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ailanthone

Product Name
ailanthone
CAS No.
981-15-7
Chemical Name
ailanthone
Synonyms
ailanthone;Δ13-Dehydrochaparrinone;Ailanthone, 10 mM in DMSO;13,21-Didehydrochaparrinone;2H-1,11c-(Epoxymethano)phenanthro[10,1-bc]pyran-5,10(3H,6aH);(1beta,11alpha,12alpha)-1,11,12-trihydroxy-11,20-epoxypicras...;11β,20-Epoxy-1β,11,12α-trihydroxypicrasa-3,13(21)-diene-2,16-dione;(1β,11β,12α)-11,20-Epoxy-1,11,12-trihydroxypicrasa-3,13(21)-diene-2,16-dione;Picrasa-3,13(21)-diene-2,16-dione,11,20-epoxy-1,11,12-trihydroxy-, (1b,11b,12a)-;Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1β,11β,12α)-
CBNumber
CB71327541
Molecular Formula
C20H24O7
Formula Weight
376.4
MOL File
981-15-7.mol
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ailanthone Property

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)
color 
White to off-white
InChIKey
WBBVXGHSWZIJST-BIKIFPNSNA-N
SMILES
[C@]123CO[C@@]4(O)[C@H](O)C(=C)C1CC(=O)O[C@]2([H])C[C@@]1([H])C(C)=CC(=O)[C@@H](O)[C@]1(C)[C@]34[H] |&1:0,3,5,14,17,24,26,28,r|
LogP
-0.760 (est)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML2143
Product name
Ailanthone
Purity
≥98% (HPLC)
Packaging
5MG
Price
$143.15
Updated
2025/07/31
Sigma-Aldrich
Product number
SML2143
Product name
Ailanthone
Purity
≥98% (HPLC)
Packaging
25MG
Price
$597
Updated
2025/07/31
Cayman Chemical
Product number
29194
Product name
Ailanthone
Packaging
5mg
Price
$116
Updated
2024/03/01
Cayman Chemical
Product number
29194
Product name
Ailanthone
Packaging
25mg
Price
$485
Updated
2024/03/01
Cayman Chemical
Product number
29194
Product name
Ailanthone
Packaging
1mg
Price
$37
Updated
2024/03/01
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ailanthone Chemical Properties,Usage,Production

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.

in vivo

Not only i.p. administration but also p.o. administration of Ailanthone has excellent efficiency for blocking the growth of CRPC xenografts. In pharmacokinetic studies, Ailanthone exhibits good solubility in water and good bioavailability (>20%). In addition, Ailanthone effectively suppresses CRPC tumour growth, despite not reaching a steady state of plasma drug concentration during the course of treatment[1].

References

[1] ADEWOLE L OKUNADE. Antiplasmodial activity of extracts and quassinoids isolated from seedlings of Ailanthus altissima (Simaroubaceae).[J]. Phytotherapy Research, 2003, 17 6: 675-677. DOI: 10.1002/ptr.1336
[2] VINCENZO DE FEO. Isolation of Phytotoxic Compounds from Tree-of-Heaven (Ailanthus altissima Swingle)[J]. Journal of Agricultural and Food Chemistry, 2003, 51 5: 1177-1180. DOI: 10.1021/jf020686+
[3] YUNDONG HE. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer[J]. Nature Communications, 2016, 7 1. DOI: 10.1038/ncomms13122

ailanthone Preparation Products And Raw materials

Raw materials

Preparation Products

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ailanthone Suppliers

China 151 France 1 United Kingdom 1 United States 10 Global 163
Tocris Bioscience
Tel
--
Fax
--
Email
customerservice@tocris.co.uk
Country
United Kingdom
ProdList
5726
Advantage
77
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View Lastest Price from ailanthone manufacturers

Career Henan Chemical Co
Product
ailanthone 981-15-7
Price
US $9.80/KG
Min. Order
1KG
Purity
≥98%
Supply Ability
20 tons
Release date
2020-01-10

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  • 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...
  • 2H-1,11c-(Epoxymethano)phenanthro[10,1-bc]pyran-5,10(3H,6aH)
  • (1R,2R,3aS,3a1S,6aR,7aS,11S,11aS,11bR)-1,2,11-Trihydroxy-8,11a-dimethyl-3-methylene-2,3,3a,4,7,7a,11,11a-octahydro-1H-1,3a1-(epoxymethano)dibenzo[de,g]chromene-5,10(6aH,11bH)-dione
  • Ailanthone, 10 mM in DMSO
  • 981-15-7
  • Diterpenoids