Cucurbitacin B

Base Information

• Chemical Name: Cucurbitacin B
• CAS No.: 6199-67-3
• Molecular Formula: C₃₂H₄₆O₈
• Molecular Weight: 558.712
• Hs Code.: 29153900
• European Community (EC) Number: 683-121-7
• UNII: 0115W5MABF
• ChEMBL ID: CHEMBL508185
• DSSTox Substance ID: DTXSID501316196
• Metabolomics Workbench ID: 34409
• Nikkaji Number: J2.419.799I,J8.359C
• NSC Number: 144154,49451
• Wikidata: Q27106259
• Mol file: 6199-67-3.mol

Synonyms:cucurbitacin B;cucurbitacin B 2-sulfate

Chemical Property of Cucurbitacin B

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.3E-22mmHg at 25°C
• Melting Point: 184-186oC
• Refractive Index: 1.568
• Boiling Point: 699.3 °C at 760 mmHg
• PKA: 12.60±0.29(Predicted)
• Flash Point: 218.7 °C
• PSA: 138.20000
• Density: 1.23 g/cm³
• LogP: 3.49930
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 558.31926842
• Heavy Atom Count: 40
• Complexity: 1210

Purity/Quality:

99% ^*data from raw suppliers

Cucurbitacin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O)O
• Isomeric SMILES: CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)C)O)O
• Description: Cucurbitacin B is a tetracyclic triterpenoid that has been shown to have a strong antitumor activity.
• Uses: Cucurbitacin B hydrate has been used: as a signal transducer and activator of transcription 3 (stat3) inhibitor to determine its effect on the expression of human lysosomal acid lipase (hLAL) in myeloid-derived suppressor cells (MDSCs).as an ecdysone receptor (EcR) antagonist injection to lower the levels of 20-hydoxyecdysone (20E) signaling in butterflies.to determine its effect on the cell viability of pancreatic cancer cell lines.

Technology Process of Cucurbitacin B

There total 1 articles about Cucurbitacin B 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:

→ Cucurbitacin B; 2.16.20-Trihydroxy-25-acetoxy-9-methyl-19-nor-lanostadien-(5.23)-trion-(3.11.22) (6199-67-3,59015-72-4)

Guidance literature:

Cucurbitacin E, Hydrolyse;

DOI:10.1007/BF00563735

Reference yield: 97.2%

cucurbitacin B (6199-67-3,59015-72-4) → cucurbitacin D (3877-86-9)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃; for 2h;

Reference yield: 80.0%

cucurbitacin B (6199-67-3,59015-72-4) + acetic anhydride (108-24-7) → 2,16,25-cucurbitacin D triacetate (37710-14-8)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2012.03.001

Downstream raw materials:

2,16,25-cucurbitacin D triacetate

C₃₃H₄₆N₂O₆S

2-deoxy-2-bromo-cucurbitacin B

C₃₂H₄₅NO₇