Chemistry:Homovanillic acid

Homovanillic acid

Structural formula of homovanillic acid Ball-and-stick model of the homovanillic acid molecule
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
KEGG	C05582 Y
MeSH	Homovanillic+acid
PubChem CID	1738
UNII	X77S6GMS36 Y
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 pictograms
GHS Signal word	Warning
GHS hazard statements	HH315Category:GHS errors, HH319Category:GHS errors, HH335Category:GHS errors
GHS precautionary statements	PP261Category:GHS errors, PP264Category:GHS errors, PP264+P265Category:GHS errors, PP271Category:GHS errors, PP280Category:GHS errors, PP302+P352Category:GHS errors, PP304+P340Category:GHS errors, PP305+P351+P338Category:GHS errors, PP319Category:GHS errors, PP321Category:GHS errors, PP332+P317Category:GHS errors, PP337+P317Category:GHS errors, PP362+P364Category:GHS errors, PP403+P233Category:GHS errors, PP405Category:GHS errors, PP501Category:GHS errors
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

Tracking categories (test):

• PairSizeSet

Homovanillic acid (HVA) is a major catecholamine metabolite 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 metabolic stress 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.

See also

• Homovanillyl alcohol

References

{{Navbox

| name = Neurotransmitter metabolism intermediates
| title = Neurotransmitter metabolic intermediates
| state = autocollapse|
| listclass = hlist

| group1 = catecholamines
  | list1 = {{Navbox|child

  | group1 = Anabolism
(tyrosine→epinephrine)
  | list1 =

• Tyrosine → Levodopa → [[Chemistry:Dop[[Chemistry:Dopamine → Norepinephrine|Norepinephrine]] → Epinephrine

  | group2 = Catabolism/
metabolites

| list2 =

dopamine:	DOPAL DOPAC MOPET Hydroxytyrosol 3-Methoxytyramine Homovanillic acid
norepinephrine:	3,4-Dihydroxymandelic acid Normetanephrine Vanillylmandelic acid 3-Methoxy-4-hydroxyphenylglycol Dihydroxyphenylethylene glycol
epinephrine:	Metanephrine

}} 

| group3 = tryptophan→serotonin

| list3 =

anabolism:	5-Hydroxytryptophan
catabolism:	5-Hydroxyindoleacetic acid

| group4 = serotonin→melatonin
| list4 =

• Normelatonin

}}