An active metabolite of norepinephrine
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3,4-Dihydroxymandelic Acid

Item No. 36369

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α,3,4-trihydroxy-benzeneacetic acid
CAS Number
775-01-9
Synonyms
  • DHMA
  • DOMA
Molecular Formula
C8H8O5
Formula Weight
184.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O=C(C(C1=CC=C(C(O)=C1)O)O)O
InChi Code
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
InChi Key
RGHMISIYKIHAJW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 mg

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    Cayman Chemical
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    Product Description

    3,4-Dihydroxymandelic acid is an active metabolite of the endogenous catecholamine (–)-norepinephrine (Item No. 16673).1 It is formed from (–)-norepinephrine via the intermediate norepinephrine aldehyde by aldehyde dehydrogenase. 3,4-Dihydroxymandelic acid scavenges superoxide radicals (IC50 = 130 nM) and reduces lipid peroxidation in cell-free assays.2 3,4-Dihydroxymandelic acid is also formed from norepinephrine by gut microbiota, such as E. coli.3 It is a chemoattractant for enterohemorrhagic E. coli that induces the expression of virulence genes when used at a concentration of 50 µM and increases the attachment of enterohemorrhagic E. coli to HeLa cells in vitro.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rang, H.P., Dale, M.M., Ritter, J.M., et al. Rang and Dale’s Pharmacology. (2012).

    2. Ley, J.P., Engelhart, K., Bernhardt, J., et al. 3,4-Dihydroxymandelic acid, a noradrenalin metabolite with powerful antioxidative potential. J. Agric. Food Chem. 50(21), 5897-5902 (2002).

    3. Sule, N., Pasupuleti, S., Kohli, N., et al. The norepinephrine metabolite 3,4-dihydroxymandelic acid is produced by the commensal microbiota and promotes chemotaxis and virulence gene expression in enterohemorrhagic Escherichia coli. Infect. Immun. 85(10), e00431-00417 (2017).