3,4-Dihydroxymandelic acid

3,4-Dihydroxymandelic acid
Names
Preferred IUPAC name
(3,4-Dihydroxyphenyl)(hydroxy)acetic acid
Other names
2-(3,4-Dihydroxyphenyl)-2-hydroxyacetic acid
Identifiers
CAS Number
  • 775-01-9 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27637 checkY
ChemSpider
  • 77371 checkY
ECHA InfoCard 100.011.154 Edit this at Wikidata
IUPHAR/BPS
  • 6633
KEGG
  • C05580 checkY
MeSH 3,4-dihydroxymandelic+acid
PubChem CID
  • 85782
UNII
  • WDP6VCX5T6 checkY
InChI
  • 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) checkY
    Key: RGHMISIYKIHAJW-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
    Key: RGHMISIYKIHAJW-UHFFFAOYAB
  • O=C(O)C(O)c1cc(O)c(O)cc1
Properties
Chemical formula
 C8H8O5
Molar mass 184.14612
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

3,4-Dihydroxymandelic acid (DHMA, DOMA) is a metabolite of norepinephrine.[1]

Norepinephrine degradation. 3,4-Dihydroxymandelic acid is shown at right. Enzymes are shown in boxes.[2]

References

  1. ^ Ley JP; Engelhart K; Bernhardt J; Bertram HJ (October 2002). "3,4-Dihydroxymandelic acid, a noradrenalin metabolite with powerful antioxidative potential". J. Agric. Food Chem. 50 (21): 5897–902. doi:10.1021/jf025667e. PMID 12358456.
  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 978-0-443-06911-6.
  • v
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Neurotransmitter metabolic intermediates
catecholamines
Anabolism
(tyrosine→epinephrine)
Catabolism/
metabolites
dopamine:
norepinephrine:
epinephrine:
tryptophan→serotonin
anabolism:
catabolism:
serotonin→melatonin


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