Homovanillic acid

Base Information

• Chemical Name: Homovanillic acid
• CAS No.: 306-08-1
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29189900
• European Community (EC) Number: 206-176-7
• NSC Number: 16682
• UNII: X77S6GMS36
• DSSTox Substance ID: DTXSID5059791
• Nikkaji Number: J61.262F
• Wikipedia: Homovanillic_acid
• Wikidata: Q903566
• NCI Thesaurus Code: C167083
• Metabolomics Workbench ID: 37081
• ChEMBL ID: CHEMBL1562
• Mol file: 306-08-1.mol

Synonyms:3 Methoxy 4 Hydroxyphenylacetic Acid;3-Methoxy-4-Hydroxyphenylacetic Acid;4 Hydroxy 3 Methoxyphenylacetic Acid;4-Hydroxy-3-Methoxyphenylacetic Acid;Acid, 3-Methoxy-4-Hydroxyphenylacetic;Acid, 4-Hydroxy-3-Methoxyphenylacetic;Acid, Homovanillic;Homovanillic Acid

Chemical Property of Homovanillic acid

Chemical Property:

• Appearance/Colour: white to beige crystalline powder
• Vapor Pressure: 4.36E-06mmHg at 25°C
• Melting Point: 142-145 °C(lit.)
• Refractive Index: 1.4209 (estimate)
• Boiling Point: 368.7 °C at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 151.9 °C
• PSA: 66.76000
• Density: 1.307 g/cm³
• LogP: 1.02790
• Storage Temp.: Store at RT.
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: soluble
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

Homovanillic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Other Biomolecules
• Canonical SMILES: COC1=C(C=CC(=C1)CC(=O)O)O
• 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: A neuroendocrine tumor marker. Dihydroxyphenylacetic Acid (DOPAC) metabolite. 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.

Technology Process of Homovanillic acid

There total 44 articles about Homovanillic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

4-hydroxy-3-methoxyphenylacetonitrile (4468-59-1) → Homovanillic acid (306-08-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 80 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.tet.2017.02.044

Reference yield: 88.0%

4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9) → Homovanillic acid (306-08-1)

Guidance literature:

With hydrogenchloride; tin(ll) chloride; In water; at 80 ℃; for 4h;

Reference yield: 71.0%

3-methoxy-4-hydroxy mandelic acid (13244-77-4,2394-20-9) → Homovanillic acid (306-08-1)

Guidance literature:

With formic acid; phosphoric acid; sodium hydrogensulfite; In water; at 100 ℃; for 9h; under 3750.3 Torr;

upstream raw materials:

4-Acetoxy-3-methoxyphenylacetaldehyde

4-(4-acetoxy-3-methoxy-benzylidene)-2-methyl-4H-oxazol-5-one

2-(4-acetoxy-3-methoxyphenyl)acetic acid

m-methoxy-p-acetoxy-α-benzoylaminocinnamic acid azlactone

Downstream raw materials:

(3,4-Dimethoxyphenyl)acetic acid

3,4-dihydroxyphenylacetate

2-(4-acetoxy-3-methoxyphenyl)acetic acid

2-(4-hydroxy-3-methoxyphenyl)acetamide

Refernces

• 1、 -. "Phenylacetic acid ester compound and use thereof". Paragraph 0059; 0065; 0066. . Retrieved 2019/03/02.
• 2、 Tang, Qingyun,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.. "Specific Residues Expand the Substrate Scope and Enhance the Regioselectivity of a Plant O-Methyltransferase". . p. 3227 - 3233. Retrieved 2019/07/04.