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CAS 2394-20-9

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Vanillylmandelic acid

Description:
Vanillylmandelic acid (VMA) is a phenolic compound that is a metabolite of catecholamines, primarily epinephrine and norepinephrine. It is characterized by its chemical structure, which includes a vanillin moiety and a mandelic acid component. VMA is typically found in urine and is used as a biomarker for certain medical conditions, particularly neuroblastoma and pheochromocytoma, as elevated levels can indicate the presence of these tumors. The compound is soluble in water and exhibits a weakly acidic nature due to the carboxylic acid group in its structure. Its presence in biological fluids is often measured through chromatographic techniques, such as high-performance liquid chromatography (HPLC). In addition to its clinical significance, VMA has been studied for its potential antioxidant properties, although its primary relevance remains in the diagnostic field. Overall, vanillylmandelic acid serves as an important indicator in the assessment of catecholamine metabolism and related disorders.
Formula:C9H10O5
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)
InChI key:InChIKey=CGQCWMIAEPEHNQ-UHFFFAOYSA-N
SMILES:C(C(O)=O)(O)C1=CC(OC)=C(O)C=C1
Synonyms:
  • (4-Hydroxy-3-methoxyphenyl)glycolic acid
  • (±)-3-Methoxy-4-hydroxymandelic acid
  • (±)-Vanilmandelic acid
  • 2-(4′-Hydroxy-3′-methoxyphenyl)-2-hydroxyethanoic acid
  • 2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
  • 3-Methoxy-4-hydroxyphenylhydroxyacetic acid
  • 4-Hydroxy-3-methoxy-<span class="text-smallcaps">DL</span>-mandelic acid
  • 4-Hydroxy-3-methoxymandelic acid
  • <span class="text-smallcaps">DL</span>-3-Methoxy-4-hydroxymandelic acid
  • <span class="text-smallcaps">DL</span>-4-Hydroxy-3-methoxymandelic acid
  • See more synonyms
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