451-13-8
Chemical Structure
Homogentisic acid
- CAS No.: 451-13-8
- Formula:C8H8O4
- Molecular Weight:168.15
IUPAC Name: 2-(2,5-dihydroxyphenyl)acetic acid
InChIKey: IGMNYECMUMZDDF-UHFFFAOYSA-N
SMILES: O=C(O)CC1=CC(O)=CC=C1O
Biological Activity: Homogentisic acid is an orally active, blood-brain barrier-permeable amyloidogenic compound that functions as both an amyloid component and a pigment precursor. Accumulation of homogentisic acid downregulates tight junction proteins (such as claudin-5, occludin, ZO-1) and impairs blood-brain barrier integrity. Homogentisic acid and its oxidation product benzoquinone acetic acid not only induce the aggregation and fibrosis of multiple proteins (such as Aβ1-42, α-synuclein, SAA, Transthyretin (TTR), atrial natriuretic peptide), but also trigger oxidative stress, damage to the Wnt/β-catenin pathway, and neurotoxicity, leading to ochronosis pigment deposition and synaptic dysfunction. At specific concentrations, homogentisic acid exerts no cytotoxicity or genotoxicity on human peripheral blood lymphocytes, and even counteracts the genotoxicity induced by Irinotecan (HY-16562). Homogentisic acid serves as an important tool molecule for investigating the mechanisms of diseases including ochronosis, secondary amyloidosis, Alzheimer's disease, and colorectal cancer[1][2][3][4][5][6][7][8].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
|
Homogentisic acid | 99.68% | Homogentisic acid is an orally active, blood-brain barrier-permeable amyloidogenic compound that functions as both an amyloid component and a pigment precursor. Accumulation of homogentisic acid downregulates tight junction proteins (such as claudin-5, occludin, ZO-1) and impairs blood-brain barrier integrity. Homogentisic acid and its oxidation product benzoquinone acetic acid not only induce the aggregation and fibrosis of multiple proteins (such as Aβ1-42, α-synuclein, SAA, Transthyretin (TTR), atrial natriuretic peptide), but also trigger oxidative stress, damage to the Wnt/β-catenin pathway, and neurotoxicity, leading to ochronosis pigment deposition and synaptic dysfunction. At specific concentrations, homogentisic acid exerts no cytotoxicity or genotoxicity on human peripheral blood lymphocytes, and even counteracts the genotoxicity induced by Irinotecan (HY-16562). Homogentisic acid serves as an important tool molecule for investigating the mechanisms of diseases including ochronosis, secondary amyloidosis, Alzheimer's disease, and colorectal cancer. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Homogentisic acid (Standard) | 99.48% | Homogentisic acid (Standard) is the analytical standard of Homogentisic acid. This product is intended for research and analytical applications. Homogentisic acid is a specific metabolite that accumulates in the urine and serum. Homogentisic acid can be used for diagnosis of alkaptonuria. Homogentisic acid is a phenolic acid. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
|
|
Homogentisic acid-13C6 | 98.57% | Homogentisic acid-13C6 is the 13C-labeled Homogentisic acid (HY-113283). Homogentisic acid is a specific metabolite that accumulates in the urine and serum. Homogentisic acid can be used for diagnosis of alkaptonuria. Homogentisic acid is a phenolic acid. | ||||||||||||||||||||
|
loading...
/
|
|||||||||||||||||||||||
- [1]. Braconi D, et al. Homogentisic acid induces aggregation and fibrillation of amyloidogenic proteins. Biochim Biophys Acta Gen Subj. 2017;1861(2):135-146. [Content Brief]
- [2]. Liu X, et al. Homogentisic Acid Disrupts the Blood-Brain Barrier and Promotes Aβ Aggregation in Alzheimer's Disease. Curr Med Sci. Published online February 5, 2026. [Content Brief]
- [3]. Zannoni VG, et al. Oxidation of homogentisic acid to ochronotic pigment in connective tissue. Biochim Biophys Acta. 1969 Feb 18;177(1):94-105. [Content Brief]
- [4]. MILCH RA, et al. Atmospheric oxidation of homogentisic acid: spectrophotometric studies. Science. 1957 Aug 2;126(3266):209-10. [Content Brief]
- [5]. Huong DT, et al. Homogentisic acid derivatives from Miliusa balansae. J Nat Prod. 2004;67(3):445-447. [Content Brief]
- [6]. Martin JP Jr, et al. Homogentisic acid autoxidation and oxygen radical generation: implications for the etiology of alkaptonuric arthritis. Free Radic Biol Med. 1987;3(4):241-250. [Content Brief]
- [7]. Bory C, et al. Diagnosis of alcaptonuria: rapid analysis of homogentisic acid by HPLC. Clin Chim Acta. 1990;189(1):7-11. [Content Brief]
- [8]. Schiavone ML, et al. Homogentisic acid affects human osteoblastic functionality by oxidative stress and alteration of the Wnt/β-catenin signaling pathway. J Cell Physiol. 2020;235(10):6808-6816. [Content Brief]