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
PubChemCID	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
logP	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 theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Homovanillic acid (HVA) is a majorcatecholaminemetabolite that is produced by a consecutive action ofmonoamine oxidase andcatechol-O-methyltransferase ondopamine.^[1] Homovanillic acid is used as areagent to detect oxidativeenzymes, and is associated withdopamine levels in thebrain.

Inpsychiatry andneuroscience,brain andcerebrospinal fluid levels of HVA are measured as a marker ofmetabolic stress caused by2-deoxy-D-glucose.^[2] HVA presence supports a diagnosis ofneuroblastoma and malignantpheochromocytoma.

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 astransgender people according to their geneticsex, both before and during cross-sex hormone administration.^[3] Differences in HVA have also been correlated totobacco usage, with smokers showing significantly lower amounts of plasma HVA.

• Homovanillyl alcohol

• Vanilloids
• Acetic acids
• Neurochemistry
• Phenolic human metabolites
• O-methylated phenols

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