Vanillylmandelic acid

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Vanillylmandelic acid
Vanilmandelic acid.svg
Identifiers
CAS number 55-10-7 YesY
PubChem 1245
ChemSpider 1207 YesY
EC number 201-701-6
MeSH Vanilmandelic+acid
ChEBI CHEBI:20106 YesY
Beilstein Reference 2213227
Jmol-3D images Image 1
Properties
Molecular formula C9H10O5
Molar mass 198.17 g mol−1
Appearance White powder
Melting point 133 °C (271 °F; 406 K)
Hazards
MSDS MSDS at Sigma Aldrich
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Vanillyl mandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings[1] and is an end-stage metabolite of the catecholamines, epinephrine, and norepinephrine. It is produced via intermediary metabolites.

Chemical Synthesis[edit]

VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla.[1] Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide.

Biological Elimination[edit]

VMA is found in the urine, along with other catecholamine metabolites, including homovanillic acid (HVA), metanephrine, and normetanephrine. In timed urine tests the quantity excreted (usually per 24 hours) is assessed along with creatinine clearance, and the quantity of cortisols, catecholamines, and metanephrines excreted is also measured.

Norepinephrine degradation. Vanillylmandelic acid is shown at top right. Enzymes are shown in boxes.[2]

Clinical significance[edit]

Urinary VMA is elevated in patients with tumors that secrete catecholamines.[3]

These urinalysis tests are used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. These tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions.

Norepinephrine is metabolised into normetanephrine and VMA. Norepinephrine is one of the hormones produced by the adrenal glands, which are found on top of the kidneys. These hormones are released into the blood during times of physical or emotional stress, which are factors that may skew the results of the test.[citation needed]

References[edit]

  1. ^ a b Fatiadi, Alexander; and Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)". Journal of Research of the National Bureau of Standards - A. Physics and Chemistry 78A (3): 411–412. doi:10.6028/jres.078A.024. Retrieved 19 December 2013. 
  2. ^ Figure 11-4 in: Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5. 
  3. ^ Magera MJ, Thompson AL, Matern D, Rinaldo P (May 2003). "Liquid chromatography-tandem mass spectrometry method for the determination of vanillylmandelic acid in urine". Clin. Chem. 49 (5): 825–6. doi:10.1373/49.5.825. PMID 12709381.