Homovanillic acid

Homovanillic acid (HVA) is a major catecholamine metabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine.^[1] Homovanillic acid is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.

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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
CAS Number	306-08-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:545959 Y
ChEMBL	ChEMBL1562 Y
ChemSpider	1675 Y
ECHA InfoCard	100.005.616
KEGG	C05582 Y
MeSH	Homovanillic+acid
PubChem CID	1738
UNII	X77S6GMS36 Y
CompTox Dashboard (EPA)	DTXSID5059791
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	182.175 g·mol−1
Appearance	white solid
Melting point	138-140 °C
Solubility in water	17 mg/mL
log P	0.33
Vapor pressure	0.00000823 mmHg
Acidity (pKa)	pKa1 = 4.41 pKa2 = 10.53
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, 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). Y verify (what is YN ?) Infobox references

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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.^{[citation needed]} 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.^[3] Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.