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ailanthone

Basic information Safety Supplier Related

ailanthone Basic information

Product Name:
ailanthone
Synonyms:
  • 11β,20-Epoxy-1β,11,12α-trihydroxypicrasa-3,13(21)-diene-2,16-dione
  • 13,21-Didehydrochaparrinone
  • ailanthone
  • Picrasa-3,13(21)-diene-2,16-dione,11,20-epoxy-1,11,12-trihydroxy-, (1b,11b,12a)-
  • (1β,11β,12α)-11,20-Epoxy-1,11,12-trihydroxypicrasa-3,13(21)-diene-2,16-dione
  • Δ13-Dehydrochaparrinone
  • Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1β,11β,12α)-
  • (1beta,11alpha,12alpha)-1,11,12-trihydroxy-11,20-epoxypicras...
CAS:
981-15-7
MF:
C20H24O7
MW:
376.4
Product Categories:
  • Diterpenoids
Mol File:
981-15-7.mol
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ailanthone Chemical Properties

Melting point:
235-237 °C
Boiling point:
641.0±55.0 °C(Predicted)
Density 
1.47
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO:100.0(Max Conc. mg/mL);265.67(Max Conc. mM)
form 
A crystalline solid
pka
11.85±0.70(Predicted)
LogP
-0.760 (est)
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ailanthone Usage And Synthesis

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.

Definition

ChEBI: Ailanthone is a triterpenoid.

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