Homovanillic acid

Homovanillic acid

Names
IUPAC name 2-(4-Hydroxy-3-methoxy-phenyl)acetic acid
Identifiers
CAS Number	306-08-1 Y
ChEBI	CHEBI:545959 Y
ChEMBL	ChEMBL1562 Y
ChemSpider	1675 Y
Jmol interactive 3D	Image
KEGG	C05582 Y
MeSH	Homovanillic+acid
PubChem	1738
InChI 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) Y Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N Y 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
SMILES O=C(O)Cc1cc(OC)c(O)cc1
Properties
Chemical formula	C9H10O4
Molar mass	182.18 g·mol−1
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

Homovanillic acid (HOC₆H₃(OCH₃)CH₂COOH; synonyms: 3-methoxy-4-hydroxyphenyl acetic acid; HVA; 4-hydroxy-3-methoxy-benzeneacetic acid; 4-hydroxy-3-methoxyphenylacetic acid) is a major catecholamine metabolite and is produced by the consecutive action of monoamine oxidase and catechol-O-methyl transferase on dopamine.^[1] It 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 metabolic stress caused by 2-deoxy-D-glucose.^[2] 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 transsexuals 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.^[3]

See also

• Homovanillyl alcohol

References