| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 1g | |||
| Other Sizes |
| Targets |
Human Endogenous Metabolite Microbial Metabolite
Vanillylmandelic acid is a product of catecholamine metabolism. It is formed from the breakdown of epinephrine and norepinephrine. As a metabolite, it is used as a marker for tumors that secrete catecholamines, such as neuroblastoma or pheochromocytoma. It also has antioxidant activity. |
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| ln Vitro |
Vanillylmandelic acid has antioxidant action; the IC50 value is calculated using the UV-Vis decolorization DPPH experiment, where the quantity of VMA needed to eliminate 50% of the initial concentration of free radical is 33*10-6 M[1].
In vitro, vanillylmandelic acid exhibits antioxidant activity with an IC50 of 33 μM for DPPH radical scavenging. It is used as a marker for catecholamine metabolism and as a precursor in the synthesis of vanilla flavorings. The compound's antioxidant properties make it useful in studies of oxidative stress and neuroprotection. |
| ln Vivo |
A significant difference is observed between the groups who received vanillylmandelic acid (intra-arterial injection during a 1-minute interval; 1, 10, and 100 mg/kg; the 60-minute observation period) and the control group. After 1, 10, and 100 mg/kg, vanillylmandelic acid reduces heart rate by 17.5%, 17.9%, and 18.9%, respectively. When wistar rats are given 1, 10, and 100 mg/kg, respectively, their mean blood pressure decreases by 13.5% in control animals and by 37%, 23%, and 26% in wistar rats[1].
In vivo, vanillylmandelic acid is the end-stage metabolite of catecholamines, including epinephrine and norepinephrine. It is excreted in urine and can be used as a marker for tumors that secrete catecholamines, such as neuroblastoma or pheochromocytoma. The compound's antioxidant activity suggests potential protective effects against oxidative stress. |
| Enzyme Assay |
In vitro enzyme assays for catecholamine metabolism involve measuring vanillylmandelic acid production from catecholamine precursors using enzymes such as monoamine oxidase and catechol-O-methyltransferase. The compound is quantified by HPLC or LC-MS/MS. Antioxidant assays (DPPH, ABTS) are used to measure the compound's radical scavenging activity.
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| Cell Assay |
For in vitro cell assays, cells are cultured in medium supplemented with vanillylmandelic acid at concentrations of 0.1-10 mM. Cell viability is assessed by MTT assay. Antioxidant effects are evaluated by measuring ROS levels using fluorescent probes and by assessing DPPH radical scavenging activity. The compound's effects on catecholamine metabolism and neuroprotection can be studied in neuronal cell models.
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| Animal Protocol |
For in vivo animal studies, vanillylmandelic acid is measured in urine and plasma as a biomarker of catecholamine metabolism. The compound is quantified by HPLC or LC-MS/MS. In neuroblastoma or pheochromocytoma models, urinary vanillylmandelic acid levels are monitored as a marker of tumor activity. Antioxidant effects are assessed by measuring oxidative stress markers in tissues.
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| ADME/Pharmacokinetics |
Vanillylmandelic acid (MW 198.17) has a molecular formula of C9H10O5. It is soluble in water and organic solvents. The compound is stable under standard storage conditions. As a catecholamine metabolite, it is produced through the action of monoamine oxidase and catechol-O-methyltransferase. It is an aromatic ether and a product of catecholamine metabolism.
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| Toxicity/Toxicokinetics |
The compound is for research use only. No specific toxicity data are available. As an endogenous metabolite of catecholamines, it is expected to have low toxicity at physiological concentrations. Standard safety precautions should be followed.
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| References |
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| Additional Infomation |
Vanillylmandelic acid is an aromatic ether, specifically the 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is a human metabolite. It is an aromatic ether, a 2-hydroxy monocarboxylic acid, belonging to the phenolic class of compounds. Functionally, it is related to mandelic acid. It is the conjugate acid of vanillylmandelic acid ester. Vanillylmandelic acid is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). It has been reported to exist in humans, patchouli, and beans, with relevant data available. Vanillylmandelic acid is an aromatic ether and a product of catecholamine metabolism. Vanillylmandelic acid can serve as a marker for catecholamine-secreting tumors (such as neuroblastoma or pheochromocytoma). It is the 3-O-methyl ether of 3,4-dihydroxymandelic acid, and is a terminal metabolite of catecholamines, adrenaline, and noradrenaline.
Vanillylmandelic acid (CAS# 55-10-7) is an endogenous metabolite and research reagent used primarily as a biomarker for catecholamine-secreting tumors such as neuroblastoma and pheochromocytoma. It has not been investigated in clinical trials nor approved as a therapeutic drug. The compound is also used in studies of catecholamine metabolism, oxidative stress, and antioxidant activity. It is a precursor in the synthesis of vanilla flavorings. |
| Molecular Formula |
C9H10O5
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|---|---|
| Molecular Weight |
198.17
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| Exact Mass |
198.052
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| CAS # |
55-10-7
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| Related CAS # |
Vanillylmandelic acid-d3;74495-70-8;Vanillylmandelic acid-d;53587-34-1
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| PubChem CID |
1245
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
421.3±45.0 °C at 760 mmHg
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| Melting Point |
132-134 °C (dec.)(lit.)
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| Flash Point |
173.7±22.2 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.606
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| LogP |
-0.11
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
205
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=C(C=CC(=C1)C(C(=O)O)O)O
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| InChi Key |
CGQCWMIAEPEHNQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
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| Chemical Name |
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 250 mg/mL (1261.54 mM)
H2O: 100 mg/mL (504.62 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 25 mg/mL (126.15 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.0462 mL | 25.2309 mL | 50.4617 mL | |
| 5 mM | 1.0092 mL | 5.0462 mL | 10.0923 mL | |
| 10 mM | 0.5046 mL | 2.5231 mL | 5.0462 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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