Homoveratric acid

Base Information

• Chemical Name: Homoveratric acid
• CAS No.: 93-40-3
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 29189090
• European Community (EC) Number: 202-244-5
• NSC Number: 27897,2753
• UNII: YY50GIT3C7
• DSSTox Substance ID: DTXSID5059086
• Nikkaji Number: J46.682D
• Wikidata: Q10395556
• Metabolomics Workbench ID: 37248
• Mol file: 93-40-3.mol

Synonyms:(3,4-dimethoxyphenyl)acetic acid

Chemical Property of Homoveratric acid

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 6.23E-05mmHg at 25°C
• Melting Point: 96-98 °C(lit.)
• Refractive Index: 1.5430 (estimate)
• Boiling Point: 331.4 °C at 760 mmHg
• PKA: pK1:4.333 (25°C)
• Flash Point: 130.2 °C
• PSA: 55.76000
• Density: 1.189 g/cm³
• LogP: 1.33090
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Homoveratric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22-36/37
• Safety Statements: 22-24/25-36/37-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC(=O)O)OC
• General Description: (3,4-Dimethoxyphenyl)acetic acid, also known as homoveratric acid, is a key starting compound used in the synthesis of benzo[c]pyrilium salts with cyclopolyether substituents. It reacts with benzo-15-crown-5 in polyphosphoric acid to form a ketone intermediate, which is further converted into benzo[c]pyrilium perchlorates and subsequently into isoquinoline derivatives. These derivatives are studied for their potential biological activity, particularly in membrane penetration and selective ion transfer.

Technology Process of Homoveratric acid

There total 56 articles about Homoveratric 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: 100.0%

C21H29NO4Si → (3,4-Dimethoxyphenyl)acetic acid (93-40-3)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In pentane; at 20 ℃;

DOI:10.1039/d0sc03676e

Reference yield: 100.0%

4,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (81447-58-7) → (3,4-Dimethoxyphenyl)acetic acid (93-40-3)

Guidance literature:

With sodium hydroxide; at 60 ℃; for 2h;

DOI:10.1021/jo00133a031

Reference yield: 95.0%

methyl (3,4-dimethoxyphenyl)acetate (15964-79-1) → (3,4-Dimethoxyphenyl)acetic acid (93-40-3)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 80 ℃; for 10h;

DOI:10.1016/j.bmcl.2014.04.057

upstream raw materials:

diazomethane

3,4-dihydroxyphenylacetate

1,2-dimethoxy-4-(2-propenyl)benzene

3,4-dimethoxyphenylacetonitrile

Downstream raw materials:

2-(3,4-dimethoxyphenyl)-1-(piperidin-1-yl)ethan-1-one

methyl (3,4-dimethoxyphenyl)acetate

(3,4-dimethoxy-phenyl)-acetic acid-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamide]

ethyl 3,4-dimethoxyphenylacetate

Refernces

BENZOPYRILIUM SALTS WITH A CYCLOPOLYETHER SUBSTITUENT

10.1007/BF00479904

The research focuses on the synthesis of benzo[c]pyrilium salts with a cyclopolyether substituent and their conversion to isoquinoline derivatives. The key chemicals involved in the research include homoveratric acid and benzo-15-crown-5 as starting compounds. These compounds react in polyphosphoric acid to form ketone I. Carboxylic acid anhydrides, specifically acetic or propionic anhydride, along with perchloric acid, are used to convert ketone I into benzo[c]pyrilium perchlorates (IIa and IIb). Finally, ammonium carbamate is employed to transform these perchlorates into the desired isoquinoline derivatives (IIIa and IIIb). The study explores the potential of these compounds for developing new biologically active substances that can penetrate biological membranes or influence selective ion transfer in living organisms.