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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:
451-13-8
Molecular Weight:
168.15
Beilstein:
2692860
EC Number:
207-192-7
MDL number:
MFCD00004324
UNSPSC Code:
12352100
PubChem Substance ID:
57654223
NACRES:
NA.22

form

crystalline

Quality Level

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

H0751-5G:
H0751-1G:
H0751-100MG:
H0751-VAR:
H0751-500MG:
H0751-BULK:
H0751-10MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7570
BCCL0048
BCCJ6366
BCCG5987
BCCC3256

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Sigma-Aldrich

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Sigma-Aldrich

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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)
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
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
Laura Tinti et al.
Rheumatology (Oxford, England), 50(2), 271-277 (2010-10-19)
Alkaptonuria (AKU) is a genetic disorder caused by lack of the enzyme responsible for breaking down homogentisic acid (HGA), an intermediate in tyrosine metabolism. HGA is deposited as a polymer, termed ochronotic pigment, in collagenous tissues. Pigmentation is progressive over
Huaixin Zheng et al.
Infection and immunity, 81(11), 4182-4191 (2013-08-28)
Iron acquisition is critical to the growth and virulence of Legionella pneumophila. Previously, we found that L. pneumophila uses both a ferrisiderophore pathway and ferrous iron transport to obtain iron. We now report that two molecules secreted by L. pneumophila
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