misleading, and is not to be used or relied on for any diagnostic or treatment purposes. Please consult your health care provider before making any healthcare decisions or for guidance about a specific medical condition. WikiMD expressly disclaims responsibility, and shall have no liability, for any damages, loss, injury, or liability whatsoever suffered as a result of your reliance on the information contained in this site. By visiting this site you agree to the foregoing terms and conditions, which may from time to time be changed or supplemented by WikiMD. If you do not agree to the foregoing terms and conditions, you should not enter or use this site. See full disclaimer.
Credits:Most images are courtesy of Wikimedia commons, and templates Wikipedia, licensed under CC BY SA or similar.
Contributors: Prab R. Tumpati, MD
