CID 280688

Base Information

• Chemical Name: CID 280688
• CAS No.: 981-15-7
• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.406
• European Community (EC) Number: 683-145-8
• NSC Number: 132792
• Wikipedia: Ailanthone
• Wikidata: Q105300637
• Mol file: 981-15-7.mol

Synonyms:ailanthone;ailantone;Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1beta,11beta,12beta)-

Chemical Property of CID 280688

Chemical Property:

• Vapor Pressure: 3.94E-19mmHg at 25°C
• Melting Point: 235-237 °C
• Refractive Index: 1.64
• Boiling Point: 641 °C at 760 mmHg
• PKA: 11.85±0.70(Predicted)
• Flash Point: 231.6 °C
• PSA: 113.29000
• Density: 1.47 g/cm³
• LogP: 0.08630
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 376.15220310
• Heavy Atom Count: 27
• Complexity: 817

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ailanthone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(=C)C4CC(=O)O3)O)(OC5)O)C)O
• Description: Ailanthone is a quassinoid that has been found in Ailanthus and has diverse biological activities. It is active against the P. falciparum strains HB-3 and Dd-2 in vitro (IC50s = 0.003 and 0.037 μg/ml, respectively). Ailanthone is phytotoxic, inhibiting radish seed germination by 88% when used at a concentration of 1 mM. It inhibits dihydrotestosterone-induced androgen receptor transcriptional activity (IC50 = 69 nM in a reporter assay), as well as the growth and colony formation of LNCaP and 22RV1 androgen receptor-expressing cells, but not androgen receptor-negative PC3 and DU145 cells, when used at a concentration of 0.1 μM. Ailanthone (2 mg/kg) reduces tumor volume in 22Rv1, LNCaP, and VCaP castration-resistant prostate cancer (CRPC) mouse xenograft models.
• Uses: Ailanthone has potent antineoplastic activity against anti-hepatocellular carcinoma (HCC) and has been shown to inhibit Huh7 cancer cell growth through cell cycle arrest and apoptosis in vitro and in vivo.

Technology Process of CID 280688

There total 1 articles about CID 280688 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:

shinjulactone A (89353-91-3) → ailanthone (981-15-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 21h; Ambient temperature;

DOI:10.1246/bcsj.56.3694

Reference yield: 40.0%

ailanthone (981-15-7) → isoailanthone (89353-80-0) + shinjulactone C (82470-74-4,130195-55-0)

Guidance literature:

In pyridine; for 20h; Heating;

DOI:10.1016/S0040-4039(00)94022-X

Reference yield: 8.0%

ailanthone (981-15-7) → chaparrinone (22611-34-3) + sinjulactone C

Guidance literature:

With pyridine; for 19h; Heating;

DOI:10.1246/bcsj.58.2357

upstream raw materials:

shinjulactone A

Downstream raw materials:

chaparrinone

3,4ξ-dihydrochaparrinone

C₂₀H₂₆O₇

isoailanthone

Refernces