Homovanillic Acid

HCID 1738CAS 306-08-1
Substructure searchFind similar structures

Basic information

Standard SMILES
COc1cc(CC(=O)O)ccc1O
InChIKey
QRMZSPFSDQBLIX-UHFFFAOYSA-N
Molecular formula
C9H10O4
Average molar mass
182.17 g/mol
Monoisotopic mass
182.0579088

Overview

Homovanillic acid is a monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. It has a role as a mouse metabolite and a human metabolite. It is a member of guaiacols and a monocarboxylic acid. It is functionally related to a (3,4-dihydroxyphenyl)acetic acid. It is a conjugate acid of a homovanillate.

Names & identifiers

Preferred name
Homovanillic Acid
IUPAC
2-(4-hydroxy-3-methoxyphenyl)acetic acid
English name
Homovanillic acid
Molecular formula
C9H10O4
Molecular weight
182.17

Names & synonyms

Homovanillic acid306-08-14-Hydroxy-3-methoxyphenylacetic acid2-(4-hydroxy-3-methoxyphenyl)acetic acidBenzeneacetic acid, 4-hydroxy-3-methoxy-Vanillacetic acid3-Methoxy-4-hydroxyphenylacetic acid4-Hydroxy-3-methoxybenzeneacetic acid(4-HYDROXY-3-METHOXYPHENYL)ACETIC ACIDAcetic acid, (4-hydroxy-3-methoxyphenyl)-X77S6GMS36DTXSID5059791
Show more names
HVAHomovanilic acidJACS-306-08-1homovanillicaciVanilacetic acidHOMOVANIUIC ACID
HMDB00118NSC-16682CHEBI:545959Acid, Homovanillic3 Methoxy 4 Hydroxyphenylacetic Acid4 Hydroxy 3 Methoxyphenylacetic AcidAcid, 3-Methoxy-4-HydroxyphenylaceticAcid, 4-Hydroxy-3-Methoxyphenylacetic

Database identifiers

CAS
306-08-1
PubChem CID
1738
DTXSID
DTXSID5059791
ChEMBL
CHEMBL1562
ChEBI
CHEBI:545959
UNII
X77S6GMS36
EC Number
206-176-7
Nikkaji
J61.262F

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
66.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Other Biomolecules
LogP0.33
Solubility17 mg/mL
Melting Point138 - 140 °C
Vapor Pressure0.00000823 [mmHg]
Physical Description · 2 items

White solid; [Merck Index] White to pale brown crystalline powder; [Alfa Aesar MSDS]

Solid

Physicochemical properties

Melting point
142 · 142-145 °C(lit.)
Boiling point
235.56 °C · 235.56°C (rough estimate)
Density
1.1634 · 1.1634 (rough estimate)
refractive index
1.4209 · 1.4209 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
DMSO (Slightly), Methanol (Slightly, Heated)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationBenzeneacetic acid, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin, respiratory tract, and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F
10-23
wgk
3
tsca
TSCA listed
hs_code
29189900
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Pharmacology

Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysAlkaptonuria

Uses & manufacturing

UsesA metabolite present in human urine; [Merck Index]
General Manufacturing InformationBenzeneacetic acid, 4-hydroxy-3-methoxy-: ACTIVE
Applications · 3 items

DescriptionHomovanillic acid (HVA) is a dopamine metabolite. It is formed via deamination of dopamine by monoamine oxidase (MAO) to produce 3,4-dihydroxyphenylacetic acid (DOPAC; ) followed by DOPAC metabolism by catechol-O-methyltransferase (COMT). HVA undergoes hydrogen peroxide-dependent oxidation in the presence of horseradish peroxidase to form a fluorescent dimer that displays excitation/emission maxima of 312/420 nm, respectively. It has been used to quantify hydrogen peroxide production in macrophages and neutrophils.

UsesFluorimetric reagent and major catecholamine metaboliteHomovanillic acid is used as a reagent in the determination of oxidative enzymes. It is associated with dopamine levels in the brain. Its presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.

UsesA neuroendocrine tumor marker. Dihydroxyphenylacetic Acid (DOPAC) metabolite.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.

Related reactions

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Linked notes

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