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Homovanillic acid

Catecholamine metabolite CAS# 306-08-1

Homovanillic acid

Catalog No. BCN1253----Order now to get a substantial discount!

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Quality Control of Homovanillic acid

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Chemical structure

Homovanillic acid

3D structure

Chemical Properties of Homovanillic acid

Cas No. 306-08-1 SDF Download SDF
PubChem ID 1738 Appearance Powder
Formula C9H10O4 M.Wt 182.17
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms HVA
Solubility Soluble to 50 mM in water and to 100 mM in DMSO
Chemical Name 2-(4-hydroxy-3-methoxyphenyl)acetic acid
SMILES COC1=C(C=CC(=C1)CC(=O)O)O
Standard InChIKey QRMZSPFSDQBLIX-UHFFFAOYSA-N
Standard InChI InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(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 Homovanillic acid

The barks of Ilex rotunda Thunb.

Biological Activity of Homovanillic acid

DescriptionHomovanillic acid is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain. Abnormalities in white matter were associated with low CSF Homovanillic acid.
In vitro

Analysis of vanillylmandelic acid and homovanillic acid by UPLC-MS/MS in serum for diagnostic testing for neuroblastoma.[Pubmed: 23830883]

Clin Chim Acta. 2013 Sep 23;424:253-7.

Vanillylmandelic acid (VMA) and Homovanillic acid (HVA) are typically measured in urine for the diagnosis and monitoring of neuroblastoma, a tumor in children <5 y. A protocol for evaluation of serum VMA and Homovanillic acid has been utilized at our institution for approximately 25 y, originally validated using high performance liquid chromatography (HPLC) with an electrochemical detector. We recently validated a serum VMA/HVA method by ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS).
METHODS AND RESULTS:
After solvent extraction and clean up with Ultrafree centrifugal filters, samples were analyzed by UPLC-MS/MS in multiple reaction monitoring mode. The assay was linear between 2 and 1000 ng/ml for VMA and Homovanillic acid . Within run and run to run CVs were <5% for VMA at all levels, <10% for HVA at high levels, and <20% at low levels. Correlation with the HPLC method was acceptable with a constant bias. The reference interval for VMA by UPLC-MS/MS was determined to be ≤20 ng/ml, and HVA≤30 ng/ml. Original patient data comparing urine to serum showed diagnostic agreement >80% for both VMA and Homovanillic acid .
CONCLUSIONS:
Correlation of VMA and Homovanillic acid was acceptable after adjustment of reference intervals. Collection of a single serum sample instead of 24-h urine collection saves time and improves accuracy of measurement due to difficulty of collecting a 24-h urine sample in infants and young children. UPLC-MS/MS also offers improved analyte specificity, improved signal to noise, and rapid analysis time.

In vivo

Homovanillic acid in cerebrospinal fluid of 1388 children with neurological disorders.[Pubmed: 23480488]

Dev Med Child Neurol. 2013 Jun;55(6):559-66.

To determine the prevalence of dopaminergic abnormalities in 1388 children with neurological disorders, and to analyse their clinical, neuroradiological, and electrophysiological characteristics.
METHODS AND RESULTS:
We studied biogenic amines in 1388 cerebrospinal fluid (CSF) samples from children with neurological disorders (mean age 3y 10mo, SD 4y 5mo; 712 males, 676 females. Correlations among CSF Homovanillic acid (HVA) values and other biochemical, clinical, neuroradiological, and electrophysiological parameters were analysed. Twenty-one patients with primary dopaminergic deficiencies were identified. Of the whole sample, 20% showed altered Homovanillic acid. We report neurological diseases with abnormal CSF Homovanillic acid values such as pontocerebellar hypoplasia, perinatal asphyxia, central nervous system infections, mitochondrial disorders, and other genetic diseases. Overlapping Homovanillic acid levels between primary and secondary dopamine deficiencies were observed. Prevalence of low CSF Homovanillic acid levels was significantly higher in neonatal patients (χ(2) =84.8, p<0.001). Abnormalities in white matter were associated with low CSF Homovanillic acid (odds ratio 2.3, 95% confidence interval 1.5-3.5).
CONCLUSIONS:
HVA abnormalities are observed in various neurological diseases, but some are probably an unspecific finding. No clear limits for CSF Homovanillic acid values pointing towards primary diseases can be stated. We report several neurological diseases showing Homovanillic acid alterations. No neuroimaging traits were associated with low Homovanillic acid values, except for white matter abnormalities.

Protocol of Homovanillic acid

Structure Identification
Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 24;118:1068-74.

Molecular structure and spectroscopic analysis of homovanillic acid and its sodium salt--NMR, FT-IR and DFT studies.[Pubmed: 24161870]

The estimation of the electronic charge distribution in metal complex or salt allows to predict what kind of deformation of the electronic system of ligand would undergo during complexation. It also permits to make more precise interpretation of mechanism by which metals affect the biochemical properties of ligands.
METHODS AND RESULTS:
Theinfluence ofsodium cation on the electronic system of Homovanillic acid was studied in this paper. Optimized geometrical structures of studied compounds were calculated by B3LYP/6-311++G(**) method. Mulliken, MK and ChelpG atomic charges were analyzed. The theoretical NMR and IR spectra were obtained. (1)H and (13)C NMR as well as FT-IR and FT-Raman spectra of studied compounds were also recorded and analyzed. The calculated parameters are compared with experimental characteristics of these molecules.

