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Key Documents

H0751

Sigma-Aldrich

Homogentisic acid

crystalline

Synonym(s):

2,5-Dihydroxyphenylacetic acid

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About This Item

Linear Formula:
(HO)2C6H3CH2CO2H
CAS Number:
Molecular Weight:
168.15
Beilstein:
2692860
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

form

crystalline

Quality Level

color

off-white to tan

mp

150-152 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)Cc1cc(O)ccc1O

InChI

1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

InChI key

IGMNYECMUMZDDF-UHFFFAOYSA-N

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General description

Homogentisic acid (HGA) is an intermediate formed during the catabolism of phenylalanine and tyrosine. Alkaptonuria, a metabolic disorder, is characterized by high levels of HGA in serum and urine due to the deficiency of the enzyme homogentisic acid oxidase, which is involved in the degradation of HGA.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Z L Hegedus et al.
Archives internationales de physiologie, de biochimie et de biophysique, 102(3), 175-181 (1994-05-01)
Homogentisic acid (HGA) spontaneously starts to undergo oxidation and polymerization soon after the beginning of incubation in human blood or plasma at 37 degrees C, and forms plasma soluble melanins (PSM). Haemolysis accompanies this process in blood. The addition of
Homogentisic acid autoxidation and oxygen radical generation: implications for the etiology of alkaptonuric arthritis.
Martin Jr, et al.
Free Radical Biology & Medicine, 3(4), 241-250 (1987)
V S Venkataseshan et al.
Modern pathology : an official journal of the United States and Canadian Academy of Pathology, Inc, 5(4), 464-471 (1992-07-01)
In alkaptonuric ochronosis, the absence of homogentisic acid oxidase results in the accumulation of homogentisic acid in the body. Associated renal failure is rare and usually occurs in the later stages of the disease. We report a 19-yr-old girl who
Yaping Wang et al.
BMC microbiology, 17(1), 122-122 (2017-05-27)
Combining experimental and computational screening methods has been of keen interest in drug discovery. In the present study, we developed an efficient screening method that has been used to screen 2100 small-molecule compounds for alanine racemase Alr-2 inhibitors. We identified
A M Taylor et al.
Arthritis and rheumatism, 63(12), 3887-3896 (2011-12-01)
Alkaptonuria is a genetic disorder of tyrosine metabolism, resulting in elevated circulating concentrations of homogentisic acid. Homogentisic acid is deposited as a polymer, termed ochronotic pigment, in collagenous tissues, especially cartilages of weight-bearing joints, leading to a severe osteoarthropathy. We

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