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Homogentisic acid

CAS# 451-13-8

Homogentisic acid

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Homogentisic acid: 5mg Please Inquire In Stock
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Quality Control of Homogentisic acid

Number of papers citing our products

Chemical structure

Homogentisic acid

3D structure

Chemical Properties of Homogentisic acid

Cas No. 451-13-8 SDF Download SDF
PubChem ID 780 Appearance Powder
Formula C8H8O4 M.Wt 168.2
Type of Compound Phenols Storage Desiccate at -20°C
Solubility DMSO : 250 mg/mL (1486.77 mM; Need ultrasonic)
Chemical Name 2-(2,5-dihydroxyphenyl)acetic acid
SMILES C1=CC(=C(C=C1O)CC(=O)O)O
Standard InChIKey IGMNYECMUMZDDF-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Homogentisic acid

The herbs of Arbutus unedo

Biological Activity of Homogentisic acid

DescriptionHomogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae, a Hyphomonas strain, and Shewanella colwelliana. Homogentisic acid shows interesting antioxidant and antiradical activities, and protective effect against thermal-cholesterol degradation. A derivative of homogentisic acid which inhibits Pfnek-1 with an IC(50) around 1.8 muM, this product is moderately active in vitro against a FcB1 P. falciparum strain (IC(50) = 12 muM).
TargetsPfnek-1 | Antifection
In vitro

Serum markers in alkaptonuria: simultaneous analysis of homogentisic acid, tyrosine and nitisinone by liquid chromatography tandem mass spectrometry.[Pubmed: 25628464]

Ann Clin Biochem. 2015 Sep;52(Pt 5):597-605.

Alkaptonuria is a rare debilitating autosomal recessive disorder of tyrosine metabolism, where deficiency of homogentisate 1,2-dioxygenase results in increased Homogentisic acid. Homogentisic acid is deposited as an ochronotic pigment in connective tissues, especially cartilage, leading to a severe early onset form of osteoarthritis, increased renal and prostatic stone formation and hardening of heart vessels. Treatment with the orphan drug, nitisinone, an inhibitor of 4-hydroxyphenylpyruvate dioxygenase has been shown to reduce urinary excretion of Homogentisic acid.
METHODS AND RESULTS:
A reverse phase liquid chromatography tandem mass spectrometry method has been developed to simultaneously analyse serum Homogentisic acid, tyrosine and nitisinone. Using matrix-matched calibration standards, two product ion transitions were identified for each compound (Homogentisic acid, tyrosine, nitisinone) and their respective isotopically labelled internal standards ((13)C6-Homogentisic acid, d2-tyrosine, (13)C6-nitisinone). Intrabatch accuracy was 94-108% for Homogentisic acid, 95-109% for tyrosine and 89-106% for nitisinone; interbatch accuracy (n = 20) was 88-108% for Homogentisic acid, 91-104% for tyrosine and 88-103% for nitisinone. Precision, both intra- and interbatch were <12% for Homogentisic acid and tyrosine, and <10% for nitisinone. Matrix effects observed with acidified serum were normalized by the internal standard (<10% coefficient of variation). Homogentisic acid, tyrosine and nitisinone proved stable after 24 h at room temp, three freeze-thaw cycles and 24 h at 4℃.
CONCLUSIONS:
The assay was linear to 500μmol/L Homogentisic acid, 2000μmol/L tyrosine and 10μmol/L nitisinone; increased range was not required for clinical samples and no carryover was observed.

Interferences of homogentisic acid (HGA) on routine clinical chemistry assays in serum and urine and the implications for biochemical monitoring of patients with alkaptonuria.[Pubmed: 24373924]

Clin Biochem. 2014 May;47(7-8):640-7.

We have assessed the effect of elevated concentrations of Homogentisic acid (HGA) as in alkaptonuria (AKU), on a range of routine chemistry tests in serum and urine.
METHODS AND RESULTS:
Homogentisic acid was added to pooled serum and a range of assays was analysed with Roche Modular chemistries. Effects on urine were assessed by diluting normal urine with urine from a patient with AKU, adding Homogentisic acid to urine and after lowering output of urinary Homogentisic acid with nitisinone treatment. Serum enzymatic creatinine showed 30% negative interference with 100μmol/L Homogentisic acid and >50% at 400μmol/L. Serum urate 100 to 480μmol/L was reduced up to 20% at 100 and to 50% with 400μmol/L Homogentisic acid. Serum cholesterol between 3 and 11mmol/L was reduced by 0.5mmol/L with 400μmol/L Homogentisic acid. Urine enzymatic creatinine and urate with >2mmol/L Homogentisic acid showed concentration dependent negative interference up to 80%. A positive interference in urine total protein by benzethonium turbidometric assay was observed, with 10mmol/L Homogentisic acid equivalent to 1g/L protein. Jaffe creatinine, Na, K, Cl, Mg, Ca, phosphate, ALT, GGT, ALP activities and urea in serum and or urine were not affected by increases in Homogentisic acid.
CONCLUSIONS:
To avoid interferences by Homogentisic acid in alkaptonuria concentration of Homogentisic acid should be established before samples are assayed with peroxidase assays and benzethonium urine protein.

Homogentisic acid Dilution Calculator

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Homogentisic acid Molarity Calculator

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Preparing Stock Solutions of Homogentisic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.9453 mL 29.7265 mL 59.453 mL 118.9061 mL 148.6326 mL
5 mM 1.1891 mL 5.9453 mL 11.8906 mL 23.7812 mL 29.7265 mL
10 mM 0.5945 mL 2.9727 mL 5.9453 mL 11.8906 mL 14.8633 mL
50 mM 0.1189 mL 0.5945 mL 1.1891 mL 2.3781 mL 2.9727 mL
100 mM 0.0595 mL 0.2973 mL 0.5945 mL 1.1891 mL 1.4863 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Homogentisic acid

Interferences of homogentisic acid (HGA) on routine clinical chemistry assays in serum and urine and the implications for biochemical monitoring of patients with alkaptonuria.[Pubmed:24373924]

Clin Biochem. 2014 May;47(7-8):640-7.

OBJECTIVES: We have assessed the effect of elevated concentrations of Homogentisic acid (HGA) as in alkaptonuria (AKU), on a range of routine chemistry tests in serum and urine. DESIGN AND METHODS: HGA was added to pooled serum and a range of assays was analysed with Roche Modular chemistries. Effects on urine were assessed by diluting normal urine with urine from a patient with AKU, adding HGA to urine and after lowering output of urinary HGA with nitisinone treatment. RESULTS: Serum enzymatic creatinine showed 30% negative interference with 100mumol/L HGA and >50% at 400mumol/L. Serum urate 100 to 480mumol/L was reduced up to 20% at 100 and to 50% with 400mumol/L HGA. Serum cholesterol between 3 and 11mmol/L was reduced by 0.5mmol/L with 400mumol/L HGA. Urine enzymatic creatinine and urate with >2mmol/L HGA showed concentration dependent negative interference up to 80%. A positive interference in urine total protein by benzethonium turbidometric assay was observed, with 10mmol/L HGA equivalent to 1g/L protein. Jaffe creatinine, Na, K, Cl, Mg, Ca, phosphate, ALT, GGT, ALP activities and urea in serum and or urine were not affected by increases in HGA. CONCLUSIONS: To avoid interferences by HGA in alkaptonuria concentration of HGA should be established before samples are assayed with peroxidase assays and benzethonium urine protein.

Serum markers in alkaptonuria: simultaneous analysis of homogentisic acid, tyrosine and nitisinone by liquid chromatography tandem mass spectrometry.[Pubmed:25628464]

Ann Clin Biochem. 2015 Sep;52(Pt 5):597-605.

BACKGROUND: Alkaptonuria is a rare debilitating autosomal recessive disorder of tyrosine metabolism, where deficiency of homogentisate 1,2-dioxygenase results in increased Homogentisic acid. Homogentisic acid is deposited as an ochronotic pigment in connective tissues, especially cartilage, leading to a severe early onset form of osteoarthritis, increased renal and prostatic stone formation and hardening of heart vessels. Treatment with the orphan drug, nitisinone, an inhibitor of 4-hydroxyphenylpyruvate dioxygenase has been shown to reduce urinary excretion of Homogentisic acid. METHOD: A reverse phase liquid chromatography tandem mass spectrometry method has been developed to simultaneously analyse serum Homogentisic acid, tyrosine and nitisinone. Using matrix-matched calibration standards, two product ion transitions were identified for each compound (Homogentisic acid, tyrosine, nitisinone) and their respective isotopically labelled internal standards ((13)C6-Homogentisic acid, d2-tyrosine, (13)C6-nitisinone). RESULTS: Intrabatch accuracy was 94-108% for Homogentisic acid, 95-109% for tyrosine and 89-106% for nitisinone; interbatch accuracy (n = 20) was 88-108% for Homogentisic acid, 91-104% for tyrosine and 88-103% for nitisinone. Precision, both intra- and interbatch were <12% for Homogentisic acid and tyrosine, and <10% for nitisinone. Matrix effects observed with acidified serum were normalized by the internal standard (<10% coefficient of variation). Homogentisic acid, tyrosine and nitisinone proved stable after 24 h at room temp, three freeze-thaw cycles and 24 h at 4. The assay was linear to 500mumol/L Homogentisic acid, 2000mumol/L tyrosine and 10mumol/L nitisinone; increased range was not required for clinical samples and no carryover was observed. CONCLUSIONS: The method developed and validated shows good precision, accuracy and linearity appropriate for the monitoring of alkaptonuria patients, pre- and post-nitisinone therapy.

Description

Homogentisic acid is a specific metabolite in urine and serum, which is used for diagnosis of alkaptonuria.

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