3,5-Diiodosalicylic acid

Base Information

• Chemical Name: 3,5-Diiodosalicylic acid
• CAS No.: 133-91-5
• Molecular Formula: C7H4I2O3
• Molecular Weight: 389.916
• Hs Code.: 29182990
• European Community (EC) Number: 205-124-0
• NSC Number: 6303
• UNII: 1496OH15B6
• DSSTox Substance ID: DTXSID3059636
• Nikkaji Number: J54.308J
• Wikidata: Q223023
• Metabolomics Workbench ID: 149108
• ChEMBL ID: CHEMBL1232243
• Mol file: 133-91-5.mol

Synonyms:3,5-diiodosalicylic acid;3,5-diiodosalicylic acid, disodium salt;3,5-diiodosalicylic acid, lithium salt;3,5-diiodosalicylic acid, monolithium salt;3,5-diiodosalicylic acid, monosodium salt;lithium di-iodosalicylate;lithium diiodosalicilate;lithium diiodosalicylate

Chemical Property of 3,5-Diiodosalicylic acid

Chemical Property:

• Appearance/Colour: Off-white to beige or grey powder
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Melting Point: 220-230 °C (dec.)(lit.)
• Boiling Point: 380.8 °C at 760 mmHg
• PKA: 2.07±0.14(Predicted)
• Flash Point: 184.1 °C
• PSA: 57.53000
• Density: 2.697 g/cm³
• LogP: 2.29960
• Storage Temp.: -20°C
• Sensitive.: Light Sensitive
• Solubility.: 0.192g/l
• Water Solubility.: 0.02 g/100mL (25 ºC)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 389.82499
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

3,5-Diiodosalicylic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1C(=O)O)O)I)I
• Uses: 3,5-Diiodosalicylic Acid is an metabolite of Aspirin (A187780), an anti-inflammatory, anti-platelet and cancer-preventive agent. 3,5-Diiodosalicylic Acid was shown to exhibit agonist activity at GPR35 , a orphan G protein coupled receptor. 3,5-Diiodosalicylic Acid is an metabolite of Aspirin (A187780), an anti-inflammatory, anti-platelet and cancer-preventive agent. 3,5-Diiodosalicylic Acid was shown to exhibit agonist activity at GPR35, a orphan G protein coupled receptor.

Technology Process of 3,5-Diiodosalicylic acid

There total 24 articles about 3,5-Diiodosalicylic 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: 95.9%

salicylic acid (69-72-7,25496-36-0,8052-31-1) → 3,5-diiodosalicylic acid (133-91-5)

Guidance literature:

With dihydrogen peroxide; iodine; trichloroacetic acid; In methanol; at 45 - 66 ℃; for 6h;

Reference yield:

3,5-diodosalicylaldehyde (2631-77-8) → 3,5-diiodosalicylic acid (133-91-5)

Guidance literature:

With permanganate(VII) ion; acetone;

Reference yield:

2-hydroxy-5-iodobenzoic acid (119-30-2) → 3,5-diiodosalicylic acid (133-91-5)

Guidance literature:

upstream raw materials:

3,5-diodosalicylaldehyde

2-hydroxy-5-iodobenzoic acid

2-hydroxy-3-iodobenzoic acid

silver salicylate

Downstream raw materials:

2-hydroxy-3,5-diiodobenzoic acid ethyl ester

2,4,6-Triiodophenol

2-hydroxy-3,5-diiodo-benzoic acid-(1H-tetrazol-5-ylamide)

2-hydroxy-3,5-diiodobenzoyl chloride

Refernces

Iodinated 1,2-diacylhydrazines, benzohydrazide-hydrazones and their analogues as dual antimicrobial and cytotoxic agents

10.1016/j.bmc.2021.116209

This research aimed to evaluate the potential of iodinated hydrazide-hydrazones and their analogues as dual antimicrobial and cytotoxic agents, addressing the increasing resistance of bacterial and fungal pathogens to existing treatments. The study synthesized and screened twenty-two iodinated hydrazide-hydrazones and ten 1,2-diacylhydrazines, along with their three reduced analogues, for their antibacterial, antifungal, and cytotoxic properties. The compounds were tested against eight bacterial and eight fungal strains, and their cytotoxicity was assessed on HepG2 and HK-2 cell lines. The study found that certain derivatives, particularly those containing the 3,5-diiodosalicylidene scaffold, exhibited potent antibacterial activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), with low minimum inhibitory concentrations (MIC) values. Some compounds also showed antifungal activity and variable degrees of cytotoxicity, with normal human cells exhibiting lower sensitivity. The research concluded that these compounds, especially those with electron-withdrawing groups like F, Cl, CF3, and NO2, have potential as antimicrobial and cytotoxic agents. The chemicals used in the process included various substituted benzohydrazides, 2-/4-hydroxy-3,5-diiodobenzaldehydes, 3,5-diiodosalicylic acid, and their derivatives, as well as reagents for biological assays and cytotoxicity tests.