Diffractaic acid

Base Information

• Chemical Name: Diffractaic acid
• CAS No.: 436-32-8
• Molecular Formula: C20H22 O7
• Molecular Weight: 374.39
• Hs Code.: 2918990090
• NSC Number: 685595,5901
• UNII: PD86RC383X
• DSSTox Substance ID: DTXSID40195883
• Nikkaji Number: J12.592J
• Wikidata: Q27185958
• Pharos Ligand ID: N45VK1MCYFTH
• Metabolomics Workbench ID: 133015
• ChEMBL ID: CHEMBL367741
• Mol file: 436-32-8.mol

Synonyms:diffractaic acid

Chemical Property of Diffractaic acid

Chemical Property:

• Vapor Pressure: 1.74E-15mmHg at 25°C
• Melting Point: 189～190℃
• Boiling Point: 604.9°Cat760mmHg
• PKA: 2.66±0.25(Predicted)
• Flash Point: 214.2°C
• PSA: 102.29000
• Density: 1.26g/cm³
• LogP: 3.56040
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 374.13655304
• Heavy Atom Count: 27
• Complexity: 536

Purity/Quality:

≥98% ^*data from raw suppliers

Diffractaic Acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1C(=O)O)O)C)OC(=O)C2=C(C(=C(C=C2C)OC)C)OC
• Description: Diffractaic acid is a lichen metabolite that has been found in P. magellanica and has diverse biological activities. It is cytotoxic to HCT116, HeLa, and MCF-7 cancer cells (IC50s = 42.2, 64.6, and 93.4 μM, respectively). Diffractaic acid inhibits growth of M. tuberculosis (MIC = 41.7 μM). In vivo, diffractaic acid (25-200 mg/kg) reduces neutrophil infiltration, lipid peroxidation, myeloperoxidase (MPx) activity, and the number of gastric lesions as well as reverses decreases in superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities induced by indomethacin in rat gastric mucosa. Diffractaic acid also has analgesic activity, reducing acetic acid-induced writhing and increasing the pressure pain threshold in mice.

Technology Process of Diffractaic acid

There total 5 articles about Diffractaic 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:

Benzyl diffractaiat (56410-45-8) → diffractaic acid (436-32-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate;

DOI:10.1016/S0223-5234(99)00132-4

Reference yield:

ethyl 2,4-dihydroxy-3,6-dimethylbenzoate (31581-32-5) → diffractaic acid (436-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / NaOCH₂Ph / 24 h / Heating

2: 83 percent / (CF₃-CO)2O / toluene / 20 °C

3: H₂; 10 percent Pd/C / ethyl acetate

With palladium on activated charcoal; hydrogen; sodium phenyl-methanolate; trifluoroacetic anhydride; In ethyl acetate; toluene; 1: transesterification / 2: Esterification / 3: Hydrogenolysis;

DOI:10.1016/S0223-5234(99)00132-4

Reference yield:

benzyl 2,4-dihydroxy-3,6-dimethylbenzoate (56410-30-1) → diffractaic acid (436-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / (CF₃-CO)2O / toluene / 20 °C

2: H₂; 10 percent Pd/C / ethyl acetate

With palladium on activated charcoal; hydrogen; trifluoroacetic anhydride; In ethyl acetate; toluene; 1: Esterification / 2: Hydrogenolysis;

DOI:10.1016/S0223-5234(99)00132-4

upstream raw materials:

Benzyl diffractaiat

ethyl 2,4-dihydroxy-3,6-dimethylbenzoate

2,4-O-dimethyl-β-orcinolcarboxylic acid

benzyl 2,4-dihydroxy-3,6-dimethylbenzoate

Downstream raw materials:

2,5-dimethyl-1,3-benzenediol

2,4-O-dimethyl-β-orcinolcarboxylic acid

2,4-dihydroxy-3,6-dimethylbenzoic acid

4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester

Refernces