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Topic summary

Homovanillic acid

Homovanillic acid
Names Preferred IUPAC name
(4-Hydroxy-3-methoxyphenyl)acetic acid
Other names
  • 2-(4-hydroxy-3-methoxyphenyl)acetic acid
  • 3-methoxy-4-hydroxyphenylacetic acid
  • 4-hydroxy-3-methoxy-benzeneacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.005.616KEGG
MeSHHomovanillic+acid
UNII
  • InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
    Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N
  • InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
    Key: QRMZSPFSDQBLIX-UHFFFAOYAZ
  • O=C(O)Cc1cc(OC)c(O)cc1
Properties C9H10O4Molar mass182.175 g·mol Appearance white solid Melting point138-140 °C 17 mg/mL log P0.33 Vapor pressure0.00000823 mmHg Acidity (pKa) pKa1 = 4.41
pKa2 = 10.53 Hazards GHS labelling: WarningH315, H319, H335P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Homovanillic acid (HVA) is a major catecholaminemetabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine. Homovanillic acid is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.

In psychiatry and neuroscience, brain and cerebrospinal fluid levels of HVA are measured as a marker of caused by 2-deoxy-D-glucose. HVA presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.

Fasting plasma levels of HVA are known to be higher in females than in males. This does not seem to be influenced by adult hormonal changes, as the pattern is retained in the elderly and post-menopausal as well as transgender people according to their genetic sex, both before and during cross-sex hormone administration. Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.

Wikipedia source