An active metabolite of (–)-norepinephrine
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Vanillylmandelic Acid

Item No. 42992

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α,4-dihydroxy-3-methoxy-benzeneacetic acid
CAS Number
55-10-7
Synonyms
  • HMMA
  • 4-Hydroxy-3-methoxymandelic Acid
  • (±)-4-Hydroxy-3-methoxymandelic Acid
  • DL-4-Hydroxy-3-methoxymandelic Acid
  • (±)-Vanillylmandelic Acid
  • DL-Vanillylmandelic Acid
  • VMA
Molecular Formula
C9H10O5
Formula Weight
198.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/mlEthanol: Slightly soluble: 0.1-1 mg/ml
SMILES
O=C(C(C1=CC=C(C(OC)=C1)O)O)O
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)
InChi Key
CGQCWMIAEPEHNQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $42

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    250 mg

    $63

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    500 mg

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    Product Description

    Vanillylmandelic acid is an active metabolite of (–)-norepinephrine (Item No. 16673).1 It is formed from (–)-norepinephrine via normetanephrine (Item No. 38792) and 4-hydroxy-3-methoxyphenylglycol (Item No. 19714) intermediates by several enzymatic reactions. Vanillylmandelic acid (10 mg/kg) reduces ventricular tachyarrhythmia severity in a rat model of myocardial ischemia injury induced by coronary artery occlusion.2 It has been used as a urinary marker for catecholamine-secreting tumors.1,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Goldstein, D.S., Eisenhofer, G., and Kopin, I.J. Sources and significance of plasma levels of catechols and their metabolites in humans. J. Pharm. Exp. Ther. 305(3), 800-811 (2003).

    2. Kolentinis, M.K., Verginadis, I.I., Simos, Y.V., et al. Vanillylmandelic acid protects against reperfusion injury in an experimental animal model of myocardial infarction. Pathophysiology 26(3-4), 343-347 (2019).

    3. Taran, F., Bernard, H., Valleix, A., et al. Competitive enzyme immunoassay for urinary vanillylmandelic acid. Clin. Chim. Acta 264, 177-192 (1997).