Homovanillic acid Dilution Calculator

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Homovanillic acid Molarity Calculator

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Preparing Stock Solutions of Homovanillic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.4894 mL 27.4469 mL 54.8938 mL 109.7876 mL 137.2345 mL
5 mM 1.0979 mL 5.4894 mL 10.9788 mL 21.9575 mL 27.4469 mL
10 mM 0.5489 mL 2.7447 mL 5.4894 mL 10.9788 mL 13.7234 mL
50 mM 0.1098 mL 0.5489 mL 1.0979 mL 2.1958 mL 2.7447 mL
100 mM 0.0549 mL 0.2745 mL 0.5489 mL 1.0979 mL 1.3723 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 Homovanillic acid

Interchangeability between 24-hour collection and single spot urines for vanillylmandelic and homovanillic acid levels in the diagnosis of neuroblastoma.[Pubmed:23813598]

Pediatr Blood Cancer. 2013 Dec;60(12):E170-2.

The determination of the two urinary catecholamine metabolites Homovanillic acid (HVA) and vanillylmandelic acid (VMA) is of crucial importance for the diagnosis and follow-up of neuroblastoma (NB). The standard practice for their measurement requires the use of 24-hour collections that are time consuming and difficult to obtain. In this article, we directly demonstrate that 24-hour collections and single spot urines are interchangeable for the determination of HVA and VMA expressed as ratio on creatinine concentration. This study can be useful for a faster management of NB at onset.

Analysis of vanillylmandelic acid and homovanillic acid by UPLC-MS/MS in serum for diagnostic testing for neuroblastoma.[Pubmed:23830883]

Clin Chim Acta. 2013 Sep 23;424:253-7.

BACKGROUND: Vanillylmandelic acid (VMA) and Homovanillic acid (HVA) are typically measured in urine for the diagnosis and monitoring of neuroblastoma, a tumor in children <5 y. A protocol for evaluation of serum VMA and HVA has been utilized at our institution for approximately 25 y, originally validated using high performance liquid chromatography (HPLC) with an electrochemical detector. We recently validated a serum VMA/HVA method by ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). METHODS: After solvent extraction and clean up with Ultrafree centrifugal filters, samples were analyzed by UPLC-MS/MS in multiple reaction monitoring mode. RESULTS: The assay was linear between 2 and 1000 ng/ml for VMA and HVA. Within run and run to run CVs were <5% for VMA at all levels, <10% for HVA at high levels, and <20% at low levels. Correlation with the HPLC method was acceptable with a constant bias. The reference interval for VMA by UPLC-MS/MS was determined to be 80% for both VMA and HVA. CONCLUSION: Correlation of VMA and HVA was acceptable after adjustment of reference intervals. Collection of a single serum sample instead of 24-h urine collection saves time and improves accuracy of measurement due to difficulty of collecting a 24-h urine sample in infants and young children. UPLC-MS/MS also offers improved analyte specificity, improved signal to noise, and rapid analysis time.

Homovanillic acid in cerebrospinal fluid of 1388 children with neurological disorders.[Pubmed:23480488]

Dev Med Child Neurol. 2013 Jun;55(6):559-66.

AIM: To determine the prevalence of dopaminergic abnormalities in 1388 children with neurological disorders, and to analyse their clinical, neuroradiological, and electrophysiological characteristics. METHOD: We studied biogenic amines in 1388 cerebrospinal fluid (CSF) samples from children with neurological disorders (mean age 3y 10mo, SD 4y 5mo; 712 males, 676 females. Correlations among CSF Homovanillic acid (HVA) values and other biochemical, clinical, neuroradiological, and electrophysiological parameters were analysed. RESULTS: Twenty-one patients with primary dopaminergic deficiencies were identified. Of the whole sample, 20% showed altered HVA. We report neurological diseases with abnormal CSF HVA values such as pontocerebellar hypoplasia, perinatal asphyxia, central nervous system infections, mitochondrial disorders, and other genetic diseases. Overlapping HVA levels between primary and secondary dopamine deficiencies were observed. Prevalence of low CSF HVA levels was significantly higher in neonatal patients (chi(2) =84.8, p<0.001). Abnormalities in white matter were associated with low CSF HVA (odds ratio 2.3, 95% confidence interval 1.5-3.5). INTERPRETATION: HVA abnormalities are observed in various neurological diseases, but some are probably an unspecific finding. No clear limits for CSF HVA values pointing towards primary diseases can be stated. We report several neurological diseases showing HVA alterations. No neuroimaging traits were associated with low HVA values, except for white matter abnormalities.

Molecular structure and spectroscopic analysis of homovanillic acid and its sodium salt--NMR, FT-IR and DFT studies.[Pubmed:24161870]

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 24;118:1068-74.

The estimation of the electronic charge distribution in metal complex or salt allows to predict what kind of deformation of the electronic system of ligand would undergo during complexation. It also permits to make more precise interpretation of mechanism by which metals affect the biochemical properties of ligands. Theinfluence ofsodium cation on the electronic system of Homovanillic acid was studied in this paper. Optimized geometrical structures of studied compounds were calculated by B3LYP/6-311++G(**) method. Mulliken, MK and ChelpG atomic charges were analyzed. The theoretical NMR and IR spectra were obtained. (1)H and (13)C NMR as well as FT-IR and FT-Raman spectra of studied compounds were also recorded and analyzed. The calculated parameters are compared with experimental characteristics of these molecules.

Description

Homovanillic acid is a dopamine metabolite found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency.

Keywords:

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