3,4-Dihydroxymandelic acid - Misplaced Pages

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3,4-Dihydroxymandelic acid
Names

IUPAC name 2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
Identifiers
CAS Number	775-01-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27637
ChemSpider	77371
ECHA InfoCard	100.011.154
KEGG	C05580
MeSH	3,4-dihydroxymandelic+acid
PubChem CID	85782
CompTox Dashboard (EPA)	DTXSID30862411
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)Key: RGHMISIYKIHAJW-UHFFFAOYSA-N 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
SMILES 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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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

References

Ley JP, Engelhart K, Bernhardt J, Bertram HJ (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Figure 11-4 in: Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5.{{cite book}}: CS1 maint: multiple names: authors list (link)

Neurotransmitter metabolic intermediates

Catecholamines

Anabolism

Phenylalanine → Tyrosine → DOPA (levodopa) → Dopamine → Norepinephrine → Epinephrine

Catabolism

Dopamine	3,4-Dihydroxyphenylacetaldehyde (DOPAL) 3,4-Dihydroxyphenylacetic acid (DOPAC) Homovanillyl alcohol Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET) 3-Methoxytyramine (3-MT) Homovanillic acid (HVA)
Norepinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) 3,4-Dihydroxymandelic acid (DHMA) Normetanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL) Vanillylmandelic acid (VMA) 3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG) 3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
Epinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) Metanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL)

Tryptophan→Serotonin

Anabolism	Tryptophan 5-Hydroxytryptophan (5-HTP)
Catabolism	5-Hydroxyindoleacetaldehyde (5-HIAL) 5-Hydroxyindoleacetic acid (5-HIAA) 5-Hydroxytryptophol (5-HTOL)

Serotonin→Melatonin

Trace amines

GABA

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