Homovanillic Acid
HVA · Homovanilic acid · 4-HYDROXY-3-METHOXYPHENYLACETIC ACID · 4-Hydroxy-3-methoxybenzeneacetic acid · Benzeneacetic acid, 4-hydroxy-3-methoxy- · JACS-306-08-1 · homovanillicaci · Vanilacetic acid
Identifiers & Physical Properties
| CAS No. | 306-08-1 |
|---|---|
| Molecular formula | C9H10O4 |
| Average molar mass | 182.17 g/mol |
| Monoisotopic mass | 182.0579088 g/mol |
| SMILES | COc1cc(CC(=O)O)ccc1O |
| InChIKey | QRMZSPFSDQBLIX-UHFFFAOYSA-N |
| PubChem CID | 1738 |
| ChEMBL | CHEMBL1562 |
| ChEBI | CHEBI:545959 |
| EC No. | 206-176-7 |
| DTXSID | DTXSID5059791 |
Chemical & Physical Properties
| XLogP | 0.4 |
|---|---|
| Topological polar surface area | 66.8 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 3 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 180 |
| Chemical classes | Biological Agents -> Other Biomolecules |
| LogP (partition coefficient) | 0.33 |
| Solubility | 17 mg/mLDMSO (Slightly), Methanol (Slightly, Heated)soluble |
| Melting point | 138 - 140 °C142-145 °C(lit.) |
| Vapor pressure | 0.00000823 [mmHg] |
| Physical Description | White solid[Merck Index] White to pale brown crystalline powder[Alfa Aesar MSDS] |
| Collision Cross Section | 134.15 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]140.75 Ų [M-H]- [CCS Type: DTMethod: stepped-field]146.2 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]145.9 Ų [M+Na]+ |
| Boiling point | 235.56°C (rough estimate) |
| Density | 1.1634 (rough estimate) |
| Refractive index | 1.4209 (estimate) |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (acidity coefficient) | 4.39±0.10(Predicted) |
| Physical state | Crystalline Powder |
| Color | White to beige |
| Merck | 14,4740 |
| BRN | 2213447 |
| Stability | Hygroscopic |
| Major applications | pharmaceutical |
| 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) |
| InChIKey | QRMZSPFSDQBLIX-UHFFFAOYSA-N |
| SMILES | COc1cc(CC(O)=O)ccc1O |
| LogP (partition coefficient) | 0.330 |
| CAS DataBase Reference | 306-08-1(CAS DataBase Reference) |
| FDA UNII | X77S6GMS36 |
| NIST Chemistry Reference | Benzeneacetic acid, 4-hydroxy-3-methoxy-(306-08-1) |
| EPA Substance Registry System | Homovanillic acid (306-08-1) |
| UNSPSC Code | 77101502 |
| NACRES | NA.47 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | 3 |
| F | 10-23 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANT |
| Customs code | 29189900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH315 (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. |
|---|---|
| Regulatory information | Benzeneacetic acid, 4-hydroxy-3-methoxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin, respiratory tract, and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 10-23 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29189900 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36 |
| Hazard class | IRRITANT |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
Description
Homovanillic 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.
Uses
Fluorimetric 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.
Uses
A neuroendocrine tumor marker. Dihydroxyphenylacetic Acid (DOPAC) metabolite.