Cantharidin

Base Information

• Chemical Name: Cantharidin
• CAS No.: 56-25-7
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID7041752
• Pharos Ligand ID: Y158V373LA4C
• ChEMBL ID: CHEMBL299846
• Mol file: 56-25-7.mol

Synonyms:4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-, (3aa,4b,7b,7aa)-;7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylicanhydride, 2,3-dimethyl- (8CI);Cantharidin (6CI,7CI);1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride;Cantharidine;Cantharone;Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione;Kantaridin;NSC 61805;

Chemical Property of Cantharidin

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00021mmHg at 25°C
• Melting Point: 215-217 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 326.869 °C at 760 mmHg
• Flash Point: 146.137 °C
• PSA: 52.60000
• Density: 1.362 g/cm³
• LogP: 0.64360
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (25 mg/ml warm), acetone (8 mg/ml), ethanol (8 m
• Water Solubility.: 30mg/L(20 oC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 318

Purity/Quality:

99%, ^*data from raw suppliers

Cantharidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T+,T
• Statements: 28-36/37/38-38-37-36-23/24/25
• Safety Statements: 53-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12C3CCC(C1(C(=O)OC2=O)C)O3
• Isomeric SMILES: C[C@]12C3CCC([C@]1(C(=O)OC2=O)C)O3
• General Description: Cantharidin is a bicyclic terpenoid compound that serves as a precursor in the synthesis of novel aminobenzylcantharidinimides, which exhibit inhibitory effects on nitric oxide (NO) induction, particularly through the para-aminobenzylic derivatives. These derivatives, such as the most potent compound 3fp, show potential as therapeutic agents by targeting inducible NO synthase (iNOS) with notable efficacy.

Technology Process of Cantharidin

There total 22 articles about Cantharidin 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: 90.0%

furan (110-00-9) + 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride (75532-25-1) → cantharidin (56-25-7)

Guidance literature:

furan; 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride; With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 50 ℃; for 19h;

In ethyl acetate; for 4h; Reagent/catalyst; Temperature; Reflux;

Reference yield: 59.0%

C10H10O4S (75538-64-6) → cantharidin (56-25-7)

Guidance literature:

With hydrogen; In ethyl acetate; under 760.051 Torr; Reflux;

Reference yield:

C10H8O4S (75532-26-2) → cantharidin (56-25-7)

Guidance literature:

With hydrogen; In water; ethyl acetate; for 4h; Reflux;

upstream raw materials:

furan

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

C₁₀H₁₀O₄S

hydrogenchloride

Downstream raw materials:

Cantharidin-N-p-tolylimid

2-[2-((1RS,2SR)-2-hydroxy-1,2-diphenyl-ethylamino)-ethyl]-3a,7a-dimethyl-(3at,7at)-hexahydro-4r,7c-epioxido-isoindole-1,3-dione

N-phenylcantharidinimide

7-oxabicyclo<2.2.1>heptane-2,3-dimethyl-2,3-dicarboxylic acid imide

Refernces

Characterization of novel aminobenzylcantharidinimides and related imides by proton NMR spectra and their effects on NO induction

10.1002/jccs.201400228

The study focuses on the synthesis and characterization of novel aminobenzylcantharidinimides and related imides using proton NMR spectra. Researchers reacted various acidic anhydrides, including cantharidin, with aminobenzylamines and triethylamine to produce a series of imides with yields ranging from 35% to 87%. These compounds were evaluated for their effects on nitric oxide (NO) induction, and the results showed that para-aminobenzylic imides were more effective in inhibiting NO synthesis compared to their ortho and meta counterparts. The most potent compound, 3fp, demonstrated 35% inhibition of inducible NO synthase (iNOS). The findings provide insights into the structure-activity relationships of these compounds and their potential as therapeutic agents.