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Vanillylmandelic acid information


Vanillylmandelic acid
Names
Preferred IUPAC name
Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
Other names
2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
α,4-Dihydroxy-3-methoxybenzeneacetic acid
VMA
Vanillomandelic acid
Vanillylmandelic acid
Vanilmandelic acid
Identifiers
CAS Number
  • 55-10-7 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
2213227
ChEBI
  • CHEBI:20106 checkY
ChemSpider
  • 1207 checkY
ECHA InfoCard 100.000.204 Edit this at Wikidata
EC Number
  • 201-701-6
IUPHAR/BPS
  • 6645
MeSH Vanilmandelic+acid
PubChem CID
  • 1245
UNII
  • 0DQI268449 checkY
CompTox Dashboard (EPA)
  • DTXSID10861583 Edit this at Wikidata
InChI
  • 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) checkY
    Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N checkY
  • 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)
SMILES
  • COC1=C(C=CC(=C1)C(C(=O)O)O)O
  • O=C(O)C(O)c1cc(OC)c(O)cc1
Properties
Chemical formula
C9H10O5
Molar mass 198.173 g/mol
Appearance White powder
Melting point 133 °C (271 °F; 406 K)
Hazards
Safety data sheet (SDS) MSDS at Sigma Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Vanillylmandelic 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.

  1. ^ Fatiadi, Alexander; Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of Standards Section A. 78A (3): 411–412. doi:10.6028/jres.078A.024. PMC 6742820. PMID 32189791. Retrieved 19 December 2013.

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Vanillylmandelic acid

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Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines...

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Catecholamine

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norepinephrine is vanillylmandelic acid (VMA) which is excreted in the urine. Dopamine catabolism leads to the production of homovanillic acid (HVA). Two catecholamines...

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Mandelic acid

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Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and...

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Vanillyl group

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group are called vanilloids, and include vanillin, vanillic acid, capsaicin, vanillylmandelic acid, etc. v t e Lee DW, Kim HN, Lee DS (June 2019). "Introduction...

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Vanilloid

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include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids...

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Vanillin

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glyoxylic acid by electrophilic aromatic substitution. The resulting vanillylmandelic acid (2) is then converted by 4-Hydroxy-3-methoxyphenylglyoxylic acid (3)...

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Methylvanillylecgonine

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more probably the result of the same metabolic pathways by which vanillylmandelic acid is formed). Salicylmethylecgonine Cocaethylene Smith, R. Martin;...

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Adrenal tumor

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levels of catecholamine hormone metabolites, such as vanillylmandelic acid (VMA) and homovanillic acid, and may produce severe watery diarrhea through production...

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Methocarbamol

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laboratory tests for 5-hydroxy-indoleacetic acid (5-HIAA) and in urinary testing for vanillylmandelic acid (VMA) using the Gitlow method. The mechanism...

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Monoamine oxidase

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noradrenaline to 3,4-Dihydroxymandelic acid;[medical citation needed] Metanephrine or normetanephrine to vanillylmandelic acid (VMA);[medical citation needed]...

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VMA

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Award, an award presented to writers of children's works in Canada Vanillylmandelic acid, a metabolite in urine which may be measured to diagnose medical...

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Menkes disease

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look for abnormalities in bone formation. Urine homovanillic acid/vanillylmandelic acid ratio has been proposed as a screening tool to support earlier...

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Neuroblastoma

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Catecholamines and their metabolites include dopamine, homovanillic acid (HVA), and/or vanillylmandelic acid (VMA). Another way to detect neuroblastoma is the...

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Aldehyde dehydrogenase

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oxidation of aldehydes. They convert aldehydes (R–C(=O)–H) to carboxylic acids (R–C(=O)–O–H). The oxygen comes from a water molecule. To date, nineteen...

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Moclobemide

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4-dihydroxyphenylacetic acid, 3,4-dihydroxyphenylethylglycol as well as 5-HIAA. Excretion of homovanillic acid and vanillylmandelic acid via urine is also reduced...

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C9H10O5

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to: Ethyl gallate, an antioxidant food additive Syringic acid, a polyphenol Vanillylmandelic acid, a catecholamine This set index page lists chemical structure...

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Norepinephrine

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by a variety of pathways. The principal end products are either Vanillylmandelic acid or a conjugated form of MHPG, both of which are thought to be biologically...

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Secondary hypertension

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excretion of epinephrine and norepinephrine and/or their metabolites (vanillylmandelic acid).[citation needed] Another cause is an exceptionally rare neurological...

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