451-13-8
451-13-8
Chemical Structure
Homogentisic acid
- No. CAS: 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].
| Referencia número | Nombre del producto | Pureza | Descripciòn | Pricing | |||||||||||||||||||
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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. | ||||||||||||||||||||
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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. | ||||||||||||||||||||
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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. | ||||||||||||||||||||
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2,4-Dihydroxyphenylacetic acid | 95.44% | 2,4-Dihydroxyphenylacetic acid (compound 3) is a natural product that can be obtained from Nigella damascene L. seeds. | ||||||||||||||||||||
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3-(2,4-Dihydroxyphenyl)propanoic acid (Standard) | ≥98% | 3-(2,4-Dihydroxyphenyl)propanoic acid (Standard) is the analytical standard of 3-(2,4-Dihydroxyphenyl)propanoic acid (HY-N1750). This product is intended for research and analytical applications. 3-(2,4-Dihydroxyphenyl) propanoic acid (DPPacid) is a competitive Tyrosinase inhibitor. It exhibits an IC50 value of 3.02 μM against mushroom tyrosinase with L-tyrosine as the substrate, an IC50 value of 62 μM with DL-DOPA as the substrate, and a Ki value of 11.5 μM. 3-(2,4-Dihydroxyphenyl) propanoic acid shows no DPPH radical scavenging activity. It can be used in studies related to ultraviolet B (UVB)-induced hyperpigmentation. | ||||||||||||||||||||
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Dihydrocaffeic acid (Standard) | 99.88% | Dihydrocaffeic acid (Standard) (3,4-Dihydroxy-benzenepropanoic acid (Standard)) is the analytical standard of Dihydrocaffeic acid (HY-N2406). This product is intended for research and analytical applications. Dihydrocaffeic acid is a microbial metabolite of flavonoids. Dihydrocaffeic acid scavenges intracellular ROS and increases nitric oxide synthase activity. Dihydrocaffeic acid reduces phosphorylation of MAPK p38 and prevent UVB-induced skin damage. Dihydrocaffeic acid has antioxidant, anti-inflammatory and anti-cartilage degradation activities. | ||||||||||||||||||||
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3,4-Dihydroxybenzeneacetic acid | 99.90% | 3,4-Dihydroxybenzeneacetic acid is the main neuronal metabolite of dopamine. | ||||||||||||||||||||
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3-Hydroxyphenylacetic acid | 99.03% | 3-Hydroxyphenylacetic acid is an orally active flavonoid metabolite produced by intestinal flora, with blood pressure-lowering activity. 3-Hydroxyphenylacetic acid can also inhibit ferroptosis by upregulating the expression of GPX4, thereby improving spermatogenic dysfunction in aged mice. In addition, abnormal levels of 3-Hydroxyphenylacetic acid are closely related to certain diseases, such as autism spectrum disorders. | ||||||||||||||||||||
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3-Chloro-4-hydroxyphenylacetic acid | 3-Chloro-4-hydroxyphenylacetic acid is a fungal metabolite. 3-Chloro-4-hydroxyphenylacetic acid is an active small molecule, that can be used as building block in synthesis of 17β-HSD2 inhibitors. | |||||||||||||||||||||
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2,5-Dihydroxybenzoic acid | 99.92% | 2,5-Dihydroxybenzoic acid is a derivative of benzoic and a powerful inhibitor of fibroblast growth factors. | ||||||||||||||||||||
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2-Hydroxyphenylacetic acid | 98.79% | 2-Hydroxyphenylacetic acid is a metabolite of Phenylalanine and Tyrosine, as well as a product of the biotransformation of Phenylacetonitrile by marine fungi. 2-Hydroxyphenylacetic acid acts as a potential biomarker for food. 2-Hydroxyphenylacetic acid slightly induces the expression of green fluorescent protein. 2-Hydroxyphenylacetic acid is used in the research of phenylketonuria and related hyperphenylalaninemia. | ||||||||||||||||||||
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Methyl 2-(2,4-dihydroxyphenyl)acetate | 98.08% | Methyl 2-(2,4-dihydroxyphenyl)acetate, a phenolic ester, is isolated from Nigella damascena seeds with selective phytotoxic effects. | ||||||||||||||||||||
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References
- [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]
