Vanillylmandelic acid is the end product of the metabolism of epinephrine and norepinephrine. Vanillylmandelic acid may also serve as a marker for neurotransmitter metabolism disorders. Vanillylmandelic acid has anti-oxidant effect, and its IC50 for scavenging DPPH free radicals is 33 μM.

Physicochemical Properties

Molecular Formula	C9H10O5
Molecular Weight	198.17
Exact Mass	198.052
CAS #	55-10-7
Related CAS #	Vanillylmandelic acid-d3;74495-70-8;Vanillylmandelic acid-d;53587-34-1
PubChem CID	1245
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Boiling Point	421.3±45.0 °C at 760 mmHg
Melting Point	132-134 °C (dec.)(lit.)
Flash Point	173.7±22.2 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.606
LogP	-0.11
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	14
Complexity	205
Defined Atom Stereocenter Count	0
InChi Key	CGQCWMIAEPEHNQ-UHFFFAOYSA-N
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)
Chemical Name	2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
HS Tariff Code	2934.99.9001
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)

Biological Activity

Targets	Human Endogenous Metabolite Microbial Metabolite
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].
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].
References	[1]. Cardiovascular effects of vanillylmandelic acid in rats. Eur J Pharmacol. 2013 Mar 5;703(1-3):46-52. [2]. Experimental and theoretical elucidation of structural and antioxidant properties of vanillylmandelic acid and its carboxylate anion. Spectrochim Acta A Mol Biomol Spectrosc. 2018 Jun 5;198:61-70.
Additional Infomation	Vanillylmandelic acid is an aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid. It has a role as a human metabolite. It is an aromatic ether, a 2-hydroxy monocarboxylic acid and a member of phenols. It is functionally related to a mandelic acid. It is a conjugate acid of a vanillylmandelate. Vanillylmandelic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Vanillylmandelic acid has been reported in Homo sapiens, Pogostemon cablin, and Phaseolus vulgaris with data available. Vanillylmandelic Acid is an aromatic ether that is a product of catecholamine metabolism. Vanillylmandelic acid may be a used as marker for tumors that secrete catecholamines, such as neuroblastoma or pheochromocytoma. A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.

Solubility Data

Solubility (In Vitro)

DMSO: 250 mg/mL (1261.54 mM) H2O: 100 mg/mL (504.62 mM)

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. 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. 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 corn oil and mix evenly. 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.  (Please use freshly prepared in vivo formulations for optimal results.)

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.