Isohomovanillic acid

Base Information

• Chemical Name: Isohomovanillic acid
• CAS No.: 1131-94-8
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29189900
• European Community (EC) Number: 670-463-7
• DSSTox Substance ID: DTXSID10150287
• Nikkaji Number: J1.169.302D
• Wikidata: Q27139116
• Metabolomics Workbench ID: 37208
• ChEMBL ID: CHEMBL1299652
• Mol file: 1131-94-8.mol

Synonyms:4-methoxy-3-hydroxyphenylacetic acid;homo-iso-vanillic acid;isohomovanillic acid

Chemical Property of Isohomovanillic acid

Chemical Property:

• Vapor Pressure: 3.59E-06mmHg at 25°C
• Melting Point: 128 °C
• Refractive Index: 1.573
• Boiling Point: 371.3 °C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 153.1 °C
• PSA: 66.76000
• Density: 1.307 g/cm³
• LogP: 1.02790
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• 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:

98% ^*data from raw suppliers

3-Hydroxy-4-methoxyphenylacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC(=O)O)O
• Uses: 3-Hydroxy-4-methoxyphenylacetic acid is a 4-O-methylated metabolite of catechol amines in man. 3-Hydroxy-4-methoxyphenylacetic acid is also a metabolite of 3,4-dihydroxyphenylalanine (DOPA) analogues as well as a metabolite of Hydroxytyrosol (H977000).

Technology Process of Isohomovanillic acid

There total 40 articles about Isohomovanillic 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: 99.0%

(3-bromo-4-methoxy-phenyl)-acetic acid (774-81-2) → homoisovanillic acid (1131-94-8)

Guidance literature:

With sodium hydroxide; copper(II) sulfate; In water; at 150 ℃; for 36h; sealed bomb;

DOI:10.1021/jo00185a061

Reference yield: 76.0%

2-bromo-4-methoxy-5-hydroxylphenylacetic acid (81038-48-4) → homoisovanillic acid (1131-94-8)

Guidance literature:

With formic acid; palladium on activated charcoal; at 100 ℃; for 3h;

DOI:10.1002/ardp.19813141203

Reference yield: 75.0%

3-hydroxy-4-methoxyphenylacetonitrile (4468-58-0) → homoisovanillic acid (1131-94-8)

Guidance literature:

With sodium hydroxide; 1.) 50 deg C, 48 h, 2.) 100 deg C;

DOI:10.1002/ardp.19813141203

upstream raw materials:

(5-hydroxy-4-methoxy-2-nitro-phenyl)-acetic acid

(3-hydroxy-4-methoxy-phenyl)-glyoxylic acid

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

(3-acetoxy-4-methoxy-phenyl)-acetonitrile

Downstream raw materials:

1-(3'-hydroxy-4'-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,6,7,8-hexahydroisoquinolin-6-one

1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

Refernces

• 1、 Yang, Kai,Luo, Shi-He,Chen, Si-Hong,Cao, Xi-Ying,Zhou, Yong-Jun,Lin, Yan-Lan,Huo, Yan-Ping,Wang, Zhao-Yang. "Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid". supporting information. p. 8133 - 8139. Retrieved 2021/10/04.
• 2、 Lee, David Y.W.,Liu, Jing,Zhang, Shuzhen,Huang, Peng,Liu-Chen, Lee-Yuan. "Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors". supporting information. p. 1437 - 1440. Retrieved 2017/03/08.