3-Hydroxy-4-methoxybenzoic acid

Base Information

• Chemical Name: 3-Hydroxy-4-methoxybenzoic acid
• CAS No.: 645-08-9
• Molecular Formula: C8H8 O4
• Molecular Weight: 168.149
• Hs Code.: 29189900
• European Community (EC) Number: 211-430-5
• UNII: A8D1DUX2PR
• DSSTox Substance ID: DTXSID40214745
• Nikkaji Number: J7.068H
• Wikidata: Q1674563
• Metabolomics Workbench ID: 62968
• ChEMBL ID: CHEMBL88700
• Mol file: 645-08-9.mol

Synonyms:isovanillic acid

Chemical Property of 3-Hydroxy-4-methoxybenzoic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystalline powder
• Vapor Pressure: 2.53E-05mmHg at 25°C
• Melting Point: 250 - 253 C
• Refractive Index: Health: 1; Flammability: 0; Reactivity: 0
• Boiling Point: 344.3 °C at 760 mmHg
• PKA: 4.35±0.10(Predicted)
• Flash Point: STABILITY
• PSA: 66.76000
• Density: 1.351 g/cm³
• LogP: 1.09900
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-4-methoxybenzoicacid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(=O)O)O
• Uses: Isovanillic acid has been used in the synthesis of opiate alkaloid precursor, dihydrothebainone.

Technology Process of 3-Hydroxy-4-methoxybenzoic acid

There total 76 articles about 3-Hydroxy-4-methoxybenzoic 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%

2-methoxy-5-cyanophenol (52805-46-6) → Isovanillic acid (645-08-9,74309-78-7)

Guidance literature:

With potassium hydroxide; for 6h; Heating;

DOI:10.1021/jo00202a014

Reference yield:

3,4-Dihydroxybenzoic acid (99-50-3) + S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) → 3-methoxy-4-hydroxybenzoic acid (121-34-6) + Isovanillic acid (645-08-9,74309-78-7) + Veratric acid (93-07-2)

Guidance literature:

With caffeic acid 3-O-methyltransferase from Catharanthus roseus; D,L-dithiothreitol; In aq. phosphate buffer; at 28 ℃; pH=7.5; regioselective reaction; Enzymatic reaction;

DOI:10.1002/cctc.201900606

Reference yield:

2-(3'-hydroxy-4'-methoxyphenyl)-2-hydroxyethanoic acid (3695-24-7,91318-74-0) → isovanillin (621-59-0) + Isovanillic acid (645-08-9,74309-78-7)

Guidance literature:

With oxygen; acetic acid; bismuth; In water; dimethyl sulfoxide; at 125 ℃; for 4h; under 760.051 Torr;

DOI:10.1002/1099-0690(200206)2002:12<1984::AID-EJOC1984>3.0.CO;2-3

upstream raw materials:

diazomethane

methanol

diethyl ether

3,4-Diacetoxy-benzoesaeure

Downstream raw materials:

3-ethoxy-4-methoxybenzoic acid

ethyl 3-hydroxy-4-methoxybenzoate

2,5-dihydroxy-4-methoxybenzoic acid

2-formyl-5-hydroxy-4-methoxy-benzoic acid

Refernces

• 1、 Singhal, Ashok K.,Barua, Nabin C.,Sharma, Ram P.,Baruah, Jogendra N.. "A CHALCONE AND AN ISOFLAVONE FROM MILLETTIA PACHYCARPA SEEDS". . p. 1005 - 1006. Retrieved 1983.
• 2、 Lee, Seul Hoo,Kim, Bongsang,Kim, Kyung-Jin. "Crystal Structure and Regiospecificity of Catechol O-Methyltransferase from Niastella koreensis". . p. 2531 - 2538. Retrieved 2021/03/09.
• 3、 Lanfranchi, Elisa,Trajkovi?, Milo?,Barta, Katalin,de Vries, Johannes G.,Janssen, Dick B.. "Exploring the Selective Demethylation of Aryl Methyl Ethers with a Pseudomonas Rieske Monooxygenase". . p. 118 - 125. Retrieved 2019/01/04